4,068 houses for sale in Dukes County

This is a Real Estate-Owned (REO)/post-foreclosure home owned or managed by a bank. All offers are considered; however, the highest and best will most likely be accepted

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This is a Real Estate-Owned (REO)/post-foreclosure home owned or managed by a bank. All offers are considered; however, the highest and best will most likely be accepted

Breathtaking property at the tip of a prominent peninsula on Sengekontacket Pond's western shoreline. Set beautifully at high elevation above the shore, this charming home and guest cottage includes jaw-dropping views of the pond, barrier dunes and Nantucket Sound. Direct from the property take your whaler or other watercraft out into the sound and beyond for endless recreational pursuits. Aside from boating, the swimming and clamming in the immediate waters are sublime. Expansive lawns slope down to the water on three sides of the residence - one of the most enchanting settings on the waterfront on Martha's Vineyard

Directly Across from Inkwell Beach, this Victorian Queen has stood the test of time. Partially insulated to extend the season, the new kitchen and bath are cozy in winter and open and bright in summer. 5 bedrooms, 1.5 baths with an outdoor shower, there's plenty of room for family and friends. The front porch has been a gathering place for 50+ years, and the views have not been expanded. So much opportunity; this house is being sold As-Is

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

Welcome to a beautifully renovated custom contemporary colonial located just 1/3 mile from the Sengekontacket Pond boat landing. Perfect for kayaking, paddleboarding, and coastal living, this builder-owned home seamlessly blends classic Vineyard charm with modern luxury. The bright, open-concept main floor features a wood-burning fireplace, custom kitchen, and direct access to a private backyard oasis with a stone patio, built-in grill, and fire pit. Spanning three finished levels, the home offers and unmatched layout versatility. The second floor features a loft that connects via a balcony to a private studio/office suite above the garage. The third-floor retreat boasts its own full bath and a private balcony with elevated views. Key upgrades include brand-new HVAC, Andersen windows, refinished hardwood floors and a MicroFAST septic system. An exceptional year-round residence or high-yield investment property with strong rental history!

4 Rock Pond Road offers a rare opportunity to enjoy the best of community-centered living in one of Martha's Vineyard's most unique and thoughtfully designed neighborhoods. Located within the Island Cohousing community in West Tisbury, this 4-bedroom, 2-bath home combines warmth, functionality, sustainability, and connection in a peaceful natural setting. Built by South Mountain Company, the home was designed with quality craftsmanship, natural light, and efficient living in mind. The expansive open living, kitchen, and dining area creates an inviting gathering space, anchored by warm cherry cabinetry, a wood stove, and oversized windows that bring the outdoors in. An atrium addition fills the home with sunlight and offers a tranquil indoor retreat year-round. Recent additions and eco-conscious features include composting toilets and a greenhouse, supporting a more sustainable and self-sufficient lifestyle. The partially finished basement offers exceptional flexibility with built-in de

Here is your opportunity to own a charming Cape close to beaches, the bike path and plenty of dining and shopping options. This home features wide plank wood floors on the first level and a full unfinished basement for storage and potential additional living space. Second level has two spacious bedrooms with cathedral ceilings and ample natural light. Rooftop widow's walk provides panoramic views. 3 bedroom septic has passed Title 5 inspection. This home is being offered as-is

Well-maintained three-bedroom, two-bath home set on a quiet road in a convenient Edgartown location. The property is bordered by more than 100 acres of conservation land, offering a peaceful setting and added privacy while remaining close to Edgartown Village, beaches, bike paths, and everyday amenities. The home features comfortable living and dining spaces along with a beautifully updated kitchen with warm wood cabinetry, granite countertops, and stainless steel appliances. Three bedrooms and two full bathrooms provide a practical layout, while the full basement offers plenty of additional storage and utility space. A well-cared-for Edgartown home with a quiet setting, conservation land in its backyard, and easy access to everything the area has to offer

A rare offering of extraordinary scale and architectural significance, this 22-acre Martha's Vineyard estate represents a category of ownership seldom available on the Island. Designed around privacy, natural beauty, and enduring craftsmanship, the living spaces encompass more than 9,500 square feet across multiple thoughtfully designed structures, creating an unparalleled setting for multigenerational living, private retreats, or legacy ownership. Altogether, the compound offers 11 bedrooms and 13 bathrooms across its collection of residences and guest accommodations. At its heart is the Robert A.M. Stern-designed main residence-an architectural work by one of America's most celebrated architects, whose residential designs are prized for their timeless elegance and lasting value. Complementing the estate is the architecturally striking Pond House, completed in 2021, featuring cathedral ceilings, exposed beams, shiplap detailing, a dramatic stone fireplace, screened porch overlooking t

Set amongst beautifully landscaped grounds and vibrant gardens, this inviting Chappaquiddick retreat offers a wonderful sense of privacy and tranquility. Stunning hydrangeas frame the property, also complemented by mature trees, colorful blooms, and established gardens, creating a beautiful setting throughout the seasons. Multiple outdoor spaces invite relaxing and entertaining, with a heated saltwater pool, completed in 2025, serving as the centerpiece. Inside, warm and inviting living spaces are filled with natural light, while shiplap details and a relaxed coastal aesthetic give the home a classic island feel. Vaulted ceilings and thoughtful attention to detail enhance the home's comfortable, refined character, while a thoughtfully designed single-level layout offers the ease and convenience of true first-floor living, with a private primary suite and separate guest wing providing an ideal sense of space and privacy. The detached studio with workshop is a hobbyist's dream, overlooki

Walk or Bike to Edgartown - Renovated and Move-In Ready. Fully furnished 3-bedroom home for year-round or vacation living, new roof and hot water heater, extensively renovated in 2014 (walls, windows, doors, insulation, gutters, siding). Open floor plan with cathedral ceilings and a wall of windows highlighting the beautiful views and natural light. Sliding doors open to a grill area and wide wraparound deck spanning three sides of the house - ideal for entertaining or relaxing outdoors. Large outdoor shower. Half-acre lot; Title V passed for 3 bedrooms. Prime location on Hamblen Way, convenient to the trails and conservation land at the Caroline Tuthill Preserve, with bike path access to Edgartown, Oak Bluffs, Vineyard Haven, and Bend in the Road Beach. Just half a mile to Upper Main Street's shops and restaurants, six-tenths of a mile to historic Edgartown Village and the waterfront. Private and peaceful, yet close to it all. Ring camera in use

Introducing a refined contemporary Chilmark beach house with water views and deeded access to Stonewall Beach on the Atlantic Ocean. The property is set within the storied Stonewall Road and Beach Association - where homes are held for generations and lifelong friendships take root - and offers a true sense of place and continuity. Built by South Mountain Company and thoughtfully renovated and significantly expanded in 2023, the home blends craftsmanship with modern comfort. Enjoy sweeping views of the Atlantic Ocean, Squibnocket Point, and Nomans Land island from both interior living spaces and outdoor vantage points. Designed for multigenerational living, the home offers multiple private zones - including a dedicated media room - allowing for both connection and retreat. This is a rare opportunity to own a meaningful piece of Chilmark-an offering not to be missed

This stunning custom-built waterfront estate offers sweeping views of Edgartown Harbor and exceptional craftsmanship throughout. Set on a private Chappaquiddick compound, the property features a beautifully designed main house, a separate one-bedroom guest house, a pool and spa, and expansive outdoor living spaces perfect for entertaining. Inside, warm wood finishes complement the home's comfortable scale, while the gourmet kitchen, spacious living room with a stone fireplace, and walls of windows showcase the spectacular harbor views. The second floor includes two queen suites, a bunkroom, and breathtaking water views from nearly every room. The finished lower level features a home theater and recreation room. A private path leads to the property's beach and deep-water dock, while a barn across the meadow offers a fitness center, guest suite, and basketball court. Cruise to Main Street Edgartown by skiff or take the nearby Chappy Ferry. This exceptional waterfront retreat offers the p

Located in the heart of downtown Oak Bluffs, this charming updated home seamlessly blends classic Vineyard character with bright, modern comfort. Greeting you from the street is an expansive wraparound porch framed by vibrant hydrangeas and a cozy second-floor balcony. Step inside to an inviting open layout featuring crisp white paneled walls, exposed painted ceiling beams, and warm hardwood floors that create an airy, light-filled atmosphere. Designed for relaxed coastal living, this partially insulated retreat offers effortless indoor-outdoor flow and functional updates throughout. Enjoy an unbeatable location directly across the street from the neighborhood playgroud and just a short, scenic walk to pristine beaches, local dining, and the ferry terminal. Whether you are seeking a summer sanctuary or an investment property, this home delivers classic island living at its best! Showings on Saturdays 1-3pm only beginning August 1

In the heart of historic Edgartown Village, where charming streets lead to the harbor and every cafe, boutique, and restaurant is just moments away, this exceptional turnkey residence offers the quintessential Martha's Vineyard lifestyle. Masterfully built by one of the Island's most respected builders, the home blends timeless New England architecture with refined craftsmanship and sophisticated modern living. Designed for effortless entertaining and everyday comfort, the sun-filled interiors feature beautifully appointed gathering spaces, a stunning chef's kitchen, elegant dining area, and gracious living room that seamlessly extend outdoors. Beyond the doors, a private backyard retreat awaits, where a heated in-ground pool, bluestone patio, and professionally landscaped gardens create an atmosphere worthy of a luxury resort-equally suited for intimate evenings or unforgettable summer celebrations. The thoughtfully designed floor plan offers four spacious bedrooms, four full baths, a

An extraordinary opportunity to own one of the Cape's most distinctive waterfront properties, this exceptional 5.3-acre estate parcel combines remarkable natural beauty, complete privacy, and an unparalleled coastal setting. At its heart is a beautifully renovated four-bedroom beach cottage, thoughtfully updated with modern amenities while preserving the character and intimacy of a classic seaside retreat. From virtually every room, expansive water views create a seamless connection to the surrounding landscape. The property's exceptional topography and scale are among its defining features. A meandering private path descends naturally through the expansive grounds, leading to approximately 450 feet of private sandy beachfront, an extraordinary stretch of shoreline offering a rare sense of seclusion and direct access to the water. Set within a conservation-minded private enclave, the property enjoys an atmosphere of discretion and exclusivity. Its distinguished setting is further enhan

Nestled in a quiet cul-de-sac within the coveted Hidden Cove neighborhood, this delightful property offers an exceptional Island lifestyle. The association delivers rare water access via a private dock on Sengekontacket Pond, plus newly resurfaced tennis and pickleball courts. The open-concept layout flows seamlessly from the fireplaced living room and kitchen through the dining area to an expansive screened porch - ideal for entertaining on warm summer evenings. A welcoming front porch provides additional outdoor living space. The main level is completed by a gracious primary suite with a full bath and a convenient half bath. The walk-out lower level features two additional bedrooms, a full bath, and laundry. A one-car garage offers excellent storage for your car, kayaks, or beach gear. Perfectly positioned between Edgartown and Oak Bluffs. Additional bedrooms possible with septic upgrade per BOH

Charming Oak Bluffs Ranch on a Peaceful Cul-de-Sac Welcome to this inviting 3-bedroom, 1.5-bath ranch-style home nestled on a generous.35-acre lot at the end of a peaceful cul-de-sac in Oak Bluffs, Massachusetts. Ideally located near the beach and town center, this property offers a wonderful blend of privacy, convenience, and classic island living. The comfortable single-level layout features three bedrooms and one-and-a-half baths, offering plenty of space for family, guests, or a relaxing Martha's Vineyard getaway. Step outside onto the sunny deck, an ideal spot for morning coffee, outdoor dining, or unwinding after a day at the beach. The lovely, spacious yard provides plenty of room for outdoor enjoyment, while the storage shed is perfect for beach equipment, bicycles, gardening tools, and seasonal belongings. Set on a quiet cul-de-sac with a desirable.35-acre lot, this home combines the tranquility of a residential setting with the convenience of being close to Oak Bluffs beaches

Wake up to breathtaking ocean views and the soothing rhythm of waves from this charming two-bedroom oceanfront cottage on East Chop. Set on approximately.21 acres of waterfront property with more than 50 feet of shoreline, this special retreat offers a rare opportunity to own a true piece of the island's coastline. Positioned directly on the water, the cottage captures the beauty of the ever-changing ocean from sunrise through sunset. Inside, the cozy two-bedroom cottage offers an inviting island escape with an intimate connection to its spectacular surroundings. Step outside and experience the salt air, gentle sea breezes, and the unmistakable magic of waterfront living. Whether you're enjoying your morning coffee while watching the boats pass, gathering with family and friends, or simply listening to the waves from your own waterfront property, this is a place designed to create lasting Martha's Vineyard memories. A rare East Chop opportunity-over 50 feet of oceanfront.21 acres of wa

Set on a private 1.34-acre parcel along a winding paved road in Oak Bluffs, this exceptional to-be-built luxury residence offers the perfect blend of modern sophistication and island charm. The home features over 3,200 square feet of beautifully crafted living space, including a first-floor primary suite, open-concept great room, gourmet kitchen with pantry, and seamless indoor-outdoor living areas. Upstairs are two additional bedroom suites, a loft-style family room/office, dedicated laundry, and flexible bonus room ideal for guests, media, or recreation. A screened porch, covered outdoor living spaces, and attached two-car garage enhance both functionality and lifestyle. Built with high-end finishes and attention to detail throughout, this stunning new construction offering presents an opportunity to own a luxury retreat with easy access to Oak Bluffs' beaches, harbor, restaurants, shops, and all the attractions that make the Vineyard such a sought-after destination

Offered fully furnished, this beautifully updated four-bedroom, two-bath home is a rare turnkey opportunity in Oak Bluffs. Thoughtfully updated and meticulously maintained, it is equally well suited as a year-round residence, vacation retreat, or investment property. Located just 0.8 miles from downtown Oak Bluffs, the home offers convenient access to beaches, restaurants, shops, ferries, and the harbor, while enjoying the privacy of a quiet residential neighborhood. Over the past decade, the property has benefited from extensive improvements, including a four-bedroom septic system, energy-efficient mini-split heating and air conditioning, updated windows, renovated bathrooms, irrigation, an outdoor shower, and countless additional upgrades that reflect exceptional pride of ownership. Fully booked for the 2026 summer season, the property provides immediate rental income from day one while offering exceptional flexibility for future personal use or continued investment. The property is

A place of serenity tucked in the woods of Chilmark. Beautifully designed and constructed home which was completely renovated in 2017/2018, large fenced in back yard with exquisite fish pond with waterfall and lighting. Kitchen has concrete countertops, sub zero refrigerator, Wolf Oven and Speed Oven. Large open formal dining area and open formal sitting area with fireplace. Beautiful reclaimed wood flooring. LED lighting throughout house, Media room with Sonos Music System, and Lutron Radio RA Switching System (can be smartphone controlled) Radiant heat in mudroom, and all bathrooms (except 1/2 bath in basement) to keep cozy in the cooler months, and a heat pump system with Boiler back up. Six bedroom septic. Close proximity to North Road and Middle Road. Beautiful home with a lot of attention to details. sq. footage is Approx

Breathtaking property at the tip of a prominent peninsula on Sengekontacket Pond's western shoreline. Set beautifully at high elevation above the shore, this charming home and guest cottage includes jaw-dropping views of the pond, barrier dunes and Nantucket Sound. Direct from the property take your whaler or other watercraft out into the sound and beyond for endless recreational pursuits. Aside from boating, the swimming and clamming in the immediate waters are sublime. Expansive lawns slope down to the water on three sides of the residence - one of the most enchanting settings on the waterfront on Martha's Vineyard

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,

Laid-back charm meets island character in this one-of-a-kind up-island beach house. Set on 5.5 acres of natural beauty, this four-bedroom, three-bath main house is full of updates, with bright, fun spaces and a relaxed summer-camp vibe. The creative layout on a single level connects sections of the house via breezy walkway, leading to a bedroom wing including a separate family room, off the primary bedroom. The expansive screened porch effectively doubles the living room, offering an enchanting area for relaxation or gatherings. Tucked just beyond the main house is a versatile barn with its own half bath, currently set up as a rec room and gym, great for guests and entertaining. There are three outdoor showers, full insulation and mini-splits throughout for heat and A/C. The yard is expansive and private, with room to dream-gardens, a pool, or just wide-open space to roam. Best part of all, ownership at Black Point Beach is included, so you can easily bike, stroll or drive down the qui

Modern Cape style home located off Tea Lane could be your special Chilmark retreat. This four bedroom, 2.5 bathroom home needs some updating but is in good condition. Living room with fireplace, dining area and family room provide space for living. Attached two bay garage allows for storage and projects. Wood working area in the basement is a plus. Enjoy the outdoors via the screened porch, large deck and the rolling lawn. Come see this property to truly appreciate it

Ideally situated on Main Street in Vineyard Haven, just moments from the Yacht Club and West Chop, this charming four-bedroom, six-bathroom home offers the perfect blend of convenience, comfort, and Island living. Set on a quarter-acre lot, the property features a private and inviting backyard-ideal for entertaining, gardening, or simply enjoying warm summer evenings. Inside, generous living spaces and a flexible floor plan provide plenty of room for family and guests alike. Enjoy the rare combination of a peaceful residential setting with the convenience of being just a short walk to downtown Vineyard Haven's shops, restaurants, ferry terminal, and harbor. Whether you're seeking a year-round residence, seasonal retreat, or investment opportunity, this well-located home captures the best of Martha's Vineyard living. A wonderful opportunity to own a home in one of Vineyard Haven's most desirable neighborhoods, where town, beaches, and West Chop are all at your doorstep. Same day and sho