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Oak Bluffs Homes for Sale

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  • 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

    (508) 205-8583

    0 Temahigan Ave Unit 22602202, Oak Bluffs, MA 02568
  • 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

    (774) 446-7075

    0 Temahigan Ave Unit 160, Oak Bluffs, MA 02568
  • 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
  • 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
  • 0-A California Ave Unit Part lot 79, Oak Bluffs, MA 02568
    0-A California Ave Unit Part lot 79, Oak Bluffs, MA 02568
    0-A California Ave Unit Part lot 79, Oak Bluffs, MA 02568
    /4

    $625,000

    • Land
    • 14,997 Sq Ft
    • $1,815,277 per Acre

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

    Oak Bluffs Buildable Lot – Prime Location. This flat 2-bedroom building lot is ideally located just moments from the Hudson Avenue access to scenic Lagoon Pond, with easy access to both Farm Neck Golf Club and downtown Oak Bluffs. Situated in a neighborhood of newly constructed homes, this lot presents an excellent opportunity to become part of a growing community in Oak Bluffs. According to the

    Andrew McElhinney Compass LLC

    0-A California Ave Unit Part lot 79, Oak Bluffs, MA 02568
  • 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
  • 26 Winthrop Ave, Oak Bluffs, MA 02557
    26 Winthrop Ave, Oak Bluffs, MA 02557
    26 Winthrop Ave, Oak Bluffs, MA 02557
    /48

    $839,000

    $60K PRICE DROP
    • 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 tons of potential. Existing one bedroom, two story house situated on a 1/3 Acre of land, a 14,810 sq.ft. level lot. Land is large enough for a house and guest house when meeting ZBA 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
  • 4 High Meadow Ln, Oak Bluffs, MA 02557
    4 High Meadow Ln, Oak Bluffs, MA 02557
    4 High Meadow Ln, Oak Bluffs, MA 02557
    /36

    $2,260,000

    $335K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 2,810 Sq Ft

    4 High Meadow Ln, Oak Bluffs, MA 02557

    Set within the coveted Meadow View Farms community, this exceptional post-and-beam residence offers timeless craftsmanship, generous living spaces, and nearly an acre of private beautifully landscaped grounds with significant potential for expansion. A full-length farmer’s porch creates a gracious arrival and provides the perfect setting to relax. Inside, the sun-drenched main level is defined by

    Kate Burnside Portfolio Properties

    4 High Meadow Ln, 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
  • 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
  • 43 Sengekontacket Rd, Oak Bluffs, MA 02557
    43 Sengekontacket Rd, Oak Bluffs, MA 02557
    43 Sengekontacket Rd, Oak Bluffs, MA 02557
    /31

    $5,995,000

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

    43 Sengekontacket Rd, Oak Bluffs, MA 02557

    Breathtaking property at the tip of a prominent peninsula on Sengekontacket Pond's western shoreline. Set beautifully at high elevation above the shore, this charming home and guest cottage includes jaw-dropping views of the pond, barrier dunes and Nantucket Sound. Direct from the property take your whaler or other watercraft out into the sound and beyond for endless recreational pursuits. Aside

    Peyton Wallace Studio Realty

    43 Sengekontacket Rd, 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
    /6

    $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 MVC-approved plans by Sullivan &

    Rose Ryley Wallace & Co. Sotheby's International Realty

    112 Dukes County 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
  • 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
  • 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
  • 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
  • 2 Lincoln Ave, Oak Bluffs, MA 02568
    2 Lincoln Ave, Oak Bluffs, MA 02568
    2 Lincoln Ave, Oak Bluffs, MA 02568
    /20

    $640,000

    • 1 Bed
    • 1 Bath
    • 354 Sq Ft

    2 Lincoln Ave, Oak Bluffs, MA 02568

    Nestled in the heart of the historic Martha’s Vineyard Camp Meeting Association, this beautifully updated suite cottage offers the rare opportunity for year-round living in Oak Bluffs’ campground community. Fully renovated in 2023, including kitchen, bath, floors and winterization, the home seamlessly blends classic Vineyard charm with modern comfort — featuring upgraded systems and finishes that

    Stacy Ickes Donnelly + Co.

    2 Lincoln Ave, Oak Bluffs, MA 02568
  • 24 Towanticut Ave Unit 188, Oak Bluffs, MA 02568
    24 Towanticut Ave Unit 188, Oak Bluffs, MA 02568
    /2

    $857,000

    • Land
    • 16,892 Sq Ft
    • $2,209,902 per Acre

    24 Towanticut Ave Unit 188, 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 Ave Unit 188, 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 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, 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
  • 385 Barnes Rd, Vineyard Haven, MA 02568
    385 Barnes Rd, Vineyard Haven, MA 02568
    385 Barnes Rd, Vineyard Haven, MA 02568
    /70

    $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
  • 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
  • 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
  • 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
  • 44 Tiffany Dr, Oak Bluffs, MA 02557
    44 Tiffany Dr, Oak Bluffs, MA 02557
    44 Tiffany Dr, Oak Bluffs, MA 02557
    /15

    $3,095,000

    $150K PRICE DROP
    • 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, Oak Bluffs. The property has been thoughtfully renovated with two new kitchens, 5 new bathrooms, 4-bedrooms (two ensuite), and all new appliances and windows. Its floor plan is great for entertaining and flows family and guests from an oversized living room with

    Perry Patterson MV Luxury Homes LLC

    44 Tiffany Dr, 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
  • 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
  • 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
  • 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
  • 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
  • 9 Brunswick Ave, Oak Bluffs, MA 02557
    9 Brunswick Ave, Oak Bluffs, MA 02557
    9 Brunswick Ave, Oak Bluffs, MA 02557
    /42

    $1,275,000

    $520K PRICE DROP
    • 3 Beds
    • 1 Bath
    • 1,033 Sq Ft

    9 Brunswick Ave, Oak Bluffs, MA 02557

    PRIME LOCATION! Beautifully Renovated in Oak Bluffs! This move-in ready home at 9 Brunswick Ave has been thoughtfully and extensively UPDATED inside and out. Enjoy peace of mind with a NEW septic system, siding, windows, water line from the street, and upgraded electrical and plumbing. The interior boasts NEW flooring, insulation, fresh paint, a stylishly renovated kitchen, and efficient new

    Alice Pierce Coldwell Banker Realty - Martha's Vineyard

    9 Brunswick Ave, 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
  • 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

    COMING SOON 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

    Marilyn Moses Ocean Park Realty Inc

    12 Samoset Ave, Oak Bluffs, MA 02557
  • 0-B California Ave Unit Part lot 79, Oak Bluffs, MA 02568
    0-B California Ave Unit Part lot 79, Oak Bluffs, MA 02568
    0-B California Ave Unit Part lot 79, Oak Bluffs, MA 02568
    /4

    $675,000

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

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

    Oak Bluffs Buildable Lot – Prime LocationThis flat 3-bedroom building lot is ideally located just moments from the Hudson Avenue access to scenic Lagoon Pond, with easy access to both Farm Neck Golf Club and downtown Oak Bluffs. Situated in a neighborhood of newly constructed homes, this lot presents an excellent opportunity to become part of a growing community in Oak Bluffs. According to

    Andrew McElhinney Compass LLC

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

    • 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
  • 111 Eastville Ave, Oak Bluffs, MA 02557
    111 Eastville Ave, Oak Bluffs, MA 02557
    111 Eastville Ave, Oak Bluffs, MA 02557
    /44

    $2,499,000

    $299K PRICE DROP
    • 6 Beds
    • 4 Baths
    • 2,400 Sq Ft

    111 Eastville Ave, Oak Bluffs, MA 02557

    LARGE PRICE DROP. THIS IS A PERFECT LOCATION FOR WEDDING PARTIES.Just steps from the beach and minutes to both Oak Bluffs and Vineyard Haven, this fully furnished, turnkey coastal retreat offers an exceptional location paired with a strong, proven rental history. Set on an oversized lot just two parcels from the shoreline, the home features six bedrooms and four bathrooms, providing generous

    Ed Charter Arrowhead Homes

    111 Eastville Ave, Oak Bluffs, MA 02557
  • 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
  • 4 Canonicus Ave, Oak Bluffs, MA 02557
    4 Canonicus Ave, Oak Bluffs, MA 02557
    4 Canonicus Ave, Oak Bluffs, MA 02557
    /44

    $5,225,000

    $100K PRICE DROP
    • 6 Beds
    • 4 Baths
    • 2,890 Sq Ft

    4 Canonicus Ave, Oak Bluffs, MA 02557

    With a striking presence overlooking Nantucket Sound and just moments from the vibrant pulse of downtown, this distinctive compound is infused with a laid-back West Coast spirit while honoring the vintage charm of Oak Bluffs. Airy and effortlessly elegant, the four-bedroom main house has been masterfully updated, introducing refined, contemporary comforts, designed for every season. Tucked to the

    Katherine Donahue Sandpiper Realty

    4 Canonicus Ave, Oak Bluffs, MA 02557

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

Why Live in Oak Bluffs
Oak Bluffs, located in the northeast of Martha’s Vineyard, is renowned for its whimsical gingerbread houses. This down-island town is a bustling port of entry during the summer season, where tourists disembark from ferry boats and explore attractions like Circuit Avenue, known for its T-shirts and fresh doughnuts. The town features gray-shingled beach houses overlooking the Nantucket Sound, and the commercial district offers pizza parlors, ice cream shops, and clothing stores. Oak Bluffs is home to the oldest platform carousel in the U.S., the Flying Horses Carousel, and hosts the Martha’s Vineyard African American Film Festival and a fireworks show every August. The Ritz Café provides nightlife with live music and karaoke, while the Sweet Life Café offers upscale dining year-round. Ocean Park, with its rolling hills and Victorian homes, and the Martha’s Vineyard Camp Meeting Association, with its brightly colored gingerbread houses, are notable landmarks. The town also has gray-shingled beach cottages, Cape Cods, and farmhouses. Martha’s Vineyard Regional High School, a highly rated institution, serves the island’s students. Health care is accessible at Mass General Brigham Martha’s Vineyard Hospital, which offers comprehensive services. Residents and visitors can enjoy sandy pathways along the Nantucket Sound, beaches like Inkwell Beach, and a skate park near the high school. Oak Bluffs is 10 minutes from Vineyard Haven, 15 minutes from Edgartown, and 15 minutes from Martha’s Vineyard Airport.
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 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 $1,550,000. If you put a 20% down payment of $310,000 and had a 30-year fixed mortgage with an interest rate of 6.47%, your estimated principal and interest payment would be $7,810 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $335K 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.

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

Oak Bluffs North Falmouth Vineyard Haven Falmouth Village
Median Home Price
$1,550,000
$1,099,000
$1,770,000
$1,100,000
Median Sale Price
$1,350,000
+17% YoY
$1,145,000
+15% YoY
$1,445,000
+13% YoY
$959,000
-4% YoY
Median Single Family Price
$1,515,000
$1,110,000
$1,762,500
$1,325,000
Median Townhouse Price
--
$1,040,000
$1,300,000
$1,900,000
Median Condo Price
$912,000
$1,012,250
$1,150,000
$620,000
Total Active Listings
70
14
64
44
Market Conditions
5 Months
Balanced Market
1 Months
Seller's Market
7 Months
Buyer's Market
3 Months
Seller's Market
How to Buy a Home How to Finance a Home How to Sell a Home

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