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28372 Canvasback Ln, Easton
$1,120,000
4 Beds ⋅ 3 Baths
Fabulous home in Oaklands, ideally located along the highly desirable Oxford Road corridor! Beautifully updated and designed for effortless entertaining, this four-bedroom Colonial offers light-filled interiors, hardwood floors, geothermal heating and cooling and exceptional indoor-outdoor living. The living room features a fireplace flanked by custom built-ins and a large bay window. A separate family room provides a more relaxed setting with exposed wood beams and raised-hearth brick fireplace. At the heart of the home, the renovated kitchen features an oversized island, abundant cabinetry, a gas range, generous storage and a dining area. Just beyond, the light-filled sunroom is a standout with a wet bar, beamed ceiling and custom built-ins making it an inviting space for gatherings throughout the year. Upstairs, the oversized primary suite includes an updated ensuite bath and expansive walk-in closet. The second bedroom features hardwood floors and its own sitting area, while two additional bedrooms and an updated full bath complete the second floor. Outside, the backyard is an entertainer’s dream, featuring a saltwater in-ground pool, outdoor kitchen, fire pit and an impressive 1,532 square feet of terraced patio space. Two sheds offer additional storage and versatility, while a separate pump house accommodates the pool equipment. An oversized attached two-car garage provides ample space for vehicles, storage and hobbies. A 26 kW whole-house generator provides added comfort and peace of mind. Residents of Oaklands also enjoy community water access and use of the community pier, completing this exceptional Oxford Road property. Please do not go down driveway without an appointment.

28372 Canvasback Ln, Easton

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

100 Pier, Oxford
$1,095,000
3 Beds ⋅ 3 Baths
Waterfront, a deeded boat slip, off-street parking, and a single-car garage with additional storage set the stage for this thoughtfully redesigned coastal retreat in the heart of Oxford. Completely renovated from top to bottom, this 3 bedroom, 2.5 bathroom home blends timeless Eastern Shore charm with luxury finishes and exceptional boating amenities. Every detail has been carefully curated, from the new hardwood flooring and fresh paint throughout to the completely remodeled gourmet kitchen featuring high-end appliances, quartz and soapstone countertops, custom cabinetry, and a butler's pantry connecting the kitchen and dining room. The dining room is anchored by a beautiful masonry fireplace with a gas insert, while the custom "Wine Snug" offers built-in wine racks, a wine refrigerator, and handcrafted wrought iron doors. Designed to maximize its setting, the home captures water views from both the front and rear, with sightlines straight through the home to the water. Upstairs, the primary suite opens to a private balcony overlooking the harbor, and the conveniently located second-floor laundry adds everyday functionality. For boating enthusiasts, the property includes a deeded 40’ boat slip accommodating with approximately 5’ MLW. Ideally located just moments from downtown Oxford, you'll enjoy easy access to marinas, the Oxford Ferry, waterfront parks, and local favorites like Doc's Sunset Grille with frequent live music. Whether you're searching for a full-time residence, weekend getaway, or luxury second home, 100 W. Pier Street offers the perfect blend of water views, boating access, modern updates, and the relaxed Eastern Shore lifestyle.

100 Pier, Oxford

Listing courtesy of Benson & Mangold, LLC. Contact:

700 S Talbot St, St Michaels
$1,075,000
3 Beds ⋅ 3 Baths
The charm of historic St Michaels comes to life in this 1890 home, completely updated for modern comfort and amenities. Each room is defined yet open, flowing into each other with ease. The dining room opens to the living space and sitting room with gas fireplace. Exposed beams and cathedral ceilings provide interest in design and skylights provide brightness and light. The beautiful, gourmet kitchen (updated recently) has quartz countertops and a breakfast nook overlooking the backyard patio and gardens. Both en suite full baths are updated and wait until you see the thoughtfully placed half bath tucked under the staircase in the foyer entry hall. Just one of the many details found throughout the home. There are multiple opportunities to take advantage of outdoor living with a light-filled sun room and screened porch leading to a spacious brick patio. The masterfully designed gardens surrounding the home provide privacy, peace and tranquility as well as a tapestry of color during the summertime. Included amidst the gardens a pergola for outdoor dining and a babbling stone water fountain. The entire back yard is fenced and lovely mature trees provide comfortable shade on this corner lot. Walk to town for shopping, waterfront dining and local events or get some exercise on the nearby St. Michaels Nature Trail. For your parking needs, there is a detached one car garage and three additional off-street, private parking spaces. To truly appreciate this lovingly cared-for home, it must be felt in person!

700 S Talbot St, St Michaels

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

140 S Washington St, Easton
$997,000
Price Improvement!!! Looking for the ideal downtown Easton location? This beautifully renovated Colonial offers a rare opportunity—perfect as a high‑end investment property or as your personal residence with an income‑producing second unit. This stunning building features two fully updated 1,000 sq. ft. units, each finished with high‑quality materials and thoughtful design. ✦ First‑Floor Unit 2 bedrooms, 2 baths Gourmet kitchen with premium finishes In‑unit washer/dryer Fireplace and hardwood floors Relaxing front porch and covered rear deck with landlord‑provided furniture Large private parking lot behind the building Easy walking distance to Easton’s restaurants, shops, and entertainment ✦ Second‑Floor Unit Offered fully furnished Mirrors the first‑floor layout and upgrades Primary bedroom with access to a second‑story balcony Turnkey and ready for immediate occupancy Together, the two units generate $5,670 per month, making this an exceptional opportunity for investors, entrepreneurs, or owner‑occupants seeking both comfort and cash flow. With its prime location and high‑end renovation, this exquisite property won’t last. Call today to schedule your private showing.

140 S Washington St, Easton

Listing courtesy of Meredith Fine Properties. Contact:

140 S Washington St, Easton
$997,000
4 Beds ⋅ 4 Baths
Just Reduced!!!! Looking for the ideal downtown Easton location? This beautifully renovated Colonial offers a rare opportunity—perfect as a high‑end investment property or as your personal residence with an income‑producing second unit. This stunning building features two fully updated 1,000 sq. ft. units, each finished with high‑quality materials and thoughtful design. ✦ First‑Floor Unit 2 bedrooms, 2 baths Gourmet kitchen with premium finishes In‑unit washer/dryer Fireplace and hardwood floors Relaxing front porch and covered rear deck with landlord‑provided furniture Large private parking lot behind the building Easy walking distance to Easton’s restaurants, shops, and entertainment ✦ Second‑Floor Unit Offered fully furnished Mirrors the first‑floor layout and upgrades Primary bedroom with access to a second‑story balcony Turnkey and ready for immediate occupancy Together, the two units generate $5670 per month, making this an exceptional opportunity for investors, entrepreneurs, or owner‑occupants seeking both comfort and cash flow. With its prime location and high‑end renovation, this exquisite property won’t last. Call today to schedule your private showing.

140 S Washington St, Easton

Listing courtesy of Meredith Fine Properties. Contact:

101 Mulberry St, Saint Michaels
$997,000
4 Beds ⋅ 3 Baths
Beautifully restored Historic Victorian in the heart of Saint Michaels. From the wide, welcoming front porch to the gated, manicured yard—complete with a hammock ideal for long afternoon naps—every space is designed for comfort and relaxation. A brick walkway leads to the custom beveled‑glass entry door and into the warm, inviting family room. Inside, the home features rich pine floors throughout, a cherry kitchen with stainless steel appliances, granite countertops, and an open flow into the charming dining room. The spacious family room includes a propane stove for cozy winter days. The first floor also offers a full laundry room and an ornate powder room. The original staircase leads to the second floor, which includes three bedrooms and a renovated marble‑tile full bath. The private third‑floor primary suite offers a peaceful retreat with its own en‑suite bath. Seller raised the home 3 feet and the lot 2 feet to help will water run-off and has a dry encapsulated crawl space with cement floor. Just one block from the water—with water views from the street—this home captures the best of small‑town living. Enjoy walking access to Saint Michaels’ restaurants, quaint shops, kayaking, swimming, boating, and biking. It’s a special property ready for unforgettable memories with family and friends. Whether you're looking for a proven investment property or a beautiful home for your family, this one stands out.

101 Mulberry St, Saint Michaels

Listing courtesy of Meredith Fine Properties. Contact:

28598 9th Dr, Easton
$995,000
4 Beds ⋅ 5 Baths
Nestled in the Easton Club along the shores of the Tred Avon river, this exquisite Craftsman-style residence offers a harmonious blend of luxury and comfort. Spanning over 3,900 square feet, this home features four spacious bedrooms and 3 full and 2 half bath that are elegantly appointed, including a primary suite with a waterside view, his and her private baths and dressing rooms.. Step inside to discover an inviting open floor plan adorned with rich hardwood floors, ceramic tile, and plush carpeting. The gourmet kitchen is a chef's dream, equipped with stainless steel Wolf gas cooktop and oven, a large island, a butlers pantry, granite counters and an eat in waterside dining nook. Enjoy cozy evenings by the gas fireplace in the living room, enhanced by bookshelves and charming wainscoting. The exterior is equally impressive, featuring extensive hardscaping, lush landscaping, and a private dock site on the Tred Avon River. Embrace outdoor living with a community pool, tennis courts, and a BBQ grill for summer gatherings. The home also boasts an immaculate three-car garage with electric vehicle charging capabilities and ample off-street parking. With water features that include a serene waterfall and a tranquil atmosphere, this home is a sanctuary for those seeking an exclusive lifestyle. Experience the perfect blend of elegance and comfort in this remarkable property.

28598 9th Dr, Easton

Listing courtesy of Coldwell Banker Realty. Contact:

29747 Easton Farms, Easton
$995,000
4 Beds ⋅ 4 Baths
This spacious 4-bedroom, 3.5-bath home offers a peaceful rural setting just minutes from downtown Easton. Set on 2+/- acres with an additional 5.92+/-acre non-buildable lot included in the sale, the property offers plenty of space both inside and out. The main level features a large living room with a stone-surround gas fireplace, formal dining room, sunroom, and a well-appointed kitchen with stainless steel appliances, and a large island that makes gathering and entertaining easy. A first-floor office or library adds flexibility, while A whole-home Sonos sound system adds another layer of convenience for everyday living and entertaining. Upstairs, the spacious primary suite includes a private bath with a tile-surround shower and soaking tub, along with three additional bedrooms, two of which have attached baths. The full basement is a standout feature, offering a dedicated workshop with ample space for projects, tools, and storage. Outside, the entertaining space continues with a large back porch, pool, hot tub, oversized shed, extended driveway, and lush landscaping. With a secluded country feel, generous indoor and outdoor gathering spaces, and easy access to downtown Easton, this property offers an exceptional balance of privacy, space, and convenience.

29747 Easton Farms, Easton

Listing courtesy of Benson & Mangold, LLC. Contact:

109 W Marengo St, Saint Michaels
$995,000
4 Beds ⋅ 3 Baths
This thoughtfully designed 4-bedroom, 3-bathroom home features an open-concept floor plan ideal for both everyday living and entertaining. The main-level primary suite provides a private retreat with a spacious walk-in closet and an en-suite bath complete with a double vanity and glass-enclosed shower. The living room is anchored by a cozy gas fireplace and flows seamlessly into the dining area and well-appointed kitchen, featuring a gas stove and stainless steel appliances. Practical amenities include a mudroom with laundry just off the attached two-car garage, a Rinnai tankless water heater, and an efficient dual-zone heat pump system with separate upstairs and downstairs climate controls. The second floor offers additional flexibility with a bedroom, full bathroom, and a large family room—perfect for guests, a home office, media room, or recreation space. Just off the recreation room, a spacious attic provides abundant storage and offers potential for future expansion. Outside, enjoy a beautifully landscaped backyard featuring a stone patio and ample garden space, creating the perfect setting for outdoor dining, gardening, or simply enjoying the peaceful surroundings. Ideally situated in the heart of St. Michaels, this home offers exceptional proximity to the area's most beloved destinations. Located less than 200 feet from the St. Michaels Nature Trail, just 0.2 miles from Chew Street Park, and only 0.2 miles from historic downtown St. Michaels, you'll enjoy convenient access to shopping, dining, waterfront attractions, and community events. Adding to the appeal, plans are underway for the future San Domingo Creek Park at the end of W Marengo Street—a proposed 7.6-acre waterfront park focused on recreation, environmental restoration, and trail connectivity that is anticipated to become the largest waterfront park in St. Michaels. Exceptional proximity to downtown St. Michaels, future recreational amenities, modern comforts, and versatile living spaces make this home a rare opportunity in one of the Eastern Shore's most sought-after communities.

109 W Marengo St, Saint Michaels

Listing courtesy of Benson & Mangold, LLC. Contact:

32675 Discovery Dr, Easton
$979,000
4 Beds ⋅ 4 Baths
Stunning and spacious, this 4703-square-foot residence rests gracefully on a meticulously landscaped 2-acre parcel adorned with majestic trees. A tranquil goldfish pond, home to over 40 fish, adds a serene touch and can remain with the property, or the owner can rehome the fish. Upon entering, you're greeted by soaring 9+ foot ceilings and an impressive cathedral ceiling in the great room, complemented by recessed lighting throughout the home. The home features cutting-edge Geo-thermal heating and central air conditioning for comfort in all seasons. Entertainment options abound, with a well-appointed wet bar complete with a fridge. Luxurious flooring finishes include marble, hardwood, and Berber carpet upstairs. Dual primary bedroom suites on the main level offer versatility, one boasting a private deck overlooking the picturesque fishpond and gas fireplace. Each suite includes a spacious walk-in closet. The home offers an intercom. A large loft with a catwalk offers a commanding view of the main living area, enhanced by a striking window wall. Relax on the screened porch or enjoy the outdoors from the expansive front porch adorned with stately columns. Or the rear exterior charm is found on the deck with brick façade and wrought-iron railings. The home office/den and convenient laundry room are on the main level for added functionality. With four bedrooms—two upstairs and two downstairs—and 3.5 bathrooms, there's ample space for family and guests alike. Crown mouldings in the lower level and large columns throughout the interior add a touch of elegance. The gourmet kitchen is a chef's delight, featuring granite countertops, all-new stainless-steel appliances, and a double-wall oven. A breakfast room and formal dining room, open and defined by elegant columns, provide flexible dining options. This home offers an open main level, kitchen, breakfast area, living room, dining room, great room and large foyer. Blacktop Driveway and parking area, and 3 car garage. Additional features are the unique advantage of being one of only three properties excluded from HOA fees. This exceptional property offers a rare blend of luxury, functionality, and serene surroundings, making it truly one-of-a-kind.

32675 Discovery Dr, Easton

Listing courtesy of Keller Williams Select Realtors of Easton. Contact:

111 Chesapeake Ave, Saint Michaels
$949,000
4 Beds ⋅ 3 Baths
Beautifully upgraded and thoughtfully designed, custom finishes, and every modern convenience. The gourmet kitchen features dual fuel gas cook top and electric oven in professional grade stove, quartz countertops, professional grade appliances, and premium appointments, flowing seamlessly into warm hardwood floors and a cozy gas fireplace beneath a striking coffered ceiling. Beautifully curated designer wallpaper accents throughout this stunning model home! Offering 4 bedrooms and 2.5 baths, the home includes a first‑floor primary suite with an ensuite spa bath, custom shower, and generous walk‑in closets. Additional highlights include Hardie Plank siding, custom black windows, a Trex deck, paved driveway, 1‑car garage, and excellent storage throughout. Located just a short walk to the heart of St. Michaels, you’ll enjoy easy access to charming shops, restaurants, waterfront activities, and year‑round festivals.

111 Chesapeake Ave, Saint Michaels

Listing courtesy of Meredith Fine Properties. Contact:

6670 Tilghman Island Rd, Sherwood
$949,000
3 Beds ⋅ 3 Baths
Price Improvement! Motivated sellers. Amazing opportunity to be on the water in Talbot County. Waterfront home situated on Back Creek in Sherwood. Conveniently located near St Michaels and Tilghman Island, the property includes views of sunsets over Poplar Island and is located minutes from restaurants, and shopping. Interior features include hickory hardwood floors, custom built-ins, crown molding, and recessed lighting. The kitchen is equipped with stainless steel appliances, a built-in pantry, and granite countertops. The open floor plan incorporates a gas fireplace and a formal dining room. The primary suite has a walk-in shower, soaking tub, and walk-in closet. An attached three-car garage provides additional space with an upstairs bonus game/theatre room. The backyard is built for fun with a swimming pool, an outdoor kitchen with bar area, gas fire features, a hot tub, and a pool house for storage and a half bath. The property also includes a 30x30 pole building with concrete floors, as well as a dock. New septic installed in 2025!

6670 Tilghman Island Rd, Sherwood

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

5734 Poplar Ln, Royal Oak
$939,900
3 Beds ⋅ 2 Baths
Boat-ready waterfront on Tar Creek, with minutes-by-water access to the Tred Avon! Welcome to a turn-key Eastern Shore weekend retreat, quietly tucked at the end of a private lane in the historic village of Bellevue, ideally positioned between St. Michaels and Oxford. This custom 2013 Cape Cod-style home sits gracefully on a tree-framed third of an acre, offering 55 feet of prime shoreline protected by an engineered bulkhead. Designed for water enthusiasts, a private 60-foot pier extends into the creek, complete with an electric lift for jet skis or small tenders, plus dockside power and water. Inside, light-filled living spaces flow across espresso-toned plank floors. Soaring cathedral ceilings, gable windows, and skylights crown the great room, where a stacked-stone gas fireplace anchors the open floor plan. The kitchen features a six-burner gas range, maple Shaker cabinetry, and a center island, adjoining a dining area that easily seats eight or more. Two sets of sliding glass doors open to the backyard deck, leading out to a stone patio, firepit, and outdoor shower. The main level includes two comfortable bedrooms, a full bath, and a laundry room. Upstairs, a skylit loft framed by cherry wood and stainless cable rails overlooks the great room. The vaulted primary suite offers dual closets, barn doors, and an en-suite bath complete with a walk-in tile shower and soapstone trough vanity. Built for low-maintenance, lock-and-leave ownership, the home features a tankless water heater, fire sprinklers, heat pump with central A/C, phone-managed Nest controls, county sewer, and a clean cement crawlspace equipped with a sump pump. Located steps from the Oxford-Bellevue Ferry. About two hours from Washington, D.C., Northern Virginia, Montgomery County, and Wilmington, with Route 301 through Delaware allowing you to bypass Bay Bridge traffic. Leave Friday, be on the water by sunset. Bring your boat!

5734 Poplar Ln, Royal Oak

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

6114 Sunset Ln, Tilghman
$939,900
3 Beds ⋅ 2 Baths
Tucked away beneath a canopy of mature trees, 6114 Sunset Lane feels like a storybook retreat along the shores of the Chesapeake Bay. A tree-lined, pebbled circular driveway welcomes you home, setting the tone for the quiet beauty and sense of escape found throughout this special waterfront property. Surrounded by nature and framed by peaceful water views, the home offers a slower, more intentional way of living. Begin your mornings with sunlight dancing across the bay, spend your afternoons enjoying the gentle rhythm of the water, and end each day beneath the soft colors of an Eastern Shore sunset. Inside, abundant natural light pours through the home, creating bright, inviting spaces that feel effortlessly connected to the surrounding landscape. The thoughtfully renovated three-bedroom, two-full-bathroom residence blends timeless character with elevated modern comfort. At the heart of the home is the beautifully renovated kitchen, where rich soapstone countertops bring natural warmth, depth, and understated sophistication to the space. Bathed in sunlight, the kitchen feels equally suited for quiet morning coffee, preparing meals with family, or gathering with friends after a day spent near the water. The renovated bathrooms continue the home’s refined design, offering calming, thoughtfully finished spaces that complement the serenity of the setting. A spacious two-car garage provides convenient parking and additional storage, while the circular driveway creates a graceful arrival with plenty of room to welcome guests. Beyond the home, the property’s lush surroundings offer an atmosphere that feels private, peaceful, and wonderfully removed from the noise of everyday life. Whether imagined as a full-time residence, a weekend escape, or a cherished gathering place for family and friends, 6114 Sunset Lane is more than a waterfront home, it is a place to exhale, reconnect with nature, and create lasting memories along the Chesapeake Bay.

6114 Sunset Ln, Tilghman

Listing courtesy of Compass. Contact:

4938 Fairbank Rd, Tilghman
$925,000
4 Beds ⋅ 3 Baths
*INCOME PRODUCING* Tucked away in the charming Fairbank community on Tilghman Island a delightful waterfront home captures the very best of Eastern Shore living. Overlooking the serene waters of Blackwalnut Cove with approximately 3’ MLW, the property blends classic cottage character with thoughtful modern enhancements. The original portion of the home reflects its roots as a cozy summer cottage, complete with a charming screened porch perfect for enjoying warm breezes and waterfront views. A connected wing was elevated 10 feet and now features a spacious two-car garage on the main level, offering abundant storage for boats, kayaks, and gear. The rear wing provides exceptional versatility with a private studio apartment—currently a licensed B&B with its own entrance—ideal for guests, rental income, or multigenerational living. Inside the main home, a wood-burning fireplace invites you to curl up on cool days and evenings, while the screened porch becomes the heart of the home during warmer months. With 4 bedrooms and 3 baths, this property offers comfort, flexibility, and the relaxed coastal lifestyle that defines the Eastern Shore. Appointment-only showings. Do not enter the property without an appointment.

4938 Fairbank Rd, Tilghman

Listing courtesy of Meredith Fine Properties. Contact:

21552 Chicken Point Rd, Tilghman
$899,000
5 Beds ⋅ 2 Baths
Located minutes from St. Michaels this waterfront property is a boater's dream. Tilghman, is a small island big on history, nature and local lore. Situated just over the Knapps Narrows Bridge this home offers a main house with first floor primary suite. The first floor is open with custom details and just perfect for hosting friends and family. A custom spiral staircase leads to a second floor with 4 additional guest bedrooms and bath. This renovated home also has a separate 3 bay garage with a 2-bedroom 2-bath water view apartment with a nice open living and dining area and total square footage of 768. The main house has an attached 1 bedroom 1 bath in-law suite. Great space for your guests or potential for a vacation rental. A nice wide-open lawn leads you to the dock with 7 boat slips. Right on the Knapps Narrows. Tilghman is the perfect place to start making your Eastern Shore Memories. New pictures to come...

21552 Chicken Point Rd, Tilghman

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

104 Stewart Ave, Oxford
$895,000
3 Beds ⋅ 3 Baths
Oxford. One owner 2,858 sq. ft home, built in 2006 is just off the Strand only a block from the Tred Avon River. Features living room and dining rooms, den, family room with woodburning fireplace off open kitchen with island and granite countertops, powder room. Second floor offers 3 spacious bedrooms including a primary suite with walk-in closet and 2 guest bedrooms and guest bath. Exterior offers 2 balconies/porches with River views, HardiPlank siding, paver driveway and more on a .18 acre lot. Hardwood flooring throughout most of the home (except 2 guest bedrooms) and 2 energy efficient heat pumps. Located in the Oxford’s historic district. This home preserves the historic character while offering a modern floor plan with 9’ ceilings and modern upgrades. Home is ready for immediate occupancy.

104 Stewart Ave, Oxford

Listing courtesy of Benson & Mangold, LLC. Contact:

21477 Island Club Rd, Tilghman
$895,000
4 Beds ⋅ 3 Baths
Price reduced SIGNIFICANTLY!! Beautiful views of Harris Creek and the Choptank River beyond provide a stunning backdrop for this beautifully maintained home in the established community of Tilghman on Chesapeake. A welcoming front porch framed by mature landscaping and colorful gardens leads into a bright, light-filled interior featuring soaring two-story ceilings, hardwood floors, crown moldings, and abundant natural light. Designed for both everyday living and entertaining, the gourmet kitchen opens to a spacious family room with a gas fireplace, breakfast area, and inviting sunroom. The adjoining rear deck, complete with a hot tub, provides a wonderful setting for outdoor entertaining while overlooking the beautifully landscaped grounds and tranquil water views. The main level also includes gracious formal living and dining rooms, as well as a private office. The upper level overlooks the family room below and features a spacious primary suite with a private balcony and luxurious ensuite bath with a jetted tub and walk-in shower. Three additional bedrooms—one currently used as a library—share a full hall bath. An attached two-car garage provides convenient parking and storage. Residents of Tilghman on Chesapeake enjoy an exceptional array of amenities, including a waterfront clubhouse, swimming pool, picnic area, community pier, and private boat slips available for lease, offering residents an ideal opportunity to enjoy the waterfront lifestyle of Maryland’s Eastern Shore.

21477 Island Club Rd, Tilghman

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

28323 Ayres Sq, Easton
$865,000
2 Beds ⋅ 3 Baths
Built in 2020 by Covell Builders, this customized Monterey Legacy offers 2,600± sq. ft. of finished living space with an appealing combination of first-floor living, flexible guest space, and distinctive architectural detail in Easton Village. The home features 2 bedrooms, 3 full baths, a private study, spacious screened porch, and attached two-car rear/side-entry garage. The private first-floor study is currently staged as a third bedroom, illustrating the versatility of the floor plan. Set on a 0.145± acre lot, the property backs to trees, while a landscaped community common area directly across the street provides an attractive outlook from the front of the home. A traditional foyer introduces the main level, where hardwood floors, crown molding, chair rail, and paneled millwork extend through the principal living areas. The private study is positioned near the entry, while the kitchen occupies the center of the home with white cabinetry, granite countertops, a large center island with seating, stainless steel appliances, and gas cooking. An adjoining butler's pantry provides generous cabinetry and counter space, glass-front display cabinets, built-in wine storage, and an under-counter beverage refrigerator. The living room features a gas fireplace and opens through French doors to a 234± sq. ft. screened porch, creating a comfortable extension of the living space and a convenient connection to the garage. The spacious first-floor primary suite includes a walk-in closet and private bath with double vanity and oversized tiled walk-in shower with frameless glass enclosure. A dedicated laundry room with utility sink and interior access to the conditioned crawlspace add everyday convenience. Upstairs, the second bedroom and full bath are joined by a spacious family room/retreat with a gas fireplace. This flexible upper level provides plenty of room for guests, media, exercise, hobbies, or additional living space. Additional features include natural gas heat and hot water, central air, a 404± sq. ft. attached two-car garage, covered front porch, brick-paver walkway, and established landscaping. Easton Village offers an array of community amenities including a clubhouse, waterside pool, fitness facilities, recreation and nature trails, open space, fishing and crabbing piers, kayak launch and storage, and marina, all convenient to downtown Easton.

28323 Ayres Sq, Easton

Listing courtesy of Benson & Mangold, LLC. Contact:

207 Brooks Ln, St Michaels
$849,900
3 Beds ⋅ 3 Baths
Charming Cape Cod in the Heart of St. Michaels Welcome to this beautifully maintained Cape Cod in the heart of St. Michaels, where newer construction, timeless charm, and exceptional indoor-outdoor living come together in a truly special property. Built in 2019, this inviting home features three generously sized bedrooms, two full bathrooms, and one half bath, with beautiful hardwood flooring throughout. Meticulously maintained and move-in ready, the home offers the comfort and quality of a newer home with the character and warmth of a classic Cape Cod. The outdoor living space is truly exceptional. Step onto the large deck, perfect for entertaining family and friends, and enjoy a private backyard that backs to peaceful woods. Gather around the fire pit, relax with a drink at your own tiki bar, or simply enjoy the tranquility of the wooded setting. It's an ideal space for summer entertaining, weekend gatherings, or quiet evenings at home. And then there's the location. Situated within walking distance of downtown St. Michaels, you can easily leave the car behind and enjoy the town's wonderful restaurants, shops, waterfront, and attractions. Few properties offer this combination of privacy and convenient in-town living. Inside, the home offers spacious bedrooms, three bathrooms, hardwood floors, and the peace of mind that comes with a 2019 build. Whether you're looking for a full-time residence, weekend retreat, or Eastern Shore getaway, this home offers an exceptional opportunity to enjoy the St. Michaels lifestyle. Property Highlights Built in 2019 3 large bedrooms 2 full bathrooms + 1 half bath Beautiful hardwood flooring throughout Beautifully maintained and move-in ready Large deck designed for entertaining Private backyard backing to woods Outdoor tiki bar Fire pit Excellent indoor-outdoor entertaining space Walk to downtown St. Michaels Close to restaurants, shops, waterfront, and attractions Rare combination of in-town convenience and private wooded setting Come discover a home where entertaining comes naturally, privacy is preserved, and the best of St. Michaels is just a short walk away. This home is also for Rent on MLS MDTA2015258

207 Brooks Ln, St Michaels

Listing courtesy of Coldwell Banker Waterman Realty. Contact:

27663 Goldsborough Neck Rd, Easton
$849,000
3 Beds ⋅ 3 Baths
Rare opportunity to own 7.46 private acres in Easton's exclusive Ashby area, with room for horses, a pool, gardens, or future expansion. This is an opportunity defined by setting, privacy, and potential. A picturesque tree-lined driveway creates a welcoming sense of arrival, leading to a classic French Provincial-style brick residence thoughtfully sited within a serene landscape of mature trees and open space. The setting offers both seclusion and flexibility, with room to reimagine, expand, or simply enjoy the natural surroundings. This well-maintained home features 3 bedrooms and 2.5 baths, with a comfortable single-level layout ready for its next chapter. Whether updated to reflect modern tastes or preserved and enhanced over time, the property presents a compelling opportunity to create a truly special Eastern Shore retreat. With acreage, architectural character, and a sought-after location as its foundation, this offering is ideally suited for those seeking space, privacy, and long-term potential in one of Talbot County’s most desirable areas. Properties like this—held and cared for over decades—are increasingly rare. A unique opportunity to shape your vision in a timeless setting. Welcome to BLEUHAVEN.

27663 Goldsborough Neck Rd, Easton

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

0000 Rustling Oaks Dr, Wye Mills
$814,990
4 Beds ⋅ 5 Baths
The Brentwood: True Executive-Style Luxury on the Eastern Shore ​Experience unparalleled scale and sophisticated design in the Brentwood, a magnificent 3,736-square-foot executive residence designed for modern luxury living. Set within a premier community featuring expansive, large home sites, this estate offers a rare and highly coveted feature for the Eastern Shore: a massive, full unfinished basement providing endless potential for future customization, a home gym, or unparalleled storage. ​The architectural design prioritizes ultimate privacy and comfort, boasting spacious bedrooms, each complete with its own private, dedicated en-suite bath. The crowning jewel of the home is the sprawling Owner’s Suite—a private sanctuary featuring an exclusive owner's sitting room, a massive walk-in closet, and a specialized wardrobe storage area designed for the ultimate organizer.Designed to blend grand indoor living with the coastal lifestyle, the Brentwood offers flexible structural options, including a sun-drenched morning room or a spacious three-car garage. Step outside to create your own private outdoor oasis on a generous home site, all while being just minutes from the scenic river for premier boating, kayaking, and outdoor water activities. The Brentwood isn’t just a home; it’s an elevated lifestyle. ​Feature & Highlight Lists ​🌟 Executive Structural Highlights ​Massive Footprint: 3,736 sq. ft. of expertly designed, wide-open living space. ​The Eastern Shore Unicorn: Rare, full unfinished basement offering incredible structural storage or future finished square footage. ​Ultimate Family/Guest Privacy: Every single bedroom features its own private, dedicated en-suite bathroom. ​Flexible Footprint: Customization options to add a bright, open morning room or expand to a 3-car garage. The Owner’s Retreat ​Private Sitting Room: A dedicated relaxation space tucked inside the primary suite. ​Expansive Walk-In Closet: A massive, boutique-style layout with a dedicated wardrobe storage area. ​🌊 Community & Lifestyle ​Large Home Sites: Generous lot sizes with ample room to engineer a custom outdoor oasis (pool, outdoor kitchen, or extensive hardscaping). ​Scenic River Access: Located just minutes from the river, offering instant access to boating, paddleboarding, and coastal outdoor recreation. The Owner’s Retreat ​Private Sitting Room: A dedicated relaxation space tucked inside the primary suite. ​Expansive Walk-In Closet: A massive, boutique-style layout with a dedicated wardrobe storage area. ​🌊 Community & Lifestyle ​Large Home Sites: Generous lot sizes with ample room to engineer a custom outdoor oasis (pool, outdoor kitchen, or extensive hardscaping). ​Scenic River Access: Located just minutes from the scenic Wye river, offering instant access to boating, paddleboarding, and coastal outdoor recreation. "Limited time" Up to $20,000 closing cost assistance if buyer uses a Koch Homes preferred lender and tile company. Talbot County maintains the communities shared treatment facility.. The other fee listed reflects the public works facility fee (sewer fee)for ongoing operation, maintenance, administration and engineering.

0000 Rustling Oaks Dr, Wye Mills

Listing courtesy of Koch Realty, Inc.. Contact:

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