Oak Bluffs Homes for Sale

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  $809,000

  • Land
  • 16,901 Sq Ft
  • $2,085,052 per Acre

  7 Highland Ave Unit 119, Vineyard Haven, MA 02568

  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 building requirements. Opportunity for buyer to design to their own specifications.

  Shera Toledo eXp Realty

  7 Highland Ave Unit 119, Vineyard Haven, MA 02568
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  $1,075,000

  Open Sat 11AM - 2PM

  • 3 Beds
  • 2 Baths
  • 1,135 Sq Ft

  21 Butler Ave Unit 1, Oak Bluffs, MA 02557

  Located within the historic Martha’s Vineyard Camp Meeting Association, this rare double-lot property combines classic Campground charm with modern comfort. Two-car off-street parking—an exceptional Campground amenity—adds convenience, while Oak Bluffs Harbor, beaches, ferries, shops, and restaurants are just moments away. The 1,135-square-foot home features painted wood floors, abundant natural

  Jennifer O'hanlon Compass

  21 Butler Ave Unit 1, Oak Bluffs, MA 02557
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  $1,895,000

  • Land
  • 1.87 Acres
  • $1,014,997 per Acre

  22 Paddock Rd Unit 85, Oak Bluffs, MA 02568

  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 beauty of Martha’s Vineyard converge.This 1.87-acre homesite represents the final opportunity to

  Marilyn Moses Ocean Park Realty Inc

  22 Paddock Rd Unit 85, Oak Bluffs, MA 02568
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  $5,100,000

  • Land
  • 2.34 Acres
  • $2,179,487 per Acre

  7 Overview Ln, Oak Bluffs, MA 02557

  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 your dream home in this sought-after location. As a homeowner in Farm Neck, you'll enjoy exclusive

  Alyssa Halisky Wallace & Co. Sotheby's International Realty

  7 Overview Ln, Oak Bluffs, MA 02557
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  $1,595,000

  • 3 Beds
  • 3.5 Baths
  • 2,739 Sq Ft

  40 Hidden Cove Road Unit 2 Unit 2, Oak Bluffs, MA 02557

  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, multi-level floor plan with open living spaces, a private primary suite, two guest bedrooms, a

  Rose Ryley Wallace & Co. Sotheby's International Realty

  40 Hidden Cove Road Unit 2 Unit 2, Oak Bluffs, MA 02557
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  $675,000

  • Land
  • 9,997 Sq Ft
  • $2,941,176 per Acre

  0-B California Ave Unit Part lot 79, Oak Bluffs, MA 02568

  Oak Bluffs Buildable Lot – Prime LocationThis 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 presents an excellent opportunity to become part of a growing community in Oak Bluffs. According to

  Andrew McElhinney Compass LLC

  0-B California Ave Unit Part lot 79, Oak Bluffs, MA 02568
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  $425,000

  • Land
  • 7,840 Sq Ft
  • $2,361,111 per Acre

  0 Heather Ln Unit 73560451, Oak Bluffs, MA 02568

  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 convenience, located just minutes from iconic Circuit Avenue, Oak Bluffs Harbor, scenic biking trails,

  Jennifer B. DaSilva Compass

  0 Heather Ln Unit 73560451, Oak Bluffs, MA 02568
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  $1,895,000

  • 4 Beds
  • 2 Baths
  • 1,760 Sq Ft

  9 Chickawaukee St, Oak Bluffs, MA 02568

  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 downtown Oak Bluffs, the home offers convenient access to beaches, restaurants, shops, ferries, and the

  Andrew McElhinney Compass LLC

  9 Chickawaukee St, Oak Bluffs, MA 02568
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  $4,850,000

  $845K PRICE DROP

  • 5 Beds
  • 4 Baths
  • 3,650 Sq Ft

  217 Barnes Rd, Vineyard Haven, MA 02568

  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, Vineyard Sound, and even distant views of Cape Cod. The property includes a renovated three-bedroom

  Elissa Lash Tea Lane Associates

  217 Barnes Rd, Vineyard Haven, MA 02568
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  $1,155,000

  $40K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,164 Sq Ft

  3 Kims Way, Oak Bluffs, MA 02557

  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. The private primary suite is thoughtfully positioned off the main living area and offers a full bath

  Alyssa Halisky Wallace & Co. Sotheby's International Realty

  3 Kims Way, Oak Bluffs, MA 02557
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  $2,650,000

  • 4 Beds
  • 2.5 Baths
  • 1,900 Sq Ft

  59 Tuckernuck Ave, Oak Bluffs, MA 02557

  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 open layout featuring crisp white paneled walls, exposed painted ceiling beams, and warm hardwood

  Jennifer DaSilva Compass | Point B

  59 Tuckernuck Ave, Oak Bluffs, MA 02557
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  $2,600,000

  $198K PRICE DROP

  • 6 Beds
  • 4 Baths
  • 2,400 Sq Ft

  111 Eastville Ave, Oak Bluffs, MA 02557

  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 parcels from the shoreline, the home features six bedrooms and four bathrooms, providing generous

  Ed Charter Arrowhead Homes

  111 Eastville Ave, Oak Bluffs, MA 02557
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  $5,225,000

  $100K PRICE DROP

  • 6 Beds
  • 4 Baths
  • 2,890 Sq Ft

  4 Canonicus Ave, Oak Bluffs, MA 02557

  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 masterfully updated, introducing refined, contemporary comforts, designed for every season. Tucked to the

  Katherine Donahue Sandpiper Realty

  4 Canonicus Ave, Oak Bluffs, MA 02557
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  $1,250,000

  • 1 Bed
  • 1 Bath
  • 855 Sq Ft

  0 Pennsylvania Ave Unit 43914, Oak Bluffs, MA 02568

  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 or seasonal residents, or businesses seeking to solve workforce housing needs along with secure

  Peyton Wallace Studio Realty

  0 Pennsylvania Ave Unit 43914, Oak Bluffs, MA 02568
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  $549,000

  $50K PRICE DROP

  • Land
  • 3,197 Sq Ft
  • $7,479,564 per Acre

  112 Dukes County Ave Unit 209, Oak Bluffs, MA 02557

  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. This level lot includes an existing poured concrete foundation and Martha’s Vineyard Commission–approved

  Rose Ryley Wallace & Co. Sotheby's

  112 Dukes County Ave Unit 209, Oak Bluffs, MA 02557
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  $2,250,000

  • 3 Beds
  • 3.5 Baths
  • 2,475 Sq Ft

  35 Double Ox Rd, Oak Bluffs, MA 02557

  Would you love to live or vacation in a brand-new home on Martha’s Vineyard?We have the LOCATION, REPUTABLE LONG-STANDING BUILDER & PROVEN TRACK RECORD!Come take a tour of the newest home under construction in the Lagoon Ridge neighborhood.Easy to show – Call now! To be built with lot purchase $695,000 and building contract approximately $1,550,000.This 3-bedroom dream home is set

  Marilyn Moses Ocean Park Realty Inc

  35 Double Ox Rd, Oak Bluffs, MA 02557
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  $869,000

  $30K PRICE DROP

  • 1 Bed
  • 1.5 Baths
  • 1,182 Sq Ft

  4 Quail Run Unit 1, Oak Bluffs, MA 02557

  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. This year-round home is filled with natural light and features a spacious deck —perfect for

  Jarrett Hurwitz Keller Williams Realty

  4 Quail Run Unit 1, Oak Bluffs, MA 02557
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  $389,900

  • 1 Bed
  • 1.5 Baths
  • 584 Sq Ft

  21 Island Inn Rd Unit 35, Oak Bluffs, MA 02568

  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 (sleeps 6) available for your families use. When you’re not here, the management team will rent

  Susan Austin Austin R.E. Properties of MV

  21 Island Inn Rd Unit 35, Oak Bluffs, MA 02568
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  $5,100,000

  • Land
  • 2.34 Acres
  • $2,182,285 per Acre

  7 Overview Ln Unit 47, Oak Bluffs, MA 02557

  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 your dream home in this sought-after location. As a homeowner in Farm Neck, you'll enjoy exclusive

  Alyssa Halisky Wallace & Co. Sotheby's

  7 Overview Ln Unit 47, Oak Bluffs, MA 02557
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  $695,000

  $55K PRICE DROP

  • Land
  • 11,417 Sq Ft
  • $2,651,660 per Acre

  35 Double Ox Rd Unit 42, Oak Bluffs, MA 02557

  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, offering sweeping sky views, vibrant sunsets, and refreshing sea breezes.The lot is ready

  Marilyn Moses Ocean Park Realty Inc

  35 Double Ox Rd Unit 42, Oak Bluffs, MA 02557
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  $3,250,000

  • 4 Beds
  • 3 Baths
  • 1,728 Sq Ft

  6 Brewster Ave, Oak Bluffs, MA 02557

  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 preserving the home’s original charm. Tucked privately at the rear of the property, the guest cottage

  Katie Donahue & Rachel Serwa Group Sandpiper Realty, Inc.

  6 Brewster Ave, Oak Bluffs, MA 02557
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  $825,000

  • 2 Beds
  • 1 Bath
  • 985 Sq Ft

  19 Perkins Ave, Oak Bluffs, MA 02557

  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, restaurants, and shops while creating your own vision in this classic Island setting.

  Katherine Donahue Sandpiper Realty

  19 Perkins Ave, Oak Bluffs, MA 02557
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  $2,995,000

  • 5 Beds
  • 1.5 Baths
  • 1,713 Sq Ft

  27 Beach Rd, Oak Bluffs, MA 02557

  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 featuring a private sandy beach, deep-water dock, and sweeping views of the harbor, the Cape, and

  Bonnie Pierce Wallace & Co. Sotheby's

  27 Beach Rd, Oak Bluffs, MA 02557
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  $1,995,000

  Open Tue 10AM - 11:30PM

  • 3 Beds
  • 2.5 Baths
  • 1,439 Sq Ft

  33 Vineyard Ave, Oak Bluffs, MA 02557

  Welcome to 33 Vineyard Avenue in Oak Bluffs, Martha's Vineyard. This fully gut renovated property 3B/2Ba in total features 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 location. The main residence in the primary showcases a light-filled interior, wood floors, beamwork, and refined

  Allison Cameron Parry Douglas Elliman of MA, LLC

  33 Vineyard Ave, Oak Bluffs, MA 02557
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  $2,295,000

  • 3 Beds
  • 2 Baths
  • 1,425 Sq Ft

  312 E Chop Dr, Oak Bluffs, MA 02557

  “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 comfort. Surrounded by lush landscaping and beautiful hydrangea and perennial gardens, the property boasts

  Alyssa Halisky Wallace & Co. Sotheby's

  312 E Chop Dr, Oak Bluffs, MA 02557
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  $3,975,000

  • 4 Beds
  • 2.5 Baths
  • 2,600 Sq Ft

  99 Ocean Ave, Oak Bluffs, MA 02557

  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, ferries, the Campground and the Tabernacle. This treasured property has been home to family and

  Perry Patterson MV Luxury Homes

  99 Ocean Ave, Oak Bluffs, MA 02557
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  $1,100,000

  • 3 Beds
  • 2 Baths
  • 1,232 Sq Ft

  54 Towanticut Ave, Oak Bluffs, MA 02568

  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 area with sliders leading to a spacious deck and outdoor shower overlooking the yard. The generous

  JoJo Lambert Island Home Realty Inc.

  54 Towanticut Ave, Oak Bluffs, MA 02568
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  $1,650,000

  $145K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 1,406 Sq Ft

  17 John Wesley Ave, Vineyard Haven, MA 02568

  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 an open-plan first floor with a large kitchen, living room, and dining area. The first floor features

  kyle Neyer Tea Lane Associates

  17 John Wesley Ave, Vineyard Haven, MA 02568
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  $5,995,000

  • 3 Beds
  • 3 Baths
  • 2,234 Sq Ft

  43 Sengekontacket Rd, Oak Bluffs, MA 02557

  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 whaler or other watercraft out into the sound and beyond for endless recreational pursuits. Aside

  Peyton Wallace Studio Realty LLC

  43 Sengekontacket Rd, Oak Bluffs, MA 02557
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  $549,000

  $50K PRICE DROP

  • Land
  • 3,049 Sq Ft
  • $7,842,857 per Acre

  112 Dukes County Ave, Oak Bluffs, MA 02557

  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.This level lot includes an existing poured concrete foundation and Martha’s Vineyard Commission–approved

  Rose Ryley Wallace & Co. Sotheby's International Realty

  112 Dukes County Ave, Oak Bluffs, MA 02557
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  $429,000

  $66K PRICE DROP

  • Land
  • 9,997 Sq Ft
  • $1,869,281 per Acre

  0 California Ave Unit 76 42933, Oak Bluffs, MA 02568

  Nice level building lot ready for your ideas on how best to create your near town home on a quiet street. This is an established neighborhood and one of the last lots left to build on. Perc test has been done. This is in Zone 2 which allows for a one bedroom home of any size. Water and electric are nearby.

  Jim Joyce Carroll & Vincent R.E.

  0 California Ave Unit 76 42933, Oak Bluffs, MA 02568
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  $2,295,000

  • 3 Beds
  • 2 Baths
  • 1,425 Sq Ft

  312 E Chop Dr, Vineyard Haven, MA 02568

  ''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 meticulously maintained, blending timeless Vineyard character with modern comfort. Surrounded by lush hydrangea and perennial gardens, the property boasts nearly 150 feet of

  Alyssa Halisky Wallace & Co. Sotheby's International Realty

  312 E Chop Dr, Vineyard Haven, MA 02568
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  $1,150,000

  • Land
  • 1.09 Acres
  • $1,055,046 per Acre

  30 Double Ox Rd Unit 33, Oak Bluffs, MA 02557

  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 enclave of just four estate parcels, the property is accessed by a welcoming paved approach. This

  Marilyn Moses Ocean Park Realty Inc

  30 Double Ox Rd Unit 33, Oak Bluffs, MA 02557
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  $4,695,000

  • 7 Beds
  • 4.5 Baths
  • 5,320 Sq Ft

  8 Fresh Pond Rd, Oak Bluffs, MA 02557

  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, paddleboarding, and swimming. Perfect for entertaining, the home showcases a dramatic great room, an

  Jarrett Hurwitz Keller Williams Realty

  8 Fresh Pond Rd, Oak Bluffs, MA 02557
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  $1,095,000

  • 3 Beds
  • 2 Baths
  • 1,764 Sq Ft

  170 Barnes Rd, Oak Bluffs, MA 02557

  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 laundry, a den with French-doors that leads to the living room with a slider opening out to the back

  Christine Rose Martha's Vineyard Island-Wide Realty

  170 Barnes Rd, Oak Bluffs, MA 02557
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  $1,349,000

  • 3 Beds
  • 2 Baths
  • 1,863 Sq Ft

  3 Troy St, Oak Bluffs, MA 02557

  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, ideal for guests or rental possibilities. The main living space features hardwood floors throughout, a

  Alyssa Halisky Wallace & Co. Sotheby's International Realty

  3 Troy St, Oak Bluffs, MA 02557

Showing Results 41 - 76, Page 2 of 2