4,068 houses for sale in Dukes County

Some properties you visit, and some properties you experience. Tucked behind mature gardens and a lush natural landscape, 41 Renear Street is a hidden Vineyard treasure - a classic 1927 cottage where timeless character, village convenience, and the beauty of the outdoors come together. Set on a generous.26-acre R10 parcel, this three-bedroom home offers the warmth and craftsmanship of an earlier era, with original architectural details, beautiful wood floors, classic moldings, built-ins, a fireplace, and sun-filled rooms framed by garden views. Thoughtfully cared for over the years, the home retains the authentic charm and easy elegance that make historic Vineyard cottages so beloved. The heart of the home is its connection to nature. Oversized windows invite the gardens inside, filling the living spaces with natural light and views of established plantings, stone pathways, and quiet outdoor sitting areas. Whether enjoying morning coffee overlooking the gardens, gathering by the firepl

Refined New Construction in Katama. Introducing the fourth custom built residence in the new Somerset development. This exceptional new construction represents a sophisticated interpretation of modern Martha's Vineyard living. With nearly 3,500 sq ft, the beautifully appointed 4-bedroom, 4.5 bath residence features light-filled interiors, 10' ceilings, gracious living spaces and clean architectural lines equally suited to relaxed summer living and year-round enjoyment. Two covered porches, an attached 2-car garage and additional space in the unfinished basement enhances the offering. The property offers the added opportunity to create an outdoor oasis, with ample room for a future pool, allowing the next owner to complete the setting with a a pool house, patio, and outdoor entertaining area tailored to their vision. Designed with the Vineyard lifestyle in mind, the home sits in close proximity to the Field Club, the bike path, and the spectacular shoreline of South Beach, while the sho

This stunning 3,200 sq. ft. architectural home features a bright, open layout defined by vaulted ceilings and rich hardwood floors. The gourmet kitchen, appointed with high-end finishes including silestone countertops, flows seamlessly into both a cozy family room and an elegant living room, anchored by a gorgeous dual-sided brick fireplace. With 4 bedrooms, 4 full bathrooms, and 2 dedicated home offices, this residence offers perfect versatility for modern living-whether you require a quiet library or a remote workspace. Step outside onto the welcoming farmer's porch to take in the beautifully manicured grounds, complete with lush perennial gardens supported by an irrigation system. The backyard serves as a true resort-style retreat, complete with an expansive in-ground pool and a hot tub spa, cabana as well as an enclosed outdoor shower. A cobblestone-lined circular driveway leads to ample guest parking and an attached two-bay garage. Combined with a full, versatile basement, this pr

This spacious 5-bedroom, 3-bathroom home is located in a quiet enclave off Main Street, Vineyard Haven. Just half a mile to the vibrant restaurant and shopping scene in the village, and even closer to the library, Owen Little Beach, and Yacht Club. Thoughtfully designed across three finished levels featuring hardwood floors, a cozy fireplace, and a seamless layout, the home is ideal for entertaining. The design is casual but practical, evidenced by the well-appointed kitchen which offers direct access to the rear deck for an eat-in or eat-out option. With separate finished living quarters on the garden level, the home easily accommodates guests, multi-generational living, or a growing family. The expansive deck invites morning coffee, summer gatherings, and peaceful evenings surrounded by nature. Mature plantings bloom on stone-scaped retaining walls and evergreen trees provide ultimate privacy. You are just moments from the harbor, shops, and ferry, and yet this property also offers s

Set along the shimmering edge of The Lagoon and Brush Pond, this rare offering captures the essence of classic island living, with expansive water views, on a little known enclave of only 9 homes. The house dates back to 1910 and was thoughtfully renovated in 2019, blending a timeless Vineyard location with all the modern comforts one would want. The house is perfectly sited to take full advantage of its beautiful location, with sweeping views from the kitchen, enclosed porch, and the expansive deck facing the water - ideal for entertaining, or quiet mornings, overlooking the lagoon. A ground floor bedroom offers convenience and flexibility, while three additional bedrooms upstairs provide ample space for family and guests, including a primary bedroom with ensuite and two bedrooms sharing another full bathroom. Beyond the home, there are three additional lots, two contiguous to the home site, allowing a yard that literally runs down to the edge of Brush Pond. Another lot is across the

Welcome to your coastal retreat in sought-after Sengekontacket, offered fully turnkey and ready to enjoy from day one. This light-filled contemporary home blends comfort, style, and exceptional community amenities in one of Martha's Vineyard's most desirable central Island locations. Designed with soaring vaulted ceilings and oversized windows, the home is flooded with natural sunlight throughout. The first floor features three spacious bedrooms and a full bath with double vanities, while warm oak and maple flooring pair elegantly with custom cherry staircases and built-ins. The open-concept second level creates the perfect gathering space for entertaining and relaxed coastal living. The kitchen, dining, and living areas flow seamlessly together and open through three sliding doors onto an expansive sun-drenched deck - ideal for alfresco dining, morning coffee, sunset cocktails, or summer entertaining. The private primary suite offers its own slider to the deck, along with a spa-like e

This charming farmhouse lies on 3-acres of land overlooking the expansive fields and horse stables, inside the gates of the exclusive Herring Creek Farm Association. The home is in lovely original form and features a large living room with fireplace, dining room, 4 bedrooms and 2 baths. Built in 1910 as one of the first houses on the storied 200-acre farm with over 2,000 ft of private Atlantic beachfront. Unparalleled beauty, expansive fields and horse pastures and the rare opportunity to walk, bike or golfcart directly to the 19 acres of private Atlantic Ocean Beach owned together with the other landowners inside the farm. All of these features along with being a short drive to downtown Edgartown, make this a very special opportunity

WATERVIEWS of Sengenotacket when you pull out of the driveway at 77 SIXTH STREET NORTH, EDGARTOWN. NEW CONSTRUCTION, with an anticipated completion date in MARCH of 2027; just in time to bring in the 2027 SPRING/SUMMER SEASON! The first floor entry offers an inviting two story foyer which opens to the living room which has a gas fireplace and wall of glass slider doors. Flowing from the living room is the open kitchen area which offers an island with seating for four. The kitchen sports Bosch appliances, an island with a built in drawer microwave, quartz countertops and an easy layout for cooking and entertaining. The kitchen then opens to a separate dining room. A half bath off the living room and a first floor primary bedroom with a luxurious private bath completes the first floor. The second floor offers a second living room and two guest bedrooms, each with their own bath. The plot is large enough to support a future detached garage. Come and enjoy! The pictures are of a similar ho

Great Location Cape Cod style year round home well maintained on a private dead end road close to Tashmoo Landing. New roof 2025, new windows, basement insulation replaced. A solid well built home ready for new owners to enjoy! Open concept kitchen to dining room. Three bedrooms and one full one half bath. Additional living area with full clean dry basement adds 768 SF with egress walkout door and large windows letting in natural light. The house has propane monitors, mini splits for cooling/heating as well as window A/C units on the second floor with backup electric baseboard. The property is in the Tashmoo Watershed and will need an enhanced system per the Town installed by the buyer. This is a fantastic area just minutes to Tashmoo landing, tennis, pickleball, boating, fishing, kayak storage, kayaking, Mink Meadows Golf, Tashmoo Town Beach, Tisbury school, Downtown Main Street and the year round Ferry Terminal

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

Set on private 3.5-acre wooded parcel, this 3-bedroom, 2-bath single-family home offers the ultimate Martha's Vineyard retreat. Nestled among mature trees, the property provides exceptional privacy and a peaceful natural setting, while remaining conveniently located to island villages, beaches, and amenities. The home is thoughtfully positioned to blend into its surroundings, featuring comfortable living spaces ideal for year-round living or seasonal enjoyment. With 3 bedrooms and 2 full baths, the layout offers flexibility for family, guests, or a home office. Custom soapstone countertops add to this home's beauty. Expansive outdoor space invites relaxation, exploration, and the potential for future enhancements, all within a serene woodland environment. An increasingly rare opportunity to own a conservation-abutting property on Martha's Vineyard-perfect as a primary residence, vacation home, or long-term investment in one of the island's most desireable natural settings

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

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

Perfectly positioned along the serene shores of Katama Bay, this property offers a front-row seat to nature's grandeur. Residents will revel in sweeping, 180-degree vistas where the tranquil waters of the bay meet the dramatic horizon of South Beach and the Atlantic Ocean. As you enter the property from Edgartown Bay Road, the home's timeless architecture and expansive front lawn make an unforgettable first impression. Inside, the home features a bright and airy open-concept layout that seamlessly blends the living, dining, and kitchen areas, all enhanced by the dramatic big sky, big water setting. Spanning three levels, the residence offers 4 bedrooms, 3 full bathrooms, and a spacious family room. Nearly every room captures breathtaking water views, creating a true connection to the surrounding coastal landscape. Step outside to the backyard lawn and follow the wooden boardwalk to your own private sandy beach. Whether launching a kayak or paddleboard for a day exploring Katama Bay

A beautiful pastoral, private family compound in West Tisbury, on 7.5 glorious acres of meadow comprised of two parcels, offers a rare opportunity. Elias Lane is a quiet country road tucked behind Misty Meadows and just minutes from West Tisbury village. The property features a lovingly maintained 4 BDR main house with a well appointed kitchen, recent sun porch addition an elegant Lew French stone fireplace. The primary bedroom is on the first floor and all the bedrooms feature peaceful meadow views. The 2 BDR post and beam barn guest house has a deck and plenty of separate storage space. There is a private tennis court and large heated swimming pool. The additional parcel is 40 Elias Lane, flat and buildable land. Build another home or sell the subdivided second lot in the future - there are so many possibilities

A rare mixed-use property on Katama Road, set right between downtown Edgartown and South Beach! Two residential apartments above - a 2BR and a 3BR, each with their own walk-up deck, in-unit laundry and dedicated parking. Both are occupied month-tomonth under self-extending leases, giving a new owner flexibility. The first floor was home to an HVAC company for nearly a decade and is now vacant and ready for its next owner: roughly 1,253 sq.ft. of office with high efficiency heat pump and A/C, plus 1,148 sq.ft. of garage and storage. Ample on-site parking with 25 designated spaces and a loading dock for your business needs. The current owners have put significant capital improvements into the building since 2017 - solar, electrical, roof,windows, integrated fire and security systems, mechanical and irrigation systems, and apt. renovations. This property has a long history of permitted commercial use well before these owners. The Edgartown Zoning Board of Appeals granted a special permit

Solid Cape-style home located one block from Sailing Camp Park and Medeiros Cove offering water access to the Lagoon and one mile to all the excitement that downtown Oak Bluffs has to offer. The first floor offers a spacious eat in kitchen that is open to the dining room. A full bathroom with laundry, a den with French-doors that leads to the living room with a slider opening out to the back deck. The second floor has a huge front-to-back primary bedroom, a large landing, full bathroom and two guest bedrooms. Although the property is in need of updates, it will be well worth the effort. There is a ton of potential here. Being offer as is

This private 17-acre Chilmark estate with ocean views, tucked away in the rolling hills and farmlands of Chilmark, offers sweeping ocean views to the south and a rare sense of seclusion and serenity. At the heart of the property is a striking modern style home, thoughtfully designed to bring the outdoors in. Expansive walls of glass flood the interior with natural light and frame panoramic views of open pastures, ancient stone walls, woodlands, and the Atlantic beyond. The four-bedroom residence features an open-concept layout that seamlessly connects indoor living spaces to a full-length deck-perfect for entertaining or simply soaking in the peaceful surroundings. Recent updates include new kitchen appliances and a high-efficiency heat pump system with central air conditioning. A true highlight of this property is the land itself. There is an extensive network of trails winding throughout the property, leading through meadows and forest, past streams, a large pond and striking glacial

Behind its classic Village facade lies a home that reimagines Edgartown living, where timeless architecture meets bright, light-filled interiors and an effortless sense of modern luxury. Just moments from Main Street and the harbor, it offers the rare opportunity to enjoy the best of the Village from a residence designed for the way people live and entertain today. Exceptional craftsmanship and thoughtfully curated finishes define every level of the home. The backyard is a true extension of the home, anchored by a fully equipped cabana, heated saltwater pool, sunken fire pit, and striking custom glass wall. A strong rental history further enhances the property's appeal, offering exceptional flexibility as a private family retreat or a compelling investment opportunity. A home where exceptional quality meets effortless living, offering a fresh and relaxed interpretation of luxury in the heart of Edgartown Village

This warm and welcoming home with exceptional outdoor living space is sited on a beautifully landscaped lot just 1.5 miles from downtown Oak Bluffs. The private backyard, designed and cultivated by Donaroma's, features a fenced lawn with irrigation, fire pit, outdoor dining area, and built-in grill-ideal for entertaining and relaxing. The open kitchen and living floor plan overlooks the backyard. Two bedrooms and a full bath on the main level. The finished lower level adds approximately 908 square feet, including a third bedroom, full bath, and den-perfect for guests, movie nights, or extended living. Medeiras Cove is approximately 0.4 miles away, offering access for kayaking, paddle boarding, and sunset views over the Lagoon. A convenient foot bath makes beach days easy. Offered furnished with a short list of exclusions, this property is ideal as a year-round home, vacation retreat, or investment property. The third bedroom, not reflected on the field card, is engineer-approved and ha

Set on over a half an acre in Edgartown's desirable Island Grove neighborhood, this three-bedroom, two-bath classic Cape offers an exceptional expansion opportunity in a convenient Katama location. The existing 1,560-square-foot home can be enjoyed as-is while plans are developed for a renovation, expansion, or new construction. With a connection to town sewer, the property can support up to seven bedrooms, creating potential for a substantial residence, pool, and accessory dwelling unit. Association tennis courts are located nearby, with Edgartown Village, South Beach, shops, restaurants, and the harbor all within easy reach. A rare opportunity to create a custom Vineyard retreat in an established neighborhood

This stunning 3,200 sq. ft. architectural home features a bright, open layout defined by vaulted ceilings and rich hardwood floors. The gourmet kitchen, appointed with high-end finishes including silestone countertops, flows seamlessly into both a cozy family room and an elegant living room, anchored by a gorgeous dual-sided brick fireplace. With 4 bedrooms, 4 full bathrooms, and 2 dedicated home offices, this residence offers perfect versatility for modern living-whether you require a quiet library or a remote workspace. Step outside onto the welcoming farmer's porch to take in the beautifully manicured grounds, complete with lush perennial gardens supported by an irrigation system. The backyard serves as a true resort-style retreat, complete with an expansive in-ground pool and a hot tub spa, cabana as well as an enclosed outdoor shower. A cobblestone-lined circular driveway leads to ample guest parking and an attached two-bay garage. Combined with a full, versatile basement, this pr

Set within the coveted Meadow View Farms community, this exceptional post-and-beam residence offers timeless craftsmanship, generous living spaces, and nearly an acre of private beautifully landscaped grounds with significant potential for expansion. A full-length farmer's porch creates a gracious arrival and provides the perfect setting to relax. Inside, the sun-drenched main level is defined by soaring cathedral ceilings, rich hardwood floors, and a striking hand-cut stone propane fireplace that anchors the open-concept living spaces. The well-appointed kitchen with casual dining area flows seamlessly into a formal dining room and an inviting living room, creating an ideal layout for both everyday living and entertaining. A spacious mudroom offers practicality and convenience after beach days or inclement weather. The primary suite is privately situated on the first floor and features abundant natural light from a bay window overlooking the backyard, a walk-in closet, and an oversize

Set along the shimmering edge of The Lagoon and Brush Pond, this rare offering captures the essence of classic island living, with expansive water views, on a little known enclave of only 9 homes. The house dates back to 1910 and was thoughtfully renovated in 2019, blending a timeless Vineyard location with all the modern comforts one would want. The house is perfectly sited to take full advantage of its beautiful location, with sweeping views from the kitchen, enclosed porch, and the expansive deck facing the water - ideal for entertaining, or quiet mornings, overlooking the lagoon. A ground floor bedroom offers convenience and flexibility, while three additional bedrooms upstairs provide ample space for family and guests, including a primary bedroom with ensuite and two bedrooms sharing another full bathroom. Beyond the home, there are three additional lots, two contiguous to the home site, allowing a yard that literally runs down to the edge of Brush Pond. Another lot is across the

Sweetened Water Farm ~ Just off the main road, past an idyllic horse barn and conserved association land, you'll find this eight-bedroom residence that sits prominently on 2.4 acres. The sprawling main house, an expanded classic Cape featuring separate living areas, both inside and out, and six bedrooms, including two first-floor en-suites, overlooks the rolling pastures with grazing horses. Private guest quarters above the detached oversized garage offer additional comfortable accommodations. Sweetened Water Farm combines the tranquility of an up-island location with the convenience of being just moments from the boutiques, restaurants, and harbor of downtown Edgartown. A home for all generations in a setting like no other

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!

Beautifully designed and built Post and Beam style home is tastefully thought out and meticulously maintained. The open living, dining and kitchen feature custom built-ins, a wood burning fireplace and a fabulous gourmet kitchen with Wolfe 8 burner professional style stove, Sub Zero refrigerator, Boshe dishwasher, soapstone counters and a butlers pantry with extra cupboards, shelving and a wine refrigerator. There are sliders that take you to an oversized deck and stairs to a blue stone patio and beautiful gardens. The screened-in porch off the living room steps out to the side yard, patio and outdoor shower. First floor Primary with walk-in closet, access to the deck and a private en-suite bathroom with beautiful tiled steam shower and large soaking tub. Second floor includes a loft with sitting room, 2 spacious bedrooms that share a full bath with shower and office, all with cathedral beamed ceilings. Many nice features throughout include white oak random width floors, marble and til

Perched atop Fulling Mill Hill this distinctive contemporary main house plus guest house offers mid-century charm and a serene retreat set on 3.3 acres of mature oak and beech forest and bordered by an ancient stone wall. Designed by renowned Yale School of Architecture Dean Paul Mitarachi, the main house features a striking circular entryway framed by mature Asiatic gardens. Step inside to discover a custom circular staircase with dramatic floor to ceiling windows, leading to the upper living area flooded with natural light from the wall of south-facing windows. The living area with high ceilings and woodstove is a comfortable place to congregate, while the kitchen and open dining areas lend themselves to modern day living. Glass sliding doors open onto a spacious 2nd story deck giving the entire living space an intimate relationship with the outdoors. On the first floor there are three total bedrooms; two bedrooms sharing a full bath plus a primary bedroom with a full bath en-suite.

Turnkey Katama Home-Beautifully furnished and move-in ready, this updated coastal retreat offers relaxed Island living with a strong rental history and effortless ownership. Outdoor highlights include a 19-foot heated swim spa and Jacuzzi set on an expansive wood deck, an outdoor shower, bluestone fire pit patio, multiple lounging spaces, decks, and wooded privacy for serene entertaining. Inside, the light-filled kitchen, living and dining area features cathedral ceilings, stainless steel appliances, granite countertops, and modern finishes. Recent improvements include a new roof, renovated bathroom, new maple flooring, refreshed interior, and updated landscaping. The thoughtful layout includes a primary bedroom with private balcony, two first-floor bedrooms with a shared full bath, and town sewer allowing expansion up to six bedrooms. Ideally located near South Beach and just minutes to Edgartown Village and Morning Glory Farm, this is a rare opportunity in a sought-after neighborhood

Stylish Chilmark retreat with sweeping water views, private beach, tennis, and walking trails. Set within the coveted Spring Point community, this beautifully renovated island home captures a rare sense of place, with natural beauty, privacy, and effortless indoor-outdoor living. Thoughtfully updated in 2022, the home blends relaxed coastal sophistication with driftwood-colored hardwood floors, a striking stone fireplace, sleek cook's kitchen, custom-tiled baths, and Sonos(R) sound. Large windows and sliding glass doors frame water views and open to private decks, while a spacious screened porch is ideal for morning coffee, summer dining, or entertaining. Landscaped grounds, a paver parking court, charming gazebo, and finished walk-out lower level add comfort and flexibility. Spring Point amenities include 68 acres of common land, ancient walking trails, two tennis courts, and Beck's Beach, a private shoreline with magnificent sunsets from the Elizabeth Islands to Gay Head Lighthouse