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LINK ID: 44868
Town: VINEYARD HAVEN
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Click here for all Vineyard Haven listings
Address:
20 Sunnyside Avenue, Vineyard Haven MA 02568
Type: Single Family Residence
$5,995,000.00
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€...
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LINK ID: 44087
Town: EDGARTOWN
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Click here for all Edgartown listings
Address:
4 Somerset Lane, Edgartown MA 02539
Type: Single Family Residence
$5,950,000.00
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...
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LINK ID: 44567
Town: VINEYARD HAVEN
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Click here for all Vineyard Haven listings
Address:
41 Hagerty Drive, Vineyard Haven MA 02568
Type: Single Family Residence
$5,950,000.00
Welcome to your Vineyard dream home in the highly sought-after West Chop neighborhood. This exceptional brand-new construction offers 6 bedrooms, 6 full baths, and 1 half bath, thoughtfully designed with timeless coastal elegance and modern luxury.
Filled with natural light, the home’s bright and...
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LINK ID: 44522
Town: AQUINNAH
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Click here for all Aquinnah listings
Address:
19 Locust Lane, Aquinnah MA 02535
Type: Single Family Residence
$5,900,000.00
There is a town at the end of Martha's Vineyard. The road narrows, the houses thin, and the light changes. This is Aquinnah; the westernmost town, clay cliffs, a lighthouse, and one of the smallest year-round populations on the Vineyard. Compound-scale offerings rarely come to market here. 19 Locust...
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LINK ID: 43366
Town: VINEYARD HAVEN
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Click here for all Vineyard Haven listings
Address:
31 Lamberts Cove Road & 0 Plum Cove Road, Vineyard Haven MA 02568
Type: Single Family Residence
$5,800,000.00
Tashmoo Farm, one of Martha’s Vineyard’s iconic properties, a take-your-breath-away landmark on Lamberts Cove Road! This country estate of over 10 acres is within close proximity of the village of Vineyard Haven with its boutiques and burgeoning restaurant scene, and yet feels secluded and remot...
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LINK ID: 44835
Town: EDGARTOWN
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Click here for all Edgartown listings
Address:
37 Plain Field Way, Edgartown MA 02539
Type: Single Family Residence
$5,795,000.00
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 ...
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CONTINGENT OFFER
STILL SHOWING
Contingent
13th September 2026
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LINK ID: 44310
Town: CHILMARK
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Click here for all Chilmark listings
Address:
17 Chockers Lane, Chilmark MA 02535
Type: Single Family Residence
$5,500,000.00
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...
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LINK ID: 44355
Town: OAK BLUFFS
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Click here for all Oak Bluffs listings
Address:
53 Circuit Avenue, Oak Bluffs MA 02557
Type: Commercial
$5,500,000.00
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...
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LINK ID: 44869
Town: OAK BLUFFS
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Click here for all Oak Bluffs listings
Address:
53 Circuit Avenue, Oak Bluffs MA 02557
Type: Multi Family
$5,500,000.00
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...
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LINK ID: 36712
Town: OAK BLUFFS
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Click here for all Oak Bluffs listings
Address:
43 Sengekontacket Road, Oak Bluffs MA 02557
Type: Single Family Residence
$5,495,000.00
Breathtaking property at the tip of a prominent peninsula on Sengekontacket Pond's western shoreline. Set beautifully at high elevation above the shore, this charming home and guest cottage includes jaw-dropping views of the pond, barrier dunes and Nantucket Sound. Direct from the property take your...
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LINK ID: 44596
Town: CHILMARK
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Click here for all Chilmark listings
Address:
8 Wauwompauque Trail, Chilmark MA 02535
Type: Single Family Residence
$5,300,000.00
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...
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LINK ID: 43452
Town: OAK BLUFFS
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Click here for all Oak Bluffs listings
Address:
4 Canonicus Avenue, Oak Bluffs MA 02557
Type: Multi Family
$5,225,000.00
With a striking presence overlooking Nantucket Sound and just moments from the vibrant pulse of downtown, this distinctive compound is infused with a laid-back West Coast spirit while honoring the vintage charm of Oak Bluffs. Airy and effortlessly elegant, the four-bedroom main house has been master...
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LINK ID: 44546
Town: CHILMARK
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Click here for all Chilmark listings
Address:
49 Gosnolds Way, Chilmark MA 02535
Type: Single Family Residence
$5,200,000.00
Set high on the north shore with panoramic waterviews of Vineyard Sound and deeded private beach access, this secluded 9.8-acre property occupies a rare setting bordered by conservation land and the Menemsha Hills trail network.
The spacious, meticulously maintained residence features a reverse floo...
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LINK ID: 44341
Town: OAK BLUFFS
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Click here for all Oak Bluffs listings
Address:
7 Overview Lane, Oak Bluffs MA 02557
Type: Unimproved Land
$5,100,000.00
A rare opportunity to own a 2.4-acre buildable lot within the prestigious Farm Neck Association. Perfectly situated overlooking the lush greens of Farm Neck Golf Club, this remarkable property also offers picturesque water views of Sengekontacket Pond and the distant Vineyard Sound. Design and build...
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LINK ID: 44917
Town: OAK BLUFFS
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Click here for all Oak Bluffs listings
Address:
3 Oak Bluffs Avenue, Oak Bluffs MA 02568
Type: Commercial
$5,000,000.00
Location, Location, Location!
A once-in-a-lifetime legacy investment opportunity in one of the most desirable and high-visibility locations on Martha’s Vineyard.
Priced to sell and positioned for success, 3 Oak Bluffs Ave is prominently situated at the corner of Seaview Ave and Oak Bluffs Ave—...
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LINK ID: 44534
Town: CHILMARK
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Click here for all Chilmark listings
Address:
35 South Bowl Road, Chilmark MA 02535
Type: Single Family Residence
$4,995,000.00
Rare opportunity in the Seven Gates Farm community of Chilmark.
Designed by acclaimed architects Jane & 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 th...
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LINK ID: 44272
Town: CHILMARK
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Click here for all Chilmark listings
Address:
44 Cencelle, Chilmark MA 02535
Type: Single Family Residence
$4,975,000.00
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...
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LINK ID: 44449
Town: CHILMARK
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Click here for all Chilmark listings
Address:
61 Stonewall Road, Chilmark 022535
Type: Single Family Residence
$4,950,000.00
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...
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LINK ID: 44722
Town: EDGARTOWN
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Click here for all Edgartown listings
Address:
31 Butlers Cove Road, Edgartown MA 02539
Type: Single Family Residence
$4,850,000.00
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 191...
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LINK ID: 44826
Town: EDGARTOWN
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Click here for all Edgartown listings
Address:
149 Litchfield Road, Edgartown MA 02539
Type: Single Family Residence
$4,725,000.00
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 ...
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LINK ID: 43954
Town: VINEYARD HAVEN
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Click here for all Vineyard Haven listings
Address:
16 Frog Hollow, Vineyard Haven MA 02568
Type: Single Family Residence
$4,695,000.00
Downtown Vineyard Haven with Harbor Views. Positioned between the energy of Main Street and the quiet prestige of West Chop, this location delivers a rare balance of downtown access, privacy, and harbor frontage.
Built in 2015, the three-bedroom, two-bath modern ranch is designed for easy first-floo...
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LINK ID: 44237
Town: OAK BLUFFS
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Click here for all Oak Bluffs listings
Address:
8 Fresh Pond Road, Oak Bluffs MA 02557
Type: Single Family Residence
$4,695,000.00
The Ultimate Oak Bluffs Compound: A rare opportunity to own a stunning seven-bedroom estate, thoughtfully designed for both luxurious living and exceptional rental potential. This expansive property features a newly built pool, lush landscaping, and direct access to Fresh Pond—ideal for kayaking, ...
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LINK ID: 44172
Town: OAK BLUFFS
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Click here for all Oak Bluffs listings
Address:
217 Barnes Road, Oak Bluffs MA 02557
Type: Single Family Residence
$4,650,000.00
This exceptional waterfront estate offers unmatched panoramic views from house and guest house with extraordinary privacy on a nearly two acre setting rarely found in this coveted Oak Bluffs location. Commanding sweeping vistas of Lagoon Pond, Vineyard Haven, Hines Point, the iconic drawbridge, Vine...
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LINK ID: 44208
Town: OAK BLUFFS
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Click here for all Oak Bluffs listings
Address:
15 Tamarack Lane, Oak Bluffs MA 02557
Type: Single Family Residence
$4,600,000.00
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...
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LINK ID: 44053
Town: EDGARTOWN
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Click here for all Edgartown listings
Address:
9 Marthas Way, Edgartown MA 02539
Type: Single Family Residence
$4,600,000.00
ONE MILE FROM HISTORIC EDGARTOWN VILLAGE; Welcome to this NEWLY CONSTRUCTED gorgeous gambrel home with a POOL that is close to SOUTH BEACH and EDGARTOWN VILLAGE! This home sits upon a flat, beautiful parcel of land with mature trees. The facade of the home presents an inviting covered porch with fre...
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LINK ID: 44853
Town: EDGARTOWN
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Click here for all Edgartown listings
Address:
170 Katama Road, Edgartown MA 02539
Type: Commercial
$4,450,000.00
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 ...
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LINK ID: 44896
Town: OAK BLUFFS
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Click here for all Oak Bluffs listings
Address:
267 Barnes Road, Oak Bluffs MA 02557
Type: Single Family Residence
$4,395,000.00
Set along 163 feet of Lagoon frontage with its own sandy beach, 267 Barnes Road offers a contemporary take on waterfront living in Oak Bluffs. Set on 1.25 acres of beautifully maintained grounds, the 4,046-square-foot residence offers generous, light-filled spaces designed to capture the water views...
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LINK ID: 43272
Town: WEST TISBURY
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Click here for all West Tisbury listings
Address:
104 Pond View Farm Road, West Tisbury MA 02575
Type: Single Family Residence
$4,300,000.00
Two homes on over three acres of waterfront on the beautiful and coveted Tisbury Great Pond. This remarkable waterfront property offers a rare opportunity to own a serene compound with two existing homes and a private permitted dock.
Both the main house and guest house boast unobstructed water view...
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LINK ID: 44904
Town: EDGARTOWN
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Click here for all Edgartown listings
Address:
148 Katama Road, Edgartown MA 02539
Type: Commercial
$4,100,000.00
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-to-month under self-extending leases, giving a new ow...
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LINK ID: 44906
Town: EDGARTOWN
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Click here for all Edgartown listings
Address:
148 Katama Road, Edgartown MA 02539
Type: Multi Family
$4,100,000.00
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-to-month under self-extending leases, giving a new ow...
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LINK ID: 44144
Town: VINEYARD HAVEN
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Click here for all Vineyard Haven listings
Address:
95 Hines Point Road, Vineyard Haven MA 02568
Type: Single Family Residence
$4,050,000.00
A rare opportunity, this Hines Point waterfront compound offers expansive views of the Lagoon and 100 feet of private beach. The home was built and has been enjoyed by the same family for gathering and summer recreation over generations. The main house offers an open first floor layout with high cei...
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LINK ID: 44879
Town: EDGARTOWN
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Click here for all Edgartown listings
Address:
33 Main Street, Edgartown MA 02539
Type: Commercial
$3,995,000.00
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...
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LINK ID: 44127
Town: EDGARTOWN
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Click here for all Edgartown listings
Address:
23 Beetle Swamp Road, Edgartown MA 02539
Type: Single Family Residence
$3,995,000.00
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 b...
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LINK ID: 44656
Town: WEST TISBURY
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Click here for all West Tisbury listings
Address:
30 & 40 Elias Lane, West Tisbury MA 02575
Type: Multi Family
$3,995,000.00
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...
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CONTINGENT OFFER
STILL SHOWING
Contingent
11th September 2026
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LINK ID: 44771
Town: OAK BLUFFS
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Click here for all Oak Bluffs listings
Address:
99 Ocean Avenue, Oak Bluffs MA 02557
Type: Single Family Residence
$3,975,000.00
A Victorian Grand Dame overlooking Ocean Park -- in a truly spectacular setting with sweeping water views from two stories of verandas. Located in Oak Bluffs most popular and exciting neighborhood and just steps from the beaches of Nantucket Sound, fine restaurants, art galleries, shopping, harbor, ...
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LINK ID: 44554
Town: CHILMARK
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Click here for all Chilmark listings
Address:
131 State Road, Chilmark MA 02535
Type: Single Family Residence
$3,950,000.00
Magical waterfront Quitsa pond cottage with private dock will change your life living on the water. Every day is special when you have an intimate relationship with Quitsa Pond. Calm, safe and breathtaking, adventure is out the doorstep and the sunsets.... Designed with the setting in mind this s...
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LINK ID: 42706
Town: EDGARTOWN
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Click here for all Edgartown listings
Address:
19 Kitts Field Circle, Edgartown MA 02539
Type: Single Family Residence
$3,950,000.00
Old World Vineyard Charm Meets Modern Katama Living. Welcome to this beautifully crafted Katama family compound, a private, thoughtfully designed estate offering timeless elegance and exceptional amenities. Nestled near Edgartown Village, this stunning property includes a four-bedroom main residence...
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LINK ID: 43929
Town: CHILMARK
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Click here for all Chilmark listings
Address:
7 Black Point Road, Chilmark MA 02535
Type: Single Family Residence
$3,950,000.00
Laid-back charm meets island character in this one-of-a-kind up-island beach house. Set on 5.5 acres of natural beauty, this four-bedroom, three-bath main house is full of updates, with bright, fun spaces and a relaxed summer-camp vibe. The creative layout on a single level connects sections of the ...
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CONTINGENT OFFER
STILL SHOWING
Contingent
25th August 2026
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LINK ID: 44616
Town: CHILMARK
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Click here for all Chilmark listings
Address:
3 Ben's Way, Chilmark MA 02535
Type: Single Family Residence
$3,900,000.00
Sited on 3.94 acres in the North Tabor Farm subdivision, this flexible 3-4 bedroom, 4 bath farmhouse offers privacy in a quiet, wooded, agricultural setting abutting working pastures. Built in 1995, this home features elegant living room and dining rooms with 12 foot ceilings and large paned windows...
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LINK ID: 44505
Town: AQUINNAH
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Click here for all Aquinnah listings
Address:
41 Moshup Trail, Aquinnah MA 02535
Type: Single Family Residence
$3,875,000.00
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...
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LINK ID: 44592
Town: EDGARTOWN
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Click here for all Edgartown listings
Address:
10 Pease Point Road, Edgartown MA 02539
Type: Unimproved Land
$3,850,000.00
PRIME 1.14 ACRE PROPERTY IN EDGARTOWN This conforming R-20 lot offers an exceptional canvas for your estate planning vision. Positioned at the end of a private drive, on an elevated parcel amid a neighborhood of distinguished new homes, the original three-bedroom, two-bath residence provides a found...
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LINK ID: 44472
Town: EDGARTOWN
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Click here for all Edgartown listings
Address:
10 Pease Point Road, Edgartown MA 02539
Type: Single Family Residence
$3,850,000.00
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 to create a tr...
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LINK ID: 43534
Town: CHILMARK
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Click here for all Chilmark listings
Address:
96 Hammett Lane, Chilmark MA 02535
Type: Single Family Residence
$3,795,000.00
This 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,...
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LINK ID: 44520
Town: WEST TISBURY
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Click here for all West Tisbury listings
Address:
31 Josiah Sachem Way, West Tisbury MA 02575
Type: Single Family Residence
$3,790,000.00
THE COMPOUND AT INDIAN HILL
Some properties are a house. This one is a world.
Set on more than three private acres along the gentle slopes of Indian Hill, this is a true multi-dwelling compound, purpose-built for the way people actually want to live now: together, apart, and on their own terms. A ma...
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LINK ID: 44615
Town: OAK BLUFFS
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Click here for all Oak Bluffs listings
Address:
9 Weston Avenue, Oak Bluffs MA 02557
Type: Single Family Residence
$3,750,000.00
This beautifully situated 4-bedroom, 3-bath home sits at the highest point of East Chop, offering sweeping views of Vineyard Sound. The property features a spacious clerestory living room with a fireplace, along with a combined family room and kitchen, also centered around a cozy fireplace. A large,...
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LINK ID: 44645
Town: WEST TISBURY
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Click here for all West Tisbury listings
Address:
131 Pond View Farm Road, West Tisbury MA 02575
Type: Unimproved Land
$3,750,000.00
Set on a picturesque peninsula along Tisbury Great Pond, this exceptional pondfront parcel offers a rare opportunity to own a piece of Martha's Vineyard's rural landscape. Currently used for equestrian activities, the expansive open acreage is nestled in one of the Island's most beautiful and unspoi...
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LINK ID: 44462
Town: EDGARTOWN
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Click here for all Edgartown listings
Address:
9 Thaxter Lane, Edgartown MA 02539
Type: Single Family Residence
$3,695,900.00
A CONTEMPORARY KATAMA RETREAT, NEWLY REFRESHED AND READY FOR SUMMER.
Set in one of Edgartown’s most coveted coastal enclaves, this contemporary retreat captures the effortless rhythm of Katama living: sun-filled interiors, generous gathering spaces, ocean breezes, and a private backyard oasis des...
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CONTINGENT OFFER
STILL SHOWING
Contingent
14th September 2026
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LINK ID: 44807
Town: EDGARTOWN
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Click here for all Edgartown listings
Address:
8 Turkeyland Cove Road, Edgartown MA 02539
Type: Unimproved Land
$3,650,000.00
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...
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LINK ID: 44477
Town: WEST TISBURY
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Click here for all West Tisbury listings
Address:
20 James Pond Way, West Tisbury MA 02575
Type: Single Family Residence
$3,600,000.00
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 ...
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LINK ID: 44695
Town: WEST TISBURY
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Click here for all West Tisbury listings
Address:
12 Brook Hollow Road, West Tisbury MA 02575
Type: Single Family Residence
$3,600,000.00
Just 9/10 of a mile from Lambert's Cove Beach, this beautifully renovated tri-level home offers over 4,000 square feet of thoughtfully designed living space with six bedrooms and six bathrooms. Expanded and extensively updated in 2023, the home provides exceptional flexibility for entertaining and a...
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Not responsible for misinformation or typographical errors.
Prices are subject to change without notice. |
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