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VIEW ALL 350 MARTHA'S VINEYARD LISTINGS ↓
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LINK ID: 44652
Town: OAK BLUFFS
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Click here for all Oak Bluffs listings
Address:
8 Pequot Avenue, Oak Bluffs MA 02557
Type: Single Family Residence
$1,925,000.00
Directly Across from Inkwell Beach, this Victorian Queen has stood the test of time.
Partially insulated to extend the season, the new kitchen and bath are cozy in winter and open and bright in summer. 5 bedrooms, 1.5 baths with an outdoor shower, there's plenty of room for family and friends.
The...
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LINK ID: 44940
Town: EDGARTOWN
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Click here for all Edgartown listings
Address:
4 Cormorant Circle, Edgartown MA 02539
Type: Single Family Residence
$1,925,000.00
Tucked at the end of a quiet cul-de-sac in the desirable Island Grove community, this charming three-bedroom, (plus bonus room), two-bathroom residence offers a private setting, association amenities and excellent proximity to Edgartown Village and Katama Beach.
Located on arguably one of the most ...
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NEW LISTING
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LINK ID: 44445
Town: CHILMARK
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Click here for all Chilmark listings
Address:
0 High Mark, Chilmark MA 02535
Type: Unimproved Land
$1,900,000.00
A rare opportunity to build a private retreat awaits at this 15 acre land parcel centrally located in Chilmark. Once part of the High Mark estate, the property features groves of mature trees planted more than 100 years ago, creating a wondrous, secluded and private setting rarely found anywhere on ...
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LINK ID: 44385
Town: WEST TISBURY
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Click here for all West Tisbury listings
Address:
63 Vineyard Meadow Farms Road, West Tisbury MA 02575
Type: Single Family Residence
$1,899,000.00
Set within the coveted Vineyard Meadow Farms community, this West Tisbury property presents a rare opportunity to own a thoughtfully configured compound in one of the island's most peaceful and sought-after settings. Privately sited on a generous parcel, the property is surrounded by natural beauty ...
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LINK ID: 44785
Town: OAK BLUFFS
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Click here for all Oak Bluffs listings
Address:
22 Paddock Road, Oak Bluffs MA 02557
Type: Unimproved Land
$1,895,000.00
An exceptional offering—the final homesite available within The Preserve at The Woodlands, one of Oak Bluffs’ most coveted residential enclaves. Create a custom coastal retreat in an extraordinary setting where architecturally designed residences, protected conservation land, and the timeless be...
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LINK ID: 44890
Town: EDGARTOWN
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Click here for all Edgartown listings
Address:
42 Marthas Road, Edgartown MA 02539
Type: Single Family Residence
$1,895,000.00
A RARE KATAMA JEWEL BOX — TURNKEY LUXURY TODAY, WITH ROOM TO GROW.
In one of Edgartown's most coveted enclaves, this beautifully reimagined three-bedroom, two-bath residence offers the ease of new construction with timeless Vineyard character. Taken down to the frame and rebuilt in 2024 by a hand...
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CONTINGENT OFFER
STILL SHOWING
Contingent
6th September 2026
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LINK ID: 44705
Town: OAK BLUFFS
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Click here for all Oak Bluffs listings
Address:
9 Chickawaukee Street, Oak Bluffs MA 02557
Type: Single Family Residence
$1,895,000.00
Offered fully furnished, this beautifully updated four-bedroom, two-bath home is a rare turnkey opportunity in Oak Bluffs. Thoughtfully updated and meticulously maintained, it is equally well suited as a year-round residence, vacation retreat, or investment property.
Located just 0.8 miles from dow...
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CONTINGENT OFFER
STILL SHOWING
Contingent
9th September 2026
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LINK ID: 44349
Town: OAK BLUFFS
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Click here for all Oak Bluffs listings
Address:
33 Vineyard Avenue, Oak Bluffs MA 02557
Type: Multi Family
$1,875,000.00
Welcome to 33 Vineyard Avenue in Oak Bluffs, Martha's Vineyard. This fully gut renovated property encompassing 3B/2Ba in total featuring a 2BR/2BA primary home plus a distinctly separate attached 1BR/1BA ADU suite - offering flexible, move-in ready living or investment potential in a prime in-town l...
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LINK ID: 44893
Town: EDGARTOWN
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Click here for all Edgartown listings
Address:
171 Upper Main Street, Edgartown MA 02539
Type: Single Family Residence
$1,850,000.00
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...
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CONTINGENT OFFER
STILL SHOWING
Contingent
3rd September 2026
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LINK ID: 44928
Town: WEST TISBURY
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Click here for all West Tisbury listings
Address:
78 Vineyard Meadow Farms Road, West Tisbury MA 02568
Type: Single Family Residence
$1,850,000.00
Situated down a long driveway, this distinctive West Tisbury property offers a rare combination of privacy, natural beauty, thoughtful design, and exceptional versatility. Designed with passive solar principles, the home takes full advantage of its orientation and abundant natural light. Exposed woo...
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LINK ID: 44113
Town: OAK BLUFFS
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Click here for all Oak Bluffs listings
Address:
22 Old Harbor Lane, Oak Bluffs MA 02557
Type: Single Family Residence
$1,850,000.00
Quintessential Waterview Farm! Built as a year round house with all the charm of the original cottages, this well-loved family home awaits a new generation. The sunny, open floor plan has two bedrooms and a full bath on each level and plenty of room to spread out. The skylit kitchen is cleverly tuck...
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CONTINGENT OFFER
STILL SHOWING
Contingent
8th September 2026
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LINK ID: 44733
Town: VINEYARD HAVEN
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Click here for all Vineyard Haven listings
Address:
0 Weaver Lane (Lot 5), Vineyard Haven MA 02568
Type: Unimproved Land
$1,800,000.00
This 1.1-acre waterfront lot is located at the end of a quiet lane abutting 20+ acres of conservation land. The level and heavily wooded lot sits high on a bluff overlooking the Lagoon. The lot has been engineered, and the bounds have been staked. A buyer would be able to connect to Town water ne...
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LINK ID: 44018
Town: OAK BLUFFS
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Click here for all Oak Bluffs listings
Address:
18 Wood Duck Way, Oak Bluffs MA 02557
Type: Single Family Residence
$1,800,000.00
Your opportunity in Sengekontacket! Being sold turnkey. This modern home has four bedrooms and three full baths. Large windows and high vaulted ceilings, the home lets in bright natural light. The first floor has three bedrooms and a full bath with double sinks. Beautiful oak and maple floors comple...
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LINK ID: 44193
Town: VINEYARD HAVEN
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Click here for all Vineyard Haven listings
Address:
79 Beach Road # B14, Vineyard Haven MA 02568
Type: Commercial
$1,799,000.00
TISBURY MARKETPLACE offers an active and well-established setting for this beloved eatery. The year 'round destination hub draws proven foot traffic and a healthy commercial environment. Rocco’s Pizzeria anchors the corner of the water view plaza with sustained history and a devoted following. Ope...
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LINK ID: 44918
Town: WEST TISBURY
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Click here for all West Tisbury listings
Address:
487 Lamberts Cove Road, West Tisbury MA 02575
Type: Single Family Residence
$1,795,000.00
This sweet four-bedroom home has fantastic energy and captures the effortless feeling of summer on Martha’s Vineyard. Set high on 2.4 acres along beloved Lamberts Cove Road, the property is just a short walk to Ice House, Lamberts Cove Beach, and Seth’s Pond. Designed for easy enjoyment, the hom...
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NEW LISTING
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LINK ID: 44556
Town: EDGARTOWN
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Click here for all Edgartown listings
Address:
99 Old Purchase Road, Edgartown MA 02539
Type: Single Family Residence
$1,775,000.00
Enjoying a private setting at the end of a quiet Edgartown cul-de-sac, this post-and-beam home is set on .71 acres with easy access to more than 25 acres of Land Bank conservation land. Conveniently located near Morning Glory Farm, the bike path, downtown Edgartown, and South Beach, the property off...
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LINK ID: 44054
Town: OAK BLUFFS
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Click here for all Oak Bluffs listings
Address:
2 Great Rock Road, Oak Bluffs MA 02557
Type: Single Family Residence
$1,765,000.00
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 buildi...
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LINK ID: 43626
Town: WEST TISBURY
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Click here for all West Tisbury listings
Address:
188 Vineyard Meadow Farms Road, West Tisbury MA 02575
Type: Single Family Residence
$1,760,000.00
House & Guesthouse near Long Point Beach! The Island's coveted south shore is just minutes from this charming West Tisbury compound, where the connection to nature is seamless. The main house sits high atop the trees and overlooks a park-like, fenced-in backyard, perfect for kids and dogs. The yard ...
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CONTINGENT OFFER
STILL SHOWING
Contingent
17th September 2026
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LINK ID: 44938
Town: OAK BLUFFS
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Click here for all Oak Bluffs listings
Address:
68 Front Street, Oak Bluffs MA 02557
Type: Single Family Residence
$1,755,000.00
Located on a quiet street in Oak Bluffs, this beautifully expanded Cape offers just over 2,800 square feet of living space, plus an additional 700+ square feet of newly finished recreation space above the two-car garage, with its own private entrance and second-floor deck. The inviting first floor i...
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NEW LISTING
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LINK ID: 44750
Town: OAK BLUFFS
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Click here for all Oak Bluffs listings
Address:
14 High Meadow Lane, Oak Bluffs MA 02557
Type: Single Family Residence
$1,750,000.00
Welcome to this sun-drenched, reverse contemporary-style home located in the lovely Meadow View Farms community! This multi-level home has boundless potential. The second level features a bright, open floor plan with cathedral ceilings, living, dining, and kitchen areas, and 3 sliding doors that tak...
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LINK ID: 44846
Town: EDGARTOWN
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Click here for all Edgartown listings
Address:
14 Donaldbin Close, Edgartown MA 02539
Type: Single Family Residence
$1,750,000.00
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 ...
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LINK ID: 44641
Town: OAK BLUFFS
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Click here for all Oak Bluffs listings
Address:
11 Beach Road, Oak Bluffs MA 02557
Type: Single Family Residence
$1,745,000.00
Wake up to breathtaking ocean views and the soothing rhythm of waves from this charming two-bedroom oceanfront cottage on East Chop. Set on approximately .21 acres of waterfront property with more than 50 feet of shoreline, this special retreat offers a rare opportunity to own a true piece of the is...
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LINK ID: 44661
Town: AQUINNAH
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Click here for all Aquinnah listings
Address:
12 Lobsterville Road, Aquinnah MA 02535
Type: Single Family Residence
$1,700,000.00
Aquinnah is a remote, culturally rich town on the western tip of Martha's Vineyard. Formerly known as Gay Head is world-renowed for its dramatic, multicolored clay cliffs and is the historic homeland of the Wampanoag Tribe.
Frank Nuovo fell in love with this piece of land and decided to build this h...
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CONTINGENT OFFER
STILL SHOWING
Contingent
17th August 2026
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LINK ID: 44067
Town: CHILMARK
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Click here for all Chilmark listings
Address:
43 North Slope Lane, Chilmark MA 02535
Type: Single Family Residence
$1,699,999.00
Set on a private 3.5-acre wooded parcel surrounded by conservation land, this 3-bedroom, 2-bath single-family home offers the ultimate Martha’s Vineyard retreat. Nestled among mature trees and protected open space, the property provides exceptional privacy and a peaceful natural setting, while rem...
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LINK ID: 44164
Town: EDGARTOWN
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Click here for all Edgartown listings
Address:
21 Schoolhouse Road, Edgartown MA 02539
Type: Single Family Residence
$1,696,000.00
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...
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LINK ID: 43364
Town: CHILMARK
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Click here for all Chilmark listings
Address:
174 Middle Road, Chilmark MA 02539
Type: Single Family Residence
$1,695,000.00
Nestled in Chilmark, this four-bedroom home blends classic Vineyard charm with modern comfort. The sunlit eat-in kitchen features dual ovens, granite countertops, and custom cherry built-ins, flowing seamlessly to a living room with a Vermont Castings wood stove and access to a covered porch and spa...
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LINK ID: 44557
Town: VINEYARD HAVEN
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Click here for all Vineyard Haven listings
Address:
41 & 0 Cook Road, Vineyard Haven MA 02568
Type: Single Family Residence
$1,690,000.00
Included in the asking price are two separate parcels: a beautifully updated 3-bedroom home and an adjacent 16,000 square foot buildable lot. No subdivision is required. The lot is ready for your plans or may be sold separately after closing, offering exceptional flexibility for a family compound, s...
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LINK ID: 44439
Town: EDGARTOWN
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Click here for all Edgartown listings
Address:
63 Division Road, Edgartown MA 02539
Type: Unimproved Land
$1,650,000.00
LOT #4 - The last lot available in this 5-lot Edgartown subdivision! Division Road is located between Meshacket and Meetinghouse Way, less than 1 mile from the center of town. This concept was thoughtfully and creatively developed in an effort to create a new and upcoming neighborhood. The new resid...
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LINK ID: 44267
Town: OAK BLUFFS
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Click here for all Oak Bluffs listings
Address:
17 John Wesley Avenue, Oak Bluffs MA 02557
Type: Single Family Residence
$1,650,000.00
Welcome to this year-round East Chop Victorian Gingerbread home, close to Oak Bluffs Harbor, Jetty Beach, and downtown. The amazing wrap-around porch is perfectly designed for spending lazy summers with friends and family. Many a party has been hosted on this generous porch, made more enticing by a...
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LINK ID: 43064
Town: VINEYARD HAVEN
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Click here for all Vineyard Haven listings
Address:
26 Union Court # 7, Vineyard Haven MA 02568
Type: Condominium
$1,625,000.00
Waterview Condo in the Heart of Downtown Vineyard Haven. Experience the best of in-town living with this newly built, thoughtfully designed 2-bedroom condo offering beautiful harbor views and luxurious modern finishes. The first level welcomes you with a primary suite featuring a full bath with a t...
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LINK ID: 44116
Town: EDGARTOWN
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Click here for all Edgartown listings
Address:
58 Road to the Plains, Edgartown MA 02539
Type: Single Family Residence
$1,625,000.00
Turnkey Katama Retreat – Welcome to this beautifully appointed, fully furnished home, offering the perfect blend of relaxed coastal living and effortless ownership. With a strong rental history and thoughtful upgrades throughout, this property is an exceptional opportunity as a year-round residenc...
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CONTINGENT OFFER
STILL SHOWING
Contingent
3rd September 2026
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LINK ID: 44919
Town: EDGARTOWN
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Click here for all Edgartown listings
Address:
31 Dodgers Hole Road, Edgartown MA 02539
Type: Single Family Residence
$1,625,000.00
Dodgers Hole - Delightful contemporary cape style home, centrally located, suitable for seasonal or year-round use. The privately sited half acre lot features a first floor primary bedroom with en-suite bath, a light filled eat-in kitchen, central A/C, full unfinished basement, a detached 18'x24' s...
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LINK ID: 44294
Town: VINEYARD HAVEN
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Click here for all Vineyard Haven listings
Address:
26 Union Court # 7, Vineyard Haven MA 02568
Type: Single Family Residence
$1,625,000.00
Waterview Condo in the Heart of Downtown Vineyard Haven. Experience the best of in-town living with this newly built, thoughtfully designed 2-bedroom condo offering beautiful harbor views and luxurious modern finishes. The first level welcomes you with a primary suite featuring a full bath with a t...
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LINK ID: 44552
Town: WEST TISBURY
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Click here for all West Tisbury listings
Address:
60A Davis Look Road, West Tisbury MA 02575
Type: Unimproved Land
$1,600,000.00
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...
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LINK ID: 44816
Town: VINEYARD HAVEN
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Click here for all Vineyard Haven listings
Address:
528 Main Street, Vineyard Haven MA 02568
Type: Single Family Residence
$1,600,000.00
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...
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LINK ID: 43281
Town: EDGARTOWN
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Click here for all Edgartown listings
Address:
501 West Tisbury Road, Edgartown MA 02539
Type: Unimproved Land
$1,595,000.00
Prime 2-acre parcel situated close to the bike path, state forest, Morning Glory Farm and Edgartown village. Per Edgartown BOH, this lot is approved to support a 5-bedroom home with a standard septic system. Additionally, with an advanced treatment system and a variance, the potential exists to expa...
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CONTINGENT OFFER
STILL SHOWING
Contingent
22nd October 2025
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LINK ID: 43800
Town: VINEYARD HAVEN
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Click here for all Vineyard Haven listings
Address:
22 Old Lighthouse Road, Vineyard Haven MA 02568
Type: Single Family Residence
$1,595,000.00
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 ...
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LINK ID: 44691
Town: OAK BLUFFS
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Click here for all Oak Bluffs listings
Address:
20 Hidden Cove Road, Oak Bluffs MA 02557
Type: Single Family Residence
$1,595,000.00
Nestled in this desirable Hidden Cove community, this contemporary residence offers a quintessential retreat centered on outdoor recreation and coastal living. Residents enjoy premier neighborhood amenities, including direct water access to Sengekontacket Pond for seamless kayaking and paddleboardin...
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PRICE CHANGE
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LINK ID: 44135
Town: WEST TISBURY
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Click here for all West Tisbury listings
Address:
26 Flint Hill Road, West Tisbury MA 02575
Type: Unimproved Land
$1,575,000.00
Stop Searching. Start Building. You've toured dozens of homes. Nothing feels right. What if your dream home on Martha's Vineyard simply hasn't been built yet? This rare 3.32-acre West Tisbury hilltop is the blank canvas you've been waiting for. Glacial boulders, open pasture, and cathedral oaks with...
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LINK ID: 44657
Town: CHILMARK
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Click here for all Chilmark listings
Address:
8 Rumpus Ridge, Chilmark MA 02535
Type: Single Family Residence
$1,550,000.00
Escape to your own getaway with mature landscaped gardens and privacy in the heart of Chilmark. Walk to the Chilmark Store, library, Chilmark Community Center, Beetlebung Farm and bank. Access to Chilmark beaches - Lucy Vincent and Squibnocket - and Menemsha Public Beach are a plus.
This four bedroo...
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LINK ID: 44931
Town: OAK BLUFFS
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Click here for all Oak Bluffs listings
Address:
8 Melrose Avenue, Oak Bluffs MA 02557
Type: Single Family Residence
$1,539,000.00
Incredible opportunity for workforce housing, live in one/rent the other, or multi generational family living. Main house has 4 levels of living space. Main floor living/kitchen/dining/full bath and laundry. 2nd floor has two bedrooms and full bath. 3rd floor is a large finished bonus room. The full...
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LINK ID: 44685
Town: WEST TISBURY
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Click here for all West Tisbury listings
Address:
150 Field View Lane, West Tisbury MA 02575
Type: Single Family Residence
$1,525,000.00
A pastoral country road leads to this enchanting wood-shingled Cape-style home, offering three bedrooms and a welcoming blend of comfort and charm. The open-concept kitchen flows into a sunken living and dining area, creating an inviting space for everyday living and entertaining. A desirable first-...
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LINK ID: 44783
Town: EDGARTOWN
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Click here for all Edgartown listings
Address:
8 Pip'n Circle, Edgartown MA 02539
Type: Single Family Residence
$1,500,000.00
CHAPPAQUIDDICK – Opportunity awaits on this conforming 3-acre parcel, featuring a year-round home with a 5-bedroom septic system, offering exceptional potential for future expansion, including a guest house. Privately tucked away off the main road, yet conveniently located just minutes from the Ch...
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LINK ID: 43832
Town: VINEYARD HAVEN
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Click here for all Vineyard Haven listings
Address:
455 State Road # 8, Vineyard Haven MA 02568
Type: Commercial
$1,500,000.00
Prime commercial opportunity in Vineyard Haven, Martha’s Vineyard’s vibrant year-round community! This 2,614± sq. ft. corner commercial condominium in popular Woodland Center Marketplace —one of the largest in a well-managed association—offers outstanding visibility and versatile space. Cur...
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LINK ID: 44891
Town: EDGARTOWN
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Click here for all Edgartown listings
Address:
36 Pine Street, Edgartown MA 02539
Type: Unimproved Land
$1,500,000.00
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...
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LINK ID: 44256
Town: WEST TISBURY
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Click here for all West Tisbury listings
Address:
111 Charles Neck Way, West Tisbury MA 02575
Type: Single Family Residence
$1,499,000.00
Tucked away on 1.6 wooded acres in West Tisbury, this classic Cape-style home offers both privacy and convenience, with easy access to the charm of Up-Island and the amenities of Down-Island. Located on a paved road near Long Point Beach, it also includes coveted access to Lambert’s Cove Beach.
Th...
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LINK ID: 44338
Town: AQUINNAH
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Click here for all Aquinnah listings
Address:
393 Lighthouse Road, Aquinnah MA 02535
Type: Single Family Residence
$1,499,000.00
Ranch style home & Guest camp situated on 1+/- acre lot. The Main House offers distant views of Lobersterville beach and the Vineyard Sound beyond. Located in the desirable Lighthouse Road area, which offers walkable/close-by beach access and quiet roads. The view can be enjoyed from the Kitchen/Liv...
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LINK ID: 44518
Town: OAK BLUFFS
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Click here for all Oak Bluffs listings
Address:
7 Ploughshare Lane, Oak Bluffs MA 02557
Type: Single Family Residence
$1,499,000.00
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...
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LINK ID: 44254
Town: VINEYARD HAVEN
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Click here for all Vineyard Haven listings
Address:
110 Clover Hill Drive, Vineyard Haven MA 02568
Type: Single Family Residence
$1,495,000.00
Minutes to downtown and the ferry, this updated year-round home checks every box buyers are asking for right now: space, flexibility, and a move-in ready setup in a highly convenient location. 3 bedrooms, 4 bathrooms, and over 3,000 sq ft of living space, including a private lower-level apartment id...
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LINK ID: 44469
Town: OAK BLUFFS
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Click here for all Oak Bluffs listings
Address:
40 Hidden Cove Road Unit 2, Oak Bluffs MA 02557
Type: Condominium
$1,495,000.00
Enjoy timeless summers at this Hidden Cove condo, where days begin with a paddle on Sengekontacket Pond, afternoons are spent between the pool and tennis courts, and evenings end on the deck after a day spent exploring the island. This three-bedroom unit has distant water views and offers an easy, m...
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PRICE CHANGE
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Prices are subject to change without notice. |
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