Oak Bluffs Properties for Sale
Address: 233 East Chop Drive | Town: Oak Bluffs | Link ID: 44725
Price: $6,900,000 | Status: Active
Perched high above the East Chop bluffs beside the historic lighthouse, this exceptional waterfront estate offers timeless character, breathtaking views, and an unmatched coastal setting. The main residence has beautifully preserved much of its original charm and features a gracious living room with... Click here for more details
Address: 53 Circuit Avenue | Town: Oak Bluffs | Link ID: 44355
Price: $5,500,000 | Status: Active
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... Click here for more details
Address: 53 Circuit Avenue | Town: Oak Bluffs | Link ID: 44869
Price: $5,500,000 | Status: Active
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... Click here for more details
Address: 31 Circuit Avenue Extension | Town: Oak Bluffs | Link ID: 44996
Price: $5,500,000 | Status: Active
The North Bluff: A rare opportunity to acquire one of Oak Bluffs’ most iconic properties. Originally built in 1913 and expanded over the years, this distinctive property occupies a prominent setting within the B-2 district, offering a unique range of residential and commercial opportunities. Cheri... Click here for more details
Address: 43 Sengekontacket Road | Town: Oak Bluffs | Link ID: 36712
Price: $5,495,000 | Status: Active
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: $5,225,000 | Status: Active
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 | Status: Active
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: 3 Oak Bluffs Avenue | Town: Oak Bluffs | Link ID: 44917
Price: $5,000,000 | Status: Active
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—... Click here for more details
Address: 8 Fresh Pond Road | Town: Oak Bluffs | Link ID: 44237
Price: $4,695,000 | Status: Active
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 | Status: Active
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: 217 Barnes Road | Town: Oak Bluffs | Link ID: 44172
Price: $4,450,000 | Status: Active
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: 267 Barnes Road | Town: Oak Bluffs | Link ID: 44896
Price: $4,395,000 | Status: Active
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... Click here for more details
Address: 9 Weston Avenue | Town: Oak Bluffs | Link ID: 44615
Price: $3,750,000 | Status: Active
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: 99 Ocean Avenue | Town: Oak Bluffs | Link ID: 44771
Price: $3,700,000 | Status: Active
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, ... Click here for more details
Address: 27 Double Ox Road | Town: Oak Bluffs | Link ID: 44528
Price: $3,400,000 | Status: Active
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: $3,100,000 | Status: Active
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: 27 Beach Road | Town: Oak Bluffs | Link ID: 44793
Price: $2,995,000 | Status: Active
WATERFRONT WITH DOCK – Nestled along the sparkling shores of Vineyard Haven Harbor, this waterfront cottage presents a rare opportunity to own a piece of Martha's Vineyard history. Originally part of the iconic Mary Guerin Inn, the home blends timeless Vineyard charm with an exceptional setting fe... Click here for more details
Address: 31 Temahigan Avenue | Town: Oak Bluffs | Link ID: 44308
Price: $2,678,000 | Status: Active
NEW CONSTRUCTION IN OAK BLUFFS WITH VINEYARD HAVEN HARBOR VIEWS Currently under construction and anticipated to be completed in Fall 2026, this thoughtfully designed four-bedroom, three-and-one-half-bath home pairs contemporary comfort with classic Vineyard character. Offering approximately 2,363 sq... Click here for more details
Address: 111 Eastville Avenue | Town: Oak Bluffs | Link ID: 36870
Price: $2,600,000 | Status: Active
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: 24 Harrison Avenue | Town: Oak Bluffs | Link ID: 44863
Price: $2,595,000 | Status: Active
East Chop with Water View! The perfect size vacation house or year round living, with all the bells and whistles, water views and located in the most desired neighborhood on East Chop! Designed by Hutker Architects, built with high quality craftsmanship by J.G. Early and landscape design by Dan Gord... Click here for more details
Address: 44 Tiffany Drive | Town: Oak Bluffs | Link ID: 44347
Price: $2,595,000 | Status: Active
Tucked away in a serene setting and set on 1.38 private acres, this beautifully renovated 4BR/4.5BA Cape offers over 4,000 sq. ft. of living space with plenty of room for a backyard pool. The main portion of the house includes a gourmet kitchen, multiple entertaining areas including living room, fam... Click here for more details
Address: 59 Tuckernuck Avenue | Town: Oak Bluffs | Link ID: 44701
Price: $2,595,000 | Status: Active
Located in the heart of downtown Oak Bluffs, this charming updated home seamlessly blends classic Vineyard character with bright, modern comfort. Greeting you from the street is an expansive wraparound porch framed by vibrant hydrangeas and a cozy second-floor balcony. Step inside to an inviting ope... Click here for more details
Address: 34 Windemere Road | Town: Oak Bluffs | Link ID: 44300
Price: $2,579,000 | Status: Active
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 | Status: Pending
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: 61 Canonicus Avenue | Town: Oak Bluffs | Link ID: 44939
Price: $2,200,000 | Status: Active
Location, location, location: This 1999 home with all the comforts of the 21 st Century is nestled on a landscaped lot within mellow surroundings. And yet … it’s located within mere moments of town, beach, bike path, bus line, parks, recreation, Farm Pond and a Land Bank trail. The situation har... Click here for more details
Address: 312 East Chop Drive | Town: Oak Bluffs | Link ID: 43898
Price: $2,195,000 | Status: Pending
“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: $2,195,000 | Status: Active
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: 51 Winemack Street & 0 Meadow Ave & Nahomon Street | Town: Oak Bluffs | Link ID: 44802
Price: $2,045,000 | Status: Active
East Chop colonial style 2BR/2BA year-round home on East Chop PLUS a separate buildable lot behind the house. The house at 51 Winemack St has a 2-bedroom Title V septic that recently passed inspection, full basement, electric baseboard heat and large yard that allows for expansion potential of the h... Click here for more details
Address: 22 Paddock Road | Town: Oak Bluffs | Link ID: 44785
Price: $1,895,000 | Status: Active
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... Click here for more details
Address: 33 Tia Anna Lane | Town: Oak Bluffs | Link ID: 44718
Price: $1,850,000 | Status: Pending
33 Tia Anna Lane has so much to offer; a charming, bright, renovated main and guest house on a half-acre in Oak Bluffs with proximity to town and walking distance to Lagoon Pond for swimming, fishing, boating and sunset enjoyment. The property is ready to enjoy, offering a turn-key home on a quiet s... Click here for more details
Address: 22 Old Harbor Lane | Town: Oak Bluffs | Link ID: 44113
Price: $1,850,000 | Status: Pending
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 | Status: Active
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: 8 Peqout Avenue | Town: Oak Bluffs | Link ID: 45003
Price: $1,775,000 | Status: Active
Set just across from iconic Inkwell Beach in Oak Bluffs’ historic Copeland District, 8 Pequot Avenue offers a rare combination of architectural character, water views and an exceptional in-town location. Built in 1870, this distinctive Victorian retains many of the period details that make this ne... Click here for more details
Address: 2 Great Rock Road | Town: Oak Bluffs | Link ID: 44054
Price: $1,765,000 | Status: Active
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: 44938
Price: $1,755,000 | Status: Active
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... Click here for more details
Address: 11 Beach Road | Town: Oak Bluffs | Link ID: 44641
Price: $1,745,000 | Status: Active
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... Click here for more details
Address: 33 Vineyard Avenue | Town: Oak Bluffs | Link ID: 44349
Price: $1,695,000 | Status: Active
33 Vineyard Avenue Oak Bluffs offers immense investment and flexible living opportunity with TWO UNITS on a fully irrigated appx 5200 sq ft lot. Fully gut renovated with all BRAND NEW; electric, plumbing, roof, septic system, and structural engineering - highlighted by elevated finishes, classic ae... Click here for more details
Address: 17 John Wesley Avenue | Town: Oak Bluffs | Link ID: 44267
Price: $1,650,000 | Status: Active
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: 13 Beach Road | Town: Oak Bluffs | Link ID: 44703
Price: $1,599,000 | Status: Pending
OAK BLUFFS Beach Road: VINEYARD HAVEN OUTER HARBOR WATERFRONT WITH DOCK… 1860’s Beach House with substantial 60’ dock built in 2004, is situated on OUTER HARBOR in private waterfront setting. Enjoy all variety of watersports, dramatic sunsets every evening, refreshing swims, or just relax on y... Click here for more details
Address: 20 Hidden Cove Road | Town: Oak Bluffs | Link ID: 44691
Price: $1,595,000 | Status: Active
Hidden Cove Retreat — Water Access, Tennis & Pickleball Set within the sought-after Hidden Cove community, a 65-acre private enclave with direct access to Sengekontacket Pond, this contemporary retreat offers an exceptional Martha’s Vineyard lifestyle. Residents enjoy a private community boat d... Click here for more details
Address: 22 Trinity Park | Town: Oak Bluffs | Link ID: 45021
Price: $1,550,000 | Status: Active
Rare Oak Bluffs Offering: TWO Detached Gingerbread Cottages which are historic jewels in the heart of Martha’s Vineyard Camp Meeting Association, (MVCMA). Located at 22 Trinity Park, this exceptional property offers a front-row view of the historic Tabernacle and its legendary festivities. The Pri... Click here for more details
Address: 8 Melrose Avenue | Town: Oak Bluffs | Link ID: 44931
Price: $1,539,000 | Status: Active
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... Click here for more details
Address: 40 Hidden Cove Road | Town: Oak Bluffs | Link ID: 44469
Price: $1,495,000 | Status: Active
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: $1,495,000 | Status: Active
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: 10 Ploughshare Lane | Town: Oak Bluffs | Link ID: 45002
Price: $1,489,000 | Status: Active
A wonderful opportunity to enjoy island living within one of Oak Bluffs’ most desirable private communities. Set on over 65 acres, Hidden Cove offers the perfect combination of privacy, recreation, and easy Vineyard living. This contemporary three-bedroom and three bath home has been thoughtfully ... Click here for more details
Address: 39 Chickawaukee Street | Town: Oak Bluffs | Link ID: 43374
Price: $1,475,000 | Status: Active
Renovated Cape style home in the desirable East Chop neighborhood of Oak Bluffs, offering the perfect combination of coastal charm, modern updates and an exceptional location. This bright and inviting 3-bedroom, 2-bath home features a spacious open floor plan, coastal-inspired décor throughout, and... Click here for more details
Address: 4 Lagrange Avenue | Town: Oak Bluffs | Link ID: 43835
Price: $1,450,000 | Status: Active
New listing tucked away on a dead end road in Oak Bluffs ~Enjoy the best of Vineyard living from this beautifully renovated Oak Bluffs home, ideally located just a short walk from a private Lagoon beach—perfect for swimming, kayaking, paddleboarding and all your favorite water activities. The invi... Click here for more details
Address: 7 Ploughshare Lane | Town: Oak Bluffs | Link ID: 44518
Price: $1,399,000 | Status: Active
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: 234 County Road | Town: Oak Bluffs | Link ID: 44895
Price: $1,375,000 | Status: Active
Surprisingly roomy Cape-style home, centrally located in Oak Bluffs and right across from the bike path. This five-bedroom house offers generously scaled living spaces throughout, including a large living room filled with natural light, an open stairway, a spacious dining room, and an updated kitche... Click here for more details
Address: 4 Periwinkle Lane | Town: Oak Bluffs | Link ID: 44907
Price: $1,295,000 | Status: Active
Stylish, thoughtfully designed ranch style home built in 2014 is bright and sunny. Tucked away in a private tranquil setting just a stroll to downtown, harbor, beaches, ferries, library, restaurants and shops, the home features solar panels, large living room with separate dining area, kitchen with ... Click here for more details
Address: 11 Stanley Street | Town: Oak Bluffs | Link ID: 44832
Price: $1,255,000 | Status: Active
Charming Oak Bluffs Ranch on a Peaceful Cul-de-Sac Welcome to this inviting 3-bedroom, 1.5-bath ranch-style home nestled on a generous .35-acre lot at the end of a peaceful cul-de-sac in Oak Bluffs, Massachusetts. Ideally located near the beach and town center, this property offers a wonderful blend... Click here for more details
Address: 0 Pennsylvania Avenue | Town: Oak Bluffs | Link ID: 43914
Price: $1,250,000 | Status: Active
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: 455 County Road | Town: Oak Bluffs | Link ID: 44903
Price: $1,200,000 | Status: Active
Lovely residential lot with a rural feel. Conforming 1.397 acre wooded lot in R3 with 150ft frontage on County Rd very close to the entrance to Meadow View Farm. Residential with bike path access along County Rd. Has been surveyed, staked & tagged. Town water available along County Rd. Electric acce... Click here for more details
Address: 170 Barnes Road | Town: Oak Bluffs | Link ID: 44775
Price: $1,195,000 | Status: Active
Solid Cape-style home located one block from Sailing Camp Park and Medeiros Cove offering water access to the Lagoon and one mile to all the excitement that downtown Oak Bluffs has to offer. The first floor offers a spacious eat in kitchen that is open to the dining room. A full bathroom with laundr... Click here for more details
Address: 30 Double Ox Road | Town: Oak Bluffs | Link ID: 44649
Price: $1,150,000 | Status: Active
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: 47 Winemack Avenue | Town: Oak Bluffs | Link ID: 44490
Price: $1,100,000 | Status: Active
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: 54 Towanticut Avenue | Town: Oak Bluffs | Link ID: 44808
Price: $1,100,000 | Status: Active
Living is easy in this beautifully maintained 3-bedroom, 2-bath air-conditioned Ranch located just one mile from the center of Oak Bluffs. Features include a spacious living room with a wood-burning fireplace, an updated kitchen with granite countertops and stainless-steel appliances, and a dining a... Click here for more details
Address: 2 Winemack Street | Town: Oak Bluffs | Link ID: 44805
Price: $1,095,000 | Status: Pending
Located at the southern end of Winemack Street, this inviting 3-bedroom, 2-bath Oak Bluffs home offers a quiet residential setting in a neighborhood of both year-round and seasonal homes, while remaining remarkably close to everything Oak Bluffs has to offer. Just approximately 1.2 miles from downto... Click here for more details
Address: 323 County Road | Town: Oak Bluffs | Link ID: 44799
Price: $1,095,000 | Status: Active
This charming Cape-style home is set on a beautifully landscaped lot filled with colorful blooming perennials, offering a peaceful setting just off the bike path. Ideally located, it's only a short ride to the town center and ferry, making it an excellent year-round residence, vacation getaway, or p... Click here for more details
Address: 0 Temahigan Avenue & Dover Street | Town: Oak Bluffs | Link ID: 43457
Price: $1,049,000 | Status: Active
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: 68 Pond View Drive | Town: Oak Bluffs | Link ID: 44714
Price: $975,000 | Status: Active
Create your ideal island retreat on this exceptional 1.068-acre parcel in Oak Bluffs. This desirable homesite comes with approved plans for a six-bedroom septic system, saving valuable time and expense as you begin the building process. The property also includes a topographic/boundary survey and so... Click here for more details
Address: 3 Dukes County Avenue | Town: Oak Bluffs | Link ID: 44841
Price: $935,000 | Status: Active
A Gem of a Marthas Vineyard Camp Meeting House Association Home, 3 Dukes County Ave. Located down from the Oak Bluffs Harbor. A couple house from Sunset Pond. Convenient to Beaches,Harbor, Resturants, Shopping, Dancing Music and walk to and from the Steamship Authority. 2 bedroom,1 queen bedroom 1 f... Click here for more details
Address: 67 Hudson Avenue | Town: Oak Bluffs | Link ID: 44201
Price: $925,000 | Status: Pending
ALL OFFERS REQUIRE COURT APPROVAL in multiple jurisdictions and may be somewhat lengthy. A straightforward offer is encouraged and may help expedite the required court approvals in multiple jurisdictions. Located in a convenient Oak Bluffs setting, this 2-bedroom, 2-bath home offers approximately 1... Click here for more details
Address: 4 Quail Run | Town: Oak Bluffs | Link ID: 44252
Price: $925,000 | Status: Active
TURN KEY OPPORTUNITY! Own your own slice of Martha's Vineyard for under a million dollars! Just book your flight/ ferry and move right in! Come enjoy the ameneties, relax and unplug. Welcome to this private, 2-bedroom, end-unit townhouse offering 1,208 sq ft of effortless coastal living. Thoughtfull... Click here for more details
Address: 37 Circuit Avenue | Town: Oak Bluffs | Link ID: 44276
Price: $879,000 | Status: Active
Intown Oak Bluffs Condo with Panoramic Rooftop Views Discover the charm of island living in this exceptional 2-bedroom, 1-bath condo in the heart of Oak Bluffs. Just under 1,000 square feet, this comfortable residence combines character, comfort, and an unbeatable in-town location. Step inside to an... Click here for more details
Address: 15 Rogers Way | Town: Oak Bluffs | Link ID: 41810
Price: $850,000 | Status: Active
Build Your Dream Home. Close to town and all that Oak Bluffs has to offer, Roger’s Way is a small enclave offering a wonderful opportunity to create your own Vineyard retreat. A paved road leads to 15 Roger’s Way, one of the last remaining lots in this desirable neighborhood. A three-bedroom sep... Click here for more details
Address: 37 Circuit Avenue | Town: Oak Bluffs | Link ID: 44275
Price: $849,000 | Status: Active
In-Town Oak Bluffs Condo with Panoramic Water Views Experience the best of island living in this charming in-town Oak Bluffs condo, offering just under 800 square feet of comfortable and versatile living space. The condo features one generously sized bedroom plus a separate sleep nook, offering flex... Click here for more details
Address: 4 Quail Run | Town: Oak Bluffs | Link ID: 44245
Price: $849,000 | Status: Active
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: 50 Canonicus Avenue | Town: Oak Bluffs | Link ID: 42877
Price: $825,000 | Status: Active
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: 7 Highland Avenue | Town: Oak Bluffs | Link ID: 44502
Price: $809,000 | Status: Active
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: 19 Perkins Avenue | Town: Oak Bluffs | Link ID: 44425
Price: $799,000 | Status: Active
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: 24 Towanticut Avenue | Town: Oak Bluffs | Link ID: 44062
Price: $789,000 | Status: Active
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: 60R Carol Lane | Town: Oak Bluffs | Link ID: 44640
Price: $785,000 | Status: Active
Charming Oak Bluffs Retreat Near Town Tucked away down a quiet lane just moments from downtown Oak Bluffs, this charming home offers the perfect blend of simplicity, comfort, and convenience. Set on just over 8,400 square feet, the property provides easy, single-story living in a sought-after Oak Bl... Click here for more details
Address: 10 Siloam Avenue | Town: Oak Bluffs | Link ID: 40546
Price: $685,000 | Status: Pending
The cottage has been maintained throughout the years, with a new roof in 2015, at which time it was insulated. The original Campground charm has been preserved thoughtfully. New mahogany boards are on front porch and a new paint job on the exterior of the cottage was done last year. The kitchen cabi... Click here for more details
Address: 0-B California Avenue | Town: Oak Bluffs | Link ID: 43507
Price: $675,000 | Status: Active
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: 35 Double Ox Road | Town: Oak Bluffs | Link ID: 43296
Price: $675,000 | Status: Active
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-A California Avenue | Town: Oak Bluffs | Link ID: 43517
Price: $625,000 | Status: Active
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: 35 Temahigan Avenue lot 5 | Town: Oak Bluffs | Link ID: 43050
Price: $595,000 | Status: Pending
Serious Seller.......Price will be discounted for cash sale................A perfect Vineyard location that is convenient to beaches, a bike path and both downtown Oak Bluffs and Vineyard Haven. This is a unique location in an area of very substantial homes. Per an island engineer, your future hous... Click here for more details
Address: 112 Dukes County Avenue | Town: Oak Bluffs | Link ID: 44094
Price: $549,000 | Status: Active
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: 109 Forest Avenue | Town: Oak Bluffs | Link ID: 45019
Price: $425,000 | Status: Active
BUILD YOUR HOME on this beautiful lot! Centrally located close to Farm Neck, bike path, and more, this property offers a wonderful opportunity to create your own home. Located in a newly created sub-division on a dead-end road, there is a baseball field right across from the property. This preserves... Click here for more details
Address: 0 Heather Lane | Town: Oak Bluffs | Link ID: 44811
Price: $399,000 | Status: Active
Rare opportunity to build your dream retreat tucked away on a quiet lane just off Wing Road. This desirable vacant lot offers the perfect blank canvas to design a custom coastal home, seasonal sanctuary, or smart island investment. Enjoy the ideal balance of residential privacy and effortless conven... Click here for more details
Address: 21 Island Inn Road | Town: Oak Bluffs | Link ID: 44749
Price: $389,900 | Status: Active
HERE'S YOUR CHANCE TO OWN A PIECE of the ISLAND!!! Live the beautiful Island Life with this gorgeous seasonal condo at the Island Inn Resort. AFFORDABLE & PRICED APPROX $100,000 less than an identical unit that Just Sold this summer!! Don't miss this delightful one and a half bedroom seasonal condo... Click here for more details
Address: 21 island Inn Road | Town: Oak Bluffs | Link ID: 44847
Price: $389,000 | Status: Active
Welcome to Unit 38G at the Island Inn, offering resort-style living in an exceptional Oak Bluffs location just steps from the beach. This desirable ground-floor end unit features a large glass slider opening to the patio, with stairs leading to the heated outdoor pool just a few feet away. Accommoda... Click here for more details
Address: 27 Island inn Road | Town: Oak Bluffs | Link ID: 44850
Price: $310,000 | Status: Active
Welcome to 27 Island Inn, Unit 10C, a comfortable one-bedroom, one-bath Martha’s Vineyard retreat offering an ideal combination of personal enjoyment and rental opportunity. Accommodating up to four guests, 10C features a queen bedroom, sofa bed, cozy living area, well-equipped kitchenette. A uniq... Click here for more details
Address: 27 Island Inn Road | Town: Oak Bluffs | Link ID: 44849
Price: $287,500 | Status: Active
Welcome to 27 Island Inn, Unit 9C, an inviting Martha’s Vineyard retreat offering the perfect combination of personal enjoyment and rental opportunity. This comfortable studio accommodates up to four guests with two double beds, a full bath, kitchenette with a 2-burner cooktop, cable TV and free W... Click here for more details
Address: 33 Island Inn Road | Town: Oak Bluffs | Link ID: 44851
Price: $260,000 | Status: Active
Welcome to 27 Island Inn, Unit 25F, a comfortable studio offering the perfect combination of a Martha’s Vineyard getaway and rental opportunity. Accommodating up to four guests, this inviting unit features two double beds, one full bath, a convenient kitchenette, cable TV and free WiFi. Island Inn... Click here for more details
Address: 27 Island Inn Road | Town: Oak Bluffs | Link ID: 44650
Price: $250,000 | Status: Active
Island Inn ....tucked behind the ever-popular Noman's Restaurant. Located off the Beach Road in Oak Bluffs. Fully furnished and updated 2nd floor studio. New: floors, appliances, television, mini-split AC and two double mattresses, Fully furnished galley kitchen. Use the convenient bike path to... Click here for more details
Address: 33 Island Inn Road | Town: Oak Bluffs | Link ID: 44790
Price: $239,000 | Status: Active
Want to own a slice of Martha's Vineyard? As an owner of this studio style "Condo-tel", you will enjoy the convenience of worry free ownership. This unit has newer flooring, an updated bathroom, updated kitchenette and a cathedral ceiling. This is casual resort style living that includes associatio... Click here for more details