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Oak Bluffs Homes for Sale

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  • 68 Pond View Dr, Oak Bluffs, MA 02557
    68 Pond View Dr, Oak Bluffs, MA 02557
    /2

    $975,000

    • Land
    • 1.07 Acres
    • $911,215 per Acre

    68 Pond View Dr, Oak Bluffs, MA 02557

    Build your Martha's Vineyard dream home on this exceptional 1.068-acre parcel in Oak Bluffs. This offering includes approved plans for a six bedroom septic system, saving valuable time in the building process. A topographic/boundary map and soil test included, providing a solid foundation for planning your future home. Subject to the Town of Oak Bluff's zoning requirements and permitting, this

    Casandra Hyland Sandpiper Realty, Inc.

    68 Pond View Dr, Oak Bluffs, MA 02557
  • 82 Pennsylvania Ave, Oak Bluffs, MA 02557
    82 Pennsylvania Ave, Oak Bluffs, MA 02557
    82 Pennsylvania Ave, Oak Bluffs, MA 02557
    /13

    $1,296,000

    • 3 Beds
    • 1.5 Baths
    • 1,144 Sq Ft

    82 Pennsylvania Ave, Oak Bluffs, MA 02557

    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 space with a spacious TV room and game area for extra entertainment, while the welcoming back deck

    Emma Kennedy Sandpiper Realty, Inc.

    82 Pennsylvania Ave, Oak Bluffs, MA 02557
  • 40 Hidden Cove Rd Unit 2, Oak Bluffs, MA 02557
    40 Hidden Cove Rd Unit 2, Oak Bluffs, MA 02557
    40 Hidden Cove Rd Unit 2, Oak Bluffs, MA 02557
    /28

    $1,595,000

    Open Tue 4PM - 5PM
    • 3 Beds
    • 3.5 Baths
    • 2,739 Sq Ft

    40 Hidden Cove Rd 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

    40 Hidden Cove Rd Unit 2, Oak Bluffs, MA 02557
  • 40 Hidden Cove Road Unit 2 Unit 2, Oak Bluffs, MA 02557
    40 Hidden Cove Road Unit 2 Unit 2, Oak Bluffs, MA 02557
    40 Hidden Cove Road Unit 2 Unit 2, Oak Bluffs, MA 02557
    /28

    $1,595,000

    Open Tue 4PM - 5PM
    • 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
  • 11 Beach Rd, Oak Bluffs, MA 02557
    11 Beach Rd, Oak Bluffs, MA 02557
    11 Beach Rd, Oak Bluffs, MA 02557
    /20

    $1,745,000

    Open Sun 1PM - 3PM
    • 2 Beds
    • 1 Bath
    • 560 Sq Ft

    11 Beach Rd, Oak Bluffs, MA 02557

    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 rare opportunity to own a slice of waterfront paradise. Designed for relaxed seaside living, the home

    Carleen Cordwell Anchor Realty of Martha's Vineyard

    11 Beach Rd, Oak Bluffs, MA 02557
  • 30 Double Ox Rd Unit 33, Oak Bluffs, MA 02557
    30 Double Ox Rd Unit 33, Oak Bluffs, MA 02557
    30 Double Ox Rd Unit 33, Oak Bluffs, MA 02557
    /7

    $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
  • 60R Carol Ln, Oak Bluffs, MA 02557
    60R Carol Ln, Oak Bluffs, MA 02557
    60R Carol Ln, Oak Bluffs, MA 02557
    /14

    $794,000

    • 2 Beds
    • 1 Bath
    • 624 Sq Ft

    60R Carol Ln, Oak Bluffs, MA 02557

    Tucked away down a quiet lane just moments from downtown Oak Bluffs, sits this charming home. Nestled on just over an 8,400 sq. ft. lot, the property offers compact single-story living, ideal for those seeking simplicity while being close to everything the island. The bright, open concept features a living area and kitchen with breakfast bar. Ample storage and a stackable washer/dryer complete

    Michele Moore Island Real Estate

    60R Carol Ln, Oak Bluffs, MA 02557
  • 33 Vineyard Ave, Oak Bluffs, MA 02557
    33 Vineyard Ave, Oak Bluffs, MA 02557
    33 Vineyard Ave, Oak Bluffs, MA 02557
    /31

    $1,995,000

    Open Wed 10:30AM - 11AM
    • 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
  • 27 Double Ox Rd, Oak Bluffs, MA 02557
    27 Double Ox Rd, Oak Bluffs, MA 02557
    27 Double Ox Rd, Oak Bluffs, MA 02557
    /12

    $3,400,000

    New Construction
    • 3 Beds
    • 4.5 Baths
    • 3,260 Sq Ft

    27 Double Ox Rd, Oak Bluffs, MA 02557

    Set on a private 1.34-acre parcel along a winding paved road in Oak Bluffs, this exceptional to-be-built luxury residence offers the perfect blend of modern sophistication and island charm. The home features over 3,200 square feet of beautifully crafted living space, including a first-floor primary suite, open-concept great room, gourmet kitchen with pantry, and seamless indoor-outdoor living

    Lesley Heidt Sandpiper Realty, Inc.

    27 Double Ox Rd, Oak Bluffs, MA 02557
  • 27 Laurel Ave, Oak Bluffs, MA 02557
    27 Laurel Ave, Oak Bluffs, MA 02557
    27 Laurel Ave, Oak Bluffs, MA 02557
    /39

    $1,575,000

    • 3 Beds
    • 3 Baths
    • 1,621 Sq Ft

    27 Laurel Ave, Oak Bluffs, MA 02557

    Located in exclusive East Chop, this sun-filled 3BR Cottage blends authentic Martha’s Vineyard charm with modern coastal living. Immaculate, fully furnished, and turn-key, this property presents a phenomenal island retreat or a lucrative investment with fantastic rental potential.The main home pairs classic character with upgraded 200-amp electric, featuring bright spaces, a large kitchen, and

    Lisa Sheehan Berkshire Hathaway HomeServices Robert Paul Properties

    27 Laurel Ave, Oak Bluffs, MA 02557
  • 9 Weston Ave, Oak Bluffs, MA 02557
    9 Weston Ave, Oak Bluffs, MA 02557
    9 Weston Ave, Oak Bluffs, MA 02557
    /37

    $3,750,000

    • 4 Beds
    • 3 Baths
    • 2,204 Sq Ft

    9 Weston Ave, Oak Bluffs, MA 02557

    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, screened porch opens onto an expansive deck, perfect for relaxing or entertaining. The first floor

    Gerrett Conover Landvest MV

    9 Weston Ave, Oak Bluffs, MA 02557
  • 28 Grovedale Rd, Oak Bluffs, MA 02557
    28 Grovedale Rd, Oak Bluffs, MA 02557
    28 Grovedale Rd, Oak Bluffs, MA 02557
    /40

    $1,750,000

    • 3 Beds
    • 3.5 Baths
    • 2,376 Sq Ft

    28 Grovedale Rd, Oak Bluffs, MA 02557

    GORGEOUS NEWER CONSTRUCTION (2023), contemporary farmhouse style home w/ classic wrap around porch & designed w/ Vineyard charm & modern comfort. And yet still there is opportunity to add value to this open concept home, w/ high ceilings, 3 en-suite BRs, laundry on each level, hardwoods throughout. Well designed, fully poured unfinished basement w/ high ceilings, wide open & w/ a separate

    David White OwnerEntry.com

    28 Grovedale Rd, Oak Bluffs, MA 02557
  • 12 Samoset Ave, Oak Bluffs, MA 02557
    12 Samoset Ave, Oak Bluffs, MA 02557
    12 Samoset Ave, Oak Bluffs, MA 02557
    /36

    $2,575,000

    • 4 Beds
    • 1.5 Baths
    • 1,606 Sq Ft

    12 Samoset Ave, Oak Bluffs, MA 02557

    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, restaurants, and all the attractions of downtown Oak Bluffs, this warm and welcoming four-bedroom home

    Marilyn Moses Ocean Park Realty Inc

    12 Samoset Ave, Oak Bluffs, MA 02557
  • 21 Butler Ave, Oak Bluffs, MA 02557
    21 Butler Ave, Oak Bluffs, MA 02557
    21 Butler Ave, Oak Bluffs, MA 02557
    /35

    $1,075,000

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

    21 Butler Ave, Oak Bluffs, MA 02557

    Located within the historic Martha’s Vineyard Camp Meeting Association, this rare double-lot property combines classic Campground charm with the comfort, privacy, and functionality of a thoughtfully modernized home. Two-car off-street parking—an exceptional Campground amenity—adds everyday convenience, while Oak Bluffs Harbor, beaches, ferries, shops, and restaurants are just moments away.

    Jennifer O'hanlon Compass LLC

    21 Butler Ave, Oak Bluffs, MA 02557
  • 47 Winemack St, Oak Bluffs, MA 02557
    47 Winemack St, Oak Bluffs, MA 02557
    47 Winemack St, Oak Bluffs, MA 02557
    /18

    $1,199,000

    • 3 Beds
    • 2 Baths
    • 1,302 Sq Ft

    47 Winemack St, Oak Bluffs, MA 02557

    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 flooring. The second home nestled in the back of the lot is an open floor plan with one bedroom, one

    Lisa Lucier Anchor Realty of MV

    47 Winemack St, Oak Bluffs, MA 02557
  • 312 E Chop Dr, Vineyard Haven, MA 02568
    312 E Chop Dr, Vineyard Haven, MA 02568
    312 E Chop Dr, Vineyard Haven, MA 02568
    /38

    $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
  • 19 Perkins Ave, Oak Bluffs, MA 02557
    19 Perkins Ave, Oak Bluffs, MA 02557
    19 Perkins Ave, Oak Bluffs, MA 02557
    /14

    $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
  • 312 E Chop Dr, Oak Bluffs, MA 02557
    312 E Chop Dr, Oak Bluffs, MA 02557
    312 E Chop Dr, Oak Bluffs, MA 02557
    /36

    $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
  • 7 Ploughshare Ln, Oak Bluffs, MA 02557
    7 Ploughshare Ln, Oak Bluffs, MA 02557
    7 Ploughshare Ln, Oak Bluffs, MA 02557
    /33

    $1,599,000

    • 3 Beds
    • 2.5 Baths
    • 1,645 Sq Ft

    7 Ploughshare Ln, Oak Bluffs, MA 02557

    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 layout flows seamlessly from the fireplaced living room and kitchen through the dining area to an

    Emma Kennedy Sandpiper Realty, Inc.

    7 Ploughshare Ln, Oak Bluffs, MA 02557
  • 3 Troy St, Oak Bluffs, MA 02557
    3 Troy St, Oak Bluffs, MA 02557
    3 Troy St, Oak Bluffs, MA 02557
    /26

    $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
  • 15 Tamarack Ln, Oak Bluffs, MA 02557
    15 Tamarack Ln, Oak Bluffs, MA 02557
    15 Tamarack Ln, Oak Bluffs, MA 02557
    /42

    $4,600,000

    $350K PRICE DROP
    • 6 Beds
    • 5.5 Baths
    • 3,998 Sq Ft

    15 Tamarack Ln, Oak Bluffs, MA 02557

    Nestled within the idyllic and highly coveted setting of Farm Neck Golf Club, 15 Tamarack Lane offers 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 over the 7th fairway and 8th tee box, across to Sengekontacket Pond, creating a peaceful backdrop of lush greens and distant water. The historic

    Stephanie Roache Donnelly + Co.

    15 Tamarack Ln, Oak Bluffs, MA 02557
  • 7 Highland Ave Unit 119, Vineyard Haven, MA 02568
    7 Highland Ave Unit 119, Vineyard Haven, MA 02568
    7 Highland Ave Unit 119, Vineyard Haven, MA 02568
    /4

    $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
  • 7 Overview Ln, Oak Bluffs, MA 02557
    7 Overview Ln, Oak Bluffs, MA 02557
    7 Overview Ln, Oak Bluffs, MA 02557
    /13

    $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
  • 61 Ocean Ave Unit 4, Oak Bluffs, MA 02557
    61 Ocean Ave Unit 4, Oak Bluffs, MA 02557
    61 Ocean Ave Unit 4, Oak Bluffs, MA 02557
    /26

    $1,299,000

    $100K PRICE DROP
    • 1 Bed
    • 1 Bath
    • 546 Sq Ft

    61 Ocean Ave Unit 4, Oak Bluffs, MA 02557

    THE BEST SEAT IN TOWN! This one-bedroom, one-bathroom condo offers incomparable, panoramic views of Vineyard Sound and the open ocean beyond, across the green expanse of Ocean Park with the Steamship Authority dock in the distance. Door to door, the ferry dock is 392 yards away. This perfect pied-a-terre is convenient to long stretches of beach, numerous shops, great and varied restaurants and

    Buder Team Sandpiper Realty, Inc.

    61 Ocean Ave Unit 4, Oak Bluffs, MA 02557
  • 44 Tiffany Dr, Oak Bluffs, MA 02557
    44 Tiffany Dr, Oak Bluffs, MA 02557
    44 Tiffany Dr, Oak Bluffs, MA 02557
    /31

    $2,900,000

    $345K PRICE DROP
    • 4 Beds
    • 4.5 Baths
    • 4,023 Sq Ft

    44 Tiffany Dr, Oak Bluffs, MA 02557

    Classic Vineyard charm meets modern luxury. Set on 1.38 private acres, this beautifully renovated 4BR/4.5BA Cape offers over 4,000 sq. ft. of living space, a gourmet kitchen, multiple entertaining areas, a screened porch, and a separate one-bedroom guest apartment above the garage. Renovations include two new kitchens (one in the apartment), 4.5 new bathrooms, 4-bedrooms (two ensuite), all new

    Perry Patterson MV Luxury Homes

    44 Tiffany Dr, Oak Bluffs, MA 02557
  • 0 Temahigan Ave Unit 160, Oak Bluffs, MA 02568
    0 Temahigan Ave Unit 160, Oak Bluffs, MA 02568
    0 Temahigan Ave Unit 160, Oak Bluffs, MA 02568
    /12

    $1,200,000

    • Land
    • 10,890 Sq Ft
    • $4,800,000 per Acre

    0 Temahigan Ave Unit 160, Oak Bluffs, MA 02568

    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 bedrooms, this exceptional property includes an approved 6-bedroom septic design, with room for a

    Agent Photo

    Rene Ben David

    Ocean Park Realty Inc

    0 Temahigan Ave Unit 160, Oak Bluffs, MA 02568
  • 0 Temahigan Ave Unit 22602202, Oak Bluffs, MA 02568
    0 Temahigan Ave Unit 22602202, Oak Bluffs, MA 02568
    0 Temahigan Ave Unit 22602202, Oak Bluffs, MA 02568
    /8

    $1,200,000

    • Land
    • 10,890 Sq Ft
    • $4,800,000 per Acre

    0 Temahigan Ave Unit 22602202, Oak Bluffs, MA 02568

    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 bedrooms, this exceptional property includes an approved 6-bedroom septic design, with room for a

    Agent Photo

    Rene Ben David

    0 Temahigan Ave Unit 22602202, Oak Bluffs, MA 02568
  • 4 Quail Run Unit 21, Oak Bluffs, MA 02557
    4 Quail Run Unit 21, Oak Bluffs, MA 02557
    4 Quail Run Unit 21, Oak Bluffs, MA 02557
    /26

    $925,000

    • 2 Beds
    • 1.5 Baths
    • 1,208 Sq Ft

    4 Quail Run Unit 21, Oak Bluffs, MA 02557

    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 relaxed island charm with modern convenience—perfect for year-round living or as an established rental

    Emma Bryant Studio Realty

    4 Quail Run Unit 21, Oak Bluffs, MA 02557
  • 22 Firehouse Ln, Oak Bluffs, MA 02557
    22 Firehouse Ln, Oak Bluffs, MA 02557
    22 Firehouse Ln, Oak Bluffs, MA 02557
    /15

    $940,000

    $10K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 1,074 Sq Ft

    22 Firehouse Ln, Oak Bluffs, MA 02557

    Tucked away on a quiet side street just 0.7 miles from Circuit Avenue, this charming Oak Bluffs cottage offers the rare combination of privacy and proximity to town. The original two-bedroom, one-bath home was thoughtfully expanded to include a bright great room that opens directly to a large fenced yard — ideal for outdoor dining, pets, or simply enjoying Vineyard summers. The property is

    Jennifer O'hanlon Compass LLC

    22 Firehouse Ln, Oak Bluffs, MA 02557
  • 8 Paddock Rd, Oak Bluffs, MA 02557
    8 Paddock Rd, Oak Bluffs, MA 02557
    8 Paddock Rd, Oak Bluffs, MA 02557
    /47

    $5,450,000

    • 4 Beds
    • 5.5 Baths
    • 3,300 Sq Ft

    8 Paddock Rd, Oak Bluffs, MA 02557

    Refined Vineyard Living in The Preserve - Set atop a knoll overlooking sweeping grassland and the pond, this exceptional residence embodies the perfect balance of classic coastal architecture and modern sophistication. Located within the prestigious enclave of The Preserve, the home offers a combination of privacy, elegance, and seamless indoor-outdoor living. At its core, an expansive great room

    Lesley Heidt Sandpiper Realty

    8 Paddock Rd, Oak Bluffs, MA 02557
  • 46 Kennebec Ave, Oak Bluffs, MA 02557
    46 Kennebec Ave, Oak Bluffs, MA 02557
    46 Kennebec Ave, Oak Bluffs, MA 02557
    /40

    $1,395,000

    • 4 Beds
    • 3 Baths
    • 1,305 Sq Ft

    46 Kennebec Ave, Oak Bluffs, MA 02557

    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 Harbor, a supermarket, and a variety of charming restaurants and shops that contribute to Oak Bluffs'

    Michael Schweikert Ocean Park Realty Inc

    46 Kennebec Ave, Oak Bluffs, MA 02557
  • 22 Old Harbor Ln, Oak Bluffs, MA 02557
    22 Old Harbor Ln, Oak Bluffs, MA 02557
    22 Old Harbor Ln, Oak Bluffs, MA 02557
    /25

    $1,850,000

    • 4 Beds
    • 2 Baths
    • 1,833 Sq Ft

    22 Old Harbor Ln, Oak Bluffs, MA 02557

    Quintessential Waterview Farm! Built as a year-round home with the charm of the original cottages, this well-loved retreat awaits its next chapter. The sunny, open floor plan offers two bedrooms and a full bath on each level, with generous gathering spaces throughout. A skylit kitchen is tucked into a corner of the main living area, where a curved wall of glass opens to a deck and private yard.

    Lisa Stewart Sandpiper Realty, Inc.

    22 Old Harbor Ln, Oak Bluffs, MA 02557
  • 7 Overview Ln Unit 47, Oak Bluffs, MA 02557
    7 Overview Ln Unit 47, Oak Bluffs, MA 02557
    7 Overview Ln Unit 47, Oak Bluffs, MA 02557
    /14

    $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
  • 26 Sea Glen Rd, Oak Bluffs, MA 02557
    26 Sea Glen Rd, Oak Bluffs, MA 02557
    26 Sea Glen Rd, Oak Bluffs, MA 02557
    /39

    $1,495,000

    $130K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 1,514 Sq Ft

    26 Sea Glen Rd, Oak Bluffs, MA 02557

    Nestled in a desirable neighborhood, this beautifully maintained cape style home offers a rare blend of charm, flexibility and convenience in a serene island setting. Thoughtfully appointed throughout, the home welcomes you with an open living room that flows effortlessly into a bright dining area, where French doors open to a private stone patio—creating an inviting connection between indoor

    Jennifer B. DaSilva Compass

    26 Sea Glen Rd, Oak Bluffs, MA 02557
  • 34 Windemere Rd, Oak Bluffs, MA 02557
    34 Windemere Rd, Oak Bluffs, MA 02557
    34 Windemere Rd, Oak Bluffs, MA 02557
    /64

    $2,579,000

    • 4 Beds
    • 2 Baths
    • 1,399 Sq Ft

    34 Windemere Rd, Oak Bluffs, MA 02557

    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 location with all the modern comforts one would want. The house is perfectly sited to take full

    Alisan Lohan-Conway Alisan Lohan-Conway Properties

    34 Windemere Rd, Oak Bluffs, MA 02557
  • 98 Farm Neck Way Unit 51, Oak Bluffs, MA 02568
    98 Farm Neck Way Unit 51, Oak Bluffs, MA 02568
    98 Farm Neck Way Unit 51, Oak Bluffs, MA 02568
    /10

    $3,750,000

    $245K PRICE DROP
    • Land
    • 1.92 Acres
    • $1,956,182 per Acre

    98 Farm Neck Way Unit 51, Oak Bluffs, MA 02568

    Farm Neck Golf Club – Undeveloped Water View Parcel with Membership A truly rare opportunity to acquire a 1.92-acre undeveloped parcel within the prestigious Farm Neck Golf Club community, one of the last remaining opportunities of its kind. This exceptional offering features sweeping water views over Sengekontacket Pond to the Vineyard Sound, creating a stunning backdrop for your future Martha’s

    Andrew McElhinney Compass LLC

    98 Farm Neck Way Unit 51, Oak Bluffs, MA 02568
  • 68 Front St, Oak Bluffs, MA 02557
    68 Front St, Oak Bluffs, MA 02557
    68 Front St, Oak Bluffs, MA 02557
    /38

    $1,755,000

    $40K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 2,695 Sq Ft

    68 Front St, Oak Bluffs, MA 02557

    Nestled at the end of a quiet street, this charming and spacious Cape-style home offers both privacy and convenience, just a short distance from the Oak Bluffs School and town center, and walking distance to the Lagoon. Thoughtfully maintained, the sun-filled main level boasts an open floor plan with large windows that frame views of the surrounding property. The generously sized kitchen features

    Jayne Isford Ocean Park Realty Inc

    68 Front St, Oak Bluffs, MA 02557
  • 385 Barnes Rd, Vineyard Haven, MA 02568
    385 Barnes Rd, Vineyard Haven, MA 02568
    385 Barnes Rd, Vineyard Haven, MA 02568
    /70

    $5,295,000

    $200K PRICE DROP
    • 3 Beds
    • 7 Baths
    • 3,608 Sq Ft

    385 Barnes Rd, Vineyard Haven, MA 02568

    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 space across three levels, the property is thoughtfully oriented to maximize light, views, and

    Stephanie Roache Donnelly + Co

    385 Barnes Rd, Vineyard Haven, MA 02568
  • 37 Circuit Ave Unit 4, Oak Bluffs, MA 02557
    37 Circuit Ave Unit 4, Oak Bluffs, MA 02557
    37 Circuit Ave Unit 4, Oak Bluffs, MA 02557
    /20

    $899,000

    • 2 Beds
    • 1 Bath
    • 990 Sq Ft

    37 Circuit Ave Unit 4, Oak Bluffs, MA 02557

    In the heart of Downtown Oak Bluffs this Restless Winds Penthouse condominium Unit #4 on 2nd floor 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 nautical feel with custom wood features and a ships ladder leading to the roof top deck. This condo packs a lot in with a full kitchen, living and dining area, a guest

    Lisa Lucier Anchor Realty of MV

    37 Circuit Ave Unit 4, Oak Bluffs, MA 02557
  • 37 Circuit Ave Unit 5, Oak Bluffs, MA 02557
    37 Circuit Ave Unit 5, Oak Bluffs, MA 02557
    37 Circuit Ave Unit 5, Oak Bluffs, MA 02557
    /27

    $869,000

    • 1 Bed
    • 1 Bath
    • 797 Sq Ft

    37 Circuit Ave Unit 5, Oak Bluffs, MA 02557

    In the heart of Downtown Oak Bluffs walk to everything from this Circuit Avenue location Unit #5 comes with an amazing roof top deck that is only shared with one other condo (#4). This well appointed sleeps 4 with custom wood features and a staircase to the roof top deck. This condo packs a lot in with a full kitchen, living and dining area,, large bedroom with alcove, a sleep nook, a tiled

    Lisa Lucier Anchor Realty of MV

    37 Circuit Ave Unit 5, Oak Bluffs, MA 02557

Showing Results 1 - 40, Page 1 of 2

Massachusetts Dukes County Marthas Vineyard Oak Bluffs

Real Estate & Homes for Sale in Oak Bluffs, Marthas Vineyard

Learn more about living in Oak Bluffs

Oak Bluffs Home Prices vs. Nearby Marthas Vineyard, MA Neighborhoods

Oak Bluffs North Falmouth Vineyard Haven Jamestown Village
Median Home Price
$1,595,000
$1,075,000
$1,750,000
$1,750,000
Median Sale Price
$1,424,500
+30% YoY
$1,235,000
+24% YoY
$1,500,000
+15% YoY
$1,350,000
Median Single Family Price
$1,600,000
$1,075,000
$1,735,000
$1,587,500
Median Condo Price
$933,000
$1,012,250
$1,175,000
$950,000
Total Active Listings
81
12
68
11
Market Conditions
5 Months of Supply
Balanced Market
1 Months of Supply
Seller's Market
8 Months of Supply
Buyer's Market
5 Months of Supply
Balanced Market

Frequently Asked Questions

Is Oak Bluffs a good place to live?
Oak Bluffs is a good place to live. Oak Bluffs is considered very car-dependent and somewhat bikeable with some transit options. Oak Bluffs is a neighborhood with a crime score of 1, making it safer than the average neighborhood in the U.S. Oak Bluffs has 5 parks for recreational activities. It is sparse in population with 2.0 people per acre and a median age of 49. The average household income is $133,511 which is above the national average. College graduates make up 46.9% of residents. A majority of residents in Oak Bluffs are home owners, with 27% of residents renting and 73% of residents owning their home. A local real estate agent serving Oak Bluffs can help you decide if this neighborhood is the right one for you. Learn more on our Oak Bluffs neighborhood guide.
Is Oak Bluffs, MA a safe neighborhood?
Oak Bluffs, MA is safer than the average neighborhood in the United States. It received a crime score of 1 out of 10.
How much do you need to make to afford a house in Oak Bluffs?
The median home price in Oak Bluffs is $1,595,000. If you put a 20% down payment of $319,000 and had a 30-year fixed mortgage with an interest rate of 6.49%, your estimated principal and interest payment would be $8,060 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $345K a year to afford the median home price in Oak Bluffs. Learn how much home you can afford with our Home Affordability Calculator. The average household income in Oak Bluffs is $134K.
What are the best public schools in Oak Bluffs?
The best public schools that serve Oak Bluffs are:
What are the best private schools in Oak Bluffs?
The best private schools that serve Oak Bluffs are:
What are the most popular zip codes in Oak Bluffs, Marthas Vineyard, MA?
The most popular zip codes in Oak Bluffs, Marthas Vineyard, MA include 02568, 02536, 02539, 02575 and 02535.
What are the most popular neighborhoods near Oak Bluffs, Marthas Vineyard, MA?
The most popular neighborhoods near Oak Bluffs, Marthas Vineyard, MA are Vineyard Haven, Edgartown, West Tisbury, Chilmark and Falmouth Village.
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