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1730 Ocean Gtwy, Trappe
$900,000
SIGNIFICANT PRICE REDUCTION!! Amazing investment opportunity!! 23.06 Acres of commercial property situated with 500 +/- ft. of direct frontage along busy Rt. 50 with 30,000+ AADT. Located less than 2 miles from the heart of Cambridge, Maryland, this versatile property features 3 vehicular ingress / egress points and is zoned Limited Commercial (LC), which is characterized by low intensity commercial, neighborhood-oriented businesses. The once bustling Talbot Landing Motel, with more than 8,000 square feet, features 4 buildings with 19 total guest rooms plus a roomy owner's suite, and could be perfect for revitalization or redevelopment. There is existing well and septic in use on the property. This is a phenomenal opportunity to acquire significant acreage along Rt.50.

1730 Ocean Gtwy, Trappe

Listing courtesy of Coldwell Banker Realty. Contact:

Selling Office: Coldwell Banker Realty.

1730 Ocean Gtwy, Trappe
$900,000
SIGNIFICANT PRICE REDUCTION!! Amazing investment opportunity!! 23.06 Acres of commercial property situated with 500 +/- ft. of direct frontage along busy Rt. 50 with 30,000+ AADT. Located less than 2 miles from the heart of Cambridge, Maryland, this versatile property features 3 vehicular ingress / egress points and is zoned Limited Commercial (LC), which is characterized by low intensity commercial, neighborhood-oriented businesses. The once bustling Talbot Landing Motel, with more than 8,000 square feet, features 4 buildings with 19 total guest rooms plus a roomy owner's suite, and could be perfect for revitalization or redevelopment. There is existing well and septic in use on the property. This is a phenomenal opportunity to acquire significant acreage along Rt.50.

1730 Ocean Gtwy, Trappe

Listing courtesy of Coldwell Banker Realty. Contact:

Selling Office: Unrepresented.

24896 Back Crk, Saint Michaels
$877,000
5 Beds ⋅ 5 Baths
Welcome to 24896 Back Creek Drive Saint Michaels, a coastal home with one of the most beautiful back yard pond views available in the entire community! This property has so much a buyer may desire--modern, coastal design, open concept living, soaring ceilings, a large fenced back yard, broad views of a beautiful pond, water access approx 0.2 miles down the community pathway to San Domingo Creek for kayaking/paddleboarding, an abundance of space, a kitchen with a spectacular gas stove and two ovens, a gas fireplace, recently planted privacy trees, an encapsulated crawl space and so much more! You will be the envy of family and/or friends as you all sit around the enormous 90" flat screen television over the fireplace to take in sporting events or shows (television conveys with the property) or when you sit around the new hardscape fire pit boasting a new, large pellet/wood burning stove (which also conveys, along with the four new Adirondack chairs)! If you prefer to take in the spectacular water view from the nice deck or the large four season sunroom, either is an excellent option! The primary suite is on the main floor with all other bedrooms upstairs. There is an option to have an upstairs primary en suite if you prefer being on the same floor as other bedrooms. This property has sold in past listed as a five bedroom property so is listed as such again. Please be advised two of the five bedrooms do not have closets; wardrobes have been used in past listing of the property. Closets can easily be built in those two bedrooms--there is tremendous space to do so. Recent seller upgrades include a newly paved driveway, fire pit hardscape and pellet/wood fire pit (which conveys with the sale of the property), kitchen cabinet handles/pulls, entire exterior of the home was power washed, The crawl space is encapsulated. This property is very close to a grocery store, coffee place, bank and gas station. St Michaels' Historic District can be reached in mere minutes by car or on foot. The Y, community pool, Miles River Yacht Club, Chesapeake Bay Maritime Museum, Inn at Perry Cabin, golf, are all in proximity.

24896 Back Crk, Saint Michaels

Listing courtesy of Meredith Fine Properties. Contact:

Selling Office: Meredith Fine Properties.

226 S Morris St, Oxford
$875,000
3 Beds ⋅ 3 Baths
This charming Victorian house is located in the Historic District of Oxford and has resided with the current owner for several decades. A front porch overlooks a beautifully landscaped garden and lawn while the rear lawn is surrounded by gardens for beauty and privacy. A stunning water fountain with trickling water works perfectly for a quiet time on the sun porch or the second floor deck with sliding shades for the late afternoon sun. A garden shed/shop and a single car garage with a studio/apartment on the second floor round out this beautifully decorated home. A full size modern kitchen with top of the line appliances, dining room, and formal living room are on the first floor. Three bedrooms and two modern baths are located on the second floor. The house enjoys the benefits of a geothermal well system, 9’ ceilings and two fireplaces. The garage and garden shed are accessed by an alley which also allows for additional off street parking, a rarity in the Historic District. All of this sits on high ground in the “X” flood zone. Enjoy easy access to local shops, restaurants, the waterfront park, Oxford Market, and the beloved Scottish Highland Creamery.

226 S Morris St, Oxford

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Unrepresented.

28715 Jacks Field Rd, Wye Mills
$875,000
5 Beds ⋅ 3 Baths
Set on a peaceful two-acre lot in Wye Mills, 28715 Jacks Field Road has been thoughtfully updated from top to bottom, offering the space, functionality, and modern finishes today’s buyers are looking for. This spacious five-bedroom, three-bath home features a newly reimagined interior with new flooring throughout, custom blinds, and a series of high-impact upgrades that elevate both everyday living and entertaining. The kitchen serves as the heart of the home, showcasing brand-new stainless steel appliances, a gas cooktop with downdraft, double ovens, new countertops, and an oversized center island with new cabinetry. Part of the kitchen and dining area has been remodeled to create a more open, connected floor plan, complemented by updated lighting throughout the kitchen, dining area, office, laundry room, and four bedrooms. The primary suite offers a relaxing retreat with heated floors in the master bath and a newly installed walk-in closet organizer. Two additional bathrooms have been completely remodeled, providing fresh, modern finishes throughout the home. Major system upgrades include two brand-new HVAC heat pump systems with new exterior components and a new asphalt driveway, ensuring both comfort and peace of mind. Practical features abound with new laundry room cabinetry, ample storage, and flexible spaces for work, guests, or hobbies. Outside, the property truly shines. A 20’ x 20’ brick-lined patio seamlessly matches the existing covered patio, creating an ideal setting for outdoor entertaining. The expansive backyard is anchored by a 16’–20’ diameter gas fire pit with stone surround, perfect for gatherings under the stars. In addition to the two-car attached garage with walk-up attic storage, the property also includes a two-car detached garage, offering exceptional storage and workspace options. With its generous acreage, extensive updates, and move-in-ready condition, 28715 Jacks Field Road delivers a rare blend of privacy, functionality, and modern comfort in a sought-after Eastern Shore setting.

28715 Jacks Field Rd, Wye Mills

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Real Estate Professionals, Inc..

8020 Easton Village Dr, Easton
$860,000
5 Beds ⋅ 4 Baths
Effortless Lifestyle — Deeded Boat Slip with Lift in Easton Village Tucked into one of Talbot County’s most coveted waterfront community, 8020 Easton Village Drive delivers what Eastern Shore buyers search for: a deeded boat slip with electric lift on the Tred Avon, a turn-key home, and close proximity to historic downtown Easton. This 5-bedroom, 3.5-bath Colonial offers a wraparound covered porch and hardwood floors throughout the main level. The open kitchen features granite counters, butcher-block island, stainless appliances, gas cooking, and a coffee bar. A formal dining room, gas-fireplace family room, main-level bonus room (5th bedroom or office), and powder room complete the first floor. Upstairs, the primary suite has vaulted ceilings, two walk-in closets, soaking tub, and double vanity, plus three additional bedrooms and two full baths. The detached two-car garage includes a private guest suite with full bath above — ideal for in-laws or visitors. Major systems include a whole-house standby generator, Rinnai tankless water heater, whole-house alarm system, as well as natural gas forced air, central A/C, and central vacuum. The home has been thoughtfully updated with an improved kitchen, along with new lighting and ceiling fans. The fenced backyard features extensive stone hardscape, a gazebo, and built-in stone grill. The rare and sought-after deeded boat slip with electric lift gives direct access to the Oxford and St Michaels' marinas via the scenic Tred Avon River. Easton Village is known for its top-notch amenities which include an in-ground pool, the clubhouse, a fitness center, kayak launch, trails, and so much more.

8020 Easton Village Dr, Easton

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: O'Conor, Mooney & Fitzgerald.

8061 N Fork Blvd, Easton
$860,000
4 Beds ⋅ 3 Baths
Welcome to 8061 N Fork Boulevard in Easton’s sought-after waterfront community! This 4-bedroom 2.5 bath modern home offers over 3,000 sq.ft. of living with an open floor plan, gas burning fireplace and finished south-facing sunroom, as well as a south-facing living room and kitchen. The kitchen is equipped with stainless steel appliances. There is also a large first floor primary suite. Built in 2019 the home has a wrap-around front porch with composite decking and a private outdoor patio with hardscaping and some unusual shrubs and plants. There is a 2-car garage in the back facing an alley. Owned-outright solar panels on the roof is the gift that keeps on giving! The panels produce more electricity than the property uses (including charging an electric car in the garage) and the excess is automatically sold every month. The first floor primary suite with plenty of windows, includes, apart from the master bedroom, a spacious bathroom with a marble soaking tub and marble double sinks and a linen closet which could be converted to a stand-up shower enclosure. There is also a walk-in closet plus a second large closet. In addition, there is a very large work room/study, that can be used as a bedroom. The second floor has a lounge with gorgeous views, two bedrooms, a full bath, and a large storage room. This ADA compliant/handicap accessible home with smart features allows for easier living. There is also a chairlift to the second floor and a wheelchair lift from the first floor down to the garage level. Enjoy resort-style community amenities including a clubhouse, pool, fitness center, six-acre park, and over 50 acres of preserved wetlands. Boaters will love the multi-slip marina. Downtown Easton’s shops, dining and entertainment are just around the corner.

8061 N Fork Blvd, Easton

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Unrepresented Buyer Office.

28391 Masters Ct, Easton
$850,000
4 Beds ⋅ 4 Baths
Easton Club. This beautiful 3300 sq. ft. home has been extensively renovated. Living room, formal dining room, upgraded kitchen with Quartz countertops, new appliances and breakfast area, family room with stone gas fireplace, 1st floor primary suite with remodeled bath, laundry room and powder room. Wood flooring throughout 1st floor. 2nd floor offers 3 bedrooms, 2 baths and large media room or 5th bedroom. Exterior features a tiered deck with awning, lawn irrigation system and extensive landscaping. Sited on a .35 acre lot backing to open space on a quiet cul-de-sac. Roof (new 2023). HVAC (new 2022). Community amenities include a pool and tennis/pickleball court. Close to downtown Easton and many amenities. Short distance to the picturesque towns of St. Michaels and Oxford. A must to see!

28391 Masters Ct, Easton

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: TTR Sotheby's International Realty.

28298 Ayres Sq, Easton
$850,000
4 Beds ⋅ 3 Baths
Easton Village. Desirable waterfront community located minutes from downtown Easton, St. Michaels and Oxford. Enjoy access to Tred Avon River, community pier, clubhouse, outdoor pool, bocce court, kayak launch, 3+ miles of trails and 50 acres of open space. This custom built one owner home features a great room with gas fireplace and wood flooring, dining room, open kitchen with granite countertops and island, study/office and 1st floor primary suite. Four season sunroom addition with casement windows, separate/split HVAC and open beam and board ceiling. 2nd floor features 3 guest bedrooms with upgraded bath with new quartzite stone vanity top, glass shower door and mirror. This home is tastefully appointed and decorated. Substantial improvements and additions have been made to landscaping with beautiful trees, unique garden, foundation and perimeter shrubs. Between garage and house there is a slate patio and narrow garden. 4' tall concrete crawl space/storage under home. List of the many upgrades in Documents for review.

28298 Ayres Sq, Easton

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Benson & Mangold, LLC.

28254 Knapps, Easton
$830,000
4 Beds ⋅ 3 Baths
Easton Village. Desirable waterfront community located minutes from downtown Easton, St. Michaels and Oxford. Enjoy access to the Tred Avon River, community pier, clubhouse, outdoor pool, bocce court, kayak launch, 3+ miles of trails and 50 acres of open space. This custom built, one owner home features a living/dining room combo, family room with gas fireplace and built-ins, open gourmet kitchen with center island, primary suite, guest bedroom or office. 2nd floor offers a large loft, 2 additional guest bedrooms, bath and attic storage. 2 car rear loading garage with built-in cabinets and work bench, screened porch, patio, fenced backyard, irrigation system and extensive landscaping. LVP flooring throughout first floor living areas. This home is beautiful and is in move-in condition.

28254 Knapps, Easton

Listing courtesy of Benson & Mangold, LLC. Contact:

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

10494 Rich Neck Rd, Claiborne
$825,000
3 Beds ⋅ 4 Baths
Built in the early 1900s and thoughtfully renovated over the past 20 years, this charming home beautifully combines historic character with modern amenities. Situated on a half-acre lot, the property features 3 bedrooms with the potential for a 4th bedroom, along with 3.5 bathrooms. Each bedroom includes its own private bath, and the bedrooms offer access to relaxing balconies. The updated kitchen is equipped with granite countertops, stainless steel appliances, and tile floors. Hardwood flooring that continues throughout the home. Outside, the property also includes a potting shed and a machine shed, providing additional storage and workspace. A standout feature is the impressive 1,500-square-foot attached garage. This two-story space includes three garage doors, three passenger doors, and a dedicated office area, offering exceptional versatility for hobbies, work, or storage. With its timeless old-world charm and carefully integrated updates, this home offers the perfect blend of classic style and modern comfort.

10494 Rich Neck Rd, Claiborne

Listing courtesy of Coldwell Banker Chesapeake Real Estate Company. Contact:

Selling Office: Chesapeake Bay Real Estate Plus, LLC.

7588 Easton Club Dr, Easton
$825,000
4 Beds ⋅ 4 Baths
Easton Club. Boasting an open layout, the home features a great room with vaulted ceiling, completely remodeled kitchen (Kitchen Creations) with quartz countertops, stainless appliances (6 burner Wolf stove, double wall oven, GE profile refrigerator, Bosch dishwasher), breakfast area and morning room with Palladian windows, formal dining room, 1st floor primary suite with walk-in closets, primary bath with soaking tub, separate shower and vanities. 1st floor office/5th bedroom and full bath. 2nd floor offers 3 more spacious bedrooms and 2 additional baths and a large family/game room perfect for guests and children. Additional features include an attached 2-car garage, asphalt driveway, screened porch, deck, lawn irrigation system and private backyard. The community includes a pool and tennis/pickleball court. Close to downtown Easton and all its amenities, on the sought-after Oxford corridor.

7588 Easton Club Dr, Easton

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Meredith Fine Properties.

8006 Parrotts, Easton
$825,000
3 Beds ⋅ 3 Baths
CONTINUE TO SHOW. CONTINGENT ON A HOUSE SALE AND 72 HOUR KICK-OUT IN EFFECT!. Perfectly positioned on a premier corner lot overlooking a tranquil park-like circle, ( Hollyday Park), this thoughtfully designed home blends refined finishes with effortless functionality. Framed by a welcoming front porch and complemented by a private side porch just off the sunlit Morning Room, this distinguished home captures the essence of relaxed coastal elegance. This 3 Bedroom 2-1/2 Bath home offers exceptional upgrades throughout. The main level Primary Suite presents a spa-inspired bath, while the Gourmet Kitchen adorned with Granite surfaces, a generous Island, upgraded Stainless Steel appliances, Silgranit Sink, "RO" System for kitchen sink and icemaker and a custom Butlers Pantry, opens seamlessy to the Living Room with a Gas Log Fireplace. A cheerful Morning Room fills with natural light and leads to a Side Porch, an ideal setting for morning coffee or evening relaxation. The Living Room and Morning Room are gracefully divided by a custom, beautifully crafted double sided built-in cabinet and glass shelving, allowing light to filter through while preserving a sense of openness between the two spaces and maintaining clear sight lines and natural light. Upstairs a versatile Loft Family Room accompanies two additional bedrooms and an ample Storage Room and Full, Tiled Bath. Enhancements include a Custom Laundry Room with top-tier Appliances, whole-house Water Filtration, Fast Hot Water Retrieval System, and an oversized Two-Car Garage with an integrated (14x10) Work Shop and a fabulous TALL Crawl Space (or Shallow Basement), finished nicely with loads of storage. PLEASE NOTE: PUBLIC RECORDS SQUARE FOOTAGE IS INCORRECT. Actual Living Area Square Footage is, 3,261 +/-Square Feet, that is, 2,095 Square Foot Main level and 1,166 Square Foot Upper level. Does not include Garage or Workshop. Located in a coveted Water-Access Community, with boat slips, pool, kayaking, and a fabulous Club House, and close to all Easton's finest amenities, this home offers a seamless blend of sophistication and comfort as well as convenience.

8006 Parrotts, Easton

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

Selling Office: Benson & Mangold, LLC.

28667 Hope Cir, Easton
$815,000
4 Beds ⋅ 4 Baths
Located in a tree-lined private community that captures the warmth of small-town charm while offering modern conveniences, this bright and sunny home blends elegance, luxury, and everyday comfort. At the heart of the home, the custom chef’s kitchen with fireplace and breakfast nook is designed to impress—perfectly appointed for everyday meals or entertaining. From the kitchen, flow easily into the formal dining room with butler’s pantry, ideal for entertaining and storage, the inviting family room with floor-to-ceiling custom bookcase and fireplace, the screened porch overlooking the fenced backyard, or the bonus room above the garage. The main-level primary suite offers a peaceful retreat, while three additional bedrooms and two full baths provide flexibility for family and guests. This home is also wired for a hot tub offering even more potential for outdoor living . The community enhances the lifestyle with walking trails, a community dock, private park, dog park, fitness center, and tennis courts. Whether savoring the quiet of the neighborhood or hosting gatherings in your spacious home, this property seamlessly combines refined living and modern convenience in one beautiful setting. HVAC #1 2023, HVAC #2 2024, WH 2025 ***NEW ROOF 2025***.

28667 Hope Cir, Easton

Listing courtesy of Cummings & Co. Realtors. Contact:

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

207 Seymour Ave, Saint Michaels
$800,000
4 Beds ⋅ 4 Baths
Experience modern living in the heart of St Michaels with this exquisitely renovated home. Completed in 2023, every aspect has been thoughtfully updated—from a chef’s kitchen and luxurious new bathrooms to pristine floors, a brand new roof, and new HVAC system. The expansive, open floorplan offers effortless flow for entertaining and everyday life. The main residence features three bedrooms and two and a half baths, complemented by a charming guest cottage with its own full bath—perfect for visitors or flexible use. Enjoy the convenience of being just steps away from boutique shops and acclaimed restaurants, making this home an unparalleled in-town retreat.

207 Seymour Ave, Saint Michaels

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

Selling Office: Non Subscribing Office.

no property photo
$799,000
4 Beds ⋅ 2 Baths
THE BEST EASTERN SHORE WATERFRONT VALUE Where mornings begin by the water and plans tend to follow the tide, this Eastern Shore retreat blends relaxed waterfront living with thoughtful design by respected local architect Pam Gardener. Warm woods and a naturally flowing layout create easy and inviting view-filled spaces where you’ll prep picnics and gather for afternoons in. Comfortable for both small gatherings and full summer house occasions, you’ll savor rainy-day reads in the home’s tranquil waterside sunroom, while rip-rapped shoreline and decking set the stage for crab feasts, firefly-lit dinners, and afternoons that drift happily off schedule. Your private pier, with floating dock and boat lift, launch adventures, provide a place to spot wildlife, and host impromptu swims. At day’s end, evenings are cozy in four restful bedrooms accommodated by two baths suiting both weekend escapes and longer stays. With generous storage, timeless finishes, and a long list of upgrades, the home feels ready to be enjoyed. While on tour, visit the canoe rack, storage shed, two car garage with EV charger, and stroll the gently sloping lawn leading to the water’s edge. Just minutes from St. Michaels’ antique shops, marinas, and winding back roads, this is Eastern Shore living at its best. 2026 is the planned year for the public sewer hook up which will enable the new owner to build a pool and expand adding more property value. Significant renovations and an addition were completed in 2001, including a new septic system. Recent upgrades feature an encapsulated crawlspace, kitchen countertops (2020), Bailey dock with oversized floating dock and sundeck (2013), added power boat lift (2023). Modern conveniences include new washer and dryer (2024), dishwasher (2022), new refrigerator (2024), leaf filter system on house and garage (2022), updated 2nd floor bathroom (2024), new well pump and bladder tank (2022), replaced waterfront portion of roof (2002) the front portion (2019), upgraded electrical service to garage and sheds, including electric vehicle charger (2024), replaced pump to house heater (2024), freshly paved asphalt driveway, new garage doors (2023).

22769 Almost Neavitt Rd, Bozman

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

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

206 N Morris St, Oxford
$799,000
3 Beds ⋅ 2 Baths
Traditional historic Oxford house on high elevation in the center of the historic district. Completely renovated in 2009-10. Back half of house is all new construction, with historic elevations and appearance preserved. Fine, high quality, functional, spacious kitchen, for serious cooks. Aga 2-oven, 5-burner stove with broiler. Stainless steel Kitchen Aid appliances, well located. Large refrigerator (upper) - freezer (lower) with high capacity ice maker. Kitchen Aid dishwasher. Very extensive kitchen-dining room storage capacity in floor to ceiling custom hickory cabinets and 2 dining room pantries. 3 full bedrooms on 2nd floor with good closets, windows and light. Full bathrooms on 1st and 2nd floors with accessible showers and original claw foot tub on 2nd, good storage and very nice fixtures. Washer and dryer laundry on 2nd floor. 2 current home offices or study rooms on the 2nd floor. In addition, the 1st floor front (book) room and back (morning) room could be used for home offices. 1st floor rear family/morning room could be converted to 1st floor bedroom, if necessary. All new plumbing, electrical and HVAC systems. Geothermal wells for very efficient all-season heating, cooling and electrical operations, with these costs rising rapidly. Conditioned, masonry 48” high crawl space for HVAC and abundant storage. Established, well-maintained lawn, garden and trees. Continually refreshed plants, flowers and herbs. Period garden shed for tools, mower and storage. Fully fenced back and side yards, with traditional Oxford pickets. Re-roofed the main part of the house before the 2009-10 renovation. Enjoy amenities including Oxford's picturesque waterfront park, shops, restaurants and marinas.

206 N Morris St, Oxford

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Benson & Mangold, LLC.

53 Londonderry Dr, Easton
$795,000
4 Beds ⋅ 4 Baths
Under Contract, can be shown for backup offers. Open House cancelled for 4/26/26. This stunning center hall colonial, in the sought after community of Thread Haven, seamlessly blends timeless architecture with a complete, top-to-bottom renovation, delivering a truly exceptional living experience in one of Easton’s most established neighborhoods. Every detail has been thoughtfully curated with an uncompromising commitment to design, quality, and craftsmanship. From the moment you enter, you are welcomed by rich heart of pine flooring, refined finishes, and a cohesive, designer-selected color palette that carries throughout the home. The traditional floor plan has been reimagined for modern living while preserving its classic charm. At the heart of the home is the show-stopping gourmet kitchen, expertly designed with all-new double-tiered custom cabinetry, pull-out drawers, and striking display features. Outfitted with GE Café smart Wi-Fi appliances, including a gas range, this space is as functional as it is beautiful. A generous center island with seating anchors the room, while a built-in window seat nestled between custom display cabinetry adds a warm, inviting touch. The kitchen flows effortlessly into the spacious family room, where a gas fireplace framed by custom built-ins creates the perfect gathering space, with direct access to the screened porch and backyard beyond. The main level also offers a beautifully appointed dining room with statement lighting and exquisite millwork, a formal living room, and a richly detailed den featuring exposed beam ceilings and wood-paneled walls, an ideal retreat for work, reading, or quiet moments. A well-placed powder room completes the main level. Upstairs, the primary suite is a true sanctuary, featuring a spa-inspired ensuite bath with dual vanities, a walk-in shower, soaking tub, and elegant tile finishes. Three additional bedrooms are thoughtfully designed with refined detailing and share a beautifully updated hall bath complete with shiplap accents, tile flooring, and a built-in laundry area with cabinetry and folding station for added convenience. A standout feature is the expansive bonus room over the garage, complete with its own full bath and charming sloped ceilings perfect as a playroom, guest suite, or private retreat. Outside, the property is equally impressive. Set on a beautifully landscaped, mature lot, the home is framed by blooming cherry blossoms and lush greenery. The fully fenced backyard offers both privacy and space, enhanced by thoughtful hardscaping, stone wall seating, and an inviting patio ideal for entertaining. The screened porch provides a peaceful vantage point to enjoy the surroundings year-round. Completing the property is an exceptional three-car garage with extra depth, offering ample space for vehicles, storage, or a workshop. This is a rare opportunity to own a fully renovated, design-forward home in an established Easton neighborhood, where classic elegance meets modern luxury in every detail. Located within Easton town limits in the community of Thread Haven, the home enjoys close proximity to all that Easton has to offer including: the newly renovated YMCA, just a few blocks to Idlewild Park and downtown amenities, and offers easy access to the best shops, restaurants, and entertainment, including the Avalon Theatre and the Academy of the Arts. A full list of upgrades & renovations is available in the documents section.

53 Londonderry Dr, Easton

Listing courtesy of Northrop Realty. Contact:

Selling Office: Bayside Realty.

24822 Swan Rd, Saint Michaels
$785,000
3 Beds ⋅ 3 Baths
Located in the sought-after Martingham community and close proximity to downtown Saint Michaels, 24822 Swan Road offers the perfect balance of privacy, convenience, and Eastern Shore charm. Designed for comfortable single-level living, the home features 3 bedrooms and 3 full baths, including a spacious primary suite with a walk-in closet and an updated en-suite bath. The main living area is open-concept and features a family room with wood burning fireplace, parquet oak flooring leading into the recently renovated kitchen which serves as the heart of the home, blending style and functionality for everyday living and entertaining. There is also a sunroom which flanks the back of the house offering plenty of natural light and access to the covered back deck. A standout feature is the large detached two-car garage with a fully finished, conditioned space above, adding an additional 1,200 square feet of living space and bringing the total finished living area to 3,600 square feet. A workshop space is attached to the back of the garage, along with an additional 12' x 16' storage shed, providing even more room for a tractor, garden equipment, or general storage. There are peaceful water views from the back porch, creating an ideal backdrop for morning coffee or relaxed evenings outdoors. Residents enjoy access to a community waterfront park with a kayak launch, right down the street. With a brand-new roof being installed (2026), public water and sewer, mature landscaping, and a location minutes from waterfront dining, marinas, boutiques, and golf, this property delivers both lifestyle and peace of mind. Whether you are seeking a full-time residence or a weekend retreat near the water, 24822 Swan Road is a rare opportunity to enjoy the very best of Saint Michaels living. See documents for full list of updates.

24822 Swan Rd, Saint Michaels

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Coldwell Banker Waterman Realty.

9359 Martingham, Saint Michaels
$775,000
4 Beds ⋅ 3 Baths
Stunning One-Level Luxury Living with Golf Course & Pond Views Perfectly positioned in one of St. Michaels' most desirable communities, this exceptional residence offers effortless one-level living with a private backyard overlooking a tranquil pond and the 4th green of The Links at Perry Cabin. Just minutes from the historic charm, fine dining, boutiques, and waterfront attractions of St. Michaels, residents enjoy exclusive access to a beautiful private waterfront park on the Miles River—a treasured amenity that embodies the best of Eastern Shore living. Meticulously maintained and thoughtfully renovated, this home is truly move-in ready. Recent improvements include a beautifully updated kitchen, renovated bathrooms, fresh interior paint, and a new roof installed in September 2025 featuring 30-year architectural shingles. Additional upgrades and features include: Main HVAC system installed in 2021 with an active service agreement New hot water heater (2024) New dishwasher (2024) Electric vehicle charging station in the garage Invisible pet fence surrounding the yard The serene setting, spectacular views, and extensive updates create a rare opportunity to enjoy a low-maintenance lifestyle in a premier St. Michaels location. Whether relaxing on the patio overlooking the pond and golf course or enjoying the community's private waterfront park, this home offers the perfect blend of luxury, comfort, and convenience. A truly turnkey property where every detail has been thoughtfully updated and impeccably maintained.

9359 Martingham, Saint Michaels

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

Selling Office: Unrepresented.

7106 Wheeler Park Cir, Easton
$775,000
4 Beds ⋅ 3 Baths
OPEN HOUSE Saturday June 27 2pm-4pm. SERIOUS 70k price reduction, best deal in Cooke's Hope Village! NEW 50 YR ROOF 2026 CertainTeed Landmark architectural shingles. Discover this exceptional listing in one of Talbot County’s most desirable neighborhoods of Cooke’s Hope. Ideally situated just off Oxford Road in Easton, the community offers numerous amenities and unmatched convenience, located only five minutes from both downtown Easton and Talbot Country Club. Set on quiet Wheeler Park Circle, one of the community’s most sought-after village locations, this home offers just under 3,000 square feet of finished living space. Broad double covered front porches create a welcoming front exterior, while at the rear of the home a large, private screened porch off the kitchen opens to a fully fenced backyard with patio—ideal for outdoor living and entertaining. The main level features a first-floor primary suite with a lovely, updated bath and huge walk-in closet. Hardwood floors enhance the rest of the first floor including the beautiful light-filled living room with gas fireplace, a formal dining room, convenient powder room and a spacious den with built ins that flows into a beautifully updated eat-in kitchen with mostly new appliances. A large separate first floor laundry/mud room provides not only washer and dryer but abundant cabinetry and a utility sink for added convenience. Upstairs, a wide hardwood hallway leads to three additional bedrooms, a full bath, and spacious fully insulated storage room complete with a mini split system, space easily finished if desired. An oversized attached two car garage, accessed by a private concrete drive from the rear alley, completes this well-designed home. Owner has meticulously maintained this property since purchase in 2018 including new kitchen appliances (2026), all hvac=two air-condition units & furnace ("TRANE" 2023), interior paint, etc. The Cooke’s Hope HOA maintains a reserve fund, manages community operations and common areas, oversees the community waterfront park and dock, and supports additional amenities including a gym, mail room, tennis/pickleball court, dog park, over three miles of walking paths, ponds, picnic areas, roads, trash service, and snow removal. The HOA has a set yearly fee for these services and provides front and side yard maintenance at a reasonable additional cost to the property owners. The community is served by Easton Utilities, providing electric, water, sewer, natural gas, and fiber optic high-speed internet. Extra refrigerator and two custom carpets for living and dining rooms included.

7106 Wheeler Park Cir, Easton

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Monument Sotheby's International Realty.

106 Grace St, Saint Michaels
$775,000
3 Beds ⋅ 2 Baths
Grace and Gratitude perfectly describe this charming historic home on Grace Street in the heart of St. Michaels! Grace St. is one of the few streets in town that isn't a through street to traffic. It starts at Talbot St & "Restaurant Row" & ends at the waterfront & walking trail off San Domingo Creek. The cozy front porch & classic Eastern Shore red front door are a prelude to the delightful interior spaces within. Beautifully renovated to include a more traditional living room which flows into a large open floor plan for the family room & dining room. The designer inspired kitchen with breakfast bar opens to the dining room & is close to the backdoor that leads out to the relaxing 12x14 screened porch. The porch overlooks a magical backyard that is an oasis for nature & centered around an adorable Victorian shed. Beautifully finished hardwood floors, moldings & gingerbread staircase make this a magazine quality home! The 2nd floor bedrooms are each unique & comfortable. Many recent improvements include: encapsulated crawlspace, bathroom renovation, On demand hot water, backyard irrigation, fireplace tile surround, electric car charger & a hot tub that's negotiable. Enjoy classic St. Michaels & all it has to offer in the enchanting neighborhood of Grace Street!

106 Grace St, Saint Michaels

Listing courtesy of Chesapeake Bay Real Estate Plus, LLC. Contact:

Selling Office: TTR Sotheby's International Realty.

24912 Back Creek Dr, St Michaels
$765,000
3 Beds ⋅ 3 Baths
Back Creek Landing home for sale in St. Michaels, MD — located in one of the town’s most desirable neighborhoods, known for its peaceful setting, friendly community, and proximity to downtown St. Michaels. This home is just minutes away by bike or golf cart, offering easy access to shops, restaurants, the harbor, and waterfront activities while still feeling private and serene. This beautifully maintained single-family home features a covered front porch, ideal for relaxing, entertaining, or enjoying quiet mornings. Inside, the flexible floor plan includes a main-level living room or home office with pocket doors, a formal dining room, and an open-concept kitchen and great room — a layout highly sought after by today’s buyers. The kitchen offers ample cabinetry, generous counter space, and a large center island with seating, making it perfect for everyday living and entertaining. The great room opens to a covered rear porch overlooking community ponds, with western exposure and sunset views. A private patio and pollinator garden enhance the outdoor living space. The first-floor primary suite is a standout feature, offering a walk-in closet with custom built-ins and an updated en-suite bath. Additional main-level highlights include a powder room, laundry room, and continuous flooring throughout, creating a seamless flow. Upstairs, you’ll find two spacious bedrooms with large closets, a full bath, and a large bonus room ideal for guests, a media room, home gym, or second family room. A walk-in attic provides excellent storage, a rare and valuable feature. Back Creek Landing is a planned residential community offering walking trails, scenic ponds, picnic areas, and water access to San Domingo Creek, complete with a community dock and kayak storage — perfect for buyers seeking the Eastern Shore lifestyle with kayaking, nature, and outdoor recreation. Freshly painted and move-in ready, this St. Michaels home combines main-level living, outdoor spaces, water access, and proximity to town — a highly desirable combination that is rarely available. 📍 St. Michaels, MD 21663 💲 $795,000 🛏 3 Bedrooms | 🛁 2.5 Bathrooms | 📐 3,166 sq ft Don’t miss your opportunity to tour this exceptional Back Creek Landing home. Schedule your private showing today.

24912 Back Creek Dr, St Michaels

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Benson & Mangold, LLC.

7015 Cheston Way, Easton
$755,000
3 Beds ⋅ 3 Baths
Move In Ready!! Please try 3-D virtual tour. This gorgeous Hanover design by Koch Homes is the needle in the haystack you've been looking for. New Construction that is 100% complete in the highly sought after Cooke's Hope community. This home focuses on main-level living, while having two bedrooms and one bath upstairs for family and friends. An open floorplan flows beautifully from the foyer entrance, past the home office, and into the dining and great room. Our 19 x 10 morning room is filled with windows to soak up the eastern shore sunlight. Get a great night's rest in the 1st floor owners suite and then hit the tennis courts (only steps away) for a match with a friend. Fishing, boating, golfing, and all outdoor activities are more enjoyable when the day starts and ends in your new Koch Home at Cooke's Hope...

7015 Cheston Way, Easton

Listing courtesy of Koch Realty, Inc.. Contact:

Selling Office: Benson & Mangold, LLC.

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