New Listings

Address: 23 Hamblen Way    Town: Edgartown    Link ID: 44900

Price: $1,175,000

Property Description:
Walk or Bike to Edgartown — Renovated & Move-In Ready. Fully furnished 3-bedroom home for year-round or vacation living, new roof & hot water heater, extensively renovated in 2014 (walls, windows, doors, insulation, gutters, siding). Open floor plan with cathedral ceilings and a wall of windows hi... Click here for more details

Address: 18 Sylvan Avenue    Town: Vineyard Haven    Link ID: 44892

Price: $2,095,000

Property Description:
COMING SOON! Welcome to 18 Sylvan Avenue, a delightful, custom-crafted four-bedroom, four-bath, contemporary-style home set at the end of a quiet neighborhood road in Vineyard Haven. Surrounded by eight acres of conservation land, the property offers a peaceful setting with a spacious wraparound dec... Click here for more details

Address: 8 Beach Plum Meadows    Town: Edgartown    Link ID: 44844

Price: $7,250,000

Property Description:
COMING SOON: 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 ... Click here for more details

Address: 14 Donalbin Close    Town: Edgartown    Link ID: 44846

Price: $1,750,000

Property Description:
Tucked into a quiet neighborhood and surrounded by mature trees, this home sits elevated on a 0.84-acre lot. With an open floorplan, the kitchen, dining, and living areas flow comfortably together, enhanced by vaulted ceilings, a stone gas fireplace, and French doors that bring in abundant natural ... Click here for more details

Address: 51 Winemack Street & 0 Meadow Ave & Nahomon Street    Town: Oak Bluffs    Link ID: 44802

Price: $2,045,000

Property Description:
East Chop colonial style 2BR/2BA year-round home on East Chop PLUS a separate buildable lot behind the house. The house at 51 Winemack St has a 2-bedroom Title V septic that recently passed inspection, full basement, electric baseboard heat and large yard that allows for expansion potential of the h... Click here for more details

Address: 36 Pine Street    Town: Edgartown    Link ID: 44891

Price: $1,500,000

Property Description:
Imagine creating your own Vineyard retreat on this almost half-acre parcel, ideally located within walking distance to downtown Edgartown. This property offers the opportunity to build a custom home within a designated building envelope, while a protected no-build area provides an added sense of pri... Click here for more details

Address: 171 Upper Main Street/9 Curtis Lane    Town: Edgartown    Link ID: 44417

Price: $1,950,000

Property Description:
A Rare Edgartown Opportunity — Privacy, Proximity & Possibility. Tucked away at the end of a private setting on Upper Main Street, this almost one acre parcel offers a rare opportunity to create your own Edgartown retreat within easy walking distance of downtown. Set well back from the road, the p... Click here for more details

Address: 171 Upper Main Street    Town: Edgartown    Link ID: 44893

Price: $1,850,000

Property Description:
A Rare in-town Edgartown Opportunity — Create Your Own Private Compound At the end of a long private driveway close to downtown Edgartown, this property offers a unique opportunity to create a special island retreat. The beginning of the driveway is less than a third of a mile to the very heart of... Click here for more details

Address: 33 Main Street    Town: Edgartown    Link ID: 44879

Price: $3,995,000

Property Description:
Rare opportunity to own a prominent commercial property on Main Street in the heart of downtown Edgartown. The first floor offers approximately 1,300 square feet of open retail space with excellent visibility on one of Martha’s Vineyard’s premier shopping streets. The second floor includes a two... Click here for more details

Address: 171 Upper Main Street    Town: Edgartown    Link ID: 44897

Price: $1,850,000

Property Description:
A Rare in-town Edgartown Opportunity — Create Your Own Private Compound At the end of a long private driveway close to downtown Edgartown, this property offers a unique opportunity to create a special island retreat. The beginning of the driveway is less than a third of a mile to the very heart of... Click here for more details

Address: 4 Lagrange Avenue    Town: Oak Bluffs    Link ID: 43835

Price: $1,450,000

Property Description:
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 invi... Click here for more details

Address: 9 Winter Street    Town: Edgartown    Link ID: 44840

Price: $2,800,000

Property Description:
Just a block off Main St, Winter Street grew alongside Edgartown's 19th Century maritime and whaling boom. In the mid 2010's local business owners began transforming the corridor, and affectionally dubbed Winter Street the "Left Bank" of Edgartown in comparison to Paris's famous boutique shopping di... Click here for more details

Address: 44 Cencelle    Town: Chilmark    Link ID: 44873

Price: $6,250,000

Property Description:
This exceptional 21-acre estate offers sweeping ocean views, remarkable privacy, and a rare opportunity to create a truly special island retreat. Tucked among the rolling hills, open farmlands, and woodlands of Chilmark, the property combines a profound sense of seclusion with extraordinary natural ... Click here for more details

Address: 0 Old Country Lane    Town: Vineyard Haven    Link ID: 44867

Price: $450,000

Property Description:
Discover peace and privacy without sacrificing location. Nestled under a serene natural tree canopy, this central wooded parcel provides a quiet setting just minutes from local shops, dining, and beautiful beaches. Ready for your custom vision.

Address: 88 Franklin Street    Town: Vineyard Haven    Link ID: 44820

Price: $2,250,000

Property Description:
Tucked away in a private, beautifully landscaped setting, this charming Vineyard farmhouse offers a wonderful blend of privacy, space, and in-town convenience. Just moments from town, the ferry, and shopping, the four-bedroom, three-bath home sits on a spacious 30,000-square-foot lot with a five-bed... Click here for more details

Address: 21 Vickers Street    Town: Edgartown    Link ID: 42743

Price: $3,075,000

Property Description:
Katama at its best! Set in one of Martha’s Vineyard’s most coveted locations, 21 Vickers Street is a classic beach home with an effortless connection to everything that makes Katama so special. Just one mile from South Beach. With the bike path, Katama General Store, and Edgartown Village close ... Click here for more details

Address: 70 Edgartown Vineyard Haven Road    Town: Vineyard Haven    Link ID: 44839

Price: $1,429,900

Property Description:
Classic Vineyard Charm Meets Effortless Island Living! Brimming w/original character and timeless appeal, this delightful 3-bedroom, 3-bath home w/1BR, 1BA ADU offers a perfect blend of historic charm + thoughtful updates in one of Martha’s Vineyard’s most sought-after communities. Original hard... Click here for more details

Address: 105 Whalers Walk    Town: Edgartown    Link ID: 44872

Price: $2,395,000

Property Description:
RENOVATED EDGARTOWN RETREAT WITH POOL, TERRACE + OUTDOOR ENTERTAINING PAVILIONS. Designed for relaxed indoor-outdoor living, this recently renovated four-bedroom, three-bath Edgartown home is set on just under an acre and centered around an exceptional backyard retreat. The heated saltwater pool wit... Click here for more details

Address: 8 Wauwompauque Trail    Town: Chilmark    Link ID: 44596

Price: $5,300,000

Property Description:
Abels Hill opportunity! Coastal living at its finest in this contemporary Abels Hill retreat, where south-facing ocean views and exceptional amenities define the lifestyle. Situated within one of Chilmark's most sought-after communities, the property enjoys exclusive access to the Atlantic Ocean, Ch... Click here for more details

Address: 20 Sunnyside Avenue    Town: Vineyard Haven    Link ID: 44868

Price: $5,995,000

Property Description:
Waterfront Estate with Deep-Water Dock & 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 dockâ€... Click here for more details

Address: 53 Circuit Avenue    Town: Oak Bluffs    Link ID: 44355

Price: $5,500,000

Property Description:
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... Click here for more details

Address: 53 Circuit Avenue    Town: Oak Bluffs    Link ID: 44869

Price: $5,500,000

Property Description:
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... Click here for more details

Address: 24 Harrison Avenue    Town: Oak Bluffs    Link ID: 44863

Price: $2,595,000

Property Description:
East Chop with Water View! The perfect size vacation house or year round living, with all the bells and whistles, water views and located in the most desired neighborhood on East Chop! Designed by Hutker Architects, built with high quality craftsmanship by J.G. Early and landscape design by Dan Gord... Click here for more details

Address: 60A Davis Look Road    Town: West Tisbury    Link ID: 44552

Price: $1,600,000

Property Description:
Over five acres of privacy in one of the Island's most sought-after settings. This 5.15-acre parcel offers a rare opportunity to build a primary residence and accessory structure on old farmland surrounded by large, mature trees. Idyllic stonewalls run along some of the property lines. Large parcel... Click here for more details

Address: 149 Litchfield Road    Town: Edgartown    Link ID: 44826

Price: $4,725,000

Property Description:
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 ... Click here for more details

Address: 2 & 6 Clements Way    Town: Edgartown    Link ID: 44852

Price: $3,300,000

Property Description:
A compelling opportunity to acquire raw land in Edgartown with exceptional development potential. Lots 4B and 4C based on the plot plan provided, each offer the potential for a five-bedroom residence, ADU/guest house, pool, and pool cabana, providing the flexibility to create a substantial Martha’... Click here for more details

Address: 59 Hagerty Drive    Town: Vineyard Haven    Link ID: 44845

Price: $6,150,000

Property Description:
Tucked away on a quiet street in coveted West Chop, this pristine property offers exceptional privacy, stunning scenery, and easy access to downtown Vineyard Haven. Designed for effortless indoor-outdoor living, this sophisticated compound combines timeless charm with every modern amenity. The first... Click here for more details

Address: 49 The Boulevard    Town: Edgartown    Link ID: 44828

Price: $2,850,000

Property Description:
A rare opportunity to own this classic waterfront property on Sengekontacket Pond, offering sweeping 180 degree views across the pond and salt marsh toward the Causeway, the iconic Jaws bridge, State Beach, Nantucket Sound and beyond. Set along the Boulevard, behind a traditional white picket fence... Click here for more details

Address: 15 Tilton Way    Town: Edgartown    Link ID: 44860

Price: $8,250,000

Property Description:
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 propo... Click here for more details

Address: 8 Turkeyland Cove Road    Town: Edgartown    Link ID: 44807

Price: $3,650,000

Property Description:
Set in the heart of Katama, this exceptional 5.5-acre building lot offers a rare opportunity to create a private island retreat surrounded by nature and conservation land. The property is bordered by 87 acres of Sheriffs Meadow conservation land and an additional 75 acres of town-owned land, providi... Click here for more details

Address: 170 Katama Road    Town: Edgartown    Link ID: 44853

Price: $4,450,000

Property Description:
Ideally situated just one-half mile from historic downtown Edgartown on the main access road to South Beach, the Katama General Store presents a rare opportunity to acquire a premier commercial property in one of Martha's Vineyard's most desirable locations. Set on 0.67 acres, the property features ... Click here for more details

Address: 37 Plain Field Way    Town: Edgartown    Link ID: 44835

Price: $5,795,000

Property Description:
SOPHISTICATED KATAMA RETREAT WITH POOL AND CUSTOM FINISHES. Tucked at the end of a lightly traveled road, this modern farmhouse offers an exceptional combination of sophisticated design, generous living spaces, and complete backyard privacy. Working closely with the builder, the owners thoughtfully ... Click here for more details

Address: 27 Island inn Road    Town: Oak Bluffs    Link ID: 44850

Price: $310,000

Property Description:
Welcome to 27 Island Inn, Unit 10C, a comfortable one-bedroom, one-bath Martha’s Vineyard retreat offering an ideal combination of personal enjoyment and rental opportunity. Accommodating up to four guests, 10C features a queen bedroom, sofa bed, cozy living area, well-equipped kitchenette. A uniq... Click here for more details

Address: 21 island Inn Road    Town: Oak Bluffs    Link ID: 44847

Price: $527,500

Property Description:
Welcome to Unit 38G at the Island Inn, offering resort-style living in an exceptional Oak Bluffs location just steps from the beach. This desirable ground-floor end unit features a large glass slider opening to the patio, with stairs leading to the heated outdoor pool just a few feet away. Accommoda... Click here for more details

Address: 27 Island Inn Road    Town: Oak Bluffs    Link ID: 44849

Price: $287,500

Property Description:
Welcome to 27 Island Inn, Unit 9C, an inviting Martha’s Vineyard retreat offering the perfect combination of personal enjoyment and rental opportunity. This comfortable studio accommodates up to four guests with two double beds, a full bath, kitchenette with a 2-burner cooktop, cable TV and free W... Click here for more details

Address: 33 Island Inn Road    Town: Oak Bluffs    Link ID: 44851

Price: $260,000

Property Description:
Welcome to 27 Island Inn, Unit 25F, a comfortable studio offering the perfect combination of a Martha’s Vineyard getaway and rental opportunity. Accommodating up to four guests, this inviting unit features two double beds, one full bath, a convenient kitchenette, cable TV and free WiFi. Island Inn... Click here for more details

Address: 36 Hines Point Road    Town: Vineyard Haven    Link ID: 44589

Price: $3,100,000

Property Description:
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 br... Click here for more details

Address: 0 Cencelle    Town: Chilmark    Link ID: 44829

Price: $1,275,000

Property Description:
Set amid the rolling farmlands of Chilmark, this beautiful parcel offers an exceptional opportunity to create your own island retreat. Framed by stone walls, wooded surroundings, and open meadow views, the property combines privacy and natural beauty in a serene rural setting with glacial erratics a... Click here for more details

Address: 124 Skiff Avenue    Town: Vineyard Haven    Link ID: 44848

Price: $725,000

Property Description:
Vineyard Haven- Walk to the Ferry from this 2 bedroom condo with pool. Located near the downtown area a desirable place for a rental property or live there year-round. The property features common grounds, picnic tables, and seating by the pool to relax and enjoy the outdoors.

Address: 74 Chase Lane    Town: Vineyard Haven    Link ID: 44715

Price: $945,000

Property Description:
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 removed and replaced and ready for new owners to enjoy ~ a solid well built home! Open concept kitchen to dining room. Three bedrooms an... Click here for more details

Address: 27 Island Inn Road    Town: Oak Bluffs    Link ID: 44650

Price: $250,000

Property Description:
Island Inn ....tucked behind the ever-popular Noman's Restaurant. Located off the Beach Road in Oak Bluffs. Fully furnished and updated 2nd floor studio. New: floors, appliances, television, mini-split AC and two double mattresses, Fully furnished galley kitchen. Use the convenient bike path to... Click here for more details

Address: 3 Dukes County Avenue    Town: Oak Bluffs    Link ID: 44841

Price: $935,000

Property Description:
A Gem of a Marthas Vineyard Camp Meeting House Association Home, 3 Dukes County Ave. Located down from the Oak Bluffs Harbor. A couple house from Sunset Pond. Convenient to Beaches,Harbor, Resturants, Shopping, Dancing Music and walk to and from the Steamship Authority. 2 bedroom,1 queen bedroom 1 f... Click here for more details

Address: 9 Codman Spring Road    Town: Edgartown    Link ID: 44843

Price: $2,500,000

Property Description:
Charming four bedroom property set on 0.88 acres along Codman Spring Road, offering a convenient location with easy access to Edgartown Village, Morning Glory, South Beach and all other island towns. Surrounded by beautiful gardens, the home features an expansive wraparound deck ideal for outdoor li... Click here for more details

Address: 11 Stanley Street    Town: Oak Bluffs    Link ID: 44832

Price: $1,255,000

Property Description:
Nestled on a cul-de-sac is this sweet 3 bedroom ranch. Located on a .34 acre lot with plenty of room to expand this solid home and still have enough space for an ADU on this spacious lot. Well maintained over the years with recent upgrades including, roof, siding, new insulation, flooring and paint.... Click here for more details

Address: 220 North Road    Town: Chilmark    Link ID: 44814

Price: $2,400,000

Property Description:
A wonderfully private, peaceful aerie in Chilmark on 3 acres (with a Guest House), featuring a spacious, high, secluded, wrap-around Deck off of the Living Room and Dining Room. The house is built into the side of a hill which allows more light and 2 areas to be considered "ground level." There is a... Click here for more details

Address: 528 Main Street    Town: Vineyard Haven    Link ID: 44816

Price: $1,800,000

Property Description:
Expanded cottage with in-law suite, garage, and detached studio. On the way to West Chop, it is equidistant to Downtown Vineyard Haven, the flagpole at West Chop, Mink Meadows Golf Club, and Vineyard Haven Yacht Club. This 4 bedroom, 4 bathroom property offers a flexible floor plan, including a priv... Click here for more details

Address: 4 Somerset Lane    Town: Edgartown    Link ID: 44087

Price: $5,950,000

Property Description:
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 b... Click here for more details

Address: 10 Norton Street    Town: Edgartown    Link ID: 44836

Price: $7,600,000

Property Description:
This classically designed Colonial home blends timeless architectural character with fresh, beautifully curated interiors. The first floor welcomes you with a large, sun-filled living room with fireplace, an inviting front parlor, a spacious kitchen with pantry, a screened porch and mudroom/laundry ... Click here for more details

Address: 4 Sand Plain Way    Town: Edgartown    Link ID: 44837

Price: $8,750,000

Property Description:
This truly remarkable Chappaquiddick property offers a rare opportunity to step back in time and experience the quintessential character of Martha’s Vineyard. The original historic home, built in 1892, is distinguished by its signature four-story tower with 270-degree water views and gracious wrap... Click here for more details

Address: 139 Chappaquiddick Road and 75 Landing Place Road    Town: Edgartown    Link ID: 44777

Price: $12,250,000

Property Description:
You truly can have it all—just over a mile from the Chappaquiddick Ferry and the shops and restaurants of Edgartown Village, yet set along one of the most spectacular stretches of beach, with a 190’ private dock with mooring and sweeping views across Edgartown Outer Harbor to the iconic Edgartow... Click here for more details

Address: 2 Winemack Street    Town: Oak Bluffs    Link ID: 44805

Price: $1,095,000

Property Description:
Located at the southern end of Winemack Street, this inviting 3-bedroom, 2-bath Oak Bluffs home offers a quiet residential setting in a neighborhood of both year-round and seasonal homes, while remaining remarkably close to everything Oak Bluffs has to offer. Just approximately 1.2 miles from downto... Click here for more details

Address: 220 North Road    Town: Chilmark    Link ID: 44663

Price: $2,400,000

Property Description:
Welcome to 220 North Road, Chilmark, an idyllic, up-island retreat featuring a 4-BR, post-and-beam, main house and 3-BR guest cottage. Set on three private acres, this verdant oasis is surrounded by preserves, walking trails and even an ancient way that leads directly from the property to Middle Lin... Click here for more details