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$2,350,000

Sited on Cox Creek with 369 feet of waterfront, this elegant contemporary residence offers 2.3 private acres, spectacular western exposure, and breathtaking sunset views. Thoughtfully designed to maximize water vistas from nearly every room, the home features 4 bedrooms, 3 full baths and 2 half baths, and approximately 4,717 square feet of refined living space. The gourmet kitchen is appointed with rich custom cabinetry, granite countertops, upgraded stainless steel appliances, and a gas cooktop, creating an ideal setting for both everyday living and entertaining. Custom hardwood flooring spans the main level, complemented by two fireplaces and timeless architectural details throughout. The luxurious main-level primary suite offers serene water views, multiple walk-in closets, and a recently renovated spa-inspired bath. A beautiful three-season room overlooks the creek, providing the perfect space to relax and enjoy the tranquil setting. There is also ample room to add a pool. Upstairs, three additional bedrooms and two full baths provide comfortable accommodations for family and guests, with three of the four bedrooms enjoying water views. The upper level has been recently updated with luxury vinyl plank flooring in place of carpet. Additional highlights include mature professional landscaping, a temperature-controlled wine room, a 3-car garage, a new roof, private pier with electric and water, boat lift, jet ski lifts, and riprap shoreline protection. Located in the desirable Southwind community, residents enjoy amenities including a boat launch, boat storage area, tennis courts, walking trails, and a clubhouse — all conveniently located near shopping, dining, and more.

4 Beds ⋅ 5 Baths

Sited on Cox Creek with 369 feet of waterfront, this elegant contemporary residence offers 2.3 private acres, spectacular western exposure, and breathtaking sunset views. Thoughtfully designed to maximize water vistas from nearly every room, the home features 4 bedrooms, 3 full baths and 2 half baths, and approximately 4,717 square feet of refined living space. The gourmet kitchen is appointed with rich custom cabinetry, granite countertops, upgraded stainless steel appliances, and a gas cooktop, creating an ideal setting for both everyday living and entertaining. Custom hardwood flooring spans the main level, complemented by two fireplaces and timeless architectural details throughout. The luxurious main-level primary suite offers serene water views, multiple walk-in closets, and a recently renovated spa-inspired bath. A beautiful three-season room overlooks the creek, providing the perfect space to relax and enjoy the tranquil setting. There is also ample room to add a pool. Upstairs, three additional bedrooms and two full baths provide comfortable accommodations for family and guests, with three of the four bedrooms enjoying water views. The upper level has been recently updated with luxury vinyl plank flooring in place of carpet. Additional highlights include mature professional landscaping, a temperature-controlled wine room, a 3-car garage, a new roof, private pier with electric and water, boat lift, jet ski lifts, and riprap shoreline protection. Located in the desirable Southwind community, residents enjoy amenities including a boat launch, boat storage area, tennis courts, walking trails, and a clubhouse — all conveniently located near shopping, dining, and more.

2832 Cox Neck Rd, Chester

Listing courtesy of Coldwell Banker Realty. Contact:

Selling Office: Chesapeake Real Estate Associates, LLC.

$2,300,000

Discover an exquisite Mediterranean-style residence nestled in the prestigious Southwind community, where luxury meets comfort while enjoying breathtaking sunset views. This stunning 4-bedroom, 3.5-bathroom home boasts 4,331 sq. ft. The gourmet kitchen features high-end stainless steel appliances, including a built-in microwave, wall oven, and a sleek cooktop, ensuring culinary excellence. Step outside to your private oasis, where a concrete pool invites relaxation amidst lush landscaping on a generous 1.2-acre lot that includes a covered built in Lynx grill and bar seating. Enjoy direct access to Cox Creek, complete with a private dock for fishing, kayaking, or simply soaking in the serene water views. With a double sided fireplace and three tankless water heater, this home combines elegance with modern convenience, making it a true sanctuary. The main living room features sky high ceilings and a wet bar making hosting a snap and flows into the added sunroom that features heated tile flooring. And the three season room off the back is the perfect gathering space with a wall of sliders to maximize the view. Meticulously maintained and thoroughy enjoyed by the original owners. The expansive rear yard and rip-rap shoreline enhance the outdoor experience, while the community amenities, including a beach, tennis/basketball courts, and fishing pier and boat launch, offer an exclusive lifestyle on Maryland's Eastern Shore.

4 Beds ⋅ 4 Baths

Discover an exquisite Mediterranean-style residence nestled in the prestigious Southwind community, where luxury meets comfort while enjoying breathtaking sunset views. This stunning 4-bedroom, 3.5-bathroom home boasts 4,331 sq. ft. The gourmet kitchen features high-end stainless steel appliances, including a built-in microwave, wall oven, and a sleek cooktop, ensuring culinary excellence. Step outside to your private oasis, where a concrete pool invites relaxation amidst lush landscaping on a generous 1.2-acre lot that includes a covered built in Lynx grill and bar seating. Enjoy direct access to Cox Creek, complete with a private dock for fishing, kayaking, or simply soaking in the serene water views. With a double sided fireplace and three tankless water heater, this home combines elegance with modern convenience, making it a true sanctuary. The main living room features sky high ceilings and a wet bar making hosting a snap and flows into the added sunroom that features heated tile flooring. And the three season room off the back is the perfect gathering space with a wall of sliders to maximize the view. Meticulously maintained and thoroughy enjoyed by the original owners. The expansive rear yard and rip-rap shoreline enhance the outdoor experience, while the community amenities, including a beach, tennis/basketball courts, and fishing pier and boat launch, offer an exclusive lifestyle on Maryland's Eastern Shore.

2882 Cox Neck Rd, Chester

Listing courtesy of Wilson Realty & Staging LLC. Contact:

Selling Office: Gunther-McClary Real Estate.

$1,850,000

This stunning waterfront, custom built home sits ideally on a little over an acre fronting Crab Alley Bay in the prestigious Southwind community. Home boast almost 10,000 square feet, between finished living space and additional expansion space. An already large home offers so much more room to grow the perfect, waterfront retreat. This gem features 6 large bedrooms and of those 4 have private baths, and walk-in closets. Original owners designed this home to highlight 8' solid wood doors, Brazilian cherry hardwood floors, high ceilings through-out the first floor, two focal point fireplaces, second floor balcony, come see it all and in vison the possibilities this property offers. This is truly a must-see property. Not to mention its LOCATION. Nestled in the Southwind community that features a clubhouse, basketball court, pickle ball court, tennis court, boat ramp, and plenty of ways to enjoy the nature.

6 Beds ⋅ 6 Baths

This stunning waterfront, custom built home sits ideally on a little over an acre fronting Crab Alley Bay in the prestigious Southwind community. Home boast almost 10,000 square feet, between finished living space and additional expansion space. An already large home offers so much more room to grow the perfect, waterfront retreat. This gem features 6 large bedrooms and of those 4 have private baths, and walk-in closets. Original owners designed this home to highlight 8' solid wood doors, Brazilian cherry hardwood floors, high ceilings through-out the first floor, two focal point fireplaces, second floor balcony, come see it all and in vison the possibilities this property offers. This is truly a must-see property. Not to mention its LOCATION. Nestled in the Southwind community that features a clubhouse, basketball court, pickle ball court, tennis court, boat ramp, and plenty of ways to enjoy the nature.

2817 Cox Neck Rd, Chester

Listing courtesy of Michael J. Bozek. Contact:

Selling Office: Non Subscribing Office.

$1,825,000

Set within Southwind, one of Kent Island’s most sought-after waterfront communities, this exceptional residence offers an elegant blend of craftsmanship and comfort with 10 foot ceilings and beautiful crown molding. Perfectly sited on an acre overlooking Crab Alley Bay and Eastern Bay, the home’s peaceful setting is enhanced by sweeping water views, mature landscaping, and a private waterside pool that invites year-round enjoyment. Inside, timeless design meets modern refinement. The first-floor primary suite provides a serene retreat, joined by two additional guest suites on the main level—each with its own ensuite bath for privacy and comfort. Upstairs, a fourth bedroom and full bath accompany a spacious living area, ideal for extended family or guests. The heart of the home is a stunning, renovated kitchen featuring rich finishes, premium appliances, and an open layout perfect for gathering. Gleaming hardwood floors flow throughout, leading to a mahogany-lined library that exudes warmth and sophistication—a true sanctuary for work or quiet reflection. Outdoor living takes center stage with a screened porch that captures cooling Bay breezes and views of the pool and shimmering water beyond. Whether entertaining or simply savoring the stillness of the shoreline, every space in this home celebrates the beauty of the Chesapeake Bay lifestyle.

4 Beds ⋅ 6 Baths

Set within Southwind, one of Kent Island’s most sought-after waterfront communities, this exceptional residence offers an elegant blend of craftsmanship and comfort with 10 foot ceilings and beautiful crown molding. Perfectly sited on an acre overlooking Crab Alley Bay and Eastern Bay, the home’s peaceful setting is enhanced by sweeping water views, mature landscaping, and a private waterside pool that invites year-round enjoyment. Inside, timeless design meets modern refinement. The first-floor primary suite provides a serene retreat, joined by two additional guest suites on the main level—each with its own ensuite bath for privacy and comfort. Upstairs, a fourth bedroom and full bath accompany a spacious living area, ideal for extended family or guests. The heart of the home is a stunning, renovated kitchen featuring rich finishes, premium appliances, and an open layout perfect for gathering. Gleaming hardwood floors flow throughout, leading to a mahogany-lined library that exudes warmth and sophistication—a true sanctuary for work or quiet reflection. Outdoor living takes center stage with a screened porch that captures cooling Bay breezes and views of the pool and shimmering water beyond. Whether entertaining or simply savoring the stillness of the shoreline, every space in this home celebrates the beauty of the Chesapeake Bay lifestyle.

2907 Cox Neck Rd E, Chester

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

Selling Office: RE/MAX Advantage Realty.

$1,125,000

Welcome to this pristine contemporary ranch in the coveted waterfront community of South Wind on Kent Island, where luxury, comfort, and resort-style living come together on 1.21 beautifully landscaped acres. From the moment you arrive, the home’s lush green lawn, vibrant gardens, and custom walkways create a picture-perfect setting worthy of a magazine cover. Inside, the open-concept floor plan is filled with natural light and highlighted by gleaming hardwood floors and exceptional upgrades throughout this 4 bedroom, 3 full bath estate. The stunning designer kitchen is truly the heart of the home, featuring crisp white cabinetry, granite countertops, an oversized center island, a premium Wolf 5-burner gas cooktop flanked by custom spice cabinets, a wall convection oven, and built-in microwave...crafted for both everyday living and effortless entertaining. Just beyond the main living areas, the inviting three-season sun porch with white tile flooring overlooks your own private backyard retreat. Step outside onto the expansive maintenance-free decking and new patio surrounding the spectacular heated gunite pool, complete with a waterfall feature and dual stair entrances, creating the ultimate outdoor oasis. The professionally designed landscaping continues throughout the property, accented with colorful plantings, mature greenery, and thoughtfully designed outdoor spaces. A custom-built shed, designed to perfectly complement the home, offers electric service and a gated outdoor storage area. Additional premium features include an oversized two-car garage with air conditioning, two-zone gas heat and central air, a whole-house generator, tankless water heater, updated crawlspace with dehumidifier, and energy-saving foil-wrapped attic insulation. The roof is only two years young, offering peace of mind for years to come. Perfectly positioned to capture serene open-space and water views, this exceptional property also includes access to South Wind’s sought-after amenities, including a community beach, boat ramp, pier, tennis courts, dry dock, and more. This is more than a home...it’s a private Kent Island retreat designed for exceptional living.

4 Beds ⋅ 3 Baths

Welcome to this pristine contemporary ranch in the coveted waterfront community of South Wind on Kent Island, where luxury, comfort, and resort-style living come together on 1.21 beautifully landscaped acres. From the moment you arrive, the home’s lush green lawn, vibrant gardens, and custom walkways create a picture-perfect setting worthy of a magazine cover. Inside, the open-concept floor plan is filled with natural light and highlighted by gleaming hardwood floors and exceptional upgrades throughout this 4 bedroom, 3 full bath estate. The stunning designer kitchen is truly the heart of the home, featuring crisp white cabinetry, granite countertops, an oversized center island, a premium Wolf 5-burner gas cooktop flanked by custom spice cabinets, a wall convection oven, and built-in microwave...crafted for both everyday living and effortless entertaining. Just beyond the main living areas, the inviting three-season sun porch with white tile flooring overlooks your own private backyard retreat. Step outside onto the expansive maintenance-free decking and new patio surrounding the spectacular heated gunite pool, complete with a waterfall feature and dual stair entrances, creating the ultimate outdoor oasis. The professionally designed landscaping continues throughout the property, accented with colorful plantings, mature greenery, and thoughtfully designed outdoor spaces. A custom-built shed, designed to perfectly complement the home, offers electric service and a gated outdoor storage area. Additional premium features include an oversized two-car garage with air conditioning, two-zone gas heat and central air, a whole-house generator, tankless water heater, updated crawlspace with dehumidifier, and energy-saving foil-wrapped attic insulation. The roof is only two years young, offering peace of mind for years to come. Perfectly positioned to capture serene open-space and water views, this exceptional property also includes access to South Wind’s sought-after amenities, including a community beach, boat ramp, pier, tennis courts, dry dock, and more. This is more than a home...it’s a private Kent Island retreat designed for exceptional living.

2812 Harvest Ct, Chester

Listing courtesy of RE/MAX Executive. Contact:

Selling Office: TTR Sotheby's International Realty.

$895,000

Welcome to Southwind, one of Kent Island's most desirable waterfront communities, where peaceful surroundings and an exceptional lifestyle come together. Perfectly positioned on 1.22 beautifully landscaped acres with water views, this inviting single-level home offers the comfort, space, and amenities you've been searching for. Inside, you'll find three spacious bedrooms and three beautifully updated full baths, creating a home that is both stylish and comfortable. Freshly painted throughout, with newly refinished hardwood floors and plush new carpeting in the bedrooms, every room feels bright, fresh, and move-in ready. The heart of the home is the welcoming kitchen, featuring gleaming granite countertops, crisp white cabinetry, a generous pantry with charming French doors, peninsula seating for casual meals and conversation, a vaulted breakfast area with a dramatic palladium window showcasing beautiful water views, and brand-new stainless steel range and refrigerator. Whether you're preparing dinner or gathering with family and friends, this space is designed to bring everyone together. The adjoining family room is warm and inviting, centered around a cozy propane fireplace and accented by custom built-in bookshelves that add both charm and functionality. A sliding glass door opens directly to the slate patio, creating an effortless connection between indoor and outdoor living. Just off the main living area, the light-filled dining room is surrounded by large windows that frame lovely water views, creating the perfect backdrop for everyday meals and special occasions. A versatile bonus sunroom offers even more living space and can easily serve as a cozy den, home office, or additional bedroom to fit your needs. Step outside to enjoy the fenced backyard and slate patio, where a remote-operated awning provides welcome shade at the touch of a button, making it the perfect spot for morning coffee, evening sunsets, or weekend barbecues. Car enthusiasts, hobbyists, and those needing extra space will appreciate the oversized four-car garage. Above, an expansive unfinished area offers endless possibilities. Already plumbed for a future bath, it's ready to become a guest suite, home office, recreation room, or whatever your imagination inspires. Energy efficiency is another standout feature, with owned solar panels and two Tesla Powerwall storage batteries helping to keep utility costs remarkably low while providing added peace of mind. Living in Southwind means more than owning a beautiful home—it's embracing a waterfront lifestyle. Residents enjoy access to the community boat launch, waterfront clubhouse, boat storage lot, pickleball and tennis courts, and scenic nature trail along the water. Whether you're launching your boat for a day on the Chesapeake Bay, enjoying an evening stroll by the shoreline, or simply relaxing at home while taking in the tranquil water views, this property offers the perfect blend of comfort, community, and coastal living.

3 Beds ⋅ 3 Baths

Welcome to Southwind, one of Kent Island's most desirable waterfront communities, where peaceful surroundings and an exceptional lifestyle come together. Perfectly positioned on 1.22 beautifully landscaped acres with water views, this inviting single-level home offers the comfort, space, and amenities you've been searching for. Inside, you'll find three spacious bedrooms and three beautifully updated full baths, creating a home that is both stylish and comfortable. Freshly painted throughout, with newly refinished hardwood floors and plush new carpeting in the bedrooms, every room feels bright, fresh, and move-in ready. The heart of the home is the welcoming kitchen, featuring gleaming granite countertops, crisp white cabinetry, a generous pantry with charming French doors, peninsula seating for casual meals and conversation, a vaulted breakfast area with a dramatic palladium window showcasing beautiful water views, and brand-new stainless steel range and refrigerator. Whether you're preparing dinner or gathering with family and friends, this space is designed to bring everyone together. The adjoining family room is warm and inviting, centered around a cozy propane fireplace and accented by custom built-in bookshelves that add both charm and functionality. A sliding glass door opens directly to the slate patio, creating an effortless connection between indoor and outdoor living. Just off the main living area, the light-filled dining room is surrounded by large windows that frame lovely water views, creating the perfect backdrop for everyday meals and special occasions. A versatile bonus sunroom offers even more living space and can easily serve as a cozy den, home office, or additional bedroom to fit your needs. Step outside to enjoy the fenced backyard and slate patio, where a remote-operated awning provides welcome shade at the touch of a button, making it the perfect spot for morning coffee, evening sunsets, or weekend barbecues. Car enthusiasts, hobbyists, and those needing extra space will appreciate the oversized four-car garage. Above, an expansive unfinished area offers endless possibilities. Already plumbed for a future bath, it's ready to become a guest suite, home office, recreation room, or whatever your imagination inspires. Energy efficiency is another standout feature, with owned solar panels and two Tesla Powerwall storage batteries helping to keep utility costs remarkably low while providing added peace of mind. Living in Southwind means more than owning a beautiful home—it's embracing a waterfront lifestyle. Residents enjoy access to the community boat launch, waterfront clubhouse, boat storage lot, pickleball and tennis courts, and scenic nature trail along the water. Whether you're launching your boat for a day on the Chesapeake Bay, enjoying an evening stroll by the shoreline, or simply relaxing at home while taking in the tranquil water views, this property offers the perfect blend of comfort, community, and coastal living.

2810 Harvest Ct, Chester

Listing courtesy of Blackwell Real Estate, LLC. Contact:

Selling Office: Redfin Corp.