4,068 houses for sale in Dukes County

Nestled in this desirable Hidden Cove community, this contemporary residence offers a quintessential retreat centered on outdoor recreation and coastal living. Residents enjoy premier neighborhood amenities, including direct water access to Sengekontacket Pond for seamless kayaking and paddleboarding, as well as community tennis courts just steps from your front door. Set on a private, wooded lot, the home showcases cedar siding, a striking wood burning fireplace, gas fireplace, an expansive wood deck, screened porch and outdoor shower for effortless post-beach relaxation. Featuring a 512 square foot finished lower level not counted in the square footage, ideal for a media room, gym and/or home office, this property perfectly combines island tranquility with an active coastal lifestyle

Set along 163 feet of Lagoon frontage with its own sandy beach, 267 Barnes Road offers a fresh, contemporary take on waterfront living in Oak Bluffs. Set on 1.25 acres, the 4,046-square-foot home balances privacy with comfortable spaces for entertaining or relaxing. Oversized windows bring Lagoon views into nearly every room. The main level features soaring ceilings, a wood-burning fireplace, wet bar, and an eat-in kitchen opening to a sunny patio. A separate two-room wing with full bath and private deck offers flexible space for an office, den, studio, or guest accommodations. Upstairs, the primary suite includes a fireplace, walk-in closets, ensuite bath, and Lagoon-facing deck. Two additional ensuite bedrooms open to a wraparound deck and 3-season porch. The refinished 2,000-square-foot walk-out lower level includes a full bath, laundry, and space for a gym, media room, or additional living area. Offered fully furnished, this waterfront retreat is ready to enjoy. Whether you are hos

This traditionally styled residence offers exceptional quality and craftsmanship in a coveted Edgartown location, situated on a corner lot just blocks from downtown and the harborfront. Thoughtfully designed for both elegant entertaining and relaxed island living, the home features beautifully proportioned interiors that flow seamlessly from one space to the next. The inviting front foyer opens to a gracious living room with fireplace and French doors leading to a deep, covered porch complete with its own fireplace. The 1st floor continues to a private den with fireplace, while the dining room and spacious kitchen/family room complete the main living spaces. Abundant windows and French doors throughout the 1st floor provide an effortless connection to the covered porch and the beautifully landscaped grounds. The 2nd floor offers 4 well-appointed bedrooms and 3 full baths providing comfortable accommodations, with most bedrooms offering access to private 2nd-floor decks. The finished lo

Welcome to this year-round East Chop Victorian Gingerbread home, close to Oak Bluffs Harbor, Jetty Beach, and downtown. The amazing wrap-around porch is perfectly designed for spending lazy summers with friends and family. Many a party has been hosted on this generous porch, made more enticing by an open-plan first floor with a large kitchen, living room, and dining area. The first floor features Victorian charm, featuring a beautiful stained glass window, painted beam ceilings, wainscoting, and built-in shelves. The second floor has 3 bedrooms, each with its own character, including a generous primary bedroom suite with vaulted ceilings, skylights, a walk-in closet, plus a full bathroom and an extra built-in closet. The 2nd bedroom has an open and airy feel with a vaulted ceiling and a screened porch affording views of the neighborhood. The final room has its own private balcony for viewing the backyard garden oasis. The lower level consists of a finished bonus room, laundry, and a fu

Tucked away on 1.6 wooded acres in West Tisbury, this classic Cape-style home offers both privacy and convenience, with easy access to the charm of Up-Island and the amenities of Down-Island. Located on a paved road near Long Point Beach, it also includes coveted access to Lambert's Cove Beach. The bright, open interior features a living and dining area with a wood-burning fireplace, a kitchen with a center island, and sliding doors that open to a spacious back deck-ideal for outdoor entertaining. The first floor includes a bedroom and a full bathroom, while the second floor offers two large bedrooms and a shared full bathroom. A full-height, dry basement provides excellent storage and potential for future expansion. The landscaped grounds create a picturesque environment, making it a perfect option for year-round living or rental investment

This custom-built Martha's Vineyard residence blends timeless elegance with contemporary luxury, offering exclusive access to Lambert's Cove Beach.At its heart is a chef's kitchen with bespoke cabinetry, honed Carrara marble, Wolf and Sub-Zero appliances, Miele dishwasher, and Hudson Valley lighting. An adjacent custom bar features Dolomite Italian granite, ideal for entertaining.The home boasts refined finishes, including wide-plank heart pine floors, three Rumford fireplaces, a powder room with Durango tile, and a primary bath retreat with Carrara marble and a freestanding soaking tub.Outdoor living is elevated by a mahogany-screened porch with a reclaimed granite hearth, alongside a mahogany-enclosed outdoor shower with Connecticut granite. Additional features include a reverse osmosis water filtration system and a three-bay garage with expansion potential. Easy expansion is possible with a 5 BR SEPTIC ALREADY IN PLACE! A rare Vineyard offering combining exceptional craftsmanship an

CLASSIC CHILMARK RETREAT. Set on nearly six acres of picturesque land, this beautifully restored and expanded modern farmhouse offers a seamless blend of timeless Vineyard character and contemporary comfort. The 3-bedroom, 3.5-bath main residence spans approximately 5,400 square feet of thoughtfully designed living space, highlighted by a sun-filled open kitchen and living area anchored by a striking central fireplace-ideal for both everyday living and entertaining. An expansive primary suite wing features a spacious bedroom, full bath, private office, half bath, and dedicated laundry. The second floor offers flexible space for a studio, office, or media room, while a classic three-season room invites relaxed enjoyment of the surrounding landscape and distant winter water views. Perfect for compound living, the property includes a guest house, solar, horse barn, fenced pasture, garage, and historic boat shed. Deeded access to Chilmark Pond and South Shore Beach completes this property

This exceptional mixed-use property occupies a premier location in the heart of Oak Bluffs thriving Circuit Avenue business district. Meticulously renovated and designed by architect Chuck Sullivan, the building offers a distinctive combination of commercial and residential spaces in one of Martha's Vineyard's most sought-after high-foot-traffic downtown locations. The Union Chapel, across the street, and the Tabernacle, behind the property, host major Island events. Every aspect of the property reflects an outstanding level of craftsmanship and attention to detail. The street level features an expansive commercial space with considerable flexibility for restaurant-bar and/or retail use (for a restauranteur, the kitchen and bar infrastructure are intact and virtually turnkey). The commercial floor includes three handicap-accessible half baths and a convenient and thoughtfully designed rear exterior loading area. The very large newly excavated basement is dry and temperate year-round, p

This North Shore beachfront estate represents one of the most breathtaking properties in all of New England. The newly built home was created on a 3.3-acre parcel of land, surrounded by specimen trees, rolling grassy meadows and is highly situated on a stable bank overlooking nearly 250 ft of sandy beach. The home, which celebrates and was imagined utilizing the 14 patterns of biophilic design, fosters positive and sustained interaction and relationships among people and the natural environment. The entrance to the home leads across enormous granite steppingstones bridging over expansive reflection ponds with two waterfalls cascading to a lower-level pond. The entry way welcomes one to open and dramatic living spaces with 10 ft ceilings and large expanses of glass facing Vineyard Sound and the surrounding landscape. In the main residence, each of the five-bedroom suites have unique features and connect with the beauty of the outdoors. The lower level of the residence offers amazing, ey

Lambert's Cove/West Tisbury- custom-built contemporary farmhouse style. 4 bedrooms and 3 bathrooms in Main and 2 bedrooms and 1 bath Guest Cottage on 3 acres in a private neighborhood. Enter Main house from the covered porch -matching custom arch doors lead you to either the mudroom/laundry room-kitchen entry, or the living room. The kitchen has Mexican tiled floor and granite counters with stainless steel appliances and gas 4 burner cooktop and double wall oven. Dining area with lots of natural light and 2 sliding glass doors lead out to the deck and patio. Off the pantry hallway, is a full bathroom (with glass block tiled shower), open Livingroom area with cathedral ceiling, with wide pine floors, home office. A slider leads to a covered porch and back deck. Au pair suite bedroom with loft and separate full 3/4 bathroom-with glass slide to deck and outdoor shower and own entrance. Another large bedroom is located just off the living room. The back of the house is wrapped with a 30x20

Waterfront Estate with Deep-Water Dock and Private Beach. Experience an exceptional Martha's Vineyard waterfront lifestyle at this rare Lagoon Pond offering, ideally located just minutes from Vineyard Haven's vibrant harbor, restaurants and shops. The property features a private deep-water dock-ideal for the avid boater-along with its own sandy beach for effortless access to the water. The refined residence was completely renovated in 2022, with interiors by Nicole Hogarty Designs. Filled with natural light and expansive water views, the home is complemented by beautifully landscaped grounds and mature specimen trees, creating a private setting for outdoor living and entertaining. Amenities include a professional-grade bocce court, cold plunge, large hot tub, and classic Island outdoor shower. A separate, stylish party barn provides a versatile setting for everything from intimate gatherings to summer celebrations. Offering an uncommon combination of privacy, waterfront access, boating

Ready - Set - Go! This gorgeous centrally located private 1.5 acre wooded property is ready for you to complete. The Town approved this property to accommodate a 9 bedroom septic system, 20' x 40' in-ground pool, a 7 bedroom main house, garage and a 2 bedroom accessory dwelling unit. The town building and board of health departments approved the house and and septic plans attached. The property includes a newly beautifully renovated 2 bedroom 2 bathroom guest house. This guest house is offered fully furnished. This listing documents include a custom landscape design plan. This very large parcel of land is well suited to get started building an investor dream or family compound

New listing tucked away on a dead end road in Oak Bluffs ~Enjoy the best of Vineyard living from this beautifully renovated Oak Bluffs home, ideally located just a short walk from a private Lagoon beach-perfect for swimming, kayaking, paddleboarding and all your favorite water activities. The inviting living area features a dramatic vaulted ceiling and gas fireplace, creating a warm and spacious gathering space. The thoughtfully designed layout offers a private first-floor primary suite, while the second floor features two additional spacious bedrooms and a full bath. Step outside to a spacious back deck, ideal for outdoor dining, entertaining or relaxing after a day at the beach. Beautifully updated for today's lifestyle, this home offers a wonderful blend of comfort, coastal living and Vineyard charm

Forty six extraordinary acres on Black Point Pond with easy access to Black Point sandy ocean beach. Magical expansive views of meadows, pond and ocean. This estate-sized property abuts 140 acres of Sheriff's Meadow conservation land, offering exceptional privacy. A simple 1041 square foot two bedroom home sits on one lot with two detached studios alongside. Close to nature, this seasonal home (April through October) was built in 1973 and evokes an earlier and simpler time. Use as is, build anew or significantly expand and/or modify the existing dwelling. There is a second abutting buildable lot with many options as well. Enjoyed as a summer retreat by one family for three generations, this is the only private home on Black Point Pond. Walking into the generous, inviting wood panelled living room, the eye is drawn to the large windows opening to expansive views. Rolling meadows, pond, and endless sea and sky. this blend of fields and water stretching into the horizon is the property's

This stunning reverse-contemporary four-bedroom custom home is perfectly situated in one of Chappaquiddick's most sought-after locations. Designed with an expansive open-concept floor plan, the airy and inviting living area flows seamlessly onto a generous wraparound deck, where sweeping, bird's-eye views capture the natural beauty that surrounds you. Thoughtfully renovated, the home blends modern updates with custom finishes to create a rare balance of style, comfort, and year-round functionality an uncommon find in this idyllic setting. Enjoy direct access to Katama Bay, just a three-minute stroll down the road. Its calm waters and sandy shoreline are ideal for swimming, boating, and shellfishing. Nearby, the Wasque Preserve offers over 200 acres. of pristine conservation land, with scenic trails, abundant wildlife, and direct ocean access. Whether you're seeking a serene coastal retreat, a multi-generational family home, or a proven investment property, 76 Washque has it all. With

Wonderful Vineyard retreat located close to coveted long point beach and wildlife reserve, only a short bike ride away. This contemporary is adorned with 4 spacious bedrooms and an open living area with cathedral ceilings. Roomy yet cozy, this home has been the gathering place for 3 generations of family and has great potential for both rentals and year round use. With the recent addition of a huge 2 car garage with super high ceilings and ADU potential, already plumbed with water and a connection to the septic, this is a great property with tons of possibilities and potential

Located under a mile from the heart of downtown Oak Bluffs, this charming property offers endless potential in a highly convenient location. Set on a level lot, the home is ready for its next chapter - whether as a summer getaway or year-round residence. Enjoy easy access to town, beaches, ferries, restaurants, and shops while creating your own vision in this classic Island setting

Two homes on over three acres of waterfront on the beautiful and coveted Tisbury Great Pond. This remarkable waterfront property offers a rare opportunity to own a serene compound with two existing homes and a private permitted dock. Both the main house and guest house boast unobstructed water views, creating a tranquil and picturesque setting perfect for birdwatching, relaxation, and year-round enjoyment. The main house features four bedrooms, two and a half bathrooms, central air conditioning, screened porch for stunning sunset views, den/sunroom with wet bar plus a spacious unfinished basement. The guest house provides an additional two bedrooms, two bathrooms and has its own separate three-bedroom septic system. The guest house has been recently updated with new roof, windows, and cedar shingle siding. Additional highlights for this property include a permitted dock for direct pond access and further access to the South shore beaches. There is no waiting period to add a pool, barn,

Set high on the north shore with panoramic views of Vineyard Sound and deeded private beach access, this secluded 9.8-acre estate enjoys a rare setting abutting conservation land and the Menemsha Hills trail network. The meticulously maintained residence features a reverse floor plan designed to maximize natural light, soaring ceilings, and stunning water views. The upper level offers an open-concept kitchen, dining, and living area, a private primary suite, office, screened porch, and expansive decks. Thoughtfully appointed with air conditioning, a whole-house generator, integrated sound system, and outdoor lighting. The grounds include a tennis court, landscaped gardens with a water feature, and several acres of open meadow surrounded by mature woodland, ensuring exceptional privacy with no visible neighboring homes. Ample room exists for a pool, and the parcel may offer subdivision potential. Ownership includes rights to Brickyard Beach

A pastoral country road leads to this enchanting wood-shingled Cape-style home, offering three bedrooms and a welcoming blend of comfort and charm. The open-concept kitchen flows into a sunken living and dining area, creating an inviting space for everyday living and entertaining. A desirable first-floor bedroom and convenient first-floor laundry add to the home's thoughtful design. Upstairs you will find two large bedrooms, a full bathroom with walk-in shower and plenty of attic storage. Set on a picturesque two-acre parcel, the property also features a detached 384-square-foot studio, which sits privately from the main house, with a private parking area, yard, and septic system, it presents wonderful possibilities for hosting family and friends or creating a private artist's studio or home office. Ideally located just minutes from Nip 'n Tuck Farm, Up-Island Cronig's Market, Conroy's Apothecary, and Main St. in Vineyard Haven. As a W. Tisbury resident, you'll also enjoy access to the

Rare opportunity in the Seven Gates Farm community of Chilmark. Designed by acclaimed architects Jane and Christian Langmuir, this exceptional home is nestled on 5.3 acres of beautifully landscaped grounds. Thoughtfully designed to embrace warmth, natural light, and its surrounding environment, the three-bedroom residence seamlessly blends natural elements with contemporary architectural details. The dramatic great room is anchored by a striking fireplace with a glacial stone hearth. The open kitchen is complemented by custom-crafted cabinetry and top-tier appliances. The primary suite includes two separate office spaces and a media space, a walk-in closet, and a spa-inspired bathroom. A private guest suite offers a full bath with a soaking tub, providing comfort and privacy for visitors. The third bedroom is currently configured as a gym and wellness space, complete with a sauna. The lower level includes an attached two-car garage. Designed with sustainability and ease of ownership in

Nestled in the heart of Chilmark, this four-bedroom home offers a blend of comfort, convenience, and timeless Vineyard charm. Thoughtfully designed with distinct, well-proportioned rooms, the home centers around an expansive, sunlit, eat-in kitchen featuring dual ovens, elegant granite countertops, and extensive custom cherry wood built-ins that combine beauty and practicality. The welcoming living room, anchored by a pristine Vermont Castings wood stove, opens seamlessly to a covered porch and spacious deck-perfect for morning coffee or evening gatherings. The spacious first-floor primary suite provides a private retreat with two en-suite baths and two walk-in closets. Upstairs, you'll find two bedrooms with beautiful wood floors, built-in drawers, and cabinets that add both charm and functionality to the rooms. These bedrooms share a hall bath, making the second floor an ideal space for family or guests. A generous bonus room above the garage offers flexible space for a home office,

This Greek Revival style home blends timeless architecture with a bright, modern open floor plan, all presented in impeccable condition. A welcoming front foyer leads into a beautifully appointed kitchen featuring high-end appliances, a large center island, and seamless flow into the dining and living areas. The living room is anchored by a fireplace and filled with natural light throughout. French doors open to a covered porch with a striking stone fireplace, overlooking a meticulously landscaped backyard with multiple patios-perfect for outdoor entertaining. Upstairs, the second floor offers a spacious primary suite complete with a private sundeck, along with two additional ensuite bedrooms and laundry room. The finished lower level adds exceptional versatility, featuring two additional bedrooms, comfortable sitting area with TV and a generously sized laundry space. A detached barn at the rear of the property includes a full basement and bathroom, as well as a large deck-ideal for a

BEACH PLUM MEADOWS: ARCHITECTURAL KATAMA COMPOUND NEAR SOUTH BEACH. Set on more than 1.6 acres in the coveted Beach Plum Meadows enclave, this distinctive property combines classic coastal architecture, private compound living, and distant views across the Katama plains to the Atlantic Ocean-all less than one mile from South Beach. The gambrel-style Main House features three light-filled levels anchored by a dramatic Great Room with soaring vaulted ceilings, gas fireplace, and sliding glass doors opening to an expansive screened porch and two south-facing decks. A third-floor crow's nest offers an ideal office or private retreat, with access to an elevated deck showcasing sweeping views toward the ocean. The open kitchen features a large center island, granite countertops, stainless appliances, and seamless flow to the dining and living areas. Four bedrooms are distributed across the compound, including two en suite primary bedrooms in the Main House and a private Carriage House suite

Set privately in one of Vineyard Haven's most tranquil enclaves, 30 Water Gate Road is a rare legacy offering defined by pastoral beauty and access to Lake Tashmoo. The nearly 5,000-square-foot residence offers five bedrooms and generous living spaces designed for gathering and quiet retreat, with an effortless indoor-outdoor flow. Bedrooms are thoughtfully arranged in separate wings, with a private primary suite overlooking neighboring lawns, gardens, and conservation land. The inviting living room is anchored by a massive wood-burning fireplace and beautiful hardwood floors, while the chef's kitchen connects seamlessly to indoor and outdoor entertaining spaces. An attached two-car garage adds convenience. Outside, wide lawns, mature plantings, a classic stone wall, and a fenced vegetable garden create a timeless Vineyard setting. A post-and-beam barn offers flexible space for storage, recreation, or a workshop. Ownership includes neighborhood tennis courts and a dock on Lake Tashmoo

Hidden Cove Gem with Serene Pond Views And Coveted Water Access - Located in the desirable Hidden Cove enclave-a 65+ acre water-access community-this inviting contemporary home offers privacy and high-end finishes with direct access to Sengekontacket Pond and Nantucket Sound. Community amenities include a private boat dock, walking trails, pickleball and tennis, all near Oak Bluffs. The sun-filled interior features a living room with vaulted ceilings, a wood-burning fireplace, and floor-to-ceiling windows. The chef's kitchen is appointed with stone countertops and Dacor(R) appliances. The second-floor primary suite boasts a private balcony with pond views and a stylish en suite bath. The garden level provides additional bedrooms and a bonus space with a Murphy bed. Outside, enjoy a bluestone terrace and two levels of decks overlooking a private yard. This move-in-ready home is offered fully furnished with over $80,000 in 2026 summer rental income already secured

Renovated Cape style home in the desirable East Chop neighborhood of Oak Bluffs, offering the perfect combination of coastal charm, modern updates and an exceptional location. This bright and inviting 3-bedroom, 2-bath home features a spacious open floor plan, coastal-inspired decor throughout, and comfortable spaces designed for relaxed Vineyard living and entertaining. A first-floor bedroom provides added flexibility, while the enclosed 120-square-foot sun porch creates a wonderful extension of the living space. Outdoor living shines with a newer mahogany outdoor shower, bluestone patio and beautifully designed walkway, all surrounded by a private setting. An unfinished basement provides approximately 720 square feet of additional space for storage and future possibilities. Walk or bike to Jetty Beach and the East Chop Lighthouse, enjoy the nearby East Chop Beach Club, or stroll to Oak Bluffs Harbor, downtown restaurants and shops. With a proven rental history and a desirable East Ch

Perched on an elevated 10.69-acre site just off picturesque North Road in Chilmark, this exceptional private compound brings together natural beauty and architectural distinction. Designed by renowned architect Patrick Ahearn, the residence enjoys dramatic views across the Menemsha Hills and Vineyard Sound toward the Elizabeth Islands, along with superb sunsets. Spanning 7,691 square feet across three levels, the home is centered on a dramatic great room with a 17-foot vaulted ceiling, fieldstone fireplace, oak post-and-beam detailing, and a custom chef's kitchen designed for both everyday living and entertaining. Expansive walls of glass and bifold doors frame the surrounding landscape and blur the line between indoors and out. Five bedrooms are complemented by two offices, a gym, bunk room, and walkout recreation room for billiards, media, and relaxation. Two additional outdoor fireplaces create intimate gathering areas, including one just off the primary suite with compelling North

HINES POINT WATERFRONT GEM with 85 feet of frontage on the Lagoon, offering ever-changing water views and the perfect vantage point to watch the Steamship Authority ferries arrive in Vineyard Haven Harbor. Enjoy the charming, timeless cottage with a one-car garage as an idyllic summer retreat, or bring your Vineyard vision to life with beautiful architectural plans by Sullivan + Associates Architects. Perched atop a gentle embankment, this exceptional property captures expansive views of the Lagoon, harbor, and town. A private staircase leads to the water's edge, where you can launch a kayak, paddleboard, or small boat and explore the Lagoon and beyond. Just a short stroll to the Martha's Vineyard Museum, downtown Vineyard Haven, shops, restaurants, and the ferry, this is a rare opportunity to own in one of the Island's most coveted waterfront locations

Perched high above the harbor on one of New England's most secluded islands, Folly on Bayberry Hill is a classic Cuttyhunk retreat offering exceptional privacy, timeless coastal character, and sweeping panoramic water views. The home's elevated setting creates a remarkable sense of openness, light, and connection to the surrounding coastal landscape. Inside, approximately 1,472 square feet of living space is filled with warm natural materials, sunlit interiors, and relaxed gathering spaces designed for effortless island living. The residence includes three bedrooms and two full bathrooms, with an additional upper-level finished living area offering flexibility for guests, workspace, or lounge space. An expansive wraparound deck and covered porch create seamless indoor/outdoor living and entertaining opportunities, while adjacent protected conservation land preserves the dramatic harbor views and provides direct access to extensive island hiking trails and open space