New Listings

Address: 7 Ploughshare Lane    Town: Oak Bluffs    Link ID: 44518

Price: $1,599,000

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

Address: 312 East Chop Drive    Town: Oak Bluffs    Link ID: 43898

Price: $2,295,000

Property Description:
“The Doll House” is a landmark East Chop waterfront retreat overlooking Crystal Lake with sweeping views of Vineyard Sound. Originally a charming fishing cottage, this iconic property has been thoughtfully renovated and impeccably maintained, blending timeless Vineyard character with modern comf... Click here for more details

Address: 52 Heath Hen Lane    Town: Vineyard Haven    Link ID: 44535

Price: $639,000

Property Description:
GOOD TO GO! This sunny 13,000-square-foot lot is ready for your Vineyard home. The property comes with a complete six-bedroom septic design prepared by Vineyard Land Surveying, allowing for both a main house and guest house. With key planning work already completed, this is an outstanding opportunit... Click here for more details

Address: 19 Perkins Avenue    Town: Oak Bluffs    Link ID: 44425

Price: $825,000

Property Description:
Located under a mile from the heart of downtown Oak Bluffs, this charming property offers endless potential in a highly convenient location. Set on a level lot, the home is ready for its next chapter — whether as a summer getaway or year-round residence. Enjoy easy access to town, beaches, ferries... Click here for more details

Address: 18 Puritan Drive    Town: Oak Bluffs    Link ID: 44527

Price: $1,895,000

Property Description:
Craving the ultimate Martha's Vineyard escape? Discover a hidden architectural gem in the serene Tower Ridge community, across the street from Farm Neck Golf Club & Cafe! This striking contemporary home perfectly blends sophisticated design with the tranquil beauty of an expansive, private lot. Step... Click here for more details

Address: 41 Moshup Trail    Town: Aquinnah    Link ID: 44505

Price: $4,000,000

Property Description:
The Best of Aquinnah: Surf, Views, and Total Privacy. There is nothing quite like the south shore of Aquinnah, and this five-bedroom home puts you right in the heart of it. Tucked away along Moshup Trail, the property, lovingly referred to as "Surfside", is all about the Atlantic views and the effor... Click here for more details

Address: 15 Second Avenue    Town: Oak Bluffs    Link ID: 44512

Price: $925,000

Property Description:
Step into this beautifully updated Vineyard cottage, where modern comfort meets coastal charm. The living room, kitchen, dining area, and first-floor full bath were all thoughtfully renovated in 2023. The living space features freshly updated furnishings, contemporary lighting, and light grey beadbo... Click here for more details

Address: 15 Forever Wild Way    Town: Edgartown    Link ID: 44540

Price: $49,000,000

Property Description:
Great Point is a remarkable 32-acre coastal estate within the coveted 200-acre Herring Creek Farm, just minutes from Edgartown Village and Harbor. Offering an extraordinary combination of location, scale, privacy, and natural beauty, the property includes architecturally significant residences and t... Click here for more details

Address: 19 Locust Lane    Town: Aquinnah    Link ID: 44522

Price: $6,950,000

Property Description:
Nestled at the western edge of Martha’s Vineyard, where the landscape opens, the pace slows, and the light takes on a character all its own, lies Aquinnah—one of the island’s most treasured and unspoiled destinations. Known for its iconic clay cliffs, rolling landscapes, and exceptionally limi... Click here for more details

Address: 20 Peases Point Way North    Town: Edgartown    Link ID: 44537

Price: $650,000

Property Description:
Perfectly situated in the heart of downtown Edgartown, this recently renovated first-floor 1-bedroom, 1-bathroom retreat offers effortless access to the village’s acclaimed shops, galleries, restaurants, Fuller Street Beach, and Edgartown Harbor. The bright, open-concept living space seamlessly co... Click here for more details

Address: 17 Katama Point Road    Town: Edgartown    Link ID: 44465

Price: $6,595,000

Property Description:
COMING SOON: COASTAL CHIC LIVING WITH POOL NEAR KATAMA BAY. Perfectly positioned in the highly coveted Edgartown Bay Road area, just moments from the Town Landing on Katama Bay, this custom-built coastal residence offers the very best of the Vineyard lifestyle—effortless, elegant, and ready for im... Click here for more details

Address: 9 Suttons Way    Town: Edgartown    Link ID: 44296

Price: $7,999,000

Property Description:
Nestled in an enviable Katama setting, this masterfully designed shingle-style farmhouse compound epitomizes the peak of casual Vineyard luxury across a manicured coastal landscape. From the sprawling covered entry porch, the front door opens into an impeccably choreographed layout where a grand ent... Click here for more details

Address: 15 Menemsha Inn Road    Town: Chilmark    Link ID: 44504

Price: $1,250,000

Property Description:
Nestled in a bucolic setting moments from the iconic Menemsha fishing village, this beautiful and fully engineered parcel is approved for a 6BR home. One of the few remaining Menemsha buildable lots makes this a rare opportunity. With room for a pool with a special permit! Surrounded by ancient sto... Click here for more details

Address: 37 Dodgers Hole Road    Town: Edgartown    Link ID: 44357

Price: $1,249,900

Property Description:
This split-level home in the highly desirable Dodger’s Hole neighborhood offers a central location with easy access to VTA bus routes, the bike path, all down-island towns and both South Beach and State Beach. The main level features a bright and open living room, dining area, and kitchen designe... Click here for more details

Address: 100 Gosnolds Way    Town: Chilmark    Link ID: 44473

Price: $3,400,000

Property Description:
Well designed and maintained home, situated on 5 acres in a private, desirable neighborhood. Open floor plan with high ceilings that allows a lot of great light into house. The screened in porch is perfect for family dinners or relaxing. Nice water views of Vineyard Sound & the Elizabeth Islands... Click here for more details

Address: 17 Chockers Lane    Town: Chilmark    Link ID: 44310

Price: $5,500,000

Property Description:
Perfectly situated on Nashaquitsa Pond, this charming two-bedroom cottage offers sweeping views of Quitsa and Menemsha Pond from a rare vantage point few properties can match. The cottage includes private beach rights to Short Beach and dock access for a mooring. Inside, hand-painted floors and a w... Click here for more details

Address: 20 James Pond Way    Town: West Tisbury    Link ID: 44477

Price: $3,600,000

Property Description:
Tucked away on 4.5 acres off Lambert’s Cove Road, this unique property offers privacy and peaceful views to James Pond. A private boardwalk leads to a boathouse with direct access to James Pond, perfect for paddling across to Lambert’s Cove and enjoying the nearby James Pond Preserve. The home ... Click here for more details

Address: 6 Wakeman Road    Town: Chilmark    Link ID: 44509

Price: $9,875,000

Property Description:
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, a... Click here for more details

Address: 3 Troy Street    Town: Oak Bluffs    Link ID: 44213

Price: $1,349,000

Property Description:
Set on a generous 0.3-acre lot in desirable Oak Bluffs, this property offers exceptional potential just moments from Vineyard Sound. A newly installed 6-bedroom septic system opens the door to a variety of expansion opportunities. The home is thoughtfully designed with two separate living areas, ide... Click here for more details

Address: 31 Josiah Sachem Way    Town: West Tisbury    Link ID: 44520

Price: $4,650,000

Property Description:
An Inspirational Oasis - Come unwind and experience a secluded multi-dwelling compound nestled along the gentle slopes of Indian Hill, where rural tranquility meets effortless island living on more than three acres of uncommon beauty. Centered around a heated saltwater pool reminiscent of a privat... Click here for more details

Address: 10 Fowler Avenue    Town: Edgartown    Link ID: 44515

Price: $3,295,000

Property Description:
Edgartown Waterfront - Enjoy sweeping water views and direct access to Sengekontacket Pond from this beautiful coastal retreat. Built in 2024, this four-bedroom, three-bath home blends classic Vineyard charm with modern coastal design and offers 95 feet of pond frontage with a private mooring. The ... Click here for more details

Address: 10 North Bog Road    Town: Edgartown    Link ID: 44333

Price: $3,195,000

Property Description:
Set on 2.2 private acres in Edgartown, this exceptional five-bedroom home with a heated saltwater pool offers the ideal blend of privacy, comfort, and convenience. Perfectly located just moments from Morning Glory Farm, South Beach, the bike path, and downtown Edgartown Village, the property provide... Click here for more details

Address: 34 Tenth Street South    Town: Edgartown    Link ID: 44517

Price: $1,225,000

Property Description:
Welcome to easy Edgartown living in this charming 3-bedroom, 2-bath ranch offering comfort, convenience, and classic Vineyard appeal. Designed for effortless single-level living, the home features a spacious living room, an open kitchen and dining area, and a thoughtful layout ideal for both everyda... Click here for more details

Address: 14 Ephriam Allen Road    Town: West Tisbury    Link ID: 44303

Price: $2,475,000

Property Description:
Abutting Cedar Tree Neck Sanctuary, this residence is one of only a few in this rural pocket of the North shore area and benefits from its privacy, miles of walking trails and natural beauty of over 400 acres of its forest, bluffs, beaches and bogs. The main 3-br home is sited at the higher elevati... Click here for more details

Address: 44 Prices Way    Town: Edgartown    Link ID: 44466

Price: $1,495,000

Property Description:
COMING SOON! CONTEMPORARY ISLAND RETREAT. As a smart opportunity for Vineyard buyers seeking a low-maintenance Island home close to Edgartown Village, this contemporary home offers easy access to shopping, services, and the bicycle path connecting the three down-Island towns. Whether used as a year-... Click here for more details

Address: 18 Point Inner Way    Town: Chilmark    Link ID: 44498

Price: $45,000,000

Property Description:
A rare offering on the shores of Menemsha Pond, this extraordinary contemporary waterfront estate redefines luxury living in Chilmark. Thoughtfully designed with striking modern architecture, walls of glass, and seamless indoor-outdoor living, this one-of-a-kind compound captures breathtaking water ... Click here for more details

Address: 9 Ridge Hill Road    Town: Chilmark    Link ID: 44058

Price: $5,850,000

Property Description:
Set on three beautifully landscaped acres, this exceptional six-bedroom property offers a seamless blend of modern farmhouse design and timeless Vineyard appeal. The estate features a five-bedroom, five and a half bathroom main residence, along with a one-bedroom guest suite above a two-car barn. T... Click here for more details

Address: 27 Knoll Drive    Town: Edgartown    Link ID: 44410

Price: $4,850,000

Property Description:
Set the tone the moment you arrive with a dramatic first-floor foyer showcasing post-and-beam construction and warm architectural character. The heart of the home is an expansive great room anchored by a gas fireplace, seamlessly flowing through French doors that open to a sun-drenched pool area—p... Click here for more details

Address: 54 Amelias Crossing    Town: Vineyard Haven    Link ID: 44464

Price: $2,595,000

Property Description:
COASTAL CHIC RETREAT IN VINEYARD HAVEN. Located less than five blocks from Main Street in Vineyard Haven, this classically styled home is perfectly positioned for easy access to restaurants, shops, the harbor, and the ferry, offering the ideal blend of in-town convenience, relaxed island living, an... Click here for more details

Address: 2 Cosmos Way    Town: Edgartown    Link ID: 44390

Price: $2,790,000

Property Description:
Tucked away on a private 1.5-acre parcel in Katama, this thoughtfully designed home offers the layout, amenities, and lifestyle buyers consistently seek in this location. With four bedrooms, 2.5 baths, and an open main living area with high ceilings and a fireplace, the home can live comfortably yea... Click here for more details

Address: 21 Schoolhouse Road    Town: Edgartown    Link ID: 44164

Price: $1,895,000

Property Description:
Located in the heart of Katama between South beach and Edgartown Village. Biking or walking distance along the the shared use path to beach or town. With 2 first floor bedrooms along with a full bath for one floor living. Second floor has 2 more bedrooms, bath along with a loft area for extra bed sp... Click here for more details

Address: 61 Wood Chips Circle    Town: Vineyard Haven    Link ID: 44510

Price: $1,195,000

Property Description:
Set on a private, wooded lot in Vineyard Haven, this recently built home offers a rare combination of immediate enjoyment and exceptional future potential. Built in 2021, the thoughtfully designed 1-bedroom residence features a bright, modern interior, energy-efficient solar panels, and a peaceful s... Click here for more details

Address: 299 Daggett Avenue Unit A    Town: Vineyard Haven    Link ID: 44426

Price: $1,249,000

Property Description:
This cheerful sun drenched three-bed & one bath home with cathedral ceilings sits on just over an acre of gently rolling land surrounded by mature pines, oaks and ornamental plantings. Inspired by Norwegian architecture, the current owner designed and built this home in 1999 with his wife who was a... Click here for more details

Address: 7 Highland Avenue    Town: Oak Bluffs    Link ID: 44502

Price: $809,000

Property Description:
Rare opportunity in East Chop. Beautiful lot in a serene, wooded area, walking distance to town, beach, and ferries. Secluded yet accessible. This is a pre-existing nonconforming lot, with a legal opinion letter attached stating buildability. Buyer to perform all due diligence regarding town buildin... Click here for more details

Address: 15 Tamarack Lane    Town: Oak Bluffs    Link ID: 44208

Price: $4,950,000

Property Description:
Nestled within the idyllic and highly coveted setting of Farm Neck Golf Club, 15 Tamarack Lane presents a rare opportunity to own a stunning 3.7 acres in one of Martha’s Vineyard’s most exclusive communities. The property enjoys picturesque views of the 7th fairway and 8th tee box, across to Sen... Click here for more details

Address: 10 Abels Neck Road    Town: Chilmark    Link ID: 44418

Price: $1,450,000

Property Description:
Nestled on a beautiful lot in the heart of Chilmark, this charming cottage is framed by mature blueberry bushes just off the deck — a true slice of island life. Perfectly positioned to enjoy the quiet calm of up-island living while remaining close to town, beaches, and all that the Vineyard has to... Click here for more details

Address: 7 Pip'n Circle    Town: Edgartown    Link ID: 44218

Price: $2,195,000

Property Description:
A true Chappaquiddick escape — where the outdoors is as much a part of the home as anything inside. Tucked within three acres of park-like grounds, meadows and woodland, this rustic yet comfortable compound of two log houses is built for friends and family who love the land, the water, and everyth... Click here for more details

Address: 14 Ridge Road    Town: Aquinnah    Link ID: 44499

Price: $1,195,000

Property Description:
Nearly 6 acres of land bordered by stonewalls on two sides. The property has been cleared, so you are able to see the level topography and mature trees. The location lends itself to a short walk to Lobsterville Beach or Red Beach on Menemsha Pond, where you can hop on your paddleboard or kayak or ge... Click here for more details

Address: 13 Young Street    Town: Edgartown    Link ID: 44411

Price: $2,950,000

Property Description:
Tucked in the heart of Katama, this classic beach house captures the essence of coastal living with the sound of the Atlantic just beyond. Designed with a reverse-style floor plan to maximize light, the home offers a seamless blend of comfort and classic Vineyard charm. The main living level is bri... Click here for more details

Address: 15 Twenty First Street North    Town: Edgartown    Link ID: 44320

Price: $2,950,000

Property Description:
Located on a quiet street just moments from Edgartown Village, this versatile compound offers a rare combination of privacy, flexibility, and proximity to some of the Island’s most treasured outdoor amenities. Set on over a half-acre, the property features a main residence and a detached guest ho... Click here for more details

Address: 225 Lamberts Cove Road    Town: West Tisbury    Link ID: 44485

Price: $1,725,000

Property Description:
This year-round home, situated less than half a mile from Lambert’s Cove Beach, boasts fine craftsmanship and character in a peaceful, private, wooded setting. Inside, the open living room features wide plank floors, cathedral ceilings with beams, and a central brick fireplace that connects seamle... Click here for more details

Address: 27 Spring Street    Town: Vineyard Haven    Link ID: 44279

Price: $2,895,000

Property Description:
Located in the William Street Historic District, this elegant Greek Revival home, built in 1842, has stood the test of time and has been thoughtfully expanded and renovated in recent years. This five-bedroom, four-bath residence combines historic character with modern comforts. The home features a ... Click here for more details

Address: 61 Ocean Avenue    Town: Oak Bluffs    Link ID: 44475

Price: $1,399,000

Property Description:
THE BEST SEAT IN TOWN! This one-bedroom, one-bathroom condo offers incomparable, panoramic views of Vineyard Sound and the open ocean beyond, across the green expanse of Ocean Park with the Steamship Authority dock in the distance. Door to door, the ferry dock is 392 yards away. This perfect pied-a-... Click here for more details

Address: 318 Lamberts Cove Road    Town: West Tisbury    Link ID: 44156

Price: $1,400,000

Property Description:
Walk to the splendid sands of Lamberts Cove Beach as well as Seth's Pond for a dip and the nearby Inn for a romantic dinner. Fabulous location. The enchanting path to the white-rimmed cove is a mere 5-minute walk away. Main house with three bedrooms,large livingroom,many-windowed kitchen, artist;s s... Click here for more details

Address: 61 Stonewall Road    Town: Chilmark    Link ID: 44449

Price: $5,450,000

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

Address: 0, 36, 38 Black Point Road    Town: Chilmark    Link ID: 43569

Price: $16,000,000

Property Description:
Forty six extraordinary acres on Black Point Pond with easy access to Black Point sandy ocean beach. Magical expansive views of meadows, pond and ocean. This estate-sized property abuts 140 acres of Sheriff’s Meadow conservation land, offering exceptional privacy. A simple 1041 square foot two bed... Click here for more details

Address: 25 Lelands Path    Town: Edgartown    Link ID: 44492

Price: $9,995,000

Property Description:
YOUR OWN PRIVATE WATERFRONT OASIS: CAPTIVATING ESTATE LIVING. This extraordinary Katama Bay waterfront retreat blends timeless coastal architecture, refined interiors, and the natural beauty of Chappaquiddick in unforgettable fashion. Designed by noted architect Patrick Ahearn, this magnificent resi... Click here for more details

Address: 0, 36, 38 Black Point Road    Town: Chilmark    Link ID: 44495

Price: $16,000,000

Property Description:
Forty six extraordinary acres on Black Point Pond with easy access to Black Point sandy ocean beach. Magical expansive views of meadows, pond and ocean. This estate-sized property abuts 140 acres of Sheriff's Meadow conservation land, offering exceptional privacy. A simple 1041 square foot two be... Click here for more details

Address: 82 Oyster Pond Road    Town: Edgartown    Link ID: 44454

Price: $3,250,000

Property Description:
A truly rare offering on Oyster Pond Rd. This property offer rights to boating and swimming in the pond plus a rare easement to access “The Barrier Beach", on the south shore. Access to the south beach is by boating down Oyster Pond.This beach access is a spectacular addition to this property. T... Click here for more details

Address: 47 Winemack Avenue    Town: Oak Bluffs    Link ID: 44490

Price: $1,199,000

Property Description:
Oak Bluffs -East Chop-Close to the beach. Two Year-round cottages on one lot. Stay in one and rent the other, the possibilities are great with this amazing opportunity to own close to the beach and just a mile to Oak Bluffs center. The front house is two bedrooms 1 bath: freshly painted with new fl... Click here for more details

Address: 26 Bijahs Way    Town: Chilmark    Link ID: 44171

Price: $2,495,000

Property Description:
This Chilmark 3 bedroom, 2 bath home has been meticulously maintained inside and out. A major addition and reconstruction of the original house was completed in 1991 and included a 22 x 43 addition. The completely new second floor added over 1,500 square feet and the work included entirely new heati... Click here for more details

Address: 44 Tiffany Drive    Town: Oak Bluffs    Link ID: 44347

Price: $3,245,000

Property Description:
This handsome, newly renovated classic Cape, is nestled on a private 1.38 acre lot in the sought after Lagoon Estates community. The property has been thoughtfully renovated with two new kitchens, 5 new bathrooms, 4-bedrooms (two ensuite), all new windows and new flooring on first floor. It's seamle... Click here for more details

Address: 139 Main Street    Town: Vineyard Haven    Link ID: 44486

Price: $3,750,000

Property Description:
Nestled just two blocks from Vineyard Haven’s working harbor, 139 Main Street is a quietly grand in-town property with the feel of a private estate. Once two separate addresses—now gracefully combined into a single half-acre parcel—this home offers rare space, privacy, and timeless character i... Click here for more details

Address: 34 Edys Island Way    Town: Chilmark    Link ID: 44243

Price: $6,250,000

Property Description:
Waterfront house and guest house with a private dock on Menemsha Pond. This location is in the heart of Menemsha, a waterfront enclave within walking distance of this classic Harbor. Built and cared for over four generations by an Island legacy family, this property is unique among Island estates fo... Click here for more details

Address: 44 Cencelle    Town: Chilmark    Link ID: 44272

Price: $5,295,000

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

Address: 103 Edgartown Bay Road    Town: Edgartown    Link ID: 44215

Price: $6,995,000

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

Address: 51 Chase Road    Town: Edgartown    Link ID: 44409

Price: $945,000

Property Description:
Edgartown opportunity! Bring your vision to this two-bedroom, one-bath ranch situated close to the heart of downtown Edgartown. This property presents a rare chance to create value in a highly sought-after location. Just minutes to downtown, with off-street parking for three vehicles, the home feat... Click here for more details

Address: 0 Temahigan Avenue & Dover Street    Town: Oak Bluffs    Link ID: 43457

Price: $1,200,000

Property Description:
Welcome to # 0 Temahigan Ave & Dover Street, Oak Bluffs. Build Your Martha’s Vineyard Dream Home. Rare opportunity to own a level, cleared corner lot in desirable Oak Bluffs, with paved roads bordering two sides, ready for construction of your Martha’s Vineyard dream home. Approved for up to 6 b... Click here for more details

Address: 10 Pease Point Road    Town: Edgartown    Link ID: 44472

Price: $3,850,000

Property Description:
NEWLY LISTED l PRIME 1.14 ACRE PROPERTY IN EDGARTOWN This conforming R-20 lot offers an exceptional canvas for your estate planning vision. Positioned on an elevated parcel amid a neighborhood of distinguished new homes, the original three-bedroom, two-bath residence provides a foundation from which... Click here for more details