Oak Bluffs Properties for Sale
Address: 400 Barnes Road | Town: Oak Bluffs | Link ID: 43551
Price: $6,395,000
Experience the quiet elegance of this rare Asian-inspired contemporary estate set on 2.42 acres in a prime Oak Bluffs location. Tucked behind a long private drive and surrounded by 234 acres of Southern Woodlands conservation land offering biking and hiking, this expansive property offers unparallel... Click here for more details
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: 217 Barnes Road | Town: Oak Bluffs | Link ID: 44172
Price: $5,695,000
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: 385 Barnes Road | Town: Oak Bluffs | Link ID: 42465
Price: $5,495,000
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: $5,325,000
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: 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: 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: 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: 33 Ocean Avenue | Town: Oak Bluffs | Link ID: 43991
Price: $2,950,000
A rare offering on iconic Ocean Park. This beautifully renovated Victorian cottage sits in the heart of historic Oak Bluffs with unencumbered views of Ocean Park and Vineyard Sound. Completely rebuilt in 2024, the 3-bedroom home blends classic Vineyard charm with modern comforts, featuring a welcomi... Click here for more details
Address: 34 Windemere Road | Town: Oak Bluffs | Link ID: 40654
Price: $2,700,000
Perfect opportunity to own a Beautiful Beach Cottage with access to Lagoon. Totally renovated in 2019. It has been designed for relaxed living and memorable entertaining. There are 3 seating areas on the deck, to enjoy dining outside, experiencing incredible waterviews and lovely sky reflections of ... Click here for more details
Address: 23 Circuit Avenue Extension | Town: Oak Bluffs | Link ID: 44170
Price: $2,600,000
Rare Opportunity with Endless Possibilities – Unmatched Harbor & Vineyard Sound Views. Location, Location, Location! A truly rare offering in the heart of Oak Bluffs, where properties like this seldom become available. Positioned directly across from the iconic Oak Bluffs Harbor, this property boa... Click here for more details
Address: 23 Circuit Avenue Extension | Town: Oak Bluffs | Link ID: 44169
Price: $2,600,000
Rare Opportunity with Endless Possibilities – Unmatched Harbor & Vineyard Sound Views. Location, Location, Location! A truly rare offering in the heart of Oak Bluffs, where properties like this seldom become available. Positioned directly across from the iconic Oak Bluffs Harbor, this property boa... Click here for more details
Address: 50 Hidden Cove Road | Town: Oak Bluffs | Link ID: 44263
Price: $2,400,000
Sengekontacket–Walk into a “turn-key” opportunity located within the desirable Hidden Cove community, centrally located to the down-Island villages, ferries, shopping and dininig, and just steps (.3 miles) from Sengekontacket Pond with access to State Beach and Nantucket Sound beyond. The lovi... Click here for more details
Address: 3 Hidden Cove Road | Town: Oak Bluffs | Link ID: 44214
Price: $2,295,000
COMING SOON: HIDDEN COVE GEM WITH SERENE POND VIEWS AND COVETED WATER ACCESS. Located in the desirable Hidden Cove enclave, a 65+ acre water-access community with direct access to Sengekontacket Pond and Nantucket Sound, this inviting contemporary home offers privacy, comfort, and high-end finishes ... 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: 12 & 14 Maple Avenue | Town: Oak Bluffs | Link ID: 43290
Price: $1,830,000
Two Historic Oak Bluffs Cottages - Prime Location – Deeded Separately Perched atop a gentle hill, surrounded by lush, established gardens in one of the island’s most storied neighborhoods, these two charming 1909 twin cottages offer a rare opportunity to own a piece of local history—just a sho... Click here for more details
Address: 18 Wood Duck Way | Town: Oak Bluffs | Link ID: 44018
Price: $1,800,000
Being sold turnkey this modern home has four bedrooms and three full baths. Large windows and high 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 complement the cherry stairs and living room built-... Click here for more details
Address: 17 John Wesley Avenue | Town: Oak Bluffs | Link ID: 44267
Price: $1,795,000
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: 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: 103 Meadow View Road | Town: Oak Bluffs | Link ID: 43994
Price: $1,750,000
Nestled on a rare, oversized 1.5-acre lot, this spacious 3-bed/2 1/2 bath contemporary home offers a perfect blend of privacy and coastal convenience. Perched elegantly upon a gentle rise, the residence is bathed in natural light and framed by a beautifully landscaped lawn with mature plantings. T... Click here for more details
Address: 38 Rogers Way | Town: Oak Bluffs | Link ID: 43756
Price: $1,595,000
Tucked away in a private desirable Oak Bluffs neighborhood yet only minutes from the charm of downtown and the incredible OB beaches, this home is a wonderful island retreat. The neighborhood is a must see to fully appreciate this property. With four levels of finished living space, it offers room... Click here for more details
Address: 5 Seths Path | Town: Oak Bluffs | Link ID: 43862
Price: $1,450,000
Desirable picturesque Deer Run location. Just steps from the bike path, this centrally located home is a perfect island retreat. You can enjoy the multi level deck and patio overlooking a wonderful in ground pool. The large lot provides for plenty of room for gardening or games and backs up to an ... Click here for more details
Address: 101 Tradewinds Road | Town: Oak Bluffs | Link ID: 43985
Price: $1,435,000
Set on just over half an acre near downtown Oak Bluffs abutting permanently preserved acres by Land Bank - a rare find in central Oak Bluffs! This home blends classic Midcentury architectural character with abundant natural light from floor-to-ceiling windows and soaring post-and-beam ceilings creat... Click here for more details
Address: 6 Stone Pound Way | Town: Oak Bluffs | Link ID: 44033
Price: $1,399,000
The ambience of this tranquil Waterfront community will inspire you immediately. This spacious 3 bedroom w/oversized family room home is affordably priced. The sun shines in the charming living room w/ brick fireplace, Palladian side windows, Rennai gas monitor & attractive hardwood floors. The amp... Click here for more details
Address: 54 Columbian Avenue | Town: Oak Bluffs | Link ID: 44084
Price: $1,295,000
Nestled in a quiet Oak Bluffs neighborhood, this charming, sun-filled four-bedroom, two-bath home sits on a spacious corner lot and offers an ideal opportunity for both seasonal and year-round living. The home features a functional layout with a cozy wood burning stove and abundant natural light thr... Click here for more details
Address: 9 Brunswick Avenue | Town: Oak Bluffs | Link ID: 43451
Price: $1,295,000
PRIME LOCATION! Beautifully Renovated in Oak Bluffs! This move-in ready home at 9 Brunswick Ave has been thoughtfully and extensively UPDATED inside and out. Enjoy peace of mind with a NEW septic system, siding, windows, water line from the street, and upgraded electrical and plumbing. The interior ... 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: 3 Kims Way | Town: Oak Bluffs | Link ID: 44108
Price: $1,195,000
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: 28 Barling Avenue | Town: Oak Bluffs | Link ID: 43825
Price: $999,000
Oak Bluffs: Home Sweet Home Situated on over a quarter acre of beautifully landscaped, level grounds with colorful perennial plantings and mature trees, this sun-filled ranch offers a perfect blend of comfort and charm. The open kitchen, dining, and living areas feature cathedral ceilings, classic v... Click here for more details
Address: 50 Canonicus Avenue | Town: Oak Bluffs | Link ID: 42877
Price: $925,000
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: 67 Hudson Avenue | Town: Oak Bluffs | Link ID: 44201
Price: $925,000
Located in a convenient Oak Bluffs setting, this 2-bedroom, 2-bath home offers approximately 1,000 square feet of living space on a generous .69-acre lot. Built in 2014, the property presents an excellent opportunity for a year-round residence, vacation getaway, or investment. The property is being ... Click here for more details
Address: 4 Quail Run | Town: Oak Bluffs | Link ID: 44245
Price: $899,000
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: 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: 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 - A Rare Opportunity to purchase an 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 prope... Click here for more details
Address: 26 Winthrop Avenue | Town: Oak Bluffs | Link ID: 42248
Price: $849,000
Hidden behind a wall of vegetation on Winthrop Avenue this is a little 'oasis' of a piece of land. One bedroom house situated on a 1/3 Acre, 14,810 sq.ft. level lot. One side of the property is lush with vegetation and the opposite side is clear. It is one lot in total and may not be subdivided. ... Click here for more details
Address: 35 Double Ox Road | Town: Oak Bluffs | Link ID: 43296
Price: $700,000
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: 56 Holmes Hole Road | Town: Oak Bluffs | Link ID: 42990
Price: $674,000
Presenting a unique opportunity to acquire a wooded level lot located on Holmes Hole Road in Oak Bluffs, encompassing a .49-acre parcel situated within a Residential Urban (RU) zoning district. This property offers a serene environment ideal for constructing a home while remaining conveniently close... 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: 21 Island Inn Road | Town: Oak Bluffs | Link ID: 43931
Price: $560,000
Own a piece of the Vineyard dream with a fully furnished, beautifully updated condo perfectly designed for comfort and vacation living at the Island Inn Country Club in Oak Bluffs. The location is just off Beach Road, a short distance to beaches, downtown Circuit Ave, and a lovely drive along Beach ... Click here for more details
Address: 0 California Avenue | Town: Oak Bluffs | Link ID: 42933
Price: $465,000
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
Address: 0 Heather Lane | Town: Oak Bluffs | Link ID: 43465
Price: $425,000
Lovely untouched piece of land waiting for you to create your own special island retreat. Property, being sold "AS IS", is nestled on a quiet dead end road off of DeBettencourt Place in Oak Bluffs. Conveniently located within walking distance to downtown OB, OB Ferry, beaches, parks, arts district ... Click here for more details