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This beautifully designed Chester Model Home offers sophisticated comfort and modern convenience, ready for immediate move-in with a flexible month-to-month leaseback opportunity. Featuring 2 bedrooms, 2.5 baths, and a 1-car garage, this home blends style and function seamlessly. Thoughtful touches include a fully furnished interior, a dry bar perfect for entertaining, and an electric fireplace that adds warmth and ambiance. A dedicated home office with elegant lited French doors provides the ideal space for work or creativity. The gourmet kitchen is equipped with a single oven, microwave, gas cooktop, range hood, dishwasher, pendant lighting, and a tile backsplash, all accented by quartz countertops that continue into the full baths. Enjoy laminate flooring throughout for easy maintenance, complemented by tile in the full baths. The owner’s bath offers a walk-in shower with a seat and handheld shower wand, plus double sinks and quartz counters for a spa-like retreat. For a full list of included features, please contact our sales representatives.

132 Wheelhouse Way, Chester

Listing courtesy of KOVO Realty. Contact:

Welcome to the Taylor, a beautifully designed home that offers the perfect blend of comfort, style, and convenience. Available now, this home features 2 bedrooms, 2.5 baths, and a spacious 3-car garage, making it ideal for those seeking both functional living and elegant design. The open-concept layout is enhanced by a cozy fireplace and decorative ceiling beams that add warmth and architectural charm to the main living area. Step outside to the screened patio, where you can relax and take in peaceful waterfront views, creating the perfect setting for morning coffee or evening gatherings. The kitchen is equipped with a full suite of appliances, and a washer and dryer are also included, allowing you to move in with ease and enjoy modern convenience from day one. The primary bath features a spacious walk-in shower, offering a comfortable and spa-inspired retreat to unwind at the end of the day. For a full list of features for this home please contact our sales representatives. Photos are for illustrative purposes only and may not represent the exact home or finishes available. Welcome to a new luxury active adult 55+ community on Maryland's Chesapeake Bay. Discover the amenity-filled, resort-style experience within 45 miles of Washington DC and Baltimore. Residents can take advantage of the community's 24,000 sq. ft. clubhouse with indoor & outdoor pools, a state-of-the-art fitness center, and multiple tennis and pickleball courts. With a full-time lifestyle director on site the community also features a well-maintained calendar of activities such as walking club, indoor and outdoor yoga sessions, mahjong club, kayaking, pickleball and more. Kent Island life is about making friends and enjoying the company of people who have worked hard and now want to enjoy all that a luxury 55+ community has to offer. Located steps from the water and minutes from Annapolis, the location also offers quick access to Rt. 50. Enjoy the convenience of nearby dining and shopping options together with the quaint charm of a small town.

$1,200,000

Welcome to the Taylor, a beautifully designed home that offers the perfect blend of comfort, style, and convenience. Available now, this home features 2 bedrooms, 2.5 baths, and a spacious 3-car garage, making it ideal for those seeking both functional living and elegant design. The open-concept layout is enhanced by a cozy fireplace and decorative ceiling beams that add warmth and architectural charm to the main living area. Step outside to the screened patio, where you can relax and take in peaceful waterfront views, creating the perfect setting for morning coffee or evening gatherings. The kitchen is equipped with a full suite of appliances, and a washer and dryer are also included, allowing you to move in with ease and enjoy modern convenience from day one. The primary bath features a spacious walk-in shower, offering a comfortable and spa-inspired retreat to unwind at the end of the day. For a full list of features for this home please contact our sales representatives. Photos are for illustrative purposes only and may not represent the exact home or finishes available. Welcome to a new luxury active adult 55+ community on Maryland's Chesapeake Bay. Discover the amenity-filled, resort-style experience within 45 miles of Washington DC and Baltimore. Residents can take advantage of the community's 24,000 sq. ft. clubhouse with indoor & outdoor pools, a state-of-the-art fitness center, and multiple tennis and pickleball courts. With a full-time lifestyle director on site the community also features a well-maintained calendar of activities such as walking club, indoor and outdoor yoga sessions, mahjong club, kayaking, pickleball and more. Kent Island life is about making friends and enjoying the company of people who have worked hard and now want to enjoy all that a luxury 55+ community has to offer. Located steps from the water and minutes from Annapolis, the location also offers quick access to Rt. 50. Enjoy the convenience of nearby dining and shopping options together with the quaint charm of a small town.

216 Kingfisher Ln, Chester

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP. Contact:

The Chester at Lot 2443 offers a thoughtfully designed open-concept layout with a projected settlement date of August 2026, making it a great opportunity for buyers planning ahead. This home includes 2 bedrooms, 2.5 baths, and a 1-car garage, delivering comfort, functionality, and efficient use of space. Highlighted features include a dedicated home office with lighted French doors, a stylish dry bar for entertaining, a cozy electric fireplace, and a convenient storage room to keep everything organized. Luxury vinyl plank flooring runs throughout the home, with tile in both full baths for durability and a polished finish. The kitchen is well equipped with a single oven, microwave, gas cooktop, range hood, dishwasher, pendant lighting, and a tile backsplash, all complemented by quartz countertops. The owner’s bath serves as a relaxing retreat with a shower featuring a built-in seat, handheld shower wand, double sinks, and quartz countertops. For a full list of features for this home, please contact our sales representatives. Photos are for illustrative purposes only and may not represent the exact home or finishes available.

$979,990

The Chester at Lot 2443 offers a thoughtfully designed open-concept layout with a projected settlement date of August 2026, making it a great opportunity for buyers planning ahead. This home includes 2 bedrooms, 2.5 baths, and a 1-car garage, delivering comfort, functionality, and efficient use of space. Highlighted features include a dedicated home office with lighted French doors, a stylish dry bar for entertaining, a cozy electric fireplace, and a convenient storage room to keep everything organized. Luxury vinyl plank flooring runs throughout the home, with tile in both full baths for durability and a polished finish. The kitchen is well equipped with a single oven, microwave, gas cooktop, range hood, dishwasher, pendant lighting, and a tile backsplash, all complemented by quartz countertops. The owner’s bath serves as a relaxing retreat with a shower featuring a built-in seat, handheld shower wand, double sinks, and quartz countertops. For a full list of features for this home, please contact our sales representatives. Photos are for illustrative purposes only and may not represent the exact home or finishes available.

176 Flagstaff Way Unit 2443, Chester

Listing courtesy of KOVO Realty. Contact:

Selling Office: Berkshire Hathaway HomeServices PenFed Realty.

$965,000

Welcome to luxury, comfort, and effortless living in the highly sought-after first section of Four Seasons at Kent Island. Offering a floor plan no longer available in the community's newer sections, this exceptional home combines thoughtful design with upscale finishes throughout. A spacious foyer welcomes you into an open and inviting layout that is perfect for both everyday living and entertaining. At the heart of the home is a stunning gourmet kitchen featuring an oversized center island that naturally becomes the gathering place for family and friends. Whether hosting indoors or enjoying the outdoors, you'll appreciate the seamless flow to the screened porch and beautifully designed patio complete with a built-in fire pit. The private primary suite is a true retreat, highlighted by an elegant tray ceiling, an impressive custom walk-in closet system, and a luxurious en-suite bath featuring a spacious walk-in shower, dual vanities, and a dedicated built-in makeup vanity. The main level also offers a second bedroom, full bath, private home office, and convenient laundry room, providing the ease of one-level living. Upstairs, guests will enjoy their own private space with an additional living area, bedroom, and full bath and access to the conditioned sky garage which is great for storage. Attached two car garage with epoxy flooring and inside access. Beyond the home, enjoy the award-winning lifestyle Four Seasons at Kent Island is known for. Residents have access to an impressive 24,000-square-foot clubhouse featuring indoor and outdoor pools, a state-of-the-art fitness center, tennis and pickleball courts, dog parks, walking trails, and an active calendar of social events—all designed for exceptional 55+ living.

Welcome to luxury, comfort, and effortless living in the highly sought-after first section of Four Seasons at Kent Island. Offering a floor plan no longer available in the community's newer sections, this exceptional home combines thoughtful design with upscale finishes throughout. A spacious foyer welcomes you into an open and inviting layout that is perfect for both everyday living and entertaining. At the heart of the home is a stunning gourmet kitchen featuring an oversized center island that naturally becomes the gathering place for family and friends. Whether hosting indoors or enjoying the outdoors, you'll appreciate the seamless flow to the screened porch and beautifully designed patio complete with a built-in fire pit. The private primary suite is a true retreat, highlighted by an elegant tray ceiling, an impressive custom walk-in closet system, and a luxurious en-suite bath featuring a spacious walk-in shower, dual vanities, and a dedicated built-in makeup vanity. The main level also offers a second bedroom, full bath, private home office, and convenient laundry room, providing the ease of one-level living. Upstairs, guests will enjoy their own private space with an additional living area, bedroom, and full bath and access to the conditioned sky garage which is great for storage. Attached two car garage with epoxy flooring and inside access. Beyond the home, enjoy the award-winning lifestyle Four Seasons at Kent Island is known for. Residents have access to an impressive 24,000-square-foot clubhouse featuring indoor and outdoor pools, a state-of-the-art fitness center, tennis and pickleball courts, dog parks, walking trails, and an active calendar of social events—all designed for exceptional 55+ living.

154 Bluebell Ct, Chester

Listing courtesy of Wilson Realty & Staging LLC. Contact:

Selling Office: Coldwell Banker Realty.

$937,990

Welcome to the Tuscaloosa, a spacious and thoughtfully designed home offering 5 bedrooms, 4.5 baths, and a 3-car garage. Scheduled for settlement in July 2026, this home delivers the perfect combination of comfort, functionality, and modern design. The main living area features a cozy fireplace with mantel and hearth, creating a warm focal point for gathering. A dedicated home office provides a quiet and productive workspace, while the screened patio extends the living area outdoors—perfect for relaxing or entertaining. Practical touches such as a utility sink add convenience to everyday living. The kitchen is designed for both style and performance, featuring a single oven, microwave, gas cooktop with range hood, dishwasher, French door refrigerator, pendant lighting, tile backsplash, and quartz countertops. Quartz countertops are also featured in the primary bath for a cohesive and elegant finish. Luxury vinyl plank flooring runs throughout the foyer, extended foyer, HovHall, kitchen, dining area, great room, home office, extra suite, primary suite, and loft. Tile flooring is featured in the full baths and laundry room, while carpet provides comfort in bedrooms 3, 4, and 5. The primary bath offers a spa-like retreat with a freestanding tub, a walk-in shower with seat and handheld shower wand, and a double-sink vanity. For a full list of features for this home please contact our sales representatives. Photos are for illustrative purposes only and may not represent the exact home or finishes available. Welcome to a new luxury active adult 55+ community on Maryland's Chesapeake Bay. Discover the amenity-filled, resort-style experience within 45 miles of Washington DC and Baltimore. Residents can take advantage of the community's 24,000 sq. ft. clubhouse with indoor & outdoor pools, a state-of-the-art fitness center, and multiple tennis and pickleball courts. With a full-time lifestyle director on site the community also features a well-maintained calendar of activities such as walking club, indoor and outdoor yoga sessions, mahjong club, kayaking, pickleball and more. Kent Island life is about making friends and enjoying the company of people who have worked hard and now want to enjoy all that a luxury 55+ community has to offer. Located steps from the water and minutes from Annapolis, the location also offers quick access to Rt. 50. Enjoy the convenience of nearby dining and shopping options together with the quaint charm of a small town.

Welcome to the Tuscaloosa, a spacious and thoughtfully designed home offering 5 bedrooms, 4.5 baths, and a 3-car garage. Scheduled for settlement in July 2026, this home delivers the perfect combination of comfort, functionality, and modern design. The main living area features a cozy fireplace with mantel and hearth, creating a warm focal point for gathering. A dedicated home office provides a quiet and productive workspace, while the screened patio extends the living area outdoors—perfect for relaxing or entertaining. Practical touches such as a utility sink add convenience to everyday living. The kitchen is designed for both style and performance, featuring a single oven, microwave, gas cooktop with range hood, dishwasher, French door refrigerator, pendant lighting, tile backsplash, and quartz countertops. Quartz countertops are also featured in the primary bath for a cohesive and elegant finish. Luxury vinyl plank flooring runs throughout the foyer, extended foyer, HovHall, kitchen, dining area, great room, home office, extra suite, primary suite, and loft. Tile flooring is featured in the full baths and laundry room, while carpet provides comfort in bedrooms 3, 4, and 5. The primary bath offers a spa-like retreat with a freestanding tub, a walk-in shower with seat and handheld shower wand, and a double-sink vanity. For a full list of features for this home please contact our sales representatives. Photos are for illustrative purposes only and may not represent the exact home or finishes available. Welcome to a new luxury active adult 55+ community on Maryland's Chesapeake Bay. Discover the amenity-filled, resort-style experience within 45 miles of Washington DC and Baltimore. Residents can take advantage of the community's 24,000 sq. ft. clubhouse with indoor & outdoor pools, a state-of-the-art fitness center, and multiple tennis and pickleball courts. With a full-time lifestyle director on site the community also features a well-maintained calendar of activities such as walking club, indoor and outdoor yoga sessions, mahjong club, kayaking, pickleball and more. Kent Island life is about making friends and enjoying the company of people who have worked hard and now want to enjoy all that a luxury 55+ community has to offer. Located steps from the water and minutes from Annapolis, the location also offers quick access to Rt. 50. Enjoy the convenience of nearby dining and shopping options together with the quaint charm of a small town.

121 Kinglet Ct, Chester

Listing courtesy of KOVO Realty. Contact:

Selling Office: Long & Foster Real Estate, Inc..

$935,000

Welcome to Four Seasons at Kent Island, where luxury and comfort meet coastal living. This stunning Santorini model at the end of a cul-de-sac with loft offers 3 bedrooms, 4 full baths, and thoughtfully curated designer upgrades throughout. From the moment you step inside, you’ll feel the ease of open-concept living — soaring 10’ ceilings, cozy gas fireplace, abundant natural light, neutral color scheme, and wide-plank LVP flooring create a calm, inviting atmosphere. An expansive glass slider opens to a beautifully hardscaped patio and covered porch with built-in outdoor kitchen, gas grill and ceiling fan—ideal for enjoying warm evenings and cool breezes. The professionally landscaped property sets this home as the gem of the community! The gourmet kitchen is the heart of the home, featuring a full suite of premium appliances, and an expansive 12’ Laza Quartz island which easily seats five, making it perfect for gathering with family or hosting friends. The primary suite offers a spa-inspired retreat with a frameless shower featuring upgraded triple windows to let the natural light in and double sinks for added functionality. An additional guest suite, formal dining room, and library/office on the main level allow for complete one-level living. Plantation shutters, recessed LED lighting, and custom closet shelving throughout offer both elegance and practicality. The walk-in pantry with planning desk, plus laundry center with front-load washer/dryer, custom cabinetry and folding space, make everyday living effortless. Up the staircase, which features a mid-level landing for ease of use, the loft offers flexibility and privacy with an additional living area, full bath, bedroom, walk-in closet, and expansive standing attic storage. With upgraded essentials like a tankless water heater, and built-in garage storage, each detail of this home is designed to elevate your lifestyle. The amenity-rich Four Seasons at Kent Island allows residents to take advantage of the community's 24,000 sq. ft. clubhouse with indoor & outdoor pools, a state-of-the-art fitness center, lounging areas, firepits, and multiple tennis and pickleball courts. With a full-time lifestyle director on site the community also features a well-maintained calendar of activities such as walking club, indoor and outdoor yoga sessions, mahjong club, kayaking, pickleball and more. Located steps from the water and minutes from Annapolis, the location also offers quick access to Rt. 50. Enjoy the convenience of nearby dining and shopping options together with the quaint charm of a small town. miss your chance to enjoy the best of relaxed, resort-style living on Kent Island. Welcome Home!

3 Beds ⋅ 4 Baths

Welcome to Four Seasons at Kent Island, where luxury and comfort meet coastal living. This stunning Santorini model at the end of a cul-de-sac with loft offers 3 bedrooms, 4 full baths, and thoughtfully curated designer upgrades throughout. From the moment you step inside, you’ll feel the ease of open-concept living — soaring 10’ ceilings, cozy gas fireplace, abundant natural light, neutral color scheme, and wide-plank LVP flooring create a calm, inviting atmosphere. An expansive glass slider opens to a beautifully hardscaped patio and covered porch with built-in outdoor kitchen, gas grill and ceiling fan—ideal for enjoying warm evenings and cool breezes. The professionally landscaped property sets this home as the gem of the community! The gourmet kitchen is the heart of the home, featuring a full suite of premium appliances, and an expansive 12’ Laza Quartz island which easily seats five, making it perfect for gathering with family or hosting friends. The primary suite offers a spa-inspired retreat with a frameless shower featuring upgraded triple windows to let the natural light in and double sinks for added functionality. An additional guest suite, formal dining room, and library/office on the main level allow for complete one-level living. Plantation shutters, recessed LED lighting, and custom closet shelving throughout offer both elegance and practicality. The walk-in pantry with planning desk, plus laundry center with front-load washer/dryer, custom cabinetry and folding space, make everyday living effortless. Up the staircase, which features a mid-level landing for ease of use, the loft offers flexibility and privacy with an additional living area, full bath, bedroom, walk-in closet, and expansive standing attic storage. With upgraded essentials like a tankless water heater, and built-in garage storage, each detail of this home is designed to elevate your lifestyle. The amenity-rich Four Seasons at Kent Island allows residents to take advantage of the community's 24,000 sq. ft. clubhouse with indoor & outdoor pools, a state-of-the-art fitness center, lounging areas, firepits, and multiple tennis and pickleball courts. With a full-time lifestyle director on site the community also features a well-maintained calendar of activities such as walking club, indoor and outdoor yoga sessions, mahjong club, kayaking, pickleball and more. Located steps from the water and minutes from Annapolis, the location also offers quick access to Rt. 50. Enjoy the convenience of nearby dining and shopping options together with the quaint charm of a small town. miss your chance to enjoy the best of relaxed, resort-style living on Kent Island. Welcome Home!

130 Sunrise Ct, Chester

Listing courtesy of Engel & Volkers Annapolis. Contact:

Selling Office: RE/MAX Executive.

$934,900

Welcome to the Tuscaloosa, a stunning 5-bedroom, 4.5-bath home designed for flexible living and modern style. With a 3-car garage, open-concept layout, and high-end finishes, this home is the perfect blend of comfort and sophistication. Enjoy thoughtful details throughout, including a cozy fireplace, versatile home office, bright loft, and a relaxing screened patio. The kitchen features a full suite of premium appliances—including a French door refrigerator, gas cooktop, and tile backsplash—topped with elegant quartz countertops. The primary suite offers a spa-inspired retreat with a frameless shower featuring a seat and handheld wand, plus double sinks for added functionality. Flooring includes Luxury Vinyl Plank on the main level, tile in all full baths and the laundry room, and plush carpet in the second-floor loft and bedrooms 3, 4, and 5. For a full list of features for this home, please contact our sales consultants. Photos are for display purposes only and may not reflect actual selections or layout. Welcome to a new luxury active adult 55+ community on Maryland's Chesapeake Bay. Discover the amenity-filled, resort-style experience within 45 miles of Washington DC and Baltimore. Residents can take advantage of the community's 24,000 sq. ft. clubhouse with indoor & outdoor pools, a state-of-the-art fitness center, and multiple tennis and pickleball courts. With a full-time lifestyle director on site the community also features a well-maintained calendar of activities such as walking club, indoor and outdoor yoga sessions, mahjong club, kayaking, pickleball and more. Kent Island life is about making friends and enjoying the company of people who have worked hard and now want to enjoy all that a luxury 55+ community has to offer. Located steps from the water and minutes from Annapolis, the location also offers quick access to Rt. 50. Enjoy the convenience of nearby dining and shopping options together with the quaint charm of a small town. *Pictures are representative of a similar home.

Welcome to the Tuscaloosa, a stunning 5-bedroom, 4.5-bath home designed for flexible living and modern style. With a 3-car garage, open-concept layout, and high-end finishes, this home is the perfect blend of comfort and sophistication. Enjoy thoughtful details throughout, including a cozy fireplace, versatile home office, bright loft, and a relaxing screened patio. The kitchen features a full suite of premium appliances—including a French door refrigerator, gas cooktop, and tile backsplash—topped with elegant quartz countertops. The primary suite offers a spa-inspired retreat with a frameless shower featuring a seat and handheld wand, plus double sinks for added functionality. Flooring includes Luxury Vinyl Plank on the main level, tile in all full baths and the laundry room, and plush carpet in the second-floor loft and bedrooms 3, 4, and 5. For a full list of features for this home, please contact our sales consultants. Photos are for display purposes only and may not reflect actual selections or layout. Welcome to a new luxury active adult 55+ community on Maryland's Chesapeake Bay. Discover the amenity-filled, resort-style experience within 45 miles of Washington DC and Baltimore. Residents can take advantage of the community's 24,000 sq. ft. clubhouse with indoor & outdoor pools, a state-of-the-art fitness center, and multiple tennis and pickleball courts. With a full-time lifestyle director on site the community also features a well-maintained calendar of activities such as walking club, indoor and outdoor yoga sessions, mahjong club, kayaking, pickleball and more. Kent Island life is about making friends and enjoying the company of people who have worked hard and now want to enjoy all that a luxury 55+ community has to offer. Located steps from the water and minutes from Annapolis, the location also offers quick access to Rt. 50. Enjoy the convenience of nearby dining and shopping options together with the quaint charm of a small town. *Pictures are representative of a similar home.

327 Kingfisher Ln, Chester

Listing courtesy of KOVO Realty. Contact:

Selling Office: Coldwell Banker Realty.

$925,000

Welcome to 132 Kestrel Lane, an exceptional home in the premier waterfront community of Four Seasons at Kent Island. Offering over 3,600 square feet of thoughtfully designed living space, this residence combines elegant design, modern functionality, and a lifestyle centered around comfort, connection, and the natural beauty of the Chesapeake Bay. From the moment you arrive, the covered front porch and charming curb appeal set the tone for what awaits inside. The grand two-story foyer opens to soaring ceilings, wide plank wood flooring, and light-filled spaces dressed in timeless plantation shutters. The main level is designed for easy living, with 10-foot ceilings that create a sense of openness and flow. At the heart of the home, the great room features cathedral ceilings, crown molding, and a gas fireplace, providing a warm gathering place for both intimate evenings and lively entertaining. The designer kitchen blends beauty and function with a large island, stainless steel appliances, a gas range, backlit cabinetry, and a beautifully lit backsplash that adds a touch of sophistication. The open-concept design extends into the breakfast area, making mornings and casual meals a delight. A screened-in porch and fenced patio create a seamless transition from indoor living to outdoor enjoyment, perfect for entertaining or simply savoring quiet moments surrounded by nature. The first-floor primary suite is a true retreat, complete with a spacious walk-in closet outfitted with built-ins and a spa-inspired bath designed with relaxation in mind. A second bedroom with its own private bathroom on the main level offers comfort and privacy for family or overnight guests, while a dedicated office provides the flexibility to work from home with ease. The convenience of a mudroom with built-ins and a first-floor laundry adds to the thoughtful design of this home. Upstairs, a large loft-style living area can serve as a media or game room, offering additional space for recreation, relaxation, or hobbies, while two generously sized bedrooms share a well-appointed bathroom. A large two-car garage with an extra storage and workshop area provides ample space for all your needs—including the perfect spot to store multiple kayaks. Every detail of this home has been carefully curated, from the crown molding to the custom finishes, creating a space that feels both refined and welcoming. Beyond the home itself, life at Four Seasons at Kent Island offers an unparalleled resort-style experience. Residents enjoy exclusive access to the Chester House Clubhouse, where a ballroom, bar and lounge, gathering spaces, and a demonstration kitchen set the stage for community and celebration. Fitness and wellness are at the forefront with indoor and outdoor pools, a state-of-the-art fitness center, yoga room, and walking paths. Outdoor amenities abound, from tennis, pickleball, and bocce courts to a kayak launch, fishing pier, and dog park. Evenings can be spent at the fire pit, tiki bar, or amphitheater, creating countless opportunities to connect with neighbors and enjoy the Chesapeake lifestyle. Perfectly situated on Kent Island, this home is more than just a place to live—it’s a way of life. Here, every day feels like a retreat, with the Chesapeake Bay as your backdrop and a vibrant community at your doorstep. Welcome to 132 Kestrel Lane, where luxury, comfort, and lifestyle meet.

4 Beds ⋅ 4 Baths

Welcome to 132 Kestrel Lane, an exceptional home in the premier waterfront community of Four Seasons at Kent Island. Offering over 3,600 square feet of thoughtfully designed living space, this residence combines elegant design, modern functionality, and a lifestyle centered around comfort, connection, and the natural beauty of the Chesapeake Bay. From the moment you arrive, the covered front porch and charming curb appeal set the tone for what awaits inside. The grand two-story foyer opens to soaring ceilings, wide plank wood flooring, and light-filled spaces dressed in timeless plantation shutters. The main level is designed for easy living, with 10-foot ceilings that create a sense of openness and flow. At the heart of the home, the great room features cathedral ceilings, crown molding, and a gas fireplace, providing a warm gathering place for both intimate evenings and lively entertaining. The designer kitchen blends beauty and function with a large island, stainless steel appliances, a gas range, backlit cabinetry, and a beautifully lit backsplash that adds a touch of sophistication. The open-concept design extends into the breakfast area, making mornings and casual meals a delight. A screened-in porch and fenced patio create a seamless transition from indoor living to outdoor enjoyment, perfect for entertaining or simply savoring quiet moments surrounded by nature. The first-floor primary suite is a true retreat, complete with a spacious walk-in closet outfitted with built-ins and a spa-inspired bath designed with relaxation in mind. A second bedroom with its own private bathroom on the main level offers comfort and privacy for family or overnight guests, while a dedicated office provides the flexibility to work from home with ease. The convenience of a mudroom with built-ins and a first-floor laundry adds to the thoughtful design of this home. Upstairs, a large loft-style living area can serve as a media or game room, offering additional space for recreation, relaxation, or hobbies, while two generously sized bedrooms share a well-appointed bathroom. A large two-car garage with an extra storage and workshop area provides ample space for all your needs—including the perfect spot to store multiple kayaks. Every detail of this home has been carefully curated, from the crown molding to the custom finishes, creating a space that feels both refined and welcoming. Beyond the home itself, life at Four Seasons at Kent Island offers an unparalleled resort-style experience. Residents enjoy exclusive access to the Chester House Clubhouse, where a ballroom, bar and lounge, gathering spaces, and a demonstration kitchen set the stage for community and celebration. Fitness and wellness are at the forefront with indoor and outdoor pools, a state-of-the-art fitness center, yoga room, and walking paths. Outdoor amenities abound, from tennis, pickleball, and bocce courts to a kayak launch, fishing pier, and dog park. Evenings can be spent at the fire pit, tiki bar, or amphitheater, creating countless opportunities to connect with neighbors and enjoy the Chesapeake lifestyle. Perfectly situated on Kent Island, this home is more than just a place to live—it’s a way of life. Here, every day feels like a retreat, with the Chesapeake Bay as your backdrop and a vibrant community at your doorstep. Welcome to 132 Kestrel Lane, where luxury, comfort, and lifestyle meet.

132 Kestrel Ln, Chester

Listing courtesy of TTR Sotheby's International Realty. Contact:

Selling Office: Berkshire Hathaway HomeServices PenFed Realty.

$919,990

Welcome to the Kerr, a beautifully designed home offering 3 bedrooms, 3 baths, and a 3-car garage. This home combines an open-concept layout with thoughtful design for both comfort and functionality. The main living area features a cozy fireplace with mantel and hearth, creating a warm and inviting focal point. A dedicated home office provides a private space for productivity, while the screened patio extends the living area outdoors—perfect for entertaining or relaxing. The kitchen is equipped for both style and performance, featuring a single oven, microwave, gas cooktop with range hood, dishwasher, French door refrigerator, pendant lighting, tile backsplash, and quartz countertops. Quartz is also featured in the owner’s bath for a cohesive, elegant finish. Hardwood flooring flows throughout the foyer, extended foyer, HovHall, kitchen, dining area, great room, home office, bedrooms 2, the primary suite, loft, and second floor, while tile is featured in all full baths and the laundry room. The primary bath includes a walk-in shower with seat and handheld shower wand and a double-sink vanity for added convenience and luxury. For a full list of features for this home, please contact our sales representatives. Photos are for illustrative purposes only and may not represent the exact home or finishes available. Welcome to a new luxury active adult 55+ community on Maryland's Chesapeake Bay. Discover the amenity-filled, resort-style experience within 45 miles of Washington DC and Baltimore. Residents can take advantage of the community's 24,000 sq. ft. clubhouse with indoor & outdoor pools, a state-of-the-art fitness center, and multiple tennis and pickleball courts. With a full-time lifestyle director on site the community also features a well-maintained calendar of activities such as walking club, indoor and outdoor yoga sessions, mahjong club, kayaking, pickleball and more. Kent Island life is about making friends and enjoying the company of people who have worked hard and now want to enjoy all that a luxury 55+ community has to offer. Located steps from the water and minutes from Annapolis, the location also offers quick access to Rt. 50. Enjoy the convenience of nearby dining and shopping options together with the quaint charm of a small town.

Welcome to the Kerr, a beautifully designed home offering 3 bedrooms, 3 baths, and a 3-car garage. This home combines an open-concept layout with thoughtful design for both comfort and functionality. The main living area features a cozy fireplace with mantel and hearth, creating a warm and inviting focal point. A dedicated home office provides a private space for productivity, while the screened patio extends the living area outdoors—perfect for entertaining or relaxing. The kitchen is equipped for both style and performance, featuring a single oven, microwave, gas cooktop with range hood, dishwasher, French door refrigerator, pendant lighting, tile backsplash, and quartz countertops. Quartz is also featured in the owner’s bath for a cohesive, elegant finish. Hardwood flooring flows throughout the foyer, extended foyer, HovHall, kitchen, dining area, great room, home office, bedrooms 2, the primary suite, loft, and second floor, while tile is featured in all full baths and the laundry room. The primary bath includes a walk-in shower with seat and handheld shower wand and a double-sink vanity for added convenience and luxury. For a full list of features for this home, please contact our sales representatives. Photos are for illustrative purposes only and may not represent the exact home or finishes available. Welcome to a new luxury active adult 55+ community on Maryland's Chesapeake Bay. Discover the amenity-filled, resort-style experience within 45 miles of Washington DC and Baltimore. Residents can take advantage of the community's 24,000 sq. ft. clubhouse with indoor & outdoor pools, a state-of-the-art fitness center, and multiple tennis and pickleball courts. With a full-time lifestyle director on site the community also features a well-maintained calendar of activities such as walking club, indoor and outdoor yoga sessions, mahjong club, kayaking, pickleball and more. Kent Island life is about making friends and enjoying the company of people who have worked hard and now want to enjoy all that a luxury 55+ community has to offer. Located steps from the water and minutes from Annapolis, the location also offers quick access to Rt. 50. Enjoy the convenience of nearby dining and shopping options together with the quaint charm of a small town.

540 Warbler Way, Chester

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP. Contact:

The Jenkins Model Home offers a beautifully crafted open-concept layout paired with high-end designer finishes throughout—now available for immediate settlement with a rent-back opportunity. Thoughtfully designed with 2 bedrooms, 2 baths, and a 2-car garage, this home blends comfort, sophistication, and convenience. Standout features include a dedicated home office, a cozy fireplace, and a screened patio ideal for indoor–outdoor living. Elevated design moments—such as feature walls, ceiling beams, and barn doors—bring custom flair to each space. As a true bonus, all model home furniture is included, offering a completely move-in-ready experience. The chef-inspired kitchen showcases a Café range, single oven, microwave, range hood, dishwasher, side-by-side refrigerator, stylish pendant lighting, and a designer tile backsplash. Quartz countertops elevate both the kitchen and the owner’s bath for a cohesive, upscale look. Hardwood flooring extends across the main level, with tile in all full baths and carpet in Bedroom 2 for added warmth. The owner’s bath features a shower with seat, handheld shower wand, and double sinks, creating a comfortable and functional retreat. For a full list of included features, please contact our sales representatives. Welcome to a new luxury active adult 55+ community on Maryland's Chesapeake Bay. Discover the amenity-filled, resort-style experience within 45 miles of Washington DC and Baltimore. Residents can take advantage of the community's 24,000 sq. ft. clubhouse with indoor & outdoor pools, a state-of-the-art fitness center, and multiple tennis and pickleball courts. With a full-time lifestyle director on site the community also features a well-maintained calendar of activities such as walking club, indoor and outdoor yoga sessions, mahjong club, kayaking, pickleball and more. Kent Island life is about making friends and enjoying the company of people who have worked hard and now want to enjoy all that a luxury 55+ community has to offer. Located steps from the water and minutes from Annapolis, the location also offers quick access to Rt. 50. Enjoy the convenience of nearby dining and shopping options together with the quaint charm of a small town.

$880,000

2 Beds ⋅ 2 Baths

The Jenkins Model Home offers a beautifully crafted open-concept layout paired with high-end designer finishes throughout—now available for immediate settlement with a rent-back opportunity. Thoughtfully designed with 2 bedrooms, 2 baths, and a 2-car garage, this home blends comfort, sophistication, and convenience. Standout features include a dedicated home office, a cozy fireplace, and a screened patio ideal for indoor–outdoor living. Elevated design moments—such as feature walls, ceiling beams, and barn doors—bring custom flair to each space. As a true bonus, all model home furniture is included, offering a completely move-in-ready experience. The chef-inspired kitchen showcases a Café range, single oven, microwave, range hood, dishwasher, side-by-side refrigerator, stylish pendant lighting, and a designer tile backsplash. Quartz countertops elevate both the kitchen and the owner’s bath for a cohesive, upscale look. Hardwood flooring extends across the main level, with tile in all full baths and carpet in Bedroom 2 for added warmth. The owner’s bath features a shower with seat, handheld shower wand, and double sinks, creating a comfortable and functional retreat. For a full list of included features, please contact our sales representatives. Welcome to a new luxury active adult 55+ community on Maryland's Chesapeake Bay. Discover the amenity-filled, resort-style experience within 45 miles of Washington DC and Baltimore. Residents can take advantage of the community's 24,000 sq. ft. clubhouse with indoor & outdoor pools, a state-of-the-art fitness center, and multiple tennis and pickleball courts. With a full-time lifestyle director on site the community also features a well-maintained calendar of activities such as walking club, indoor and outdoor yoga sessions, mahjong club, kayaking, pickleball and more. Kent Island life is about making friends and enjoying the company of people who have worked hard and now want to enjoy all that a luxury 55+ community has to offer. Located steps from the water and minutes from Annapolis, the location also offers quick access to Rt. 50. Enjoy the convenience of nearby dining and shopping options together with the quaint charm of a small town.

127 Flycatcher Way, Chester

Listing courtesy of KOVO Realty. Contact:

The Tuscaloosa, located on Lot 588, is scheduled for an April 2026 settlement and offers generous space with 5 bedrooms, 4.5 baths, and a 3-car garage—ideal for growing households and effortless entertaining. Designed with both comfort and function in mind, this home includes a private home office, a screened patio for relaxed outdoor living, and a striking stone fireplace complemented by ceiling beams that add warmth and character to the main living area. The kitchen is beautifully appointed with a gas cooktop, single oven, microwave, range hood, dishwasher, French door refrigerator, pendant lighting, and a tile backsplash, all finished with quartz countertops that extend into the owner’s bath. Hardwood flooring welcomes you through the foyer and flows into the kitchen, dining area, great room, and hallways, while tile flooring enhances all full baths and the laundry room. Plush carpeted spaces include the owner’s bedroom, extra suite, home office, loft, and bedrooms 3–5. The owner’s suite features a spa-inspired Plus shower with seat, handheld shower wand, frameless shower doors, and dual sinks, creating a relaxing retreat at the end of the day. For a full list of features for this home, please contact our sales representatives. Photos are for illustrative purposes only and may show options, upgrades, or features not included in this home. Welcome to a new luxury active adult 55+ community on Maryland's Chesapeake Bay. Discover the amenity-filled, resort-style experience within 45 miles of Washington DC and Baltimore. Residents can take advantage of the community's 24,000 sq. ft. clubhouse with indoor & outdoor pools, a state-of-the-art fitness center, and multiple tennis and pickleball courts. With a full-time lifestyle director on site the community also features a well-maintained calendar of activities such as walking club, indoor and outdoor yoga sessions, mahjong club, kayaking, pickleball and more. Kent Island life is about making friends and enjoying the company of people who have worked hard and now want to enjoy all that a luxury 55+ community has to offer. Located steps from the water and minutes from Annapolis, the location also offers quick access to Rt. 50. Enjoy the convenience of nearby dining and shopping options together with the quaint charm of a small town.

$879,990

The Tuscaloosa, located on Lot 588, is scheduled for an April 2026 settlement and offers generous space with 5 bedrooms, 4.5 baths, and a 3-car garage—ideal for growing households and effortless entertaining. Designed with both comfort and function in mind, this home includes a private home office, a screened patio for relaxed outdoor living, and a striking stone fireplace complemented by ceiling beams that add warmth and character to the main living area. The kitchen is beautifully appointed with a gas cooktop, single oven, microwave, range hood, dishwasher, French door refrigerator, pendant lighting, and a tile backsplash, all finished with quartz countertops that extend into the owner’s bath. Hardwood flooring welcomes you through the foyer and flows into the kitchen, dining area, great room, and hallways, while tile flooring enhances all full baths and the laundry room. Plush carpeted spaces include the owner’s bedroom, extra suite, home office, loft, and bedrooms 3–5. The owner’s suite features a spa-inspired Plus shower with seat, handheld shower wand, frameless shower doors, and dual sinks, creating a relaxing retreat at the end of the day. For a full list of features for this home, please contact our sales representatives. Photos are for illustrative purposes only and may show options, upgrades, or features not included in this home. Welcome to a new luxury active adult 55+ community on Maryland's Chesapeake Bay. Discover the amenity-filled, resort-style experience within 45 miles of Washington DC and Baltimore. Residents can take advantage of the community's 24,000 sq. ft. clubhouse with indoor & outdoor pools, a state-of-the-art fitness center, and multiple tennis and pickleball courts. With a full-time lifestyle director on site the community also features a well-maintained calendar of activities such as walking club, indoor and outdoor yoga sessions, mahjong club, kayaking, pickleball and more. Kent Island life is about making friends and enjoying the company of people who have worked hard and now want to enjoy all that a luxury 55+ community has to offer. Located steps from the water and minutes from Annapolis, the location also offers quick access to Rt. 50. Enjoy the convenience of nearby dining and shopping options together with the quaint charm of a small town.

311 Kingfisher Ln, Chester

Listing courtesy of KOVO Realty. Contact:

The Kerr on Lot 529 offers a well-balanced layout with thoughtfully selected finishes, scheduled for a March 2026 settlement. Featuring 3 bedrooms, 3 baths, and a 3-car garage, this home provides flexibility, functionality, and refined comfort throughout. Notable highlights include a dedicated home office, a screened patio for relaxed outdoor living, and a shiplap-accented fireplace that anchors the great room with warmth and character. These features make the home equally suited for everyday living and entertaining. The kitchen is fully equipped with a single oven, microwave, gas cooktop, range hood, dishwasher, French door refrigerator, pendant lighting, and tile backsplash, all complemented by Quartz countertops that continue into the owner’s bath for a cohesive, upscale look. Hardwood flooring extends through the foyer, extended foyer, kitchen, dining area, great room, and HovHall, with tile in all full baths and the laundry room. Plush carpet in the owner’s bedroom, extra suite, Bedroom 2, and loft adds comfort in private spaces. The owner’s bath features a shower with seat, handheld shower wand, and double sinks, creating a spa-inspired retreat. For a full list of included features, please contact our sales representatives. Photos are for illustrative purposes only and may not represent the exact home or finishes available. Welcome to a new luxury active adult 55+ community on Maryland's Chesapeake Bay. Discover the amenity-filled, resort-style experience within 45 miles of Washington DC and Baltimore. Residents can take advantage of the community's 24,000 sq. ft. clubhouse with indoor & outdoor pools, a state-of-the-art fitness center, and multiple tennis and pickleball courts. With a full-time lifestyle director on site the community also features a well-maintained calendar of activities such as walking club, indoor and outdoor yoga sessions, mahjong club, kayaking, pickleball and more. Kent Island life is about making friends and enjoying the company of people who have worked hard and now want to enjoy all that a luxury 55+ community has to offer. Located steps from the water and minutes from Annapolis, the location also offers quick access to Rt. 50. Enjoy the convenience of nearby dining and shopping options together with the quaint charm of a small town.

$879,990

The Kerr on Lot 529 offers a well-balanced layout with thoughtfully selected finishes, scheduled for a March 2026 settlement. Featuring 3 bedrooms, 3 baths, and a 3-car garage, this home provides flexibility, functionality, and refined comfort throughout. Notable highlights include a dedicated home office, a screened patio for relaxed outdoor living, and a shiplap-accented fireplace that anchors the great room with warmth and character. These features make the home equally suited for everyday living and entertaining. The kitchen is fully equipped with a single oven, microwave, gas cooktop, range hood, dishwasher, French door refrigerator, pendant lighting, and tile backsplash, all complemented by Quartz countertops that continue into the owner’s bath for a cohesive, upscale look. Hardwood flooring extends through the foyer, extended foyer, kitchen, dining area, great room, and HovHall, with tile in all full baths and the laundry room. Plush carpet in the owner’s bedroom, extra suite, Bedroom 2, and loft adds comfort in private spaces. The owner’s bath features a shower with seat, handheld shower wand, and double sinks, creating a spa-inspired retreat. For a full list of included features, please contact our sales representatives. Photos are for illustrative purposes only and may not represent the exact home or finishes available. Welcome to a new luxury active adult 55+ community on Maryland's Chesapeake Bay. Discover the amenity-filled, resort-style experience within 45 miles of Washington DC and Baltimore. Residents can take advantage of the community's 24,000 sq. ft. clubhouse with indoor & outdoor pools, a state-of-the-art fitness center, and multiple tennis and pickleball courts. With a full-time lifestyle director on site the community also features a well-maintained calendar of activities such as walking club, indoor and outdoor yoga sessions, mahjong club, kayaking, pickleball and more. Kent Island life is about making friends and enjoying the company of people who have worked hard and now want to enjoy all that a luxury 55+ community has to offer. Located steps from the water and minutes from Annapolis, the location also offers quick access to Rt. 50. Enjoy the convenience of nearby dining and shopping options together with the quaint charm of a small town.

141 Redstart Dr, Chester

Listing courtesy of KOVO Realty. Contact:

The Severn, located on Lot 2424, is scheduled for a August 2026 settlement and offers a well-designed layout with 3 bedrooms, 2.5 baths, and a 1-car garage—perfect for low-maintenance living without sacrificing style. This home features a welcoming electric fireplace, a convenient dry bar for entertaining, and a dedicated storage room to keep everything organized. The kitchen is thoughtfully equipped with a gas cooktop, single oven, microwave, range hood, dishwasher, pendant lighting, and a tile backsplash, all paired with sleek quartz countertops. Throughout the home, LVP flooring provides durability and a cohesive look, with tile flooring in both full baths. The primary bath offers a relaxing retreat with a walk-in shower featuring a seat and handheld shower wand, dual sinks, and quartz countertops. For a full list of features for this home, please contact our sales representatives. Photos are for illustrative purposes only and may not represent the exact home or finishes available.

$875,000

The Severn, located on Lot 2424, is scheduled for a August 2026 settlement and offers a well-designed layout with 3 bedrooms, 2.5 baths, and a 1-car garage—perfect for low-maintenance living without sacrificing style. This home features a welcoming electric fireplace, a convenient dry bar for entertaining, and a dedicated storage room to keep everything organized. The kitchen is thoughtfully equipped with a gas cooktop, single oven, microwave, range hood, dishwasher, pendant lighting, and a tile backsplash, all paired with sleek quartz countertops. Throughout the home, LVP flooring provides durability and a cohesive look, with tile flooring in both full baths. The primary bath offers a relaxing retreat with a walk-in shower featuring a seat and handheld shower wand, dual sinks, and quartz countertops. For a full list of features for this home, please contact our sales representatives. Photos are for illustrative purposes only and may not represent the exact home or finishes available.

176 Flagstaff Way Unit 2424, Chester

Listing courtesy of KOVO Realty. Contact:

Selling Office: RE/MAX Executive.

$860,000

Welcome to the Kerr, a beautifully designed home offering 3 bedrooms, 3 baths, and a 3-car garage. Scheduled for settlement in July 2026, this home combines an open-concept layout with thoughtful design for both comfort and functionality. The main living area features a cozy fireplace with mantel and hearth, creating a warm and inviting focal point. A dedicated home office provides a private space for productivity, while the screened patio extends the living area outdoors—perfect for entertaining or relaxing. The kitchen is equipped for both style and performance, featuring a single oven, microwave, gas cooktop with range hood, dishwasher, French door refrigerator, pendant lighting, tile backsplash, and quartz countertops. Quartz is also featured in the owner’s bath for a cohesive, elegant finish. Hardwood flooring flows throughout the foyer, extended foyer, HovHall, kitchen, dining area, great room, home office, bedrooms 2, the primary suite, loft, and second floor, while tile is featured in all full baths and the laundry room. The primary bath includes a walk-in shower with seat and handheld shower wand and a double-sink vanity for added convenience and luxury. For a full list of features for this home, please contact our sales representatives. Photos are for illustrative purposes only and may not represent the exact home or finishes available. Welcome to a new luxury active adult 55+ community on Maryland's Chesapeake Bay. Discover the amenity-filled, resort-style experience within 45 miles of Washington DC and Baltimore. Residents can take advantage of the community's 24,000 sq. ft. clubhouse with indoor & outdoor pools, a state-of-the-art fitness center, and multiple tennis and pickleball courts. With a full-time lifestyle director on site the community also features a well-maintained calendar of activities such as walking club, indoor and outdoor yoga sessions, mahjong club, kayaking, pickleball and more. Kent Island life is about making friends and enjoying the company of people who have worked hard and now want to enjoy all that a luxury 55+ community has to offer. Located steps from the water and minutes from Annapolis, the location also offers quick access to Rt. 50. Enjoy the convenience of nearby dining and shopping options together with the quaint charm of a small town.

Welcome to the Kerr, a beautifully designed home offering 3 bedrooms, 3 baths, and a 3-car garage. Scheduled for settlement in July 2026, this home combines an open-concept layout with thoughtful design for both comfort and functionality. The main living area features a cozy fireplace with mantel and hearth, creating a warm and inviting focal point. A dedicated home office provides a private space for productivity, while the screened patio extends the living area outdoors—perfect for entertaining or relaxing. The kitchen is equipped for both style and performance, featuring a single oven, microwave, gas cooktop with range hood, dishwasher, French door refrigerator, pendant lighting, tile backsplash, and quartz countertops. Quartz is also featured in the owner’s bath for a cohesive, elegant finish. Hardwood flooring flows throughout the foyer, extended foyer, HovHall, kitchen, dining area, great room, home office, bedrooms 2, the primary suite, loft, and second floor, while tile is featured in all full baths and the laundry room. The primary bath includes a walk-in shower with seat and handheld shower wand and a double-sink vanity for added convenience and luxury. For a full list of features for this home, please contact our sales representatives. Photos are for illustrative purposes only and may not represent the exact home or finishes available. Welcome to a new luxury active adult 55+ community on Maryland's Chesapeake Bay. Discover the amenity-filled, resort-style experience within 45 miles of Washington DC and Baltimore. Residents can take advantage of the community's 24,000 sq. ft. clubhouse with indoor & outdoor pools, a state-of-the-art fitness center, and multiple tennis and pickleball courts. With a full-time lifestyle director on site the community also features a well-maintained calendar of activities such as walking club, indoor and outdoor yoga sessions, mahjong club, kayaking, pickleball and more. Kent Island life is about making friends and enjoying the company of people who have worked hard and now want to enjoy all that a luxury 55+ community has to offer. Located steps from the water and minutes from Annapolis, the location also offers quick access to Rt. 50. Enjoy the convenience of nearby dining and shopping options together with the quaint charm of a small town.

307 Kingfisher Ln, Chester

Listing courtesy of KOVO Realty. Contact:

Discover the charm and versatility of the Kerr, a thoughtfully designed 3-bedroom, 3-bath home offering an open layout, high-end finishes, and spaces tailored for comfort. With a 3-car garage and flexible rooms throughout, this home adapts beautifully to everyday living or entertaining. The main level features durable Luxury Vinyl Plank flooring, a warm fireplace, and a screened patio for year-round relaxation. A dedicated home office offers privacy and productivity, while the spacious loft upstairs provides extra space for lounging, hobbies, or guests. In the kitchen, you'll find a complete stainless appliance suite, including a French door refrigerator, gas cooktop, and wall oven, all paired with quartz countertops, pendant lighting, and a designer tile backsplash. Retreat to the primary bath with its walk-in shower featuring a seat and handheld shower wand, double sinks, and quartz surfaces. Flooring includes tile in all full baths and the laundry room, plus plush carpet in the upstairs loft and bedroom for cozy comfort. For a full list of features for this home, please contact our sales representatives. Photos are for display purposes only and may not reflect actual selections or layout. Welcome to a new luxury active adult 55+ community on Maryland's Chesapeake Bay. Discover the amenity-filled, resort-style experience within 45 miles of Washington DC and Baltimore. Residents can take advantage of the community's 24,000 sq. ft. clubhouse with indoor & outdoor pools, a state-of-the-art fitness center, and multiple tennis and pickleball courts. With a full-time lifestyle director on site the community also features a well-maintained calendar of activities such as walking club, indoor and outdoor yoga sessions, mahjong club, kayaking, pickleball and more. Kent Island life is about making friends and enjoying the company of people who have worked hard and now want to enjoy all that a luxury 55+ community has to offer. Located steps from the water and minutes from Annapolis, the location also offers quick access to Rt. 50. Enjoy the convenience of nearby dining and shopping options together with the quaint charm of a small town. *Pictures are representative of a similar home.

$844,900

Discover the charm and versatility of the Kerr, a thoughtfully designed 3-bedroom, 3-bath home offering an open layout, high-end finishes, and spaces tailored for comfort. With a 3-car garage and flexible rooms throughout, this home adapts beautifully to everyday living or entertaining. The main level features durable Luxury Vinyl Plank flooring, a warm fireplace, and a screened patio for year-round relaxation. A dedicated home office offers privacy and productivity, while the spacious loft upstairs provides extra space for lounging, hobbies, or guests. In the kitchen, you'll find a complete stainless appliance suite, including a French door refrigerator, gas cooktop, and wall oven, all paired with quartz countertops, pendant lighting, and a designer tile backsplash. Retreat to the primary bath with its walk-in shower featuring a seat and handheld shower wand, double sinks, and quartz surfaces. Flooring includes tile in all full baths and the laundry room, plus plush carpet in the upstairs loft and bedroom for cozy comfort. For a full list of features for this home, please contact our sales representatives. Photos are for display purposes only and may not reflect actual selections or layout. Welcome to a new luxury active adult 55+ community on Maryland's Chesapeake Bay. Discover the amenity-filled, resort-style experience within 45 miles of Washington DC and Baltimore. Residents can take advantage of the community's 24,000 sq. ft. clubhouse with indoor & outdoor pools, a state-of-the-art fitness center, and multiple tennis and pickleball courts. With a full-time lifestyle director on site the community also features a well-maintained calendar of activities such as walking club, indoor and outdoor yoga sessions, mahjong club, kayaking, pickleball and more. Kent Island life is about making friends and enjoying the company of people who have worked hard and now want to enjoy all that a luxury 55+ community has to offer. Located steps from the water and minutes from Annapolis, the location also offers quick access to Rt. 50. Enjoy the convenience of nearby dining and shopping options together with the quaint charm of a small town. *Pictures are representative of a similar home.

164 Redstart Dr, Chester

Listing courtesy of KOVO Realty. Contact:

Selling Office: Berkshire Hathaway HomeServices PenFed Realty.

$834,990

The Tuscaloosa home offers a thoughtfully designed layout with elevated finishes throughout, with a projected settlement of April 2026. Featuring 2 bedrooms, 2.5 baths, and a 3-car garage, this home blends everyday functionality with timeless style. Standout features include a dedicated home office, a screened patio perfect for outdoor relaxation, and a shiplap-accented fireplace paired with ceiling beams that add warmth and architectural character to the great room. The kitchen is well-appointed with a single oven, microwave, gas cooktop, range hood, dishwasher, French door refrigerator, pendant lighting, and a tile backsplash, all finished with Quartz countertops that continue into the owner’s bath for a cohesive, upscale look. Luxury Vinyl Plank flooring flows through the foyer, extended foyer, kitchen, dining area, great room, HovHall, owner’s suite, and extra suite, while tile enhances all full baths. Carpeted secondary spaces provide comfort in additional bedrooms and the loft. The owner’s bath features a shower with seat, handheld shower wand, and double sinks, creating a relaxing retreat. For a full list of included features, please contact our sales representatives. Photos are for illustrative purposes only and may not represent the exact home or finishes available. Welcome to a new luxury active adult 55+ community on Maryland's Chesapeake Bay. Discover the amenity-filled, resort-style experience within 45 miles of Washington DC and Baltimore. Residents can take advantage of the community's 24,000 sq. ft. clubhouse with indoor & outdoor pools, a state-of-the-art fitness center, and multiple tennis and pickleball courts. With a full-time lifestyle director on site the community also features a well-maintained calendar of activities such as walking club, indoor and outdoor yoga sessions, mahjong club, kayaking, pickleball and more. Kent Island life is about making friends and enjoying the company of people who have worked hard and now want to enjoy all that a luxury 55+ community has to offer. Located steps from the water and minutes from Annapolis, the location also offers quick access to Rt. 50. Enjoy the convenience of nearby dining and shopping options together with the quaint charm of a small town.

The Tuscaloosa home offers a thoughtfully designed layout with elevated finishes throughout, with a projected settlement of April 2026. Featuring 2 bedrooms, 2.5 baths, and a 3-car garage, this home blends everyday functionality with timeless style. Standout features include a dedicated home office, a screened patio perfect for outdoor relaxation, and a shiplap-accented fireplace paired with ceiling beams that add warmth and architectural character to the great room. The kitchen is well-appointed with a single oven, microwave, gas cooktop, range hood, dishwasher, French door refrigerator, pendant lighting, and a tile backsplash, all finished with Quartz countertops that continue into the owner’s bath for a cohesive, upscale look. Luxury Vinyl Plank flooring flows through the foyer, extended foyer, kitchen, dining area, great room, HovHall, owner’s suite, and extra suite, while tile enhances all full baths. Carpeted secondary spaces provide comfort in additional bedrooms and the loft. The owner’s bath features a shower with seat, handheld shower wand, and double sinks, creating a relaxing retreat. For a full list of included features, please contact our sales representatives. Photos are for illustrative purposes only and may not represent the exact home or finishes available. Welcome to a new luxury active adult 55+ community on Maryland's Chesapeake Bay. Discover the amenity-filled, resort-style experience within 45 miles of Washington DC and Baltimore. Residents can take advantage of the community's 24,000 sq. ft. clubhouse with indoor & outdoor pools, a state-of-the-art fitness center, and multiple tennis and pickleball courts. With a full-time lifestyle director on site the community also features a well-maintained calendar of activities such as walking club, indoor and outdoor yoga sessions, mahjong club, kayaking, pickleball and more. Kent Island life is about making friends and enjoying the company of people who have worked hard and now want to enjoy all that a luxury 55+ community has to offer. Located steps from the water and minutes from Annapolis, the location also offers quick access to Rt. 50. Enjoy the convenience of nearby dining and shopping options together with the quaint charm of a small town.

110 Kinglet Ct, Chester

Listing courtesy of KOVO Realty. Contact:

This stunning Taylor home offers an inviting open floor plan designed for both comfort and functionality. Featuring 2 bedrooms, 2.5 baths, and a spacious 3-car garage, this home perfectly blends everyday ease with elevated style. Highlights include a dedicated home office, a cozy screened patio for outdoor relaxation, and a dramatic 2-story stone fireplace that serves as the heart of the great room. The gourmet kitchen is equipped with a single oven, microwave, gas cooktop, range hood, dishwasher, French door refrigerator, pendant lighting, and a stylish tile backsplash. Elegant quartz countertops extend through the kitchen and owner’s bath. Luxury vinyl plank flooring enhances the main level, with tile in all full baths and the laundry room, and plush carpet in the extra suite and upstairs loft. The owner’s bath features a spacious shower with a seat and handheld shower wand, plus double sinks for convenience. For a full list of included features, please contact our sales representatives. Photos are for illustrative purposes only and may not represent the exact home or finishes available. Welcome to a new luxury active adult 55+ community on Maryland's Chesapeake Bay. Discover the amenity-filled, resort-style experience within 45 miles of Washington DC and Baltimore. Residents can take advantage of the community's 24,000 sq. ft. clubhouse with indoor & outdoor pools, a state-of-the-art fitness center, and multiple tennis and pickleball courts. With a full-time lifestyle director on site the community also features a well-maintained calendar of activities such as walking club, indoor and outdoor yoga sessions, mahjong club, kayaking, pickleball and more. Kent Island life is about making friends and enjoying the company of people who have worked hard and now want to enjoy all that a luxury 55+ community has to offer. Located steps from the water and minutes from Annapolis, the location also offers quick access to Rt. 50. Enjoy the convenience of nearby dining and shopping options together with the quaint charm of a small town.

$834,990

This stunning Taylor home offers an inviting open floor plan designed for both comfort and functionality. Featuring 2 bedrooms, 2.5 baths, and a spacious 3-car garage, this home perfectly blends everyday ease with elevated style. Highlights include a dedicated home office, a cozy screened patio for outdoor relaxation, and a dramatic 2-story stone fireplace that serves as the heart of the great room. The gourmet kitchen is equipped with a single oven, microwave, gas cooktop, range hood, dishwasher, French door refrigerator, pendant lighting, and a stylish tile backsplash. Elegant quartz countertops extend through the kitchen and owner’s bath. Luxury vinyl plank flooring enhances the main level, with tile in all full baths and the laundry room, and plush carpet in the extra suite and upstairs loft. The owner’s bath features a spacious shower with a seat and handheld shower wand, plus double sinks for convenience. For a full list of included features, please contact our sales representatives. Photos are for illustrative purposes only and may not represent the exact home or finishes available. Welcome to a new luxury active adult 55+ community on Maryland's Chesapeake Bay. Discover the amenity-filled, resort-style experience within 45 miles of Washington DC and Baltimore. Residents can take advantage of the community's 24,000 sq. ft. clubhouse with indoor & outdoor pools, a state-of-the-art fitness center, and multiple tennis and pickleball courts. With a full-time lifestyle director on site the community also features a well-maintained calendar of activities such as walking club, indoor and outdoor yoga sessions, mahjong club, kayaking, pickleball and more. Kent Island life is about making friends and enjoying the company of people who have worked hard and now want to enjoy all that a luxury 55+ community has to offer. Located steps from the water and minutes from Annapolis, the location also offers quick access to Rt. 50. Enjoy the convenience of nearby dining and shopping options together with the quaint charm of a small town.

117 Redstart Dr, Chester

Listing courtesy of KOVO Realty. Contact:

10K price reduction!!! Better Than New – $175K+ in Upgrades and Lifestyle Ready Now Four Seasons at Kent Island – Killarney with Loft Model Why wait months—and spend thousands more—for a base-level new build when you can move into your dream home today? This beautifully enhanced Killarney with Loft model in sought-after Phase I delivers over $100K in builder upgrades plus $75K in custom renovations—a total investment of $175K+—all included. To replicate this home new through the builder would exceed $1 million. For added peace of mind, the sellers are including a two-year full-service home warranty, and an invisible fence is already installed and included. Exceptional Interior & Outdoor Living The gourmet kitchen is a showstopper with a 10’ white quartz island, dry bar, SMART stainless appliances, InstaHot water dispenser, and walk-in pantry. A marble-mantled electric fireplace anchors the open-concept living area and flows to the builder-upgraded screened porch overlooking a private backyard retreat. Entertain year-round on the expansive 40' × 15' paver patio with built-in gas fire pit, gas grill, and wood-burning pizza oven—all part of the $175K+ in thoughtful upgrades that make this home truly turnkey. The spa-inspired primary suite features a fully renovated bath (2025) with new flooring, lighting, towel warmer, and upgraded fixtures. Additional highlights include Pinnacle concrete coatings on the front and screened porches, a new front door, $5K+ in custom window treatments, all-new main-level lighting, a guest en-suite, and a loft with third bedroom and full bath. A Community & Lifestyle Second to None Four Seasons at Kent Island offers a 24,000 sq ft waterfront clubhouse with indoor and outdoor pools, a fitness center, yoga studio, game room, library, tiki bar, and outdoor amphitheater. Lighted pickleball and tennis courts, bocce, a dog park, a pier with transient slips, 4+ miles of walking trails, and direct access to the Cross Island Trail complete the resort experience. A full-time lifestyle director curates events from crab feasts and live music to holiday gatherings and fitness classes. The Smarter Choice: Waiting vs. Ready Skip construction delays, surprise upgrade costs, and months of dust and noise. This home is fully finished, beautifully landscaped, and move-in ready now. Proven resale strength in an established section of the neighborhood protects your equity and provides quiet streets and friendly neighbors from day one. This is the definition of turnkey luxury—offering comfort, style, and an unmatched Chesapeake Bay lifestyle today. Schedule your private showing and experience why this home is truly better than new.

$825,000

10K price reduction!!! Better Than New – $175K+ in Upgrades and Lifestyle Ready Now Four Seasons at Kent Island – Killarney with Loft Model Why wait months—and spend thousands more—for a base-level new build when you can move into your dream home today? This beautifully enhanced Killarney with Loft model in sought-after Phase I delivers over $100K in builder upgrades plus $75K in custom renovations—a total investment of $175K+—all included. To replicate this home new through the builder would exceed $1 million. For added peace of mind, the sellers are including a two-year full-service home warranty, and an invisible fence is already installed and included. Exceptional Interior & Outdoor Living The gourmet kitchen is a showstopper with a 10’ white quartz island, dry bar, SMART stainless appliances, InstaHot water dispenser, and walk-in pantry. A marble-mantled electric fireplace anchors the open-concept living area and flows to the builder-upgraded screened porch overlooking a private backyard retreat. Entertain year-round on the expansive 40' × 15' paver patio with built-in gas fire pit, gas grill, and wood-burning pizza oven—all part of the $175K+ in thoughtful upgrades that make this home truly turnkey. The spa-inspired primary suite features a fully renovated bath (2025) with new flooring, lighting, towel warmer, and upgraded fixtures. Additional highlights include Pinnacle concrete coatings on the front and screened porches, a new front door, $5K+ in custom window treatments, all-new main-level lighting, a guest en-suite, and a loft with third bedroom and full bath. A Community & Lifestyle Second to None Four Seasons at Kent Island offers a 24,000 sq ft waterfront clubhouse with indoor and outdoor pools, a fitness center, yoga studio, game room, library, tiki bar, and outdoor amphitheater. Lighted pickleball and tennis courts, bocce, a dog park, a pier with transient slips, 4+ miles of walking trails, and direct access to the Cross Island Trail complete the resort experience. A full-time lifestyle director curates events from crab feasts and live music to holiday gatherings and fitness classes. The Smarter Choice: Waiting vs. Ready Skip construction delays, surprise upgrade costs, and months of dust and noise. This home is fully finished, beautifully landscaped, and move-in ready now. Proven resale strength in an established section of the neighborhood protects your equity and provides quiet streets and friendly neighbors from day one. This is the definition of turnkey luxury—offering comfort, style, and an unmatched Chesapeake Bay lifestyle today. Schedule your private showing and experience why this home is truly better than new.

124 Nauset Ln, Chester

Listing courtesy of RE/MAX Executive. Contact:

Selling Office: Compass.

$799,990

The Simone at Lot 547 features a well-balanced open-concept floorplan with a projected settlement date of March 2026, offering both style and functionality for modern living. This home includes 4 bedrooms, 3 baths, and a 2-car garage, with flexible spaces designed to adapt to everyday needs. Notable highlights include a dedicated home office and a welcoming shiplap-accented fireplace that anchors the main living area. Luxury vinyl plank flooring flows through the foyer, extended foyer, kitchen, dining area, great room, Bedroom 2, the owner’s suite, and the HovHall, while tile finishes enhance all full baths and the laundry room. Plush carpet adds comfort to the loft, second floor, and Bedrooms 3 and 4. The kitchen is thoughtfully equipped with a single oven, microwave, gas cooktop, range hood, dishwasher, French door refrigerator, pendant lighting, and a tile backsplash, all paired with quartz countertops that continue into the owner’s bath. The owner’s bath is designed for comfort with a shower featuring a built-in seat, handheld shower wand, and double sinks. For a full list of features for this home, please contact our sales representatives. Photos are for illustrative purposes only and may not represent the exact home or finishes available. Welcome to a new luxury active adult 55+ community on Maryland's Chesapeake Bay. Discover the amenity-filled, resort-style experience within 45 miles of Washington DC and Baltimore. Residents can take advantage of the community's 24,000 sq. ft. clubhouse with indoor & outdoor pools, a state-of-the-art fitness center, and multiple tennis and pickleball courts. With a full-time lifestyle director on site the community also features a well-maintained calendar of activities such as walking club, indoor and outdoor yoga sessions, mahjong club, kayaking, pickleball and more. Kent Island life is about making friends and enjoying the company of people who have worked hard and now want to enjoy all that a luxury 55+ community has to offer. Located steps from the water and minutes from Annapolis, the location also offers quick access to Rt. 50. Enjoy the convenience of nearby dining and shopping options together with the quaint charm of a small town.

4 Beds ⋅ 3 Baths

The Simone at Lot 547 features a well-balanced open-concept floorplan with a projected settlement date of March 2026, offering both style and functionality for modern living. This home includes 4 bedrooms, 3 baths, and a 2-car garage, with flexible spaces designed to adapt to everyday needs. Notable highlights include a dedicated home office and a welcoming shiplap-accented fireplace that anchors the main living area. Luxury vinyl plank flooring flows through the foyer, extended foyer, kitchen, dining area, great room, Bedroom 2, the owner’s suite, and the HovHall, while tile finishes enhance all full baths and the laundry room. Plush carpet adds comfort to the loft, second floor, and Bedrooms 3 and 4. The kitchen is thoughtfully equipped with a single oven, microwave, gas cooktop, range hood, dishwasher, French door refrigerator, pendant lighting, and a tile backsplash, all paired with quartz countertops that continue into the owner’s bath. The owner’s bath is designed for comfort with a shower featuring a built-in seat, handheld shower wand, and double sinks. For a full list of features for this home, please contact our sales representatives. Photos are for illustrative purposes only and may not represent the exact home or finishes available. Welcome to a new luxury active adult 55+ community on Maryland's Chesapeake Bay. Discover the amenity-filled, resort-style experience within 45 miles of Washington DC and Baltimore. Residents can take advantage of the community's 24,000 sq. ft. clubhouse with indoor & outdoor pools, a state-of-the-art fitness center, and multiple tennis and pickleball courts. With a full-time lifestyle director on site the community also features a well-maintained calendar of activities such as walking club, indoor and outdoor yoga sessions, mahjong club, kayaking, pickleball and more. Kent Island life is about making friends and enjoying the company of people who have worked hard and now want to enjoy all that a luxury 55+ community has to offer. Located steps from the water and minutes from Annapolis, the location also offers quick access to Rt. 50. Enjoy the convenience of nearby dining and shopping options together with the quaint charm of a small town.

259 Redstart Dr, Chester

Listing courtesy of KOVO Realty. Contact:

Selling Office: The KW Collective.

$799,990

Introducing the Kerr with a projected settlement date of January 2026. This home offers 3 bedrooms, 3 baths, and a spacious 3-car garage. Notable features include a home office, a screened patio, and a striking 1-story fireplace. The kitchen is beautifully appointed with a single oven, microwave, gas cooktop, range hood, dishwasher, French door refrigerator, pendant lights, and a tile backsplash, complemented by quartz countertops in both the kitchen and owner’s bath. The flooring showcases LVP throughout the main level and loft, with tile in all full baths. The owner’s bath highlights a walk-in shower with a seat, handheld shower wand, double sinks, and quartz countertops, creating a retreat-like experience. For a full list of features for this home, please contact our sales representatives. Photos are for illustrative purposes only and may not represent the exact home or finishes available. Welcome to a new luxury active adult 55+ community on Maryland's Chesapeake Bay. Discover the amenity-filled, resort-style experience within 45 miles of Washington DC and Baltimore. Residents can take advantage of the community's 24,000 sq. ft. clubhouse with indoor & outdoor pools, a state-of-the-art fitness center, and multiple tennis and pickleball courts. With a full-time lifestyle director on site the community also features a well-maintained calendar of activities such as walking club, indoor and outdoor yoga sessions, mahjong club, kayaking, pickleball and more. Kent Island life is about making friends and enjoying the company of people who have worked hard and now want to enjoy all that a luxury 55+ community has to offer. Located steps from the water and minutes from Annapolis, the location also offers quick access to Rt. 50. Enjoy the convenience of nearby dining and shopping options together with the quaint charm of a small town.

Introducing the Kerr with a projected settlement date of January 2026. This home offers 3 bedrooms, 3 baths, and a spacious 3-car garage. Notable features include a home office, a screened patio, and a striking 1-story fireplace. The kitchen is beautifully appointed with a single oven, microwave, gas cooktop, range hood, dishwasher, French door refrigerator, pendant lights, and a tile backsplash, complemented by quartz countertops in both the kitchen and owner’s bath. The flooring showcases LVP throughout the main level and loft, with tile in all full baths. The owner’s bath highlights a walk-in shower with a seat, handheld shower wand, double sinks, and quartz countertops, creating a retreat-like experience. For a full list of features for this home, please contact our sales representatives. Photos are for illustrative purposes only and may not represent the exact home or finishes available. Welcome to a new luxury active adult 55+ community on Maryland's Chesapeake Bay. Discover the amenity-filled, resort-style experience within 45 miles of Washington DC and Baltimore. Residents can take advantage of the community's 24,000 sq. ft. clubhouse with indoor & outdoor pools, a state-of-the-art fitness center, and multiple tennis and pickleball courts. With a full-time lifestyle director on site the community also features a well-maintained calendar of activities such as walking club, indoor and outdoor yoga sessions, mahjong club, kayaking, pickleball and more. Kent Island life is about making friends and enjoying the company of people who have worked hard and now want to enjoy all that a luxury 55+ community has to offer. Located steps from the water and minutes from Annapolis, the location also offers quick access to Rt. 50. Enjoy the convenience of nearby dining and shopping options together with the quaint charm of a small town.

519 Warbler Way, Chester

Listing courtesy of KOVO Realty. Contact:

Selling Office: TTR Sotheby's International Realty.

$799,500

Like-new luxury living in Four Seasons at Kent Island. Completed in August and only lightly lived in, this 2,800 sq ft home offers 4 bedrooms and 3 baths with a pristine, move-in-ready feel. Highlights include luxury vinyl plank flooring, quartz countertops, and over $20,000 in custom window treatments, can you say "plantation shutters". Professionally decorated throughout—with the option to purchase furnishings—this home is truly turn-key and ready today. Enjoy peek-a-boo Chester River views and an unbeatable location so close to the clubhouse you can see it. Plus, the builder’s full warranty remains in place through August 2026 for added peace of mind. Residents enjoy Four Seasons’ resort-style amenities: waterfront clubhouse, indoor & outdoor pools, fitness center, pickleball & tennis, walking trails, and a vibrant social calendar. Effortless luxury, prime location, island living at its best.

4 Beds ⋅ 3 Baths

Like-new luxury living in Four Seasons at Kent Island. Completed in August and only lightly lived in, this 2,800 sq ft home offers 4 bedrooms and 3 baths with a pristine, move-in-ready feel. Highlights include luxury vinyl plank flooring, quartz countertops, and over $20,000 in custom window treatments, can you say "plantation shutters". Professionally decorated throughout—with the option to purchase furnishings—this home is truly turn-key and ready today. Enjoy peek-a-boo Chester River views and an unbeatable location so close to the clubhouse you can see it. Plus, the builder’s full warranty remains in place through August 2026 for added peace of mind. Residents enjoy Four Seasons’ resort-style amenities: waterfront clubhouse, indoor & outdoor pools, fitness center, pickleball & tennis, walking trails, and a vibrant social calendar. Effortless luxury, prime location, island living at its best.

528 Warbler Way, Chester

Listing courtesy of RE/MAX Executive. Contact:

Selling Office: Keller Williams Flagship.

$799,000

Welcome to 136 Nauset Lane, an upgraded Lille model in Four Seasons at Kent Island, a premier 55+ resort-style community. Situated on a corner lot, this Coastal Traditional home offers the ease of main-level living, flexible space for guests and an impressive list of thoughtful upgrades already in place. LVP flooring flows throughout the main level, where a private office with custom California Closets built-ins provides a dedicated work or hobby space. The open-concept kitchen and family room create an inviting heart of the home, complemented by a light-filled sunroom. The kitchen features a generous island, Café/Monogram stainless steel appliances, built-in microwave, pantry, dry bar and cabinetry with double pull-out shelving. The refrigerator was replaced in 2026. Just beyond the sunroom, a screened porch with a ceiling fan opens to a beautiful paver patio with a remote-controlled electric awning, creating multiple spaces to relax, entertain and enjoy the outdoors. The spacious main-level primary suite features a large walk-in closet professionally designed by California Closets. The primary bath offers a walk-in shower, private water closet, linen closet and additional cabinetry for storage. A second bedroom and full bath are also conveniently located on the main level. Upstairs, a third bedroom, full bath and sitting area provide a private and comfortable space for overnight guests. Thoughtful upgrades continue throughout the home with ceiling fans in all three bedrooms and the family room, a California Closets-designed coat closet, central vacuum, Ethernet connections in most rooms, whole-house Wi-Fi distribution, security system, smart thermostat, remote-access garage door, Speed Queen washer and dryer and EV charging in the garage. The lawn irrigation system draws water from the community pond, with seasonal winterization handled by the HOA. Then there is the Four Seasons lifestyle. At the center of the community is the impressive 24,000-square-foot waterfront Chester House clubhouse, complemented by indoor and outdoor resort-style pools, spa, modern fitness center, yoga room, pickleball and tennis courts, bocce ball, walking paths and an outdoor amphitheater. Enjoy the beach area with fire pits, or head to the 450-foot fishing pier and kayak launch to get out on the water. A full-time lifestyle director keeps the social calendar active with activities and events throughout the year. It’s resort-style living designed to be enjoyed every day. With very few new homes remaining in the community, why wait months for new construction? 136 Nauset Lane is move-in ready with an extensive list of upgrades already completed, offering the opportunity to start enjoying the Four Seasons at Kent Island lifestyle now.

Welcome to 136 Nauset Lane, an upgraded Lille model in Four Seasons at Kent Island, a premier 55+ resort-style community. Situated on a corner lot, this Coastal Traditional home offers the ease of main-level living, flexible space for guests and an impressive list of thoughtful upgrades already in place. LVP flooring flows throughout the main level, where a private office with custom California Closets built-ins provides a dedicated work or hobby space. The open-concept kitchen and family room create an inviting heart of the home, complemented by a light-filled sunroom. The kitchen features a generous island, Café/Monogram stainless steel appliances, built-in microwave, pantry, dry bar and cabinetry with double pull-out shelving. The refrigerator was replaced in 2026. Just beyond the sunroom, a screened porch with a ceiling fan opens to a beautiful paver patio with a remote-controlled electric awning, creating multiple spaces to relax, entertain and enjoy the outdoors. The spacious main-level primary suite features a large walk-in closet professionally designed by California Closets. The primary bath offers a walk-in shower, private water closet, linen closet and additional cabinetry for storage. A second bedroom and full bath are also conveniently located on the main level. Upstairs, a third bedroom, full bath and sitting area provide a private and comfortable space for overnight guests. Thoughtful upgrades continue throughout the home with ceiling fans in all three bedrooms and the family room, a California Closets-designed coat closet, central vacuum, Ethernet connections in most rooms, whole-house Wi-Fi distribution, security system, smart thermostat, remote-access garage door, Speed Queen washer and dryer and EV charging in the garage. The lawn irrigation system draws water from the community pond, with seasonal winterization handled by the HOA. Then there is the Four Seasons lifestyle. At the center of the community is the impressive 24,000-square-foot waterfront Chester House clubhouse, complemented by indoor and outdoor resort-style pools, spa, modern fitness center, yoga room, pickleball and tennis courts, bocce ball, walking paths and an outdoor amphitheater. Enjoy the beach area with fire pits, or head to the 450-foot fishing pier and kayak launch to get out on the water. A full-time lifestyle director keeps the social calendar active with activities and events throughout the year. It’s resort-style living designed to be enjoyed every day. With very few new homes remaining in the community, why wait months for new construction? 136 Nauset Lane is move-in ready with an extensive list of upgrades already completed, offering the opportunity to start enjoying the Four Seasons at Kent Island lifestyle now.

136 Nauset Ln, Chester

Listing courtesy of RE/MAX One. Contact:

Selling Office: Samson Properties.

$787,500

If you’ve ever dreamed of waking up and feeling like you’re on vacation—but with the comforts of home—welcome to 135 Nauset Lane. Tucked into a quiet corner of Kent Island’s Four Seasons community, this home isn’t just beautiful—it’s part of a lifestyle that’s hard to find and even harder to leave. The sellers were first drawn here by the energy of the community and the resort-style amenities. But what really sold them was the way this home made everyday life feel easy, peaceful, and a little bit indulgent. From the moment you walk through the front door, the open layout just flows. The gourmet kitchen is the heart of the home—with a massive island, double ovens, gas cooktop, and more cabinet space than you’ll know what to do with. It opens to a sunny dining area and a living room that invites you to sink in and stay awhile. Downstairs, you’ll find two spacious bedrooms, including a primary suite that feels like a retreat. The spa-like bathroom, walk-in closet, and tray ceiling add a touch of everyday luxury. There’s also a den that can flex into a home office, reading room, or whatever you need it to be. Upstairs is a private guest suite with a third bedroom, full bath, and a bonus loft space that’s perfect for movie nights or extra living space. But the magic continues outside. The oversized patio was made for entertaining—complete with a built-in firepit, gas line for your grill , and even a five-person Thermospa hot tub. Whether it’s coffee in the morning or wine after sunset, this is where you’ll want to be. Other thoughtful touches? There’s a heated and cooled garage with extra space for a third vehicle or golf cart, and a sky basement for bonus storage. Throughout the home, you'll find upgrades like luxury vinyl plank flooring, under-cabinet kitchen lighting, custom bathroom finishes, recessed lighting, and so much more. And then there’s the community. Four Seasons at Kent Island is truly one-of-a-kind. Want to start your day with yoga? Go for a paddle on the river? Meet friends at the outdoor bar to catch the game by the firepit? It's all here. There’s a 24,000 sq ft clubhouse, both indoor and outdoor pools, a state-of-the-art gym, game room, pickleball and tennis courts, walking and biking trails, a pier for fishing and boating, a kayak launch, and even a dog park. The community is tucked away, peaceful and private—but you're just minutes from restaurants, wineries, breweries, and shops. And if you ever need a city fix, Annapolis and Easton are an easy 20-30 minute drive away. The best way to describe this home and community? It’s a place where life slows down in the best way. Where neighbors become friends. Where the to-do list gets a lot shorter—and the “want-to-do” list gets a whole lot longer. So if you're looking for more than just a new house—if you're ready for a new chapter filled with connection, ease, and everyday joy—135 Nauset Lane might be exactly what you’ve been waiting for.

If you’ve ever dreamed of waking up and feeling like you’re on vacation—but with the comforts of home—welcome to 135 Nauset Lane. Tucked into a quiet corner of Kent Island’s Four Seasons community, this home isn’t just beautiful—it’s part of a lifestyle that’s hard to find and even harder to leave. The sellers were first drawn here by the energy of the community and the resort-style amenities. But what really sold them was the way this home made everyday life feel easy, peaceful, and a little bit indulgent. From the moment you walk through the front door, the open layout just flows. The gourmet kitchen is the heart of the home—with a massive island, double ovens, gas cooktop, and more cabinet space than you’ll know what to do with. It opens to a sunny dining area and a living room that invites you to sink in and stay awhile. Downstairs, you’ll find two spacious bedrooms, including a primary suite that feels like a retreat. The spa-like bathroom, walk-in closet, and tray ceiling add a touch of everyday luxury. There’s also a den that can flex into a home office, reading room, or whatever you need it to be. Upstairs is a private guest suite with a third bedroom, full bath, and a bonus loft space that’s perfect for movie nights or extra living space. But the magic continues outside. The oversized patio was made for entertaining—complete with a built-in firepit, gas line for your grill , and even a five-person Thermospa hot tub. Whether it’s coffee in the morning or wine after sunset, this is where you’ll want to be. Other thoughtful touches? There’s a heated and cooled garage with extra space for a third vehicle or golf cart, and a sky basement for bonus storage. Throughout the home, you'll find upgrades like luxury vinyl plank flooring, under-cabinet kitchen lighting, custom bathroom finishes, recessed lighting, and so much more. And then there’s the community. Four Seasons at Kent Island is truly one-of-a-kind. Want to start your day with yoga? Go for a paddle on the river? Meet friends at the outdoor bar to catch the game by the firepit? It's all here. There’s a 24,000 sq ft clubhouse, both indoor and outdoor pools, a state-of-the-art gym, game room, pickleball and tennis courts, walking and biking trails, a pier for fishing and boating, a kayak launch, and even a dog park. The community is tucked away, peaceful and private—but you're just minutes from restaurants, wineries, breweries, and shops. And if you ever need a city fix, Annapolis and Easton are an easy 20-30 minute drive away. The best way to describe this home and community? It’s a place where life slows down in the best way. Where neighbors become friends. Where the to-do list gets a lot shorter—and the “want-to-do” list gets a whole lot longer. So if you're looking for more than just a new house—if you're ready for a new chapter filled with connection, ease, and everyday joy—135 Nauset Lane might be exactly what you’ve been waiting for.

135 Nauset Ln, Chester

Listing courtesy of Real Broker, LLC - Annapolis. Contact:

Selling Office: Real Broker, LLC.

$784,990

Ready NOW! This stunning Kerr home offers an inviting open floor plan designed for both comfort and functionality. Featuring 3 bedrooms, 3 baths, and a spacious 3-car garage, this home perfectly blends everyday ease with elevated style. Highlights include a dedicated home office, a cozy screened patio for outdoor relaxation, and a dramatic 2-story stone fireplace that serves as the heart of the great room. The gourmet kitchen is equipped with a single oven, microwave, gas cooktop, range hood, dishwasher, French door refrigerator, pendant lighting, and a stylish tile backsplash. Elegant quartz countertops extend through the kitchen and owner’s bath. Luxury vinyl plank flooring enhances the main level, with tile in all full baths and the laundry room, and plush carpet in the extra suite and upstairs loft. The owner’s bath features a spacious shower with a seat and handheld shower wand, plus double sinks for convenience. For a full list of included features, please contact our sales representatives. Photos are for illustrative purposes only and may not represent the exact home or finishes available. Welcome to a new luxury active adult 55+ community on Maryland's Chesapeake Bay. Discover the amenity-filled, resort-style experience within 45 miles of Washington DC and Baltimore. Residents can take advantage of the community's 24,000 sq. ft. clubhouse with indoor & outdoor pools, a state-of-the-art fitness center, and multiple tennis and pickleball courts. With a full-time lifestyle director on site the community also features a well-maintained calendar of activities such as walking club, indoor and outdoor yoga sessions, mahjong club, kayaking, pickleball and more. Kent Island life is about making friends and enjoying the company of people who have worked hard and now want to enjoy all that a luxury 55+ community has to offer. Located steps from the water and minutes from Annapolis, the location also offers quick access to Rt. 50. Enjoy the convenience of nearby dining and shopping options together with the quaint charm of a small town.

Ready NOW! This stunning Kerr home offers an inviting open floor plan designed for both comfort and functionality. Featuring 3 bedrooms, 3 baths, and a spacious 3-car garage, this home perfectly blends everyday ease with elevated style. Highlights include a dedicated home office, a cozy screened patio for outdoor relaxation, and a dramatic 2-story stone fireplace that serves as the heart of the great room. The gourmet kitchen is equipped with a single oven, microwave, gas cooktop, range hood, dishwasher, French door refrigerator, pendant lighting, and a stylish tile backsplash. Elegant quartz countertops extend through the kitchen and owner’s bath. Luxury vinyl plank flooring enhances the main level, with tile in all full baths and the laundry room, and plush carpet in the extra suite and upstairs loft. The owner’s bath features a spacious shower with a seat and handheld shower wand, plus double sinks for convenience. For a full list of included features, please contact our sales representatives. Photos are for illustrative purposes only and may not represent the exact home or finishes available. Welcome to a new luxury active adult 55+ community on Maryland's Chesapeake Bay. Discover the amenity-filled, resort-style experience within 45 miles of Washington DC and Baltimore. Residents can take advantage of the community's 24,000 sq. ft. clubhouse with indoor & outdoor pools, a state-of-the-art fitness center, and multiple tennis and pickleball courts. With a full-time lifestyle director on site the community also features a well-maintained calendar of activities such as walking club, indoor and outdoor yoga sessions, mahjong club, kayaking, pickleball and more. Kent Island life is about making friends and enjoying the company of people who have worked hard and now want to enjoy all that a luxury 55+ community has to offer. Located steps from the water and minutes from Annapolis, the location also offers quick access to Rt. 50. Enjoy the convenience of nearby dining and shopping options together with the quaint charm of a small town.

527 Warbler Way, Chester

Listing courtesy of KOVO Realty. Contact:

Selling Office: Real Broker, LLC.

$780,000

The Simone is a beautifully designed home with a projected settlement of May 2026, offering the space and features you are looking for. With 4 bedrooms, 3 full baths, and a 2-car garage, this home balances everyday comfort with thoughtful design details. A dedicated home office provides the perfect space for remote work or study, while the great room is anchored by a striking two-story shiplap fireplace with a granite surround, creating a warm and inviting focal point. The kitchen is well-appointed with a gas cooktop, single oven, microwave, range hood, dishwasher, French-door refrigerator, and pendant lighting, complemented by a tile backsplash and quartz countertops that continue into the owner’s bath. LVP flooring flows through the foyer, kitchen, dining area, great room, owner’s suite, and bedroom two, while tile finishes the full baths and laundry room. Plush carpeted spaces in the loft, second floor, and additional bedrooms add comfort where it counts. The owner’s bath features a spa-like shower with seating, a handheld wand, and double sinks for added convenience. For a full list of features for this home, please contact our sales representatives. Photos are for illustrative purposes only and may not represent the exact home or finishes available. Welcome to a new luxury active adult 55+ community on Maryland's Chesapeake Bay. Discover the amenity-filled, resort-style experience within 45 miles of Washington DC and Baltimore. Residents can take advantage of the community's 24,000 sq. ft. clubhouse with indoor & outdoor pools, a state-of-the-art fitness center, and multiple tennis and pickleball courts. With a full-time lifestyle director on site the community also features a well-maintained calendar of activities such as walking club, indoor and outdoor yoga sessions, mahjong club, kayaking, pickleball and more. Kent Island life is about making friends and enjoying the company of people who have worked hard and now want to enjoy all that a luxury 55+ community has to offer. Located steps from the water and minutes from Annapolis, the location also offers quick access to Rt. 50. Enjoy the convenience of nearby dining and shopping options together with the quaint charm of a small town.

4 Beds ⋅ 3 Baths

The Simone is a beautifully designed home with a projected settlement of May 2026, offering the space and features you are looking for. With 4 bedrooms, 3 full baths, and a 2-car garage, this home balances everyday comfort with thoughtful design details. A dedicated home office provides the perfect space for remote work or study, while the great room is anchored by a striking two-story shiplap fireplace with a granite surround, creating a warm and inviting focal point. The kitchen is well-appointed with a gas cooktop, single oven, microwave, range hood, dishwasher, French-door refrigerator, and pendant lighting, complemented by a tile backsplash and quartz countertops that continue into the owner’s bath. LVP flooring flows through the foyer, kitchen, dining area, great room, owner’s suite, and bedroom two, while tile finishes the full baths and laundry room. Plush carpeted spaces in the loft, second floor, and additional bedrooms add comfort where it counts. The owner’s bath features a spa-like shower with seating, a handheld wand, and double sinks for added convenience. For a full list of features for this home, please contact our sales representatives. Photos are for illustrative purposes only and may not represent the exact home or finishes available. Welcome to a new luxury active adult 55+ community on Maryland's Chesapeake Bay. Discover the amenity-filled, resort-style experience within 45 miles of Washington DC and Baltimore. Residents can take advantage of the community's 24,000 sq. ft. clubhouse with indoor & outdoor pools, a state-of-the-art fitness center, and multiple tennis and pickleball courts. With a full-time lifestyle director on site the community also features a well-maintained calendar of activities such as walking club, indoor and outdoor yoga sessions, mahjong club, kayaking, pickleball and more. Kent Island life is about making friends and enjoying the company of people who have worked hard and now want to enjoy all that a luxury 55+ community has to offer. Located steps from the water and minutes from Annapolis, the location also offers quick access to Rt. 50. Enjoy the convenience of nearby dining and shopping options together with the quaint charm of a small town.

255 Redstart Dr, Chester

Listing courtesy of KOVO Realty. Contact:

Selling Office: Long & Foster Real Estate, Inc..

$775,000

2 Beds ⋅ 2 Baths

169 Harrier Way, Chester

Listing courtesy of CENTURY 21 New Millennium. Contact:

$769,990

Welcome to the Kerr, a beautifully designed home offering 3 bedrooms, 3 baths, and a 3-car garage. Scheduled for settlement in July 2026, this home combines an open-concept layout with thoughtful design for both comfort and functionality. The main living area features a cozy fireplace with mantel and hearth, creating a warm and inviting focal point. A dedicated home office provides a private space for productivity, while the screened patio extends the living area outdoors—perfect for entertaining or relaxing. The kitchen is equipped for both style and performance, featuring a single oven, microwave, gas cooktop with range hood, dishwasher, French door refrigerator, pendant lighting, tile backsplash, and quartz countertops. Quartz is also featured in the owner’s bath for a cohesive, elegant finish. Hardwood flooring flows throughout the foyer, extended foyer, HovHall, kitchen, dining area, great room, home office, bedrooms 2, the primary suite, loft, and second floor, while tile is featured in all full baths and the laundry room. The primary bath includes a walk-in shower with seat and handheld shower wand and a double-sink vanity for added convenience and luxury. For a full list of features for this home, please contact our sales representatives. Photos are for illustrative purposes only and may not represent the exact home or finishes available. Welcome to a new luxury active adult 55+ community on Maryland's Chesapeake Bay. Discover the amenity-filled, resort-style experience within 45 miles of Washington DC and Baltimore. Residents can take advantage of the community's 24,000 sq. ft. clubhouse with indoor & outdoor pools, a state-of-the-art fitness center, and multiple tennis and pickleball courts. With a full-time lifestyle director on site the community also features a well-maintained calendar of activities such as walking club, indoor and outdoor yoga sessions, mahjong club, kayaking, pickleball and more. Kent Island life is about making friends and enjoying the company of people who have worked hard and now want to enjoy all that a luxury 55+ community has to offer. Located steps from the water and minutes from Annapolis, the location also offers quick access to Rt. 50. Enjoy the convenience of nearby dining and shopping options together with the quaint charm of a small town.

Welcome to the Kerr, a beautifully designed home offering 3 bedrooms, 3 baths, and a 3-car garage. Scheduled for settlement in July 2026, this home combines an open-concept layout with thoughtful design for both comfort and functionality. The main living area features a cozy fireplace with mantel and hearth, creating a warm and inviting focal point. A dedicated home office provides a private space for productivity, while the screened patio extends the living area outdoors—perfect for entertaining or relaxing. The kitchen is equipped for both style and performance, featuring a single oven, microwave, gas cooktop with range hood, dishwasher, French door refrigerator, pendant lighting, tile backsplash, and quartz countertops. Quartz is also featured in the owner’s bath for a cohesive, elegant finish. Hardwood flooring flows throughout the foyer, extended foyer, HovHall, kitchen, dining area, great room, home office, bedrooms 2, the primary suite, loft, and second floor, while tile is featured in all full baths and the laundry room. The primary bath includes a walk-in shower with seat and handheld shower wand and a double-sink vanity for added convenience and luxury. For a full list of features for this home, please contact our sales representatives. Photos are for illustrative purposes only and may not represent the exact home or finishes available. Welcome to a new luxury active adult 55+ community on Maryland's Chesapeake Bay. Discover the amenity-filled, resort-style experience within 45 miles of Washington DC and Baltimore. Residents can take advantage of the community's 24,000 sq. ft. clubhouse with indoor & outdoor pools, a state-of-the-art fitness center, and multiple tennis and pickleball courts. With a full-time lifestyle director on site the community also features a well-maintained calendar of activities such as walking club, indoor and outdoor yoga sessions, mahjong club, kayaking, pickleball and more. Kent Island life is about making friends and enjoying the company of people who have worked hard and now want to enjoy all that a luxury 55+ community has to offer. Located steps from the water and minutes from Annapolis, the location also offers quick access to Rt. 50. Enjoy the convenience of nearby dining and shopping options together with the quaint charm of a small town.

539 Warbler Way, Chester

Listing courtesy of KOVO Realty. Contact:

The Chester at Lot 2433 offers a thoughtfully designed open-concept layout with a projected settlement date of August 2026, making it an excellent opportunity for buyers planning ahead. This home features 2 bedrooms, 2.5 baths, and a 1-car garage, delivering comfort, functionality, and efficient use of space. Standout features include a dedicated home office with lighted French doors, a dry bar ideal for entertaining, an electric fireplace for added ambiance, and a convenient storage room to keep everything organized. Luxury vinyl plank flooring runs throughout the home, with tile in both full baths for durability and easy maintenance. The kitchen is well-appointed with a single oven, microwave, gas cooktop, range hood, dishwasher, pendant lighting, and a tile backsplash, all complemented by quartz countertops. The owner’s bath features a shower with seat, handheld shower wand, double sinks, and quartz countertops, creating a comfortable and refined retreat. For a full list of features for this home, please contact our sales representatives. Photos are for illustrative purposes only and may not represent the exact home or finishes available.

$769,990

The Chester at Lot 2433 offers a thoughtfully designed open-concept layout with a projected settlement date of August 2026, making it an excellent opportunity for buyers planning ahead. This home features 2 bedrooms, 2.5 baths, and a 1-car garage, delivering comfort, functionality, and efficient use of space. Standout features include a dedicated home office with lighted French doors, a dry bar ideal for entertaining, an electric fireplace for added ambiance, and a convenient storage room to keep everything organized. Luxury vinyl plank flooring runs throughout the home, with tile in both full baths for durability and easy maintenance. The kitchen is well-appointed with a single oven, microwave, gas cooktop, range hood, dishwasher, pendant lighting, and a tile backsplash, all complemented by quartz countertops. The owner’s bath features a shower with seat, handheld shower wand, double sinks, and quartz countertops, creating a comfortable and refined retreat. For a full list of features for this home, please contact our sales representatives. Photos are for illustrative purposes only and may not represent the exact home or finishes available.

176 Flagstaff Way Unit 2433, Chester

Listing courtesy of KOVO Realty. Contact:

Selling Office: KW Metro Center.

$769,900

Welcome home to the Chester, a beautifully crafted 2-bedroom, 2.5-bath residence with a 1-car garage, offering low-maintenance luxury and stylish finishes throughout. Ideal for full-time living or a lock-and-leave lifestyle, this home delivers comfort, flexibility, and charm in every room. Inside, you’ll find a dedicated home office with lighted French doors, perfect for remote work or a peaceful study. Elevated details include tray ceilings in both the great room and primary suite, a built-in dry bar, and a cozy electric fireplace that anchors the main living space. The chef-inspired kitchen features a gas cooktop, wall oven, microwave, range hood, and French door refrigerator, framed by tile backsplash, quartz countertops, and elegant pendant lighting. Durable laminate flooring flows throughout the home, with tile in both full baths. The primary bath offers a frameless walk-in shower with a seat, handheld shower wand, double sinks, and quartz countertops, giving your daily routine a spa-like upgrade. For a full list of features for this home, please contact our sales representatives. Photos are for display purposes only and may not reflect actual selections or layout.

Welcome home to the Chester, a beautifully crafted 2-bedroom, 2.5-bath residence with a 1-car garage, offering low-maintenance luxury and stylish finishes throughout. Ideal for full-time living or a lock-and-leave lifestyle, this home delivers comfort, flexibility, and charm in every room. Inside, you’ll find a dedicated home office with lighted French doors, perfect for remote work or a peaceful study. Elevated details include tray ceilings in both the great room and primary suite, a built-in dry bar, and a cozy electric fireplace that anchors the main living space. The chef-inspired kitchen features a gas cooktop, wall oven, microwave, range hood, and French door refrigerator, framed by tile backsplash, quartz countertops, and elegant pendant lighting. Durable laminate flooring flows throughout the home, with tile in both full baths. The primary bath offers a frameless walk-in shower with a seat, handheld shower wand, double sinks, and quartz countertops, giving your daily routine a spa-like upgrade. For a full list of features for this home, please contact our sales representatives. Photos are for display purposes only and may not reflect actual selections or layout.

201 Switchgrass Way Unit 1443, Chester

Listing courtesy of KOVO Realty. Contact:

Selling Office: Unrepresented Buyer Office.

$768,900

Experience the perfect balance of function and finesse in the Chester, a 2-bedroom, 2.5-bath home with a 1-car garage, designed for effortless living and elevated comfort. Thoughtfully laid out, this home includes a stylish home office with lighted French doors, a dry bar for entertaining, and a welcoming electric fireplace to anchor the living space. Elegant tray ceilings in both the great room and primary suite add a sophisticated touch. The chef’s kitchen features a gas cooktop, wall oven, microwave, range hood, and dishwasher, all surrounded by quartz countertops, a tile backsplash, and warm pendant lighting. Laminate flooring flows seamlessly throughout the home, with tile in the two full baths for added durability. In the primary bathroom, unwind in the frameless walk-in shower with a seat and handheld wand, paired with double sinks and quartz countertops for a refined retreat. For a full list of features for this home, please contact our sales representatives. Photos are for display purposes only and may not reflect actual selections or layout.