Oak Bluffs Properties for Sale
Address: 43 Sengekontacket Road | Town: Oak Bluffs | Link ID: 36712
Price: $5,995,000
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... Click here for more details
Address: 8 Paddock Road | Town: Oak Bluffs | Link ID: 44395
Price: $5,450,000
Refined Vineyard Living in The Preserve - Set atop a knoll overlooking sweeping grassland and the pond, this exceptional residence embodies the perfect balance of classic coastal architecture and modern sophistication. Located within the prestigious enclave of The Preserve, the home offers a combina... Click here for more details
Address: 385 Barnes Road | Town: Oak Bluffs | Link ID: 42465
Price: $5,295,000
SPECTACULAR WATERFRONT ESCAPE WITH POOL AND UNFORGETTABLE SUNSETS. Set along a coveted stretch of Lagoon frontage, this beautifully designed waterfront home captures the essence of relaxed luxury on Martha’s Vineyard. With 125 feet of private sandy beachfront and over 5,400 square feet of living s... Click here for more details
Address: 4 Canonicus Avenue | Town: Oak Bluffs | Link ID: 43452
Price: $5,225,000
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... Click here for more details
Address: 7 Overview Lane | Town: Oak Bluffs | Link ID: 44341
Price: $5,100,000
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... Click here for more details
Address: 217 Barnes Road | Town: Oak Bluffs | Link ID: 44172
Price: $4,850,000
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... Click here for more details
Address: 8 Fresh Pond Road | Town: Oak Bluffs | Link ID: 44237
Price: $4,695,000
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, ... Click here for more details
Address: 15 Tamarack Lane | Town: Oak Bluffs | Link ID: 44208
Price: $4,600,000
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: 28 Beach Road | Town: Oak Bluffs | Link ID: 44234
Price: $3,750,000
Location, Location, location....This is rare opportunity to own a water front property with 240 degree views of the Harbor and Sound. The property is 5 minutes from either Ferry terminal and walking distance to East beach . The house is suitable for year round living , seasonal income and comfort th... Click here for more details
Address: 9 Weston Avenue | Town: Oak Bluffs | Link ID: 44615
Price: $3,750,000
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,... Click here for more details
Address: 98 Farm Neck Way | Town: Oak Bluffs | Link ID: 44316
Price: $3,750,000
Farm Neck Golf Club – Undeveloped Water View Parcel with Membership A truly rare opportunity to acquire a 1.92-acre undeveloped parcel within the prestigious Farm Neck Golf Club community, one of the last remaining opportunities of its kind. This exceptional offering features sweeping water views... Click here for more details
Address: 27 Double Ox Road | Town: Oak Bluffs | Link ID: 44528
Price: $3,400,000
Set on a private 1.34-acre parcel along a winding paved road in Oak Bluffs, this exceptional to-be-built residence offers the perfect blend of sophistication and refined Vineyard style. The spacious floor plan offers over 3,200 square feet of living space, highlighted by a first-floor primary suite... Click here for more details
Address: 6 Brewster Avenue | Town: Oak Bluffs | Link ID: 42895
Price: $3,250,000
Enjoy sweeping water views from this beautifully updated East Chop Victorian, featuring a charming guest cottage. Renovated in 2010, the main home effortlessly blends historic character with modern comfort. The kitchen and bathrooms have been thoughtfully updated, enhancing functionality while prese... Click here for more details
Address: 44 Tiffany Drive | Town: Oak Bluffs | Link ID: 44347
Price: $2,900,000
Classic Vineyard charm meets modern luxury. Set on 1.38 private acres, this beautifully renovated 4BR/4.5BA Cape offers over 4,000 sq. ft. of living space, a gourmet kitchen, multiple entertaining areas, a screened porch, and a separate one-bedroom guest apartment above the garage. Renovations inclu... Click here for more details
Address: 34 Windemere Road | Town: Oak Bluffs | Link ID: 44300
Price: $2,579,000
Set along the shimmering edge of The Lagoon and Brush Pond, this rare offering captures the essence of classic island living, with expansive water views, on a little known enclave of only 9 homes. The house dates back to 1910 and was thoughtfully renovated in 2019, blending a timeless Vineyard loca... Click here for more details
Address: 12 Samoset Avenue | Town: Oak Bluffs | Link ID: 44579
Price: $2,575,000
Classic Oak Bluffs Victorian Steps from Beach, Harbor & Town.. Built in 1875 by famed architect Samuel Pratt, this Classic Oak Bluffs Victorian offers a rare opportunity to own a piece of Vineyard history just one block from the sandy beach. Located moments from the harbor, ferries, shops, restauran... Click here for more details
Address: 312 East Chop Drive | Town: Oak Bluffs | Link ID: 43898
Price: $2,295,000
“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: 4 High Meadow Lane | Town: Oak Bluffs | Link ID: 42967
Price: $2,260,000
Set within the coveted Meadow View Farms community, this exceptional post-and-beam residence offers timeless craftsmanship, generous living spaces, and nearly an acre of private beautifully landscaped grounds with significant potential for expansion. A full-length farmer’s porch creates a graciou... Click here for more details
Address: 35 Double OX Road | Town: Oak Bluffs | Link ID: 43866
Price: $2,250,000
Would you love to live or vacation in a brand-new home on Martha’s Vineyard? We have the LOCATION, REPUTABLE LONG-STANDING BUILDER & PROVEN TRACK RECORD! Come take a tour of the newest home under construction in the Lagoon Ridge neighborhood. Easy to show – Call now! To be built with lot purchas... Click here for more details
Address: 111 Eastville Avenue | Town: Oak Bluffs | Link ID: 36870
Price: $2,118,000
LARGE PRICE DROP. THIS IS A PERFECT LOCATION FOR WEDDING PARTIES. Just steps from the beach and minutes to both Oak Bluffs and Vineyard Haven, this fully furnished, turnkey coastal retreat offers an exceptional location paired with a strong, proven rental history. Set on an oversized lot just two ... Click here for more details
Address: 33 Vineyard Avenue | Town: Oak Bluffs | Link ID: 44349
Price: $1,995,000
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... Click here for more details
Address: 22 Old Harbor Lane | Town: Oak Bluffs | Link ID: 44113
Price: $1,850,000
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... Click here for more details
Address: 18 Wood Duck Way | Town: Oak Bluffs | Link ID: 44018
Price: $1,800,000
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... Click here for more details
Address: 2 Great Rock Road | Town: Oak Bluffs | Link ID: 44054
Price: $1,765,000
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... Click here for more details
Address: 68 Front Street | Town: Oak Bluffs | Link ID: 44077
Price: $1,755,000
Nestled at the end of a quiet street, this charming and spacious Cape-style home offers both privacy and convenience, just a short distance from the Oak Bluffs School and town center, and walking distance to the Lagoon. Thoughtfully maintained, the sun-filled main level boasts an open floor plan wit... Click here for more details
Address: 11 Beach Road | Town: Oak Bluffs | Link ID: 44641
Price: $1,745,000
Oceanfront Cottage on .21 acre of waterfront property and over 50ft of shoreline on East Chop. Wake up to breathtaking ocean views and the soothing sound of waves from this charming two-bedroom oceanfront cottage. Perfectly positioned along the shoreline, this inviting coastal retreat offers the ra... Click here for more details
Address: 17 John Wesley Avenue | Town: Oak Bluffs | Link ID: 44267
Price: $1,690,000
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... Click here for more details
Address: 7 Ploughshare Lane | Town: Oak Bluffs | Link ID: 44518
Price: $1,599,000
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: 40 Hidden Cove Road | Town: Oak Bluffs | Link ID: 44469
Price: $1,595,000
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... Click here for more details
Address: 40 Hidden Cove Road | Town: Oak Bluffs | Link ID: 44671
Price: $1,595,000
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... Click here for more details
Address: 26 Sea Glen Road | Town: Oak Bluffs | Link ID: 44199
Price: $1,495,000
Nestled in a desirable neighborhood, this beautifully maintained cape style home offers a rare blend of charm, flexibility and convenience in a serene island setting. Thoughtfully appointed throughout, the home welcomes you with an open living room that flows effortlessly into a bright dining area, ... Click here for more details
Address: 46 Kennebec Avenue | Town: Oak Bluffs | Link ID: 44374
Price: $1,395,000
This exquisite Victorian home, lovingly preserved by the same family for over a generation, stands in outstanding condition and is perfectly situated in the vibrant heart of Oak Bluffs Center. Enjoy the convenience of being just steps away from the Public Beach, Steamship Authority, Oak Bluffs Harbo... Click here for more details
Address: 3 Troy Street | Town: Oak Bluffs | Link ID: 44213
Price: $1,349,000
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: 61 Ocean Avenue | Town: Oak Bluffs | Link ID: 44475
Price: $1,299,000
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: 6 Stone Pound Way | Town: Oak Bluffs | Link ID: 44033
Price: $1,299,000
$100,000 PRICE REDUCTION !!! You cannot get all these amenities in another property in this price range!! Hidden Cove Waterfront community is a peaceful tranquil neighborhood. This spacious 3 bedroom w/oversized family room home is VERY affordably priced. The sun shines in through skylights & the... Click here for more details
Address: 0 Pennsylvania Avenue | Town: Oak Bluffs | Link ID: 43914
Price: $1,250,000
Unique new construction opportunity on Pennsylvania Ave in Oak Bluffs! Offered preconstruction so there is the ability to customize, this modern carriage house includes a spacious 1-bedroom apartment (855 sq ft with full kitchen, living room and bathroom) above a 2-car garage. Ideal for year round o... Click here for more details
Address: 0 Temahigan Avenue & Dover Street | Town: Oak Bluffs | Link ID: 43457
Price: $1,200,000
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: 47 Winemack Avenue | Town: Oak Bluffs | Link ID: 44490
Price: $1,199,000
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: 3 Kims Way | Town: Oak Bluffs | Link ID: 44108
Price: $1,155,000
Recently updated Oak Bluffs ranch-style home ideally located near Downtown and Oak Bluffs Harbor. Step inside to discover vaulted ceilings and an airy open floor plan that seamlessly connects the living room, dining area, and a spacious kitchen featuring granite countertops and updated appliances. T... Click here for more details
Address: 30 Double Ox Road | Town: Oak Bluffs | Link ID: 44649
Price: $1,150,000
Create an extraordinary Martha's Vineyard estate in the exclusive Lagoon Ridge community of Oak Bluffs. This mostly wooded estate parcel of over one acre features gently rolling topography, providing an exceptional canvas for a custom-designed luxury residence. Privately situated within an intimate ... Click here for more details
Address: 21 Butler Avenue | Town: Oak Bluffs | Link ID: 44599
Price: $1,075,000
Located within the historic Martha’s Vineyard Camp Meeting Association, this rare double-lot property combines classic Campground charm with the comfort, privacy, and functionality of a thoughtfully modernized home. Two-car off-street parking—an exceptional Campground amenity—adds everyday con... Click here for more details
Address: 22 Firehouse Lane | Town: Oak Bluffs | Link ID: 44342
Price: $940,000
Tucked away on a quiet side street just 0.7 miles from Circuit Avenue, this charming Oak Bluffs cottage offers the rare combination of privacy and proximity to town. The original two-bedroom, one-bath home was thoughtfully expanded to include a bright great room that opens directly to a large fence... Click here for more details
Address: 4 Quail Run | Town: Oak Bluffs | Link ID: 44252
Price: $925,000
Welcome to this FULLY FURNISHED, private, 2-bedroom, end-unit townhouse offering 1,208 sq ft of effortless coastal living. With seasonal rentals already in place this opportunity is the defenition of TURN KEY. Thoughtfully designed with both comfort and style in mind, this coastal retreat blends rel... Click here for more details
Address: 50 Canonicus Avenue | Town: Oak Bluffs | Link ID: 42877
Price: $899,000
Rare Opportunity to Be in a Special Location and Neighborhood! Loved by generations, this quintessential Vineyard cottage has been in the same family since its creation in 1900. Step back in time and enjoy easy cottage living of yesteryear with modern updates including newer windows and electrical. ... Click here for more details
Address: 37 Circuit Avenue | Town: Oak Bluffs | Link ID: 44276
Price: $899,000
In the heart of Downtown Oak Bluffs- Restless Winds Condominium Unit #4 comes with an amazing roof top deck that is only shared with one other condo (#5). This spacious unit just under 1,000 sq. ft. has a ships feel with custom wood features and a ships ladder leading to the roof top deck. This cond... Click here for more details
Address: 4 Quail Run | Town: Oak Bluffs | Link ID: 44245
Price: $869,000
Located in a desirable waterfront community, this newly painted end-unit condo offers 1 bedroom plus a versatile loft and 1.5 bathrooms, combining comfort with easy, low-maintenance ownership. Residents enjoy a community dock, pond access, kayak storage, boat launch, a clubhouse, and tennis courts. ... Click here for more details
Address: 37 Circuit Avenue | Town: Oak Bluffs | Link ID: 44275
Price: $869,000
In the heart of Downtown Oak Bluffs Restless Winds Unit #5 comes with an amazing roof top deck shared with only one other condo (unit #4). You're in the middle of it all with this great location, yet you have easy access to a private and peaceful deck overlooking the town of Oak Bluffs and the surro... Click here for more details
Address: 24 Towanticut Avenue | Town: Oak Bluffs | Link ID: 44062
Price: $857,000
OAK BLUFFS - EIGHT (8) BEDROOM LOT. This already cleared, oversized lot, 16,895sq.ft., (more than 1/3 acre) comes with an Approved Eight (8) Bedroom Septic Design, ready to build. Exceptional potential for a spacious custom home, family compound, or a rental property. Utilities are available by t... Click here for more details
Address: 26 Winthrop Avenue | Town: Oak Bluffs | Link ID: 42248
Price: $839,000
This little gem is waiting to be polished. Hidden behind a wall of vegetation on Winthrop Avenue, an 'oasis', with tons of potential. Existing one bedroom, two story house situated on a 1/3 Acre of land, a 14,810 sq.ft. level lot. Land is large enough for a house and guest house when meeting ZBA ... Click here for more details
Address: 19 Perkins Avenue | Town: Oak Bluffs | Link ID: 44425
Price: $825,000
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: 7 Highland Avenue | Town: Oak Bluffs | Link ID: 44502
Price: $809,000
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: 60R Carol Lane | Town: Oak Bluffs | Link ID: 44640
Price: $794,000
Tucked away down a quiet lane just moments from downtown Oak Bluffs, sits this charming home. Nestled on just over an 8,400 sq. ft. lot, the property offers compact single-story living, ideal for those seeking simplicity while being close to everything the island. The bright, open concept features... Click here for more details
Address: 35 Double Ox Road | Town: Oak Bluffs | Link ID: 43296
Price: $695,000
GOING, GOING… GONE! This is the LAST 3-bedroom lot available in Cluster C. 12 lots SOLD 9 homes already built. Welcome to Lagoon Ridge Oak Bluffs’ newest and most sought-after neighborhood. This exceptional 3-bedroom building lot sits on a lofty setting approximately 95 feet above Lagoon Pond, ... Click here for more details
Address: 0-B California Avenue | Town: Oak Bluffs | Link ID: 43507
Price: $675,000
Oak Bluffs Buildable Lot – Prime Location This flat 3-bedroom building lot is ideally located just moments from the Hudson Avenue access to scenic Lagoon Pond, with easy access to both Farm Neck Golf Club and downtown Oak Bluffs. Situated in a neighborhood of newly constructed homes, this lot pres... Click here for more details
Address: 2 Lincoln Avenue | Town: Oak Bluffs | Link ID: 43836
Price: $640,000
Nestled in the heart of the historic Martha’s Vineyard Camp Meeting Association, this beautifully updated suite cottage offers the rare opportunity for year-round living in Oak Bluffs’ campground community. Fully renovated in 2023, including kitchen, bath, floors and winterization, the home seam... Click here for more details
Address: 0-A California Avenue | Town: Oak Bluffs | Link ID: 43517
Price: $625,000
Oak Bluffs Buildable Lot – Prime Location. This flat 2-bedroom building lot is ideally located just moments from the Hudson Avenue access to scenic Lagoon Pond, with easy access to both Farm Neck Golf Club and downtown Oak Bluffs. Situated in a neighborhood of newly constructed homes, this lot pre... Click here for more details
Address: 112 Dukes County Avenue | Town: Oak Bluffs | Link ID: 44094
Price: $599,000
Downtown Oak Bluffs B1-zoned parcel offering a rare mixed-use development opportunity in one of Martha’s Vineyard’s most iconic and active locations. Conveniently located near Inkwell Beach, Oak Bluffs Harbor, the Steamship Authority, day-trip ferry services, Circuit Avenue, and Ocean Park. Thi... Click here for more details
Address: 0 California Avenue | Town: Oak Bluffs | Link ID: 42933
Price: $429,000
Nice level building lot ready for your ideas on how best to create your near town home on a quiet street. This is an established neighborhood and one of the last lots left to build on. Perc test has been done. This is in Zone 2 which allows for a one bedroom home of any size. Water and electric are ... Click here for more details