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Newest Homes for Sale in Oak Bluffs

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  • 24 Harrison Ave, Oak Bluffs, MA 02557
    24 Harrison Ave, Oak Bluffs, MA 02557
    24 Harrison Ave, Oak Bluffs, MA 02557
    /23

    $2,595,000

    • 2 Beds
    • 3 Baths
    • 1,586 Sq Ft

    24 Harrison Ave, Oak Bluffs, MA 02557

    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 Gordon Landscape Architects. This recently completed cozy 2BR/2.5 BA with solar panels providing

    Perry Patterson MV Luxury Homes

    24 Harrison Ave, Oak Bluffs, MA 02557
  • 53 Circuit Ave, Oak Bluffs, MA 02557
    53 Circuit Ave, Oak Bluffs, MA 02557
    53 Circuit Ave, Oak Bluffs, MA 02557
    /75

    $5,500,000

    • 6 Beds
    • 6 Baths
    • 5,706 Sq Ft

    53 Circuit Ave, Oak Bluffs, MA 02557

    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 Vineyard's most sought-after high-foot-traffic downtown locations. The Union Chapel, across the

    Stephanie Roache Donnelly + Co

    53 Circuit Ave, Oak Bluffs, MA 02557
  • 27 Beach Rd, Oak Bluffs, MA 02557
    27 Beach Rd, Oak Bluffs, MA 02557
    27 Beach Rd, Oak Bluffs, MA 02557
    /31

    $2,995,000

    • 4 Beds
    • 1.5 Baths
    • 3,462 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 International Realty

    27 Beach Rd, Oak Bluffs, MA 02557
  • 33 Island Inn Rd Unit 25F, Oak Bluffs, MA 02568
    33 Island Inn Rd Unit 25F, Oak Bluffs, MA 02568
    33 Island Inn Rd Unit 25F, Oak Bluffs, MA 02568
    /27

    $260,000

    • 1 Bed
    • 1 Bath
    • 319 Sq Ft

    33 Island Inn Rd Unit 25F, Oak Bluffs, MA 02568

    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 is a seasonal resort, open April through October, offering a relaxed, pet-friendly setting with a

    Agent Photo

    Rene Ben David

    Ocean Park Realty Inc

    33 Island Inn Rd Unit 25F, Oak Bluffs, MA 02568
  • 21 Island Inn Rd Unit 38G, Oak Bluffs, MA 02568
    21 Island Inn Rd Unit 38G, Oak Bluffs, MA 02568
    21 Island Inn Rd Unit 38G, Oak Bluffs, MA 02568
    /43

    $527,500

    • 1 Bed
    • 1.5 Baths
    • 590 Sq Ft

    21 Island Inn Rd Unit 38G, Oak Bluffs, MA 02568

    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. Accommodating up to six guests, the unit features one bedroom with a queen bed, a separate sleeping area

    Agent Photo

    Rene Ben David

    Ocean Park Realty Inc

    21 Island Inn Rd Unit 38G, Oak Bluffs, MA 02568
  • 27 Island Inn Rd Unit 9C, Oak Bluffs, MA 02568
    27 Island Inn Rd Unit 9C, Oak Bluffs, MA 02568
    27 Island Inn Rd Unit 9C, Oak Bluffs, MA 02568
    /41

    $287,500

    • 1 Bed
    • 1 Bath
    • 388 Sq Ft

    27 Island Inn Rd Unit 9C, Oak Bluffs, MA 02568

    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 WiFi. A unique opportunity is adjoining Unit 10C, a separate 1-bedroom, 1-bath suite accommodating up

    Agent Photo

    Rene Ben David

    Ocean Park Realty Inc

    27 Island Inn Rd Unit 9C, Oak Bluffs, MA 02568
  • 27 Island Inn Rd Unit 10C, Oak Bluffs, MA 02568
    27 Island Inn Rd Unit 10C, Oak Bluffs, MA 02568
    27 Island Inn Rd Unit 10C, Oak Bluffs, MA 02568
    /32

    $310,000

    • 1 Bed
    • 1 Bath
    • 419 Sq Ft

    27 Island Inn Rd Unit 10C, Oak Bluffs, MA 02568

    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 unique feature is the adjoining door to Unit 9C, a studio with two double beds, full bath and

    Agent Photo

    Rene Ben David

    Ocean Park Realty Inc

    27 Island Inn Rd Unit 10C, Oak Bluffs, MA 02568
  • 27 Island Inn Rd Unit D17, Oak Bluffs, MA 02568
    27 Island Inn Rd Unit D17, Oak Bluffs, MA 02568
    27 Island Inn Rd Unit D17, Oak Bluffs, MA 02568
    /18

    $250,000

    • 1 Bed
    • 1 Bath
    • 331 Sq Ft

    27 Island Inn Rd Unit D17, Oak Bluffs, MA 02568

    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 State Beach and then further on into Edgartown ...OR a short distance north to Oak Bluffs center, ferry

    Patti Dean Wiggy's Pond Real Estate

    27 Island Inn Rd Unit D17, Oak Bluffs, MA 02568
  • 11 Stanley St, Oak Bluffs, MA 02557
    11 Stanley St, Oak Bluffs, MA 02557
    11 Stanley St, Oak Bluffs, MA 02557
    /18

    $1,255,000

    • 3 Beds
    • 1.5 Baths
    • 912 Sq Ft

    11 Stanley St, Oak Bluffs, MA 02557

    Nestled on a cul-de-sac is this sweet 3 bedroom ranch. Located on a .34 acre lot with plenty of room to expand this solid home and still have enough space for an ADU on this spacious lot. Well maintained over the years with recent upgrades including, roof, siding, new insulation, flooring and paint. Natural light floods the house from the bank of windows in the living room to the sliding glass

    Lisa Lucier Anchor Realty of Martha's Vineyard

    11 Stanley St, Oak Bluffs, MA 02557
  • 3 Dukes County Ave, Oak Bluffs, MA 02557
    3 Dukes County Ave, Oak Bluffs, MA 02557
    3 Dukes County Ave, Oak Bluffs, MA 02557
    /24

    $935,000

    • 2 Beds
    • 1 Bath
    • 763 Sq Ft

    3 Dukes County Ave, Oak Bluffs, MA 02557

    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 full bed and twin bunk room with built in wardrobe and desk bathroom. Bathroom shower bath

    Karen Trotier Laer Realty Partners

    3 Dukes County Ave, Oak Bluffs, MA 02557
  • 2 Winemack St, Oak Bluffs, MA 02557
    2 Winemack St, Oak Bluffs, MA 02557
    2 Winemack St, Oak Bluffs, MA 02557
    /28

    $1,095,000

    Open Sun 11AM - 1PM $100K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,456 Sq Ft

    2 Winemack St, Oak Bluffs, MA 02557

    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 downtown, you’ll enjoy convenient access to the ferries, Oak Bluffs Harbor, beaches, shopping,

    Agent Photo

    Rene Ben David

    Ocean Park Realty Inc

    2 Winemack St, Oak Bluffs, MA 02557
  • 20 Hidden Cove Rd, Oak Bluffs, MA 02557
    20 Hidden Cove Rd, Oak Bluffs, MA 02557
    20 Hidden Cove Rd, Oak Bluffs, MA 02557
    /45

    $1,625,000

    • 4 Beds
    • 3 Baths
    • 1,898 Sq Ft

    20 Hidden Cove Rd, Oak Bluffs, MA 02557

    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 paddleboarding, as well as community tennis courts just steps from your front door. Set on a private, wooded

    Jennifer DaSilva Compass | Point B

    20 Hidden Cove Rd, Oak Bluffs, MA 02557
  • 14 High Meadow Ln, Oak Bluffs, MA 02557
    14 High Meadow Ln, Oak Bluffs, MA 02557
    14 High Meadow Ln, Oak Bluffs, MA 02557
    /37

    $1,750,000

    • 3 Beds
    • 4 Baths
    • 1,932 Sq Ft

    14 High Meadow Ln, Oak Bluffs, MA 02557

    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 take you outside to the upper deck. Open the sliders to the expansive deck and you will almost double

    Jennifer DaSilva Compass | Point B

    14 High Meadow Ln, Oak Bluffs, MA 02557
  • 61 Winemack St, Oak Bluffs, MA 02557
    61 Winemack St, Oak Bluffs, MA 02557
    61 Winemack St, Oak Bluffs, MA 02557
    /7

    $850,000

    • 2 Beds
    • 1 Bath
    • 992 Sq Ft

    61 Winemack St, Oak Bluffs, MA 02557

    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 ideally located just 0.9 miles from the East Chop Lighthouse, 1.3 miles from the East Chop Beach Club,

    Andrew McElhinney Compass LLC

    61 Winemack St, Oak Bluffs, MA 02557
  • 54 Towanticut Ave, Oak Bluffs, MA 02568
    54 Towanticut Ave, Oak Bluffs, MA 02568
    54 Towanticut Ave, Oak Bluffs, MA 02568
    /23

    $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
  • 0 Heather Ln Unit 56, Oak Bluffs, MA 02568
    0 Heather Ln Unit 56, Oak Bluffs, MA 02568
    /2

    $425,000

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

    0 Heather Ln Unit 56, 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 DaSilva Compass | Point B

    0 Heather Ln Unit 56, Oak Bluffs, MA 02568
  • 0 Heather Ln Unit 73560451, Oak Bluffs, MA 02568
    0 Heather Ln Unit 73560451, Oak Bluffs, MA 02568
    /2

    $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
  • 323 County Rd, Oak Bluffs, MA 02557
    323 County Rd, Oak Bluffs, MA 02557
    323 County Rd, Oak Bluffs, MA 02557
    /33

    $1,225,000

    • 1 Bed
    • 2 Baths
    • 1,428 Sq Ft

    323 County Rd, Oak Bluffs, MA 02557

    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 proven income-producing investment. The home features a bright, open-concept kitchen, dining, and

    Nancy Beckwith Anchor Realty of Martha's Vineyard

    323 County Rd, Oak Bluffs, MA 02557
  • 170 Barnes Rd, Oak Bluffs, MA 02557
    170 Barnes Rd, Oak Bluffs, MA 02557
    170 Barnes Rd, Oak Bluffs, MA 02557
    /19

    $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
  • 99 Ocean Ave, Oak Bluffs, MA 02557
    99 Ocean Ave, Oak Bluffs, MA 02557
    99 Ocean Ave, Oak Bluffs, MA 02557
    /36

    $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
  • 33 Island Inn Rd Unit F 22, Oak Bluffs, MA 02568
    33 Island Inn Rd Unit F 22, Oak Bluffs, MA 02568
    33 Island Inn Rd Unit F 22, Oak Bluffs, MA 02568
    /18

    $239,000

    • 1 Bed
    • 1 Bath
    • 316 Sq Ft

    33 Island Inn Rd Unit F 22, Oak Bluffs, MA 02568

    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 association pool, 3 tennis courts, playground, and shared grilling area. This wonderful location borders Farm

    Rene Jackson Island Real Estate

    33 Island Inn Rd Unit F 22, Oak Bluffs, MA 02568
  • 22 Paddock Rd Unit 85, Oak Bluffs, MA 02568
    22 Paddock Rd Unit 85, Oak Bluffs, MA 02568
    22 Paddock Rd Unit 85, Oak Bluffs, MA 02568
    /6

    $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
  • 43 Sengekontacket Rd, Oak Bluffs, MA 02557
    43 Sengekontacket Rd, Oak Bluffs, MA 02557
    43 Sengekontacket Rd, Oak Bluffs, MA 02557
    /25

    $5,495,000

    $500K PRICE DROP
    • 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
  • 21 Island Inn Rd Unit 35, Oak Bluffs, MA 02568
    21 Island Inn Rd Unit 35, Oak Bluffs, MA 02568
    21 Island Inn Rd Unit 35, Oak Bluffs, MA 02568
    /37

    $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
  • 59 Tuckernuck Ave, Oak Bluffs, MA 02557
    59 Tuckernuck Ave, Oak Bluffs, MA 02557
    59 Tuckernuck Ave, Oak Bluffs, MA 02557
    /51

    $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
  • 24 Towanticut St, Oak Bluffs, MA 02568
    24 Towanticut St, Oak Bluffs, MA 02568
    24 Towanticut St, Oak Bluffs, MA 02568
    /5

    $789,000

    • Land
    • 16,988 Sq Ft
    • $2,023,077 per Acre

    24 Towanticut St, Oak Bluffs, MA 02568

    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 the lot, which significantly reduces development costs and time. Convenient access from both Towanticut

    Alisan Lohan - Conway Alisan Lohan - Conway Properties

    24 Towanticut St, Oak Bluffs, MA 02568
  • 28 Beach Rd, Oak Bluffs, MA 02557
    28 Beach Rd, Oak Bluffs, MA 02557
    28 Beach Rd, Oak Bluffs, MA 02557
    /40

    $3,675,000

    • 4 Beds
    • 2.5 Baths
    • 1,800 Sq Ft

    28 Beach Rd, Oak Bluffs, MA 02557

    Enjoy Spectacular Views From This Chic Island Retreat. Wake up to panoramic Vineyard Sound views, watch the Steamship ferries cross to Woods Hole, and enjoy sunsets stretching down the Lagoon. This turnkey 4-bedroom, 2.5-bath home is designed to embrace its remarkable waterfront setting, with covered decks on both sides capturing ocean breezes and water views from nearly every room. The first

    Agent Photo

    Wendy Harman

    Compass

    28 Beach Rd, Oak Bluffs, MA 02557
  • 9 Chickawaukee St, Oak Bluffs, MA 02568
    9 Chickawaukee St, Oak Bluffs, MA 02568
    9 Chickawaukee St, Oak Bluffs, MA 02568
    /21

    $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
  • 68 Pond View Dr Unit 2, Oak Bluffs, MA 02557
    68 Pond View Dr Unit 2, Oak Bluffs, MA 02557
    68 Pond View Dr Unit 2, Oak Bluffs, MA 02557
    /6

    $975,000

    • Land
    • 1.07 Acres
    • $912,921 per Acre

    68 Pond View Dr Unit 2, Oak Bluffs, MA 02557

    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 soil test, providing a strong foundation for planning and development.Subject to the Town of

    Casandra Hyland Sandpiper Realty

    68 Pond View Dr Unit 2, Oak Bluffs, MA 02557
  • 8 Pequot Ave, Oak Bluffs, MA 02557
    8 Pequot Ave, Oak Bluffs, MA 02557
    8 Pequot Ave, Oak Bluffs, MA 02557
    /15

    $1,925,000

    • 5 Beds
    • 1 Bath
    • 2,232 Sq Ft

    8 Pequot Ave, Oak Bluffs, MA 02557

    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 front porch has been a gathering place for 50+ years, and the views have not been expanded. So much

    Kerry Quinlan-Potter Breakwater MV

    8 Pequot Ave, Oak Bluffs, MA 02557
  • 68 Pond View Dr, Oak Bluffs, MA 02557
    68 Pond View Dr, Oak Bluffs, MA 02557
    68 Pond View Dr, Oak Bluffs, MA 02557
    /6

    $975,000

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

    68 Pond View Dr, Oak Bluffs, MA 02557

    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 soil test, providing a strong foundation for planning and development. Subject to the Town of Oak

    Casandra Hyland Sandpiper Realty, Inc.

    68 Pond View Dr, Oak Bluffs, MA 02557
  • 26 Winthrop Ave, Oak Bluffs, MA 02557
    26 Winthrop Ave, Oak Bluffs, MA 02557
    26 Winthrop Ave, Oak Bluffs, MA 02557
    /28

    $839,000

    • 1 Bed
    • 1 Bath
    • 804 Sq Ft

    26 Winthrop Ave, Oak Bluffs, MA 02557

    This little gem is waiting to be polished. Hidden behind a wall of vegetation on Winthrop Avenue, an 'oasis', with lots 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 requirements, or build a new house and leave existing structure as an Accessory Dwelling Unit when in

    Alisan Lohan - Conway Alisan Lohan - Conway Properties

    26 Winthrop 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
    /32

    $1,595,000

    • 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 International Realty

    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

    • 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 02568
    11 Beach Rd, Oak Bluffs, MA 02568
    11 Beach Rd, Oak Bluffs, MA 02568
    /20

    $1,745,000

    • 2 Beds
    • 1 Bath
    • 560 Sq Ft

    11 Beach Rd, Oak Bluffs, MA 02568

    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 02568
  • 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
    /2

    $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
    /29

    $1,875,000

    $120K PRICE DROP
    • 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

    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
  • 9 Weston Ave, Oak Bluffs, MA 02568
    9 Weston Ave, Oak Bluffs, MA 02568
    9 Weston Ave, Oak Bluffs, MA 02568
    /37

    $3,750,000

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

    9 Weston Ave, Oak Bluffs, MA 02568

    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 02568

Showing Results 1 - 40, Page 1 of 3

Massachusetts Dukes County

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

Learn more about living in Oak Bluffs

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

Oak Bluffs Vineyard Haven West Tisbury
Median Home Price
$1,595,000
$1,800,000
$1,895,000
Median Sale Price
$1,297,500
+7% YoY
$1,470,000
+16% YoY
$1,537,500
-11% YoY
Median Single Family Price
$1,625,000
$1,895,000
$1,800,000
Median Condo Price
$869,000
$975,000
--
Total Active Listings
92 listings
90 listings
33 listings
Market Conditions
7 Months of Supply
Buyer's Market
9 Months of Supply
Buyer's Market
8 Months of Supply
Buyer's 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 6.65%, your estimated principal and interest payment would be $8,190 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $351K 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 Woods Hole.
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