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: 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: 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: 113 Dukes County Avenue | Town: Oak Bluffs | Link ID: 43846
Price: $2,289,000
UNIQUE IN-TOWN INVESTMENT opportunity in the heart of Oak Bluffs. This COMMERCIALLY ZONED B1 property offers flexibility and a strong existing rental history. Built in 2017, the MULTI-FAMILY building combines modern efficiency with an unbeatable location — just a short stroll to Oak Bluffs harbor,... 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: 7 Upper Meadow Lane | Town: Oak Bluffs | Link ID: 43262
Price: $1,799,000
Meadowview Farms — This home is ideal for those who love to host lively gatherings! Set at the end of a quiet cul-de-sac, this spacious Colonial offers over 3,200 sq ft designed for comfortable living and easy entertaining. The home features four bedrooms and 2.5 baths, including a primary suite w... 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: 56 Garvin Street | Town: Oak Bluffs | Link ID: 44143
Price: $1,350,000
Single Story Bungalow — Turnkey & Walkable Lifestyle! Welcome to this beautifully updated home offering effortless single-level living and a bright, open layout designed for comfort and functionality. Turnkey and thoughtfully renovated, the property seamlessly blends classic charm with modern upgr... 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: 22 Montgomery Square | Town: Oak Bluffs | Link ID: 44151
Price: $895,000
Located in the heart of Wesleyan Grove within the historic Martha’s Vineyard Camp Meeting Association, this enchanting year-round Victorian cottage captures the timeless charm and vibrant spirit of Oak Bluffs living. Just steps from lively Circuit Avenue, picturesque Oak Bluffs Harbor, and sandy b... 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
Welcome to Lagoon Ridge.....Oak Bluffs’ newest and most sought-after neighborhood! Build your 3 bedroom dream home on this lofty setting, 95 feet above Lagoon Pond, featuring sweeping sky views, colorful sunsets, and refreshing salty sea breezes. This exceptional building lot is among the last o... 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: 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: 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