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Oak Bluffs Homes for Sale

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  • 3 Troy St, Oak Bluffs, MA 02557
    3 Troy St, Oak Bluffs, MA 02557
    3 Troy St, Oak Bluffs, MA 02557
    /27

    $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

    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
    /66

    $4,950,000

    • 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 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 Sengekontacket Pond, offering a serene 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
  • 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.

    Katie Donahue & Rachel Serwa Group Sandpiper Realty, Inc.

    19 Perkins Ave, 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

    $1,399,000

    • 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
  • 47 Winemack St, Oak Bluffs, MA 02557
    47 Winemack St, Oak Bluffs, MA 02557
    47 Winemack St, Oak Bluffs, MA 02557
    /37

    $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

    Agent Photo

    Lisa Lucier

    Anchor Realty of Martha's Vineyard

    (508) 905-5649

    47 Winemack St, 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
    /30

    $3,245,000

    • 4 Beds
    • 4.5 Baths
    • 3,927 Sq Ft

    44 Tiffany Dr, Oak Bluffs, MA 02557

    This handsome, newly renovated classic Cape, is nestled on a private 1.38 acre lot in the sought after Lagoon Estates community. The property has been thoughtfully renovated with two new kitchens, 5 new bathrooms, 4-bedrooms (two ensuite), all new windows and new flooring on first floor. It's seamless floor plan is great for entertaining and flows family and guests from an oversized living room

    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

    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

    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
  • 150 E Chop Dr, Oak Bluffs, MA 02568
    150 E Chop Dr, Oak Bluffs, MA 02568
    150 E Chop Dr, Oak Bluffs, MA 02568
    /41

    $8,900,000

    • 8 Beds
    • 9 Baths
    • 8,170 Sq Ft

    150 E Chop Dr, Oak Bluffs, MA 02568

    BIG BLUFF- Recognized for its architectural significance and featured in leading design publications, this home stands as one of the Vineyard’s most notable coastal residences. Set along the prestigious shoreline of East Chop, this estate represents a rare convergence of architectural pedigree, craftsmanship, and irreplaceable setting. Designed by Hutker Architects, built by J.G. Early, and

    Andrew McElhinney Compass LLC

    150 E Chop Dr, Oak Bluffs, MA 02568
  • 22 Firehouse Ln, Oak Bluffs, MA 02557
    22 Firehouse Ln, Oak Bluffs, MA 02557
    22 Firehouse Ln, Oak Bluffs, MA 02557
    /15

    $950,000

    • 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
  • 66 Barnes Rd, Vineyard Haven, MA 02568
    66 Barnes Rd, Vineyard Haven, MA 02568
    66 Barnes Rd, Vineyard Haven, MA 02568
    /30

    $1,245,000

    • 2 Beds
    • 2 Baths
    • 1,752 Sq Ft

    66 Barnes Rd, Vineyard Haven, MA 02568

    Oak Bluffs~ Classic Cape charm meets modern efficiency in this move-in-ready 2 bedroom plus finished bonus space in basement. Thoughtfully maintained and beautifully presented, the home features sun-filled living spaces, an updated kitchen, and comfortable bedrooms designed for easy everyday living. Enjoy year-round comfort with energy-efficient mini-split systems providing both heating and air

    Marilyn Moses Ocean Park Realty Inc

    66 Barnes Rd, Vineyard Haven, MA 02568
  • 33 Vineyard Ave, Oak Bluffs, MA 02557
    33 Vineyard Ave, Oak Bluffs, MA 02557
    33 Vineyard Ave, Oak Bluffs, MA 02557
    /33

    $1,995,000

    • 3 Beds
    • 2.5 Baths
    • 1,431 Sq Ft

    33 Vineyard Ave, Oak Bluffs, MA 02557

    Welcome to 33 Vineyard Avenue in Oak Bluffs, Martha’s Vineyard. This fully renovated property features a 2BR/2BA primary home plus a separate 1BR/1BA suite—offering flexible, move-in ready living or investment potential in a prime in-town location. The main residence showcases a light-filled interior, wood floors, beamwork, and refined finishes throughout. Open living flows to a gourmet kitchen

    Allison Cameron Parry Douglas Elliman Real Estate - Nantucket

    33 Vineyard Ave, 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
    /27

    $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
  • 7 Overview Ln, Oak Bluffs, MA 02557
    7 Overview Ln, Oak Bluffs, MA 02557
    7 Overview Ln, Oak Bluffs, MA 02557
    /14

    $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 on Martha's Vineyard. 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,

    Alyssa Halisky Wallace & Co. Sotheby's International Realty

    7 Overview Ln, 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
    /36

    $1,595,000

    $30K 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
  • 3 Hidden Cove Rd, Oak Bluffs, MA 02557
    3 Hidden Cove Rd, Oak Bluffs, MA 02557
    3 Hidden Cove Rd, Oak Bluffs, MA 02557
    /41

    $2,295,000

    • 4 Beds
    • 3.5 Baths
    • 3,016 Sq Ft

    3 Hidden Cove Rd, Oak Bluffs, MA 02557

    Hidden Cove Gem with Serene Pond Views And Coveted Water Access - Located in the desirable Hidden Cove enclave—a 65+ acre water-access community—this inviting contemporary home offers privacy and high-end finishes with direct access to Sengekontacket Pond and Nantucket Sound. Community amenities include a private boat dock, walking trails, pickleball and tennis, all near Oak Bluffs. The

    Agent Photo

    Wendy Harman

    Compass

    (508) 456-9911

    3 Hidden Cove 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

    $3,995,000

    • Land
    • 1.92 Acres
    • $2,083,985 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
  • 309 Barnes Rd, Oak Bluffs, MA 02557
    309 Barnes Rd, Oak Bluffs, MA 02557
    309 Barnes Rd, Oak Bluffs, MA 02557
    /32

    $3,125,000

    • 3 Beds
    • 2 Baths
    • 1,569 Sq Ft

    309 Barnes Rd, Oak Bluffs, MA 02557

    Your Vineyard summer begins the moment you arrive. This rare, fully furnished waterfront retreat offers 175' of private shorefront on Lagoon Pond — one of Martha's Vineyard's most coveted settings. Taken to the studs in 2022 and reimagined by architect Ramsay Gourd, this bright coastal escape features soaring vaulted ceilings, white shiplap, and painted beams. Glass sliders open to bluestone

    Dawn Bellante Sandpiper Realty, Inc.

    309 Barnes Rd, Oak Bluffs, MA 02557
  • 68 Front St, Oak Bluffs, MA 02557
    68 Front St, Oak Bluffs, MA 02557
    68 Front St, Oak Bluffs, MA 02557
    /38

    $1,795,000

    • 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
    /60

    $5,495,000

    • 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 5, Oak Bluffs, MA 02557
    37 Circuit Ave Unit 5, Oak Bluffs, MA 02557
    37 Circuit Ave Unit 5, Oak Bluffs, MA 02557
    /21

    $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 Restless Winds Unit #5 comes with an amazing roof top deck shared with only one other condo (unit #4). You're in the middle of it all with this great location, yet you have easy access to a private and peaceful deck overlooking the town of Oak Bluffs and the surrounding waters. This incredible space takes you to another level of relaxation and a birds eye view

    Agent Photo

    Lisa Lucier

    Anchor Realty of Martha's Vineyard

    (508) 544-0253

    37 Circuit Ave Unit 5, Oak Bluffs, MA 02557
  • 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
    /24

    $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- Restless Winds Condominium Unit #4 comes with an amazing roof top deck that is only shared with one other condo (#5). This spacious unit just under 1,000 sq. ft. has a ships feel with custom wood features and a ships ladder leading to the roof top deck. This condo packs a lot in with a full kitchen, living and dining area, a guest bedroom, a tiled bathroom

    Agent Photo

    Lisa Lucier

    Anchor Realty of Martha's Vineyard

    (508) 546-9282

    37 Circuit Ave Unit 4, Oak Bluffs, MA 02557
  • 217 Barnes Rd, Vineyard Haven, MA 02568
    217 Barnes Rd, Vineyard Haven, MA 02568
    217 Barnes Rd, Vineyard Haven, MA 02568
    /60

    $5,250,000

    $445K 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
  • 6 Stone Pound Way, Oak Bluffs, MA 02557
    6 Stone Pound Way, Oak Bluffs, MA 02557
    6 Stone Pound Way, Oak Bluffs, MA 02557
    /24

    $1,399,000

    Open Sat 10:30AM - 12:30PM
    • 3 Beds
    • 2 Baths
    • 1,897 Sq Ft

    6 Stone Pound Way, Oak Bluffs, MA 02557

    The ambience of this tranquil Hidden Cove Waterfront community will inspire you immediately. This spacious 3 bedroom w/oversized family room home is affordably priced. The sun shines in the charming living room w/ brick fireplace, Palladian side windows, Rennai gas monitor & attractive hardwood floors. The ample chefs kitchen extends w/L shaped counter & snack bar. The dining area is adjacent

    Susan Austin Austin R.E. Properties of MV

    6 Stone Pound Way, Oak Bluffs, MA 02557
  • 17 John Wesley Ave, Vineyard Haven, MA 02568
    17 John Wesley Ave, Vineyard Haven, MA 02568
    17 John Wesley Ave, Vineyard Haven, MA 02568
    /46

    $1,765,000

    $30K 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
  • 4 Quail Run Unit 1, Oak Bluffs, MA 02557
    4 Quail Run Unit 1, Oak Bluffs, MA 02557
    4 Quail Run Unit 1, Oak Bluffs, MA 02557
    /23

    $899,000

    • 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
  • 28 Beach Rd, Oak Bluffs, MA 02557
    28 Beach Rd, Oak Bluffs, MA 02557
    28 Beach Rd, Oak Bluffs, MA 02557
    /33

    $3,750,000

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

    28 Beach Rd, Oak Bluffs, MA 02557

    Location, Location, location....This is rare opportunity to own a water front property with 240 degree views of the Harbor and Sound. The property is 5 minutes from either Ferry terminal and walking distance to East beach . The house is suitable for year round living , seasonal income and comfort through and through

    Scott Lewis Lewis Real Estate Services, LLC

    28 Beach Rd, Oak Bluffs, MA 02557
  • 8 Fresh Pond Rd, Oak Bluffs, MA 02557
    8 Fresh Pond Rd, Oak Bluffs, MA 02557
    8 Fresh Pond Rd, Oak Bluffs, MA 02557
    /36

    $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
  • 2 Great Rock Rd, Oak Bluffs, MA 02568
    2 Great Rock Rd, Oak Bluffs, MA 02568
    2 Great Rock Rd, Oak Bluffs, MA 02568
    /45

    $1,765,000

    • 2 Beds
    • 2 Baths
    • 890 Sq Ft

    2 Great Rock Rd, Oak Bluffs, MA 02568

    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 building and board of health departments approved the house and and septic plans attached. The property

    Susan Lemoie-Zarba Premier Properties

    2 Great Rock Rd, Oak Bluffs, MA 02568
  • 18 Wood Duck Way, Edgartown, MA 02539
    18 Wood Duck Way, Edgartown, MA 02539
    18 Wood Duck Way, Edgartown, MA 02539
    /23

    $1,800,000

    • 4 Beds
    • 3 Baths
    • 2,864 Sq Ft

    18 Wood Duck Way, Edgartown, MA 02539

    Welcome to your coastal retreat in sought-after Sengekontacket, offered fully turnkey and ready to enjoy from day one. This light-filled contemporary home blends comfort, style, and exceptional community amenities in one of Martha's Vineyard's most desirable central Island locations.Designed with soaring vaulted ceilings and oversized windows, the home is flooded with natural sunlight throughout.

    Janna O'Loughlin Portfolio Properties

    18 Wood Duck Way, Edgartown, MA 02539
  • 7 Highland Ave, Vineyard Haven, MA 02568
    7 Highland Ave, Vineyard Haven, MA 02568
    7 Highland Ave, Vineyard Haven, MA 02568
    /4

    $809,000

    • Land
    • 16,988 Sq Ft
    • $2,074,359 per Acre

    7 Highland Ave, 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, LLC

    7 Highland Ave, Vineyard Haven, MA 02568
  • 112 Dukes County Ave Unit 209, Oak Bluffs, MA 02557
    112 Dukes County Ave Unit 209, Oak Bluffs, MA 02557
    112 Dukes County Ave Unit 209, Oak Bluffs, MA 02557
    /7

    $599,000

    • Land
    • 3,197 Sq Ft
    • $8,160,763 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
  • 112 Dukes County Ave, Oak Bluffs, MA 02557
    112 Dukes County Ave, Oak Bluffs, MA 02557
    112 Dukes County Ave, Oak Bluffs, MA 02557
    /7

    $599,000

    • Land
    • 3,049 Sq Ft
    • $8,557,143 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
  • 3 Kims Way, Oak Bluffs, MA 02557
    3 Kims Way, Oak Bluffs, MA 02557
    3 Kims Way, Oak Bluffs, MA 02557
    /16

    $1,195,000

    • 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

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

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 1.6 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 26.7% of residents renting and 73.3% 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 $1,600,000. If you put a 20% down payment of $320,000 and had a 30-year fixed mortgage with an interest rate of 6.51%, your estimated principal and interest payment would be $8,100 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $347K 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, 02539, 02536, 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.

Home Trends in Oak Bluffs, MA

On average, homes in Oak Bluffs, Marthas Vineyard sell after 90 days on the market compared to the national average of 58 days. The median sale price for homes in Oak Bluffs, Marthas Vineyard over the last 12 months is $1,449,000, up 25% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$1,449,000
Median Single Family Sale Price
$1,595,000
Median 2 Bedroom Sale Price
$933,000
Median 1 Bedroom Sale Price
$884,000
Average Price Per Sq Ft
$995
Number of Homes for Sale
44
Last 12 months Home Sales
102
Months of Supply
5.20
Median List Price
$1,600,000
Median Change From 1st List Price
6%
Median Home Sale Price YoY Change
25%
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