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SEARCH RESULTS: 83 Listings
OAK BLUFFS - All Property Types
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Town: OAK BLUFFS | All Oak Bluffs listings
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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Town: OAK BLUFFS | All Oak Bluffs listings
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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Town: OAK BLUFFS | All Oak Bluffs listings
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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Town: OAK BLUFFS | All Oak Bluffs listings
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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Town: OAK BLUFFS | All Oak Bluffs listings
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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Town: OAK BLUFFS | All Oak Bluffs listings
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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Town: OAK BLUFFS | All Oak Bluffs listings
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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Town: OAK BLUFFS | All Oak Bluffs listings
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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Town: OAK BLUFFS | All Oak Bluffs listings
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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Town: OAK BLUFFS | All Oak Bluffs listings
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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Town: OAK BLUFFS | All Oak Bluffs listings
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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Town: OAK BLUFFS | All Oak Bluffs listings
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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Town: OAK BLUFFS | All Oak Bluffs listings
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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Town: OAK BLUFFS | All Oak Bluffs listings
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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Town: OAK BLUFFS | All Oak Bluffs listings
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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Town: OAK BLUFFS | All Oak Bluffs listings
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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Town: OAK BLUFFS | All Oak Bluffs listings
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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Town: OAK BLUFFS | All Oak Bluffs listings
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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Town: OAK BLUFFS | All Oak Bluffs listings
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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Town: OAK BLUFFS | All Oak Bluffs listings
Address:
44 Tiffany Drive, Oak Bluffs MA 02557
Type: Single Family Residence
$2,595,000.00
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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PRICE CHANGE |
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Town: OAK BLUFFS | All Oak Bluffs listings
Address:
59 Tuckernuck Avenue, Oak Bluffs MA 02557
Type: Single Family Residence
$2,595,000.00
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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PRICE CHANGE |
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Town: OAK BLUFFS | All Oak Bluffs listings
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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Town: OAK BLUFFS | All Oak Bluffs listings
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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CONTINGENT OFFER
STILL SHOWING
Contingent
3rd September 2026
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Town: OAK BLUFFS | All Oak Bluffs listings
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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Town: OAK BLUFFS | All Oak Bluffs listings
Address:
61 Canonicus Avenue, Oak Bluffs MA 02557
Type: Single Family Residence
$2,200,000.00
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...
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Town: OAK BLUFFS | All Oak Bluffs listings
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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CONTINGENT OFFER
STILL SHOWING
Contingent
26th August 2026
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Town: OAK BLUFFS | All Oak Bluffs listings
Address:
15 Pequot Avenue, Oak Bluffs MA 02557
Type: Single Family Residence
$2,150,000.00
Oak Bluffs Copeland District -Just One Block from the Beach!
Discover the perfect coastal getaway in this spacious 5-bedroom, 3½-bathroom home, ideally located just one block from the beach and within easy walking distance of the town center.
Spend your days enjoying the sand and surf, then stroll ...
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NEW LISTING |
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Town: OAK BLUFFS | All Oak Bluffs listings
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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Town: OAK BLUFFS | All Oak Bluffs listings
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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Town: OAK BLUFFS | All Oak Bluffs listings
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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Town: OAK BLUFFS | All Oak Bluffs listings
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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CONTINGENT OFFER
STILL SHOWING
Contingent
9th September 2026
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Town: OAK BLUFFS | All Oak Bluffs listings
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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Town: OAK BLUFFS | All Oak Bluffs listings
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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CONTINGENT OFFER
STILL SHOWING
Contingent
8th September 2026
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Town: OAK BLUFFS | All Oak Bluffs listings
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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Town: OAK BLUFFS | All Oak Bluffs listings
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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Town: OAK BLUFFS | All Oak Bluffs listings
Address:
68 Front Street, Oak Bluffs MA 02557
Type: Single Family Residence
$1,755,000.00
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...
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NEW LISTING |
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Town: OAK BLUFFS | All Oak Bluffs listings
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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Town: OAK BLUFFS | All Oak Bluffs listings
Address:
11 Beach Road, Oak Bluffs MA 02557
Type: Single Family Residence
$1,745,000.00
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...
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Town: OAK BLUFFS | All Oak Bluffs listings
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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Town: OAK BLUFFS | All Oak Bluffs listings
Address:
20 Hidden Cove Road, Oak Bluffs MA 02557
Type: Single Family Residence
$1,595,000.00
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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Town: OAK BLUFFS | All Oak Bluffs listings
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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Town: OAK BLUFFS | All Oak Bluffs listings
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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Town: OAK BLUFFS | All Oak Bluffs listings
Address:
40 Hidden Cove Road Unit 2, Oak Bluffs MA 02557
Type: Condominium
$1,495,000.00
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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Town: OAK BLUFFS | All Oak Bluffs listings
Address:
40 Hidden Cove Road Unit 2, Oak Bluffs MA 02557
Type: Single Family Residence
$1,495,000.00
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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PRICE CHANGE |
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Town: OAK BLUFFS | All Oak Bluffs listings
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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Town: OAK BLUFFS | All Oak Bluffs listings
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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Town: OAK BLUFFS | All Oak Bluffs listings
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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CONTINGENT OFFER
STILL SHOWING
Contingent
16th August 2026
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Town: OAK BLUFFS | All Oak Bluffs listings
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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CONTINGENT OFFER
STILL SHOWING
Contingent
24th August 2026
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Town: OAK BLUFFS | All Oak Bluffs listings
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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Town: OAK BLUFFS | All Oak Bluffs listings
Address:
11 Stanley Street, Oak Bluffs MA 02557
Type: Single Family Residence
$1,255,000.00
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...
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Town: OAK BLUFFS | All Oak Bluffs listings
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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Town: OAK BLUFFS | All Oak Bluffs listings
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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Town: OAK BLUFFS | All Oak Bluffs listings
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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Town: OAK BLUFFS | All Oak Bluffs listings
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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Town: OAK BLUFFS | All Oak Bluffs listings
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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Town: OAK BLUFFS | All Oak Bluffs listings
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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Town: OAK BLUFFS | All Oak Bluffs listings
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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Town: OAK BLUFFS | All Oak Bluffs listings
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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Town: OAK BLUFFS | All Oak Bluffs listings
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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Town: OAK BLUFFS | All Oak Bluffs listings
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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Town: OAK BLUFFS | All Oak Bluffs listings
Address:
37 Circuit Avenue # 4, Oak Bluffs MA 02557
Type: Condominium
$879,000.00
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...
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Town: OAK BLUFFS | All Oak Bluffs listings
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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CONTINGENT OFFER
STILL SHOWING
Contingent
1st September 2026
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Town: OAK BLUFFS | All Oak Bluffs listings
Address:
15 Rogers Way, Oak Bluffs MA 02557
Type: Unimproved Land
$850,000.00
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...
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Town: OAK BLUFFS | All Oak Bluffs listings
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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Town: OAK BLUFFS | All Oak Bluffs listings
Address:
37 Circuit Avenue # 5, Oak Bluffs MA 02557
Type: Condominium
$849,000.00
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...
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Town: OAK BLUFFS | All Oak Bluffs listings
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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Town: OAK BLUFFS | All Oak Bluffs listings
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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CONTINGENT OFFER
STILL SHOWING
Contingent
12th September 2026
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Town: OAK BLUFFS | All Oak Bluffs listings
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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Town: OAK BLUFFS | All Oak Bluffs listings
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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Town: OAK BLUFFS | All Oak Bluffs listings
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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Town: OAK BLUFFS | All Oak Bluffs listings
Address:
60R Carol Lane, Oak Bluffs MA 02557
Type: Single Family Residence
$785,000.00
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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Town: OAK BLUFFS | All Oak Bluffs listings
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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Town: OAK BLUFFS | All Oak Bluffs listings
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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Town: OAK BLUFFS | All Oak Bluffs listings
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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Town: OAK BLUFFS | All Oak Bluffs listings
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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Town: OAK BLUFFS | All Oak Bluffs listings
Address:
0 Heather Lane, Oak Bluffs MA 02257
Type: Unimproved Land
$399,000.00
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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PRICE CHANGE |
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Town: OAK BLUFFS | All Oak Bluffs listings
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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Town: OAK BLUFFS | All Oak Bluffs listings
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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Town: OAK BLUFFS | All Oak Bluffs listings
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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Town: OAK BLUFFS | All Oak Bluffs listings
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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Town: OAK BLUFFS | All Oak Bluffs listings
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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Town: OAK BLUFFS | All Oak Bluffs listings
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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Town: OAK BLUFFS | All Oak Bluffs listings
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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