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SEARCH RESULTS: 86 Listings
Oak Bluffs - All Property Types
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LINK ID: 44725
Town: Oak Bluffs
Address: 233 East Chop Drive, Oak Bluffs MA 02557
Type: Single Family Residence
$6,900,000.00
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...
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LINK ID: 44355
Town: Oak Bluffs
Address: 53 Circuit Avenue, Oak Bluffs MA 02557
Type: Commercial
$5,500,000.00
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...
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LINK ID: 44869
Town: Oak Bluffs
Address: 53 Circuit Avenue, Oak Bluffs MA 02557
Type: Multi Family
$5,500,000.00
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...
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LINK ID: 36712
Town: Oak Bluffs
Address: 43 Sengekontacket Road, Oak Bluffs MA 02557
Type: Single Family Residence
$5,495,000.00
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...
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LINK ID: 42465
Town: Oak Bluffs
Address: 385 Barnes Road, Oak Bluffs MA 02557
Type: Single Family Residence
$5,295,000.00
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...
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LINK ID: 43452
Town: Oak Bluffs
Address: 4 Canonicus Avenue, Oak Bluffs MA 02557
Type: Multi Family
$5,225,000.00
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...
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LINK ID: 44341
Town: Oak Bluffs
Address: 7 Overview Lane, Oak Bluffs MA 02557
Type: Unimproved Land
$5,100,000.00
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...
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LINK ID: 44917
Town: Oak Bluffs
Address: 3 Oak Bluffs Avenue, Oak Bluffs MA 02568
Type: Commercial
$5,000,000.00
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—...
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LINK ID: 44237
Town: Oak Bluffs
Address: 8 Fresh Pond Road, Oak Bluffs MA 02557
Type: Single Family Residence
$4,695,000.00
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, ...
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LINK ID: 44172
Town: Oak Bluffs
Address: 217 Barnes Road, Oak Bluffs MA 02557
Type: Single Family Residence
$4,650,000.00
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...
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LINK ID: 44208
Town: Oak Bluffs
Address: 15 Tamarack Lane, Oak Bluffs MA 02557
Type: Single Family Residence
$4,600,000.00
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...
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LINK ID: 44896
Town: Oak Bluffs
Address: 267 Barnes Road, Oak Bluffs MA 02557
Type: Single Family Residence
$4,395,000.00
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...
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LINK ID: 44771
Town: Oak Bluffs
Address: 99 Ocean Avenue, Oak Bluffs MA 02557
Type: Single Family Residence
$3,975,000.00
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, ...
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LINK ID: 44615
Town: Oak Bluffs
Address: 9 Weston Avenue, Oak Bluffs MA 02557
Type: Single Family Residence
$3,750,000.00
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,...
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LINK ID: 44528
Town: Oak Bluffs
Address: 27 Double Ox Road, Oak Bluffs MA 02557
Type: Single Family Residence
$3,400,000.00
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...
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LINK ID: 42895
Town: Oak Bluffs
Address: 6 Brewster Avenue, Oak Bluffs MA 02557
Type: Single Family Residence
$3,100,000.00
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...
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LINK ID: 44793
Town: Oak Bluffs
Address: 27 Beach Road, Oak Bluffs MA 02557
Type: Single Family Residence
$2,995,000.00
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...
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LINK ID: 44347
Town: Oak Bluffs
Address: 44 Tiffany Drive, Oak Bluffs MA 02557
Type: Single Family Residence
$2,800,000.00
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...
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LINK ID: 44308
Town: Oak Bluffs
Address: 31 Temahigan Avenue, Oak Bluffs MA 02557
Type: Single Family Residence
$2,678,000.00
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...
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LINK ID: 44701
Town: Oak Bluffs
Address: 59 Tuckernuck Avenue, Oak Bluffs MA 02557
Type: Single Family Residence
$2,650,000.00
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...
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LINK ID: 36870
Town: Oak Bluffs
Address: 111 Eastville Avenue, Oak Bluffs MA 02557
Type: Single Family Residence
$2,600,000.00
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 ...
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LINK ID: 44863
Town: Oak Bluffs
Address: 24 Harrison Avenue, Oak Bluffs MA 02557
Type: Single Family Residence
$2,595,000.00
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...
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LINK ID: 44300
Town: Oak Bluffs
Address: 34 Windemere Road, Oak Bluffs MA 02557
Type: Single Family Residence
$2,579,000.00
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...
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LINK ID: 44579
Town: Oak Bluffs
Address: 12 Samoset Avenue, Oak Bluffs MA 02557
Type: Single Family Residence
$2,575,000.00
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...
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LINK ID: 44263
Town: Oak Bluffs
Address: 50 Hidden Cove Road, Oak Bluffs MA 02557
Type: Single Family Residence
$2,400,000.00
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...
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LINK ID: 42967
Town: Oak Bluffs
Address: 4 High Meadow Lane, Oak Bluffs MA 02557
Type: Single Family Residence
$2,260,000.00
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...
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LINK ID: 43898
Town: Oak Bluffs
Address: 312 East Chop Drive, Oak Bluffs MA 02557
Type: Single Family Residence
$2,195,000.00
“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...
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LINK ID: 44802
Town: Oak Bluffs
Address: 51 Winemack Street & 0 Meadow Ave & Nahomon Street, Oak Bluffs MA 02557
Type: Single Family Residence
$2,045,000.00
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...
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LINK ID: 44652
Town: Oak Bluffs
Address: 8 Pequot Avenue, Oak Bluffs MA 02557
Type: Single Family Residence
$1,925,000.00
Directly Across from Inkwell Beach, this Victorian Queen has stood the test of time.
Partially insulated to extend the season, the new kitchen and bath are cozy in winter and open and bright in summer. 5 bedrooms, 1.5 baths with an outdoor shower, there's plenty of room for family and friends.
The...
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LINK ID: 44785
Town: Oak Bluffs
Address: 22 Paddock Road, Oak Bluffs MA 02557
Type: Unimproved Land
$1,895,000.00
An exceptional offering—the final homesite available within The Preserve at The Woodlands, one of Oak Bluffs’ most coveted residential enclaves. Create a custom coastal retreat in an extraordinary setting where architecturally designed residences, protected conservation land, and the timeless be...
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LINK ID: 44705
Town: Oak Bluffs
Address: 9 Chickawaukee Street, Oak Bluffs MA 02557
Type: Single Family Residence
$1,895,000.00
Offered fully furnished, this beautifully updated four-bedroom, two-bath home is a rare turnkey opportunity in Oak Bluffs. Thoughtfully updated and meticulously maintained, it is equally well suited as a year-round residence, vacation retreat, or investment property.
Located just 0.8 miles from dow...
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LINK ID: 44349
Town: Oak Bluffs
Address: 33 Vineyard Avenue, Oak Bluffs MA 02557
Type: Multi Family
$1,875,000.00
Welcome to 33 Vineyard Avenue in Oak Bluffs, Martha's Vineyard. This fully gut renovated property encompassing 3B/2Ba in total featuring a 2BR/2BA primary home plus a distinctly separate attached 1BR/1BA ADU suite - offering flexible, move-in ready living or investment potential in a prime in-town l...
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LINK ID: 44113
Town: Oak Bluffs
Address: 22 Old Harbor Lane, Oak Bluffs MA 02557
Type: Single Family Residence
$1,850,000.00
Quintessential Waterview Farm! Built as a year round house with all the charm of the original cottages, this well-loved family home awaits a new generation. The sunny, open floor plan has two bedrooms and a full bath on each level and plenty of room to spread out. The skylit kitchen is cleverly tuck...
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LINK ID: 44018
Town: Oak Bluffs
Address: 18 Wood Duck Way, Oak Bluffs MA 02557
Type: Single Family Residence
$1,800,000.00
Your opportunity in Sengekontacket! Being sold turnkey. This modern home has four bedrooms and three full baths. Large windows and high vaulted ceilings, the home lets in bright natural light. The first floor has three bedrooms and a full bath with double sinks. Beautiful oak and maple floors comple...
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LINK ID: 44054
Town: Oak Bluffs
Address: 2 Great Rock Road, Oak Bluffs MA 02557
Type: Single Family Residence
$1,765,000.00
Ready - Set - Go! This gorgeous centrally located private 1.5 acre wooded property is ready for you to complete. The Town approved this property to accommodate a 9 bedroom septic system, 20' x 40' in-ground pool, a 7 bedroom main house, garage and a 2 bedroom accessory dwelling unit. The town buildi...
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LINK ID: 44750
Town: Oak Bluffs
Address: 14 High Meadow Lane, Oak Bluffs MA 02557
Type: Single Family Residence
$1,750,000.00
Welcome to this sun-drenched, reverse contemporary-style home located in the lovely Meadow View Farms community! This multi-level home has boundless potential. The second level features a bright, open floor plan with cathedral ceilings, living, dining, and kitchen areas, and 3 sliding doors that tak...
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LINK ID: 44641
Town: Oak Bluffs
Address: 11 Beach Road, Oak Bluffs MA 02557
Type: Single Family Residence
$1,745,000.00
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...
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LINK ID: 44267
Town: Oak Bluffs
Address: 17 John Wesley Avenue, Oak Bluffs MA 02557
Type: Single Family Residence
$1,650,000.00
Welcome to this year-round East Chop Victorian Gingerbread home, close to Oak Bluffs Harbor, Jetty Beach, and downtown. The amazing wrap-around porch is perfectly designed for spending lazy summers with friends and family. Many a party has been hosted on this generous porch, made more enticing by a...
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LINK ID: 44691
Town: Oak Bluffs
Address: 20 Hidden Cove Road, Oak Bluffs MA 02557
Type: Single Family Residence
$1,625,000.00
Nestled in this desirable Hidden Cove community, this contemporary residence offers a quintessential retreat centered on outdoor recreation and coastal living. Residents enjoy premier neighborhood amenities, including direct water access to Sengekontacket Pond for seamless kayaking and paddleboardin...
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LINK ID: 44703
Town: Oak Bluffs
Address: 13 Beach Road, Oak Bluffs MA 02557
Type: Single Family Residence
$1,599,000.00
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...
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LINK ID: 44671
Town: Oak Bluffs
Address: 40 Hidden Cove Road Unit 2, Oak Bluffs MA 02557
Type: Single Family Residence
$1,595,000.00
Enjoy timeless summers at this Hidden Cove condo, where days begin with a paddle on Sengekontacket Pond, afternoons are spent between the pool and tennis courts, and evenings end on the deck after a day spent exploring the island. This three-bedroom unit has distant water views and offers an easy, m...
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LINK ID: 44469
Town: Oak Bluffs
Address: 40 Hidden Cove Road Unit 2, Oak Bluffs MA 02557
Type: Condominium
$1,595,000.00
Enjoy timeless summers at this Hidden Cove condo, where days begin with a paddle on Sengekontacket Pond, afternoons are spent between the pool and tennis courts, and evenings end on the deck after a day spent exploring the island. This three-bedroom unit has distant water views and offers an easy, m...
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LINK ID: 44931
Town: Oak Bluffs
Address: 8 Melrose Avenue, Oak Bluffs MA 02557
Type: Single Family Residence
$1,539,000.00
Incredible opportunity for workforce housing, live in one/rent the other, or multi generational family living. Main house has 4 levels of living space. Main floor living/kitchen/dining/full bath and laundry. 2nd floor has two bedrooms and full bath. 3rd floor is a large finished bonus room. The full...
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LINK ID: 44518
Town: Oak Bluffs
Address: 7 Ploughshare Lane, Oak Bluffs MA 02557
Type: Single Family Residence
$1,499,000.00
Nestled in a quiet cul-de-sac within the coveted Hidden Cove neighborhood, this delightful property offers an exceptional Island lifestyle. The association delivers rare water access via a private dock on Sengekontacket Pond, plus newly resurfaced tennis and pickleball courts. The open-concept layou...
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LINK ID: 43835
Town: Oak Bluffs
Address: 4 Lagrange Avenue, Oak Bluffs MA 02557
Type: Single Family Residence
$1,450,000.00
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...
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LINK ID: 44374
Town: Oak Bluffs
Address: 46 Kennebec Avenue, Oak Bluffs MA 02557
Type: Single Family Residence
$1,350,000.00
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...
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LINK ID: 44658
Town: Oak Bluffs
Address: 82 Pennsylvania Avenue, Oak Bluffs MA 02557
Type: Single Family Residence
$1,296,000.00
Discover the charm of this inviting single-story ranch with a large, finished basement, perfect as a vacation retreat or year-round home. Extensively renovated, this charming 3-bedroom, 1.5-bath home offers comfort and effortless living. The finished basement adds nearly another 1000 SF of living sp...
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LINK ID: 44759
Town: Oak Bluffs
Address: 66 Hudson Avenue, Oak Bluffs MA 02557
Type: Single Family Residence
$1,296,000.00
This warm and welcoming home with exceptional outdoor living space is sited on a beautifully landscaped lot just 1.5 miles from downtown Oak Bluffs. The private backyard, designed and cultivated by Donaroma’s, features a fenced lawn with irrigation, fire pit, outdoor dining area, and built-in gril...
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LINK ID: 44213
Town: Oak Bluffs
Address: 3 Troy Street, Oak Bluffs MA 02557
Type: Single Family Residence
$1,295,000.00
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...
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LINK ID: 44907
Town: Oak Bluffs
Address: 4 Periwinkle Lane, Oak Bluffs MA 02557
Type: Single Family Residence
$1,295,000.00
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 ...
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LINK ID: 44832
Town: Oak Bluffs
Address: 11 Stanley Street, Oak Bluffs MA 02557
Type: Single Family Residence
$1,255,000.00
Nestled on a cul-de-sac is this sweet 3 bedroom ranch. Located on a .34 acre lot with plenty of room to expand this solid home and still have enough space for an ADU on this spacious lot. Well maintained over the years with recent upgrades including, roof, siding, new insulation, flooring and paint....
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LINK ID: 43914
Town: Oak Bluffs
Address: 0 Pennsylvania Avenue, Oak Bluffs MA 02557
Type: Single Family Residence
$1,250,000.00
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...
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LINK ID: 44799
Town: Oak Bluffs
Address: 323 County Road, Oak Bluffs MA 02557
Type: Single Family Residence
$1,225,000.00
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...
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LINK ID: 44775
Town: Oak Bluffs
Address: 170 Barnes Road, Oak Bluffs MA 02557
Type: Single Family Residence
$1,195,000.00
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...
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LINK ID: 44108
Town: Oak Bluffs
Address: 3 Kims Way, Oak Bluffs MA 02557
Type: Single Family Residence
$1,155,000.00
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...
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LINK ID: 44649
Town: Oak Bluffs
Address: 30 Double Ox Road, Oak Bluffs MA 02557
Type: Unimproved Land
$1,150,000.00
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 ...
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LINK ID: 44808
Town: Oak Bluffs
Address: 54 Towanticut Avenue, Oak Bluffs MA 02557
Type: Single Family Residence
$1,100,000.00
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...
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LINK ID: 44490
Town: Oak Bluffs
Address: 47 Winemack Avenue, Oak Bluffs MA 02557
Type: Single Family Residence
$1,100,000.00
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...
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LINK ID: 44805
Town: Oak Bluffs
Address: 2 Winemack Street, Oak Bluffs MA 02557
Type: Single Family Residence
$1,095,000.00
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...
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LINK ID: 43457
Town: Oak Bluffs
Address: 0 Temahigan Avenue & Dover Street, Oak Bluffs MA 02557
Type: Unimproved Land
$1,049,000.00
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...
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LINK ID: 44714
Town: Oak Bluffs
Address: 68 Pond View Drive, Oak Bluffs MA 02557
Type: Unimproved Land
$975,000.00
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...
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LINK ID: 44841
Town: Oak Bluffs
Address: 3 Dukes County Avenue, Oak Bluffs MA 02557
Type: Single Family Residence
$935,000.00
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...
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LINK ID: 44252
Town: Oak Bluffs
Address: 4 Quail Run # 21, Oak Bluffs MA 02557
Type: Condominium
$925,000.00
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...
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LINK ID: 44201
Town: Oak Bluffs
Address: 67 Hudson Avenue, Oak Bluffs MA 02557
Type: Single Family Residence
$925,000.00
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...
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LINK ID: 44276
Town: Oak Bluffs
Address: 37 Circuit Avenue # 4, Oak Bluffs MA 02557
Type: Condominium
$879,000.00
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...
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LINK ID: 44815
Town: Oak Bluffs
Address: 61 Winemack Street, Oak Bluffs MA 02557
Type: Single Family Residence
$850,000.00
Located in Oak Bluffs' desirable East Chop neighborhood, this 10,000± sq. ft. R2-zoned property offers an exceptional opportunity to renovate or build new (subject to applicable approvals). The existing two-bedroom, one-bath home is being sold as is.
The level lot features a spacious yard and is i...
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LINK ID: 42877
Town: Oak Bluffs
Address: 50 Canonicus Avenue, Oak Bluffs MA 02557
Type: Single Family Residence
$849,000.00
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. ...
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LINK ID: 44245
Town: Oak Bluffs
Address: 4 Quail Run # 1, Oak Bluffs MA 02557
Type: Condominium
$849,000.00
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. ...
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LINK ID: 44275
Town: Oak Bluffs
Address: 37 Circuit Avenue # 5, Oak Bluffs MA 02557
Type: Condominium
$849,000.00
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...
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LINK ID: 42248
Town: Oak Bluffs
Address: 26 Winthrop Avenue, Oak Bluffs MA 02557
Type: Single Family Residence
$839,000.00
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 ...
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LINK ID: 44425
Town: Oak Bluffs
Address: 19 Perkins Avenue, Oak Bluffs MA 02557
Type: Single Family Residence
$825,000.00
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...
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LINK ID: 44502
Town: Oak Bluffs
Address: 7 Highland Avenue, Oak Bluffs MA 02557
Type: Unimproved Land
$809,000.00
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...
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LINK ID: 44640
Town: Oak Bluffs
Address: 60R Carol Lane, Oak Bluffs MA 02557
Type: Single Family Residence
$794,000.00
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...
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LINK ID: 44062
Town: Oak Bluffs
Address: 24 Towanticut Avenue, Oak Bluffs MA 02557
Type: Unimproved Land
$789,000.00
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...
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LINK ID: 43296
Town: Oak Bluffs
Address: 35 Double Ox Road, Oak Bluffs MA 02557
Type: Unimproved Land
$685,000.00
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, ...
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LINK ID: 43507
Town: Oak Bluffs
Address: 0-B California Avenue, Oak Bluffs MA 02557
Type: Unimproved Land
$675,000.00
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...
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LINK ID: 43517
Town: Oak Bluffs
Address: 0-A California Avenue, Oak Bluffs MA 02557
Type: Unimproved Land
$625,000.00
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...
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LINK ID: 44094
Town: Oak Bluffs
Address: 112 Dukes County Avenue, Oak Bluffs MA 02557
Type: Unimproved Land
$549,000.00
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...
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LINK ID: 44811
Town: Oak Bluffs
Address: 0 Heather Lane, Oak Bluffs MA 02257
Type: Unimproved Land
$425,000.00
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...
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LINK ID: 44749
Town: Oak Bluffs
Address: 21 Island Inn Road # 35G, Oak Bluffs MA 02557
Type: Condominium
$389,900.00
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...
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LINK ID: 44847
Town: Oak Bluffs
Address: 21 island Inn Road # 38G, Oak Bluffs MA 02557
Type: Condominium
$389,000.00
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...
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LINK ID: 44850
Town: Oak Bluffs
Address: 27 Island inn Road # 10C, Oak Bluffs MA 02557
Type: Condominium
$310,000.00
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...
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LINK ID: 44849
Town: Oak Bluffs
Address: 27 Island Inn Road # 9C, Oak Bluffs MA 02557
Type: Condominium
$287,500.00
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...
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LINK ID: 44851
Town: Oak Bluffs
Address: 33 Island Inn Road # 25F, Oak Bluffs MA 02557
Type: Condominium
$260,000.00
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...
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LINK ID: 44650
Town: Oak Bluffs
Address: 27 Island Inn Road # D17, Oak Bluffs MA 02557
Type: Condominium
$250,000.00
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...
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LINK ID: 44790
Town: Oak Bluffs
Address: 33 Island Inn Road # F22, Oak Bluffs MA 02557
Type: Condominium
$239,000.00
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...
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