1,855 houses for sale in Dukes County

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

Contemporary Island Retreat - A smart opportunity for buyers seeking a low-maintenance Vineyard home near Edgartown Village, this contemporary retreat offers convenient access to shopping, services and the bike path connecting the three down-Island towns. Ideal as a year-round residence, seasonal getaway or potential, the home features an open living and dining area, efficient kitchen and welcoming living room with wood-burning fireplace. Outdoor living includes a sunny south-facing front deck, newer rear deck for grilling and dining, and a second-floor balcony perfect for morning coffee. Natural landscaping keeps upkeep simple, while a detached Party/Game Shed with French doors opens to the backyard and firepit area, offering flexible bonus space for entertaining, remote work or relaxing after a day at the beach or in town

Contemporary Island Retreat - A smart opportunity for buyers seeking a low-maintenance Vineyard home near Edgartown Village, this contemporary retreat offers convenient access to shopping, services and the bike path connecting the three down-Island towns. Ideal as a year-round residence, seasonal getaway or potential, the home features an open living and dining area, efficient kitchen and welcoming living room with wood-burning fireplace. Outdoor living includes a sunny south-facing front deck, newer rear deck for grilling and dining, and a second-floor balcony perfect for morning coffee. Natural landscaping keeps upkeep simple, while a detached Party/Game Shed with French doors opens to the backyard and firepit area, offering flexible bonus space for entertaining, remote work or relaxing after a day at the beach or in town

Coastal chic living with pool and pool house near Katama Bay. Perfectly positioned in the coveted Edgartown Bay Road area, moments from the Town Landing, this custom-built residence offers effortless Vineyard living with exceptional craftsmanship and turnkey convenience. Designed as a builder's own home, the property features shiplap paneling, a custom fieldstone wall with wood-burning fireplace, designer finishes, and a fresh coastal palette. Offered fully furnished with contents valued at $200,000+, it is ready for immediate enjoyment, rental income, or summer living. Outdoor amenities include an inviting covered porch, expansive rear deck, custom gunite pool with PebbleTec(R), detached pool house with wet bar and half bath, and outdoor shower. Launch kayaks or a boat nearby, enjoy Katama Bay, or head to South Beach. With rental income history averaging $225,000-$250,000 per year, this rare offering combines lifestyle, location, and investment appeal

Set on 60 acres along one of the most private and unspoiled stretches of Atlantic coastline in Chilmark, this exceptional estate offers a rare combination of scale, privacy, and enduring coastal beauty. With over 800 feet of direct ocean frontage, the property commands expansive views while maintaining a true sense of seclusion, an increasingly scarce offering on Martha's Vineyard. A gated drive winds through scenic farmland and open fields, running along the edge of Quenames Cove before arriving at your own white sand beach and the Atlantic Ocean. The setting is defined by open land and natural surroundings, creating a sense of space, privacy, and uninterrupted views. The compound consists of five thoughtfully crafted structures. The original 1842 Farmhouse has been meticulously restored and fully modernized, preserving its original character while introducing thoughtful updates, modern systems, and high-quality finishes. A detached structure offers flexible space for a gym or additio

Nestled on a private 1.7-acre parcel in the Bold Meadow neighborhood, this classic Cape offers a perfect blend of comfort and Vineyard charm. Surrounded by mature woodlands, association land, and State Forest, the property provides a serene retreat just moments from Edgartown. The main level is thoughtfully designed for both relaxation and entertaining, featuring a formal living room with a fireplace and a separate TV/family room. The kitchen includes stainless steel appliances, quartz countertops, and a breakfast bar. An eat-in area opens to a spacious mahogany deck, complete with outdoor seating and beautifully landscaped gardens. The first-floor primary suite features vaulted, beamed ceilings and offers a private retreat with an en-suite bath. An additional bedroom/office and a fully renovated hall bath are also located on this level. Upstairs, 2 guest bedrooms share a full bath, while a loft above the two-car garage provides a flexible bonus space

This classic Edgartown Colonial is ideally situated in the heart of the village, just a short stroll from Fuller Street Beach, as well as Edgartown's acclaimed restaurants, boutiques, and harbor. Designed for comfortable coastal living and effortless entertaining, the open-concept floor plan flows seamlessly throughout the home. Offering 10 well-appointed rooms, the residence features six bedrooms, four full bathrooms, and two powder rooms. The gourmet kitchen opens to the spacious living and dining areas, creating an inviting gathering space that extends through French doors to a generous bluestone patio. The beautifully landscaped yard is highlighted by a private, thoughtfully sited swimming pool, providing a peaceful outdoor retreat perfect for relaxing or entertaining

A contemporary Katama retreat, newly refreshed and ready for summer. Set in one of Edgartown's most coveted coastal enclaves, moments from South Beach, this tri-level home offers sun-filled interiors, generous gathering spaces, strong rental appeal, and a private backyard oasis with an 18x40-foot saltwater pool. The dramatic open-concept living level features vaulted ceilings, a wood-burning fireplace, updated kitchen with quartz countertops and stainless appliances, and walls of sliding glass doors opening to newly completed decks and railings. Three finished levels provide comfortable bedrooms, flexible bonus areas, and room for guests to spread out. Recent improvements include fresh interior paint, new sliding glass doors, railroad ties, and completed exterior updates. Outside, enjoy a bluestone terrace, outdoor shower, lush plantings, expansive decks, and resort-style pool setting. An attached two-car garage with finished bonus space above adds versatility. Ideal as a year-round ho

Martha's Vineyard has many wonderful properties but only a few are irreplaceable. Menemsha Harbor is authentic and irreplaceable and this property, Topmast, is the highest and most spacious lot with lovely yard and rare privacy. Topmast was designed and built by master craftsmen in 2016 with unusual quality and care and only occupied a few days each year so virtually brand new. Included close by is a 37+ ft end dock space with 4+ ft low tide draft which makes Topmast arguably the finest Menemsha Harbor home and property. The breathtaking 180 degree views of Menemsha Harbor, Village and Pond, the Aquinnah coastline and Lighthouse and Elizabeth Islands are only rivaled by the dramatic sunsets year round. Topmast is unique as a family home or a special addition to a grand property. (see great video on LINK and Tea Lane web page)

ENJOY THE SEA BREEZES AND SPECTACULAR VIEWS. Wake up to the ever-changing beauty of Vineyard Sound, watch the ferries cross in the distance toward Woods Hole, and end the day with sunset views stretching down the Lagoon. Designed to celebrate its extraordinary setting, this 4-bedroom, 2.5-bath home offers a rare lifestyle defined by light, water, and effortless indoor-outdoor living. With commanding views from nearly every room, the home invites you to slow down and take in the scenery from every angle. Two levels of covered decks overlook Vineyard Sound, while two additional levels of decks face the Lagoon, creating multiple outdoor spaces for morning coffee, afternoon reading, summer entertaining, or quiet evenings under the stars. The first level offers three comfortable bedrooms, a spacious family room, a full bath with laundry, and generous storage - ideal for hosting family and friends after a day at the beach, on the boat, or exploring the Island. Upstairs, the sun-filled open l

Built in 1900, this beautiful South Water Street home is ideally located where the road begins its gentle rise up the hill. The original street-facing portion of the residence showcases classic Victorian architecture, complete with a charming covered front porch that reflects its timeless character. Thoughtfully expanded over the years, the home now offers five bedrooms and three bathrooms, providing generous living space while maintaining its historic appeal. Perfectly positioned on a large, beautifully landscaped lot, the property features expansive lawn areas, a majestic shade tree, and glimpses of Edgartown Harbor. A detached garage with a guest house adds flexibility for visitors or extended family, while ample off-street parking enhances convenience. The home is well maintained and presents an exceptional opportunity for thoughtful updates, with plenty of room to add a swimming pool if desired. This is a rare offering that combines historic charm, an outstanding location, and exc

WATERFRONT WITH DOCK - Nestled along the sparkling shores of Vineyard Haven Harbor, this waterfront cottage presents a rare opportunity to own a piece of Martha's Vineyard history. Originally part of the iconic Mary Guerin Inn, the home blends timeless Vineyard charm with an exceptional setting featuring a private sandy beach, deep-water dock, and sweeping views of the harbor, the Cape, and Nantucket Sound. The home offers five bedrooms, one full bathroom, and one half bathroom, with an open concept living and dining area where walls of windows capture the harbor views and abundant natural light. The kitchen is ideally positioned for effortless indoor and outdoor entertaining. Rich in character, the home retains many original architectural details while benefiting from thoughtful updates, including all new windows, a new roof, beautiful mahogany porches, and new cedar shingles. Whether enjoyed as a treasured family retreat or reimagined into your dream waterfront escape, the possibilit

Located on Upper Main Street in Edgartown's BII zoning district, this versatile property is currently home to Lucky Hank's restaurant. Set on a desirable lot with a large private parking area, and in a coveted high-visibility location. The building offers a turnkey restaurant space and thriving business complete with a fully equipped commercial kitchen on the first floor. Upstairs, you'll find one bedroom with an ensuite full bathroom, currently being used as the office. There is also an additional room being used for restaurant storage. With the flexibility to convert the property back to residential use, if desired, this is a rare opportunity in a prime location that should not be overlooked! This offering is for the real estate and the business. Please inquire with listing agent for additional details and information

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

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

Located on a quiet street just minutes from Edgartown Village, this versatile compound offers privacy, flexibility, and close proximity to the Island's best outdoor amenities. Set on over half an acre, the property includes a main house and detached guest house with separate driveways and mature landscaping.The main home features an open kitchen and dining area, sunken living room, and three bedrooms, plus a finished lower level for added living space. Outdoor highlights include a deck, heated pool, patio, pool house, and outdoor shower.The guest house was built in 2011 and provides additional living space, multiple baths, a garage, and its own private setting. Near conservation land and water access, and just 1.5 miles to town, this property offers strong rental potential and exceptional versatility

A rare legacy offering in the heart of Edgartown Village, this extraordinary in-town compound is among the largest on Martha's Vineyard. Originally built in 1835 and masterfully renovated, it blends historic character with refined modern luxury just moments from Edgartown Harbor, dining, and shopping. Spanning two lots, the property features 10 bedrooms and 14 baths, designed for elegant entertaining and everyday living. The main residence showcases oak floors, nickel board walls, premium appliances, and seamless indoor-outdoor flow with a screened patio. The chef's kitchen includes dual dishwashers, a Miele coffee bar, and wine storage, while a custom bar can convert to a secondary kitchen. Highlights include multiple living areas, en-suite bedrooms, a luxurious primary suite, bunk room, and a finished lower level with media room and wine cellar. Outdoors, a pool, spa, cabana, and carriage house create a private coastal retreat

Fresh, stylish, and fun best describe this inviting four-bedroom Edgartown home with a newly completed pool! Thoughtfully renovated from top to bottom, the interior offers warm, functional living spaces where every detail has been carefully considered. The same level of attention carries outdoors to a true backyard oasis, complete with a heated saltwater pool, multiple patios, a pergola, and an expansive lawn perfect for entertaining or relaxing. Connected to town sewer, the property is approved for up to seven bedrooms-offering exceptional flexibility for future expansion and added value. The location affords both privacy and convenience, with all downtown amenities and South Beach within easy reach. Whether for personal enjoyment or as an investment opportunity, this turn-key property checks all the boxes

Set in a spectacular water view setting with private beach access, this exceptional coastal compound offers a rare blend of privacy, flexibility, and breathtaking scenery. The property is thoughtfully composed of a beautifully appointed main residence, a separate guest house, an artist's studio, and a detached garage with an additional bedroom above - creating the ideal retreat for extended family, guests, or creative living. Expansive water views are showcased throughout the property, with inviting indoor and outdoor spaces designed to capture the natural beauty of the shoreline. Whether enjoying morning coffee overlooking the water, entertaining on warm summer evenings, or taking a short stroll to the private dock on Chilmark Pond, or boating over to the private sandy Atlantic Ocean beach,every aspect of this property embraces relaxed year-round coastal living. A truly unique offering, this compound presents an extraordinary opportunity to own a multi-generational retreat in an idyll

Welcome to an extraordinary waterfront retreat, where luxury meets nature perfectly. This exclusive property offers unparalleled access to breathtaking views, serene landscapes, and the soothing sounds of water lapping against the shore. Squibnocket Farm Road is renowned for its unspoiled beauty and tranquility. This sophisticated gated community offers a sense of seclusion while remaining within a reasonable distance from essential amenities and entertainment options. Whether you're looking for a year-round residence or a vacation getaway, this waterfront home in Squibnocket is an idyllic sanctuary to create unforgettable memories with family and friends

Stylized Private Waterfront Retreat close to town perched along the tranquil shores of the beloved Tisbury Great Pond, this stunning Hutker-designed waterfront home is a seamless blend of coastal elegance and timeless island charm. Designed to capture the essence of Vineyard living, the home features intimate water views, sun-drenched interiors, and carefully curated finishes throughout. From the moment you arrive, you're greeted by a graceful balance of architecture that blends with the landscape and affords contemporary touches. Vaulted ceilings, exposed beams, and hardwood floors create a warm, welcoming atmosphere, while expansive windows invite natural light and frame views of the water and extensive gardens. Off of the kitchen is a generous screened in porch which serves as an additional living space with views to the Tisbury Great Pond and manicured lawn. This is a sweet connector space to the primary bedroom wing which includes a private deck, spacious bathroom and walk-in clos

NEWLY BUILT 4-BEDROOM HOME WITH POOL - 10-Minute WALK TO TOWN, Enjoy modern living in this beautifully furnished, recently built 4-bedroom home featuring a heated saltwater pool and a stylish 20' x 30' entertainment barn-all just a short walk to downtown Edgartown.The home offers two floors of bright, elegant living space with 3.5 beautifully designed bathrooms, an open kitchen and family room, a dining area overlooking the pool, and two laundry areas for added convenience. The sleeping arrangements include an upstairs primary suite with a king bed and an ensuite bathroom with both a tub and a shower. Also upstairs are a front bedroom with two twin beds and a middle bedroom with full-size bunk beds and a trundle. The first-floor guest suite provides added privacy with a queen bed and an ensuite bathroom. The home includes two ensuite bathrooms, a shared upstairs bathroom between the secondary bedrooms, and a convenient main-floor powder room. The open family room, complete with a firep

Built in 1900, this beautiful South Water Street home is ideally located where the road begins its gentle rise up the hill. The original street-facing portion of the residence showcases classic Victorian architecture, complete with a charming covered front porch that reflects its timeless character. Thoughtfully expanded over the years, the home now offers five bedrooms and three bathrooms, providing generous living space while maintaining its historic appeal. Perfectly positioned on a large, beautifully landscaped lot, the property features expansive lawn areas, a majestic shade tree, and glimpses of Edgartown Harbor. A detached garage with a guest house adds flexibility for visitors or extended family, while ample off-street parking enhances convenience. The home is well maintained and presents an exceptional opportunity for thoughtful updates, with plenty of room to add a swimming pool if desired. This is a rare offering that combines historic charm, an outstanding location, and exc

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

Set against roughly ten acres of undeveloped meadow, this beautifully renovated Colonial delivers a coveted Vineyard experience: countryside privacy just minutes from the heart of Edgartown. Bike to Main Street or coast down to Morning Glory Farm, then return to the calm of a home wrapped in open field and mature plantings, as inviting in the quiet of winter as it is at the height of summer. A Hutker Architects design built by Stedman Construction, the home was extensively renovated and expanded, adding over 1,000 square feet along with a new roof, windows, hardwood floors, central air, and fresh cedar shingles. At its center, a sunlit kitchen anchored by an oversized island, made for gathering, opens to a family room wrapped in windows, flowing to the gardens and patio beyond. Three wood-burning fireplaces, in the family room, living room, and primary suite, carry warmth through the seasons. A gracious dining room, elegant living room, and a first-floor office, laundry, and full bath