Modern & Contemporary Homes for Sale in Dukes County MA

Brand new construction in the heart of downtown Vineyard Haven! This pristine and thoughtfully designed 3-bedroom, 3-bathroom home offers modern downtown living just steps away from the ferry terminal, restaurants, shops and all that Vineyard Haven has to offer. Where luxury meets sophisticated coastal charm complete with an open floor plan, luxury kitchen featuring quartz countertops, custom

Madelyn Silvia Wallace & Co. Sotheby's International Realty

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

Katie Donahue & Rachel Serwa Group Sandpiper Realty, Inc.

Nestled in the heart of Katama, 60 Crocker Drive offers a discerning buyer a unique opportunity to renovate a house and guest house. Bring your creativity. With 2 pre-existing structures and a total of 3 bedrooms, you can renovate the existing structures or start from scratch to make it your own. The main house is a reverse-style home with a garage underneath. The guest house is an A-frame home.

Michele Moore Island Real Estate

Perched on 2.7 acres in one of Aquinnah’s most stunning settings, this coastal retreat captures sweeping views over the Atlantic and Noman’s Land. The main level offers an open living/dining/kitchen wrapped in windows and opening to a wraparound mahogany deck—ideal for sunrise coffee and sunset dinners. A Viking-equipped kitchen and a spacious ocean-facing primary suite complete this floor. The

Jennifer O'hanlon Compass

This distinguished home in Edgartown’s Bold Meadow neighborhood features light-filled interiors highlighted by south-facing windows in a cathedral-ceilinged Great Room that flows into a new sunroom. The main house offers 3 bedrooms, complemented by a spacious detached 900-sf guest apartment above an oversized garage, ideal for hosting. Recent upgrades include a renovated kitchen, updated primary

Bonnie Pierce Wallace & Co. Sotheby's International Realty

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

Sheila Morse Island Real Estate

Experience the elegance of this rare Asian-inspired contemporary estate set on 2.42 acres in a prime location. Tucked behind a long private drive and surrounded by 234 acres of Southern Woodlands conservation land offering biking and hiking, this expansive property offers unparalleled privacy just minutes from Featherstone Center for the Arts, Farm Neck Golf Club and the island’s finest beaches.

Jennifer B. DaSilva Compass

Quintessential Waterview Farm! Built as a year-round home with the charm of the original cottages, this well-loved retreat awaits its next chapter. The sunny, open floor plan offers two bedrooms and a full bath on each level, with generous gathering spaces throughout. A skylit kitchen is tucked into a corner of the main living area, where a curved wall of glass opens to a deck and private yard.

Lisa Stewart Sandpiper Realty, Inc.

Prime Martha’s Vineyard location! Nestled on 1.4 acres in the desirable Vineyard Meadow Farms neighborhood, this property offers privacy, convenience, and potential. Ideally situated in West Tisbury near Edgartown and Vineyard Haven, residents enjoy easy access to shops, restaurants, and the island’s scenic beaches—including eligibility for Lambert’s Cove Beach through West Tisbury residency. The

Maranda Post Compass

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,

Stephanie Roache Donnelly + Co.

This four-bedroom cape-style home offers a comfortable and convenient lifestyle, ideally located just off the bike path with easy access to town and the bus route. Designed with an open floor plan, the main living area provides a seamless flow between the kitchen, dining, and living spaces--perfect for everyday living and entertaining. The first floor features two well-sized bedrooms and a full

Sheila Morse Island Real Estate

In a peaceful Vineyard Haven setting just moments from town, 50 Lantern Lane offers a refined take on classic island living. Privately sited in a quiet enclave yet only one mile from Main Street, Owen Park Beach, and dining and just 1.2 miles from the ferry—this property blends convenience with serenity. The three bedroom, two bath residence spans 1,040 square feet and features a thoughtfully

Madelyn Silvia Wallace & Co. Sotheby's International Realty

Contemporary Home plus ADU! The crashing surf of Long Point is minutes from this charming West Tisbury property, appropriately referred to as "Pinch Me" by the owners. Here, the connection to nature is seamless. The main house sits atop the trees and overlooks a sprawling lawn from two decks. Inside is open with natural light from windows and skylights. The kitchen flows to the dining area, which

Idalyn Macchia Gilstad Wallace & Co. Sotheby's International Realty

Pristine and superbly maintained, this three-bedroom home and two-bedroom guest house has tremendous upside potential and a substantial rental history. This property is tied to town sewer and will allow for up to 7 bedrooms. One additional bedroom in the main house is possible within the existing footprint with appropriate town approvals. There is an additional 668 sq. ft. of finished space in

Buder Team Sandpiper Realty, Inc.

Beautifully designed and built Post & 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

Brenda Galligan Karen M. Overtoom R.E.