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Oak Bluffs Homes for Sale

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  • 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
    /32

    $985,000

    • 2 Beds
    • 1 Bath
    • 990 Sq Ft

    37 Circuit Ave Unit 4, Oak Bluffs, MA 02557

    Downtown Oak Bluffs Located right in the heart of town. Unit #4 A penthouse condo with a semi-private rooftop deck (shared with unit 5 only). This spacious condo has a panoramic view of the town and surrounding waters sitting high above it all with outdoor seating and separate entrances from either condo. This solid deck adds a whole other dimension to this already desirable unit.The interior

    Agent Photo

    Lisa Lucier

    Anchor Realty of Martha's Vineyard

    (508) 514-5238

    37 Circuit Ave Unit 4, Oak Bluffs, MA 02557
  • 37 Circuit Ave Unit 5, Oak Bluffs, MA 02557
    37 Circuit Ave Unit 5, Oak Bluffs, MA 02557
    37 Circuit Ave Unit 5, Oak Bluffs, MA 02557
    /24

    $935,000

    • 1 Bed
    • 1 Bath
    • 797 Sq Ft

    37 Circuit Ave Unit 5, Oak Bluffs, MA 02557

    Downtown Oak Bluffs centrally located in the heart of Oak Bluffs. Steps from ferries, shops, restaurants and beaches from this penthouse condo. Escape the hustle and bustle on your semi private rooftop deck shared only with (unit 4 also for sale). Panoramic views of the Nantucket and Vineyard Sounds await you while you relax on the deck or enjoy dinner al fresco. The condo features all wood

    Agent Photo

    Lisa Lucier

    Anchor Realty of MV

    (508) 422-4131

    37 Circuit Ave Unit 5, Oak Bluffs, MA 02557
  • 34 Massasoit Ave, Oak Bluffs, MA 02568
    34 Massasoit Ave, Oak Bluffs, MA 02568
    34 Massasoit Ave, Oak Bluffs, MA 02568
    /34

    $2,700,000

    • 6 Beds
    • 2.5 Baths
    • 1,666 Sq Ft

    34 Massasoit Ave, Oak Bluffs, MA 02568

    This is the last B1 undeveloped commercial property on Circuit Avenue's main strip. Previous development plans included mixed use with commercial store front and condos above. Located on the corner of Circuit Ave and Massasoit this property has an existing Victorian home with 6 bedrooms, and 3.5 bathrooms, perfect for a weekly rental or employee housing. Right in the heart of Oak Bluffs walk to

    Agent Photo

    Lisa Lucier

    Anchor Realty of MV

    (508) 348-7972

    34 Massasoit Ave, Oak Bluffs, MA 02568
  • 70 Carol Ln, Oak Bluffs, MA 02557
    70 Carol Ln, Oak Bluffs, MA 02557
    70 Carol Ln, Oak Bluffs, MA 02557
    /45

    $1,250,000

    • 2 Beds
    • 3 Baths
    • 1,500 Sq Ft

    70 Carol Ln, Oak Bluffs, MA 02557

    Oak Bluffs location that is central to everything down Island. Situated on a 1/3 acre lot this ranch home with a finished basement has been recently renovated. The first floor has 1500 sq feet with of a large open kitchen, dining area, and living room with plenty of room for large gatherings. The primary bedroom has a bathroom on suite. Another bedroom has easy access to the hall bath. The

    Agent Photo

    Lisa Lucier

    Anchor Realty of Martha's Vineyard

    (508) 456-5742

    70 Carol Ln, 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
    /22

    $1,250,000

    • 2 Beds
    • 1 Bath
    • 742 Sq Ft

    47 Winemack St, Oak Bluffs, MA 02557

    Oak Bluffs -East Chop-Close to the ocean. Two 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 bath, and a

    Agent Photo

    Lisa Lucier

    Anchor Realty of MV

    (508) 403-9601

    47 Winemack St, Oak Bluffs, MA 02557
  • 11 John Wesley Ave, Oak Bluffs, MA 02568
    11 John Wesley Ave, Oak Bluffs, MA 02568
    11 John Wesley Ave, Oak Bluffs, MA 02568
    /32

    $1,550,000

    • 4 Beds
    • 2 Baths
    • 1,304 Sq Ft

    11 John Wesley Ave, Oak Bluffs, MA 02568

    East Chop Living in this 4 Bedroom Victorian home perched near the shoreline in Oak Bluffs-just a short stroll to the harbor, the shores of East Chop beaches, and the shops and restaurants of downtown Oak Bluffs. Built in 1905, and updated throughout the years, with its Victorian architecture softened by time and salt air, giving it an inviting, warm charm.The exterior features a wide

    Agent Photo

    Lisa Lucier

    Anchor Realty of Martha's Vineyard

    (508) 682-5574

    11 John Wesley Ave, Oak Bluffs, MA 02568
  • 9 Brunswick Ave, Oak Bluffs, MA 02557
    9 Brunswick Ave, Oak Bluffs, MA 02557
    9 Brunswick Ave, Oak Bluffs, MA 02557
    /21

    $1,795,000

    • 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

    Agent Photo

    Alice Pierce

    Coldwell Banker Realty - Hingham

    (870) 917-0672

    9 Brunswick Ave, 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
    /42

    $5,995,000 Open Sun 1:30PM - 3:30PM

    • 3 Beds
    • 6 Baths
    • 3,608 Sq Ft

    385 Barnes Rd, Vineyard Haven, MA 02568

    Indulge in luxurious living at this exquisite waterfront retreat featuring a private 125-foot sandy beach. Over 5,400 sq ft on three floors blend elegance with indoor-outdoor living. The grand foyer leads to dramatic interiors with high ceilings and floor-to-ceiling windows showcasing stunning water views. Highlights include a striking stone fireplace, custom built-ins, gourmet kitchen with stone

    Agent Photo

    Wendy Harman

    Compass

    (508) 274-5363

    385 Barnes Rd, Vineyard Haven, MA 02568
  • 44 Tiffany Dr, Oak Bluffs, MA 02557
    44 Tiffany Dr, Oak Bluffs, MA 02557
    44 Tiffany Dr, Oak Bluffs, MA 02557
    /40

    $1,925,000

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

    44 Tiffany Dr, Oak Bluffs, MA 02557

    Nestled within the desirable Lagoon Estates development and set on a beautifully wooded 1.38-acre lot abutting Land Bank property, this expansive and sun-filled home offers versatile living space and a flexible floor plan. The main house features generously sized rooms enhanced by large windows that flood the interior with natural light. The kitchen boasts white cabinetry, a wall-mounted

    Nora Jardin Island Real Estate

    44 Tiffany Dr, Oak Bluffs, MA 02557
  • 26 Tia Anna Ln, Oak Bluffs, MA 02557
    26 Tia Anna Ln, Oak Bluffs, MA 02557
    26 Tia Anna Ln, Oak Bluffs, MA 02557
    /41

    $1,995,000

    • 3 Beds
    • 3 Baths
    • 2,210 Sq Ft

    26 Tia Anna Ln, Oak Bluffs, MA 02557

    Welcome to 26 Tia Anna Lane! This immaculate, fully renovated home is move-in ready and stylishly appointed. Set on a beautifully landscaped 0.30-acre lot with vibrant plantings, it features Hardi Plank siding, a Mahogany farmer's porch, and a backyard pergola. Inside, whitewashed wood and soaring ceilings complement first-growth Southern Pine floors with pegged and bunged details. The sunlit

    Marilyn Moses Ocean Park Realty, Inc.

    26 Tia Anna Ln, Oak Bluffs, MA 02557
  • 35 Tower Ridge Rd, Oak Bluffs, MA 02557
    35 Tower Ridge Rd, Oak Bluffs, MA 02557
    35 Tower Ridge Rd, Oak Bluffs, MA 02557
    /42

    $2,125,000

    • 3 Beds
    • 4 Baths
    • 2,558 Sq Ft

    35 Tower Ridge Rd, Oak Bluffs, MA 02557

    Thoughtfully designed post-and-beam home that blends character with modern comfort and flexible living in Tower Ridge. The open-concept main floor features spacious gathering areas, while the finished basement offers a quiet retreat for work, relaxation, or play. The outdoor living space is just as inviting, with an oversized deck overlooking mature plantings and a generous side yard--perfect for

    Katherine Donahue Sandpiper Realty Inc

    35 Tower Ridge Rd, Oak Bluffs, MA 02557
  • 50 Hidden Cove Rd, Edgartown, MA 02539
    50 Hidden Cove Rd, Edgartown, MA 02539
    50 Hidden Cove Rd, Edgartown, MA 02539
    /46

    $2,495,000

    • 5 Beds
    • 4 Baths
    • 3,873 Sq Ft

    50 Hidden Cove Rd, Edgartown, MA 02539

    Sengekontacket–Walk into a “turn-key” opportunity in the desirable Hidden Cove community, just steps (.3 miles) from Sengekontacket Pond with access to State Beach and Nantucket Sound beyond. The lovingly-maintained 4 bedroom, 2.5 bath, 2 car garage main home sits high on the 1.5 acre property offering an abundance of natural light that flows into the open living and entertaining spaces. The

    Sean Federowicz Landmarks at TODAY Real Estate

    50 Hidden Cove Rd, Edgartown, MA 02539
  • 5 Bayes Hill Cir, Vineyard Haven, MA 02568
    5 Bayes Hill Cir, Vineyard Haven, MA 02568
    5 Bayes Hill Cir, Vineyard Haven, MA 02568
    /46

    $2,050,000

    • 4 Beds
    • 2.5 Baths
    • 2,855 Sq Ft

    5 Bayes Hill Cir, Vineyard Haven, MA 02568

    On a quiet cul-de-sac in the Bayes Hill neighborhood is this spacious traditional Colonial-style home adorned with charm. As you enter the home from the idyllic covered porch, you are welcomed into the foyer. The home is filled with intimate spaces while offering the opportunity for larger parties to gather. The living room has built-in shelving that flank the gas fireplace and it is connected to

    Michele Moore Island Real Estate

    5 Bayes Hill Cir, Vineyard Haven, MA 02568
  • 16 Atlantic Ave, Oak Bluffs, MA 02557
    16 Atlantic Ave, Oak Bluffs, MA 02557
    16 Atlantic Ave, Oak Bluffs, MA 02557
    /39

    $2,495,000

    • 5 Beds
    • 2.5 Baths
    • 2,577 Sq Ft

    16 Atlantic Ave, Oak Bluffs, MA 02557

    East Chop - Tucked away on a quiet lane just moments from the iconic East Chop Lighthouse and breathtaking bluff views, this timeless retreat invites you to embrace the slower pace of island life. The main residence is a stately four-bedroom, classic summer home, rich in character and nostalgic charm. At the rear of the property, a one-bedroom guest house provides privacy and, perhaps most

    Katherine Donahue Sandpiper Realty Inc

    16 Atlantic Ave, 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

    $2,748,000

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

    111 Eastville Ave, Oak Bluffs, MA 02557

    JUST REDUCED!! Steps to the beach- Minutes to downtown Oak Bluffs and Vineyard Haven. This is a perfect location.FULLY FURNISHED, TURNKEY, with an impressive rental history. Situated on an oversized lot that is two parcels away from the beach. This home offers six bedrooms and four

    Ed Charter Arrowhead Homes

    111 Eastville Ave, Oak Bluffs, MA 02557
  • 10 Wood Duck Way, Oak Bluffs, MA 02557
    10 Wood Duck Way, Oak Bluffs, MA 02557
    10 Wood Duck Way, Oak Bluffs, MA 02557
    /42

    $2,500,000

    • 4 Beds
    • 3.5 Baths
    • 1 Sq Ft

    10 Wood Duck Way, Oak Bluffs, MA 02557

    Perched on a hill, this waterfront house encompasses three levels of living. Thoughtfully designed and well cared for, this home provides calming water views and direct access to Wiggy's freshwater Pond from almost every room. The main level boasts a kitchen fitted with high-end appliances and opens to the dining room, deck, and airy living room with exposed beams, a gas fireplace, and large

    Marcia Sullivan Garvey Donnelly + Co.

    10 Wood Duck Way, Oak Bluffs, MA 02557
  • 71 Netock Ave, Oak Bluffs, MA 02557
    71 Netock Ave, Oak Bluffs, MA 02557
    71 Netock Ave, Oak Bluffs, MA 02557
    /19

    $2,295,000

    • 4 Beds
    • 5 Baths
    • 2,820 Sq Ft

    71 Netock Ave, Oak Bluffs, MA 02557

    On the doorstep of vibrant Oak Bluffs, discover this exquisitely renovated 4-bed home w/separate, office or studio space, ensconced in professionally landscaped grounds. Blending modern comfort w/timeless island charm, house features wide plank white oak floors, beautiful ceiling height & natural light, open-concept living-dining space w/new kitchen, 1st-floor primary bedroom w/ensuite bath,

    Ellen Valentgas Sotheby's International Realty

    71 Netock Ave, Oak Bluffs, MA 02557
  • 4 Dempster Park, Oak Bluffs, MA 02568
    4 Dempster Park, Oak Bluffs, MA 02568
    4 Dempster Park, Oak Bluffs, MA 02568
    /30

    $2,195,000

    • 4 Beds
    • 2.5 Baths
    • 1,825 Sq Ft

    4 Dempster Park, Oak Bluffs, MA 02568

    This handsome, meticulously maintained 4-bedroom gambrel roof house, nestled in one of the prime locations of East Chop, has had substantial renovations and upgrades over the years since 2017. First floor includes large living room with dining area and Rumford wood burning fireplace that opens out to a front porch and deck running the length of the house and which wraps around to the rear patio.

    Perry Patterson MV Luxury Homes LLC

    4 Dempster Park, Oak Bluffs, MA 02568
  • 22 Greenleaf Ave, Oak Bluffs, MA 02557
    22 Greenleaf Ave, Oak Bluffs, MA 02557
    22 Greenleaf Ave, Oak Bluffs, MA 02557
    /37

    $2,290,000

    • 3 Beds
    • 2 Baths
    • 1,608 Sq Ft

    22 Greenleaf Ave, Oak Bluffs, MA 02557

    Tucked away on one of Oak Bluffs' most sought-after streets, Fairview on Greenleaf Avenue offers an extraordinary location with stunning views of Sunset Lake, Oak Bluffs Harbor, and Nantucket Sound. From the highest point on Greenleaf, enjoy vibrant sunrises and a front-row seat to the town's iconic fireworks.This home blends classic Vineyard character with thoughtful design by Island architect

    Jennifer O'hanlon Compass

    22 Greenleaf Ave, Oak Bluffs, MA 02557
  • 22 Greenleaf Ave, Oak Bluffs, MA 02539
    22 Greenleaf Ave, Oak Bluffs, MA 02539
    22 Greenleaf Ave, Oak Bluffs, MA 02539
    /39

    $2,290,000

    • 3 Beds
    • 2 Baths
    • 1,608 Sq Ft

    22 Greenleaf Ave, Oak Bluffs, MA 02539

    Tucked away on one of the most sought-after streets in Oak Bluffs, Fairview on Greenleaf Avenue offers an extraordinary location steeped in history and charm. With unparalleled views stretching across Sunset Lake, Oak Bluffs Harbor, and Nantucket Sound, this property captures the essence of coastal living on Martha’s Vineyard. From the highest vantage point on Greenleaf, enjoy sunrises that fill

    Jen O'Hanlon Compass | The O'Hanlon Group

    22 Greenleaf Ave, Oak Bluffs, MA 02539
  • 23 Circuit Avenue Extension, Oak Bluffs, MA 02557
    23 Circuit Avenue Extension, Oak Bluffs, MA 02557
    23 Circuit Avenue Extension, Oak Bluffs, MA 02557
    /21

    $3,100,000

    • 3 Beds
    • 1 Bath
    • 1 Sq Ft

    23 Circuit Avenue Extension, Oak Bluffs, MA 02557

    Rare Opportunity with Endless Possibilities - Unmatched Harbor & Vineyard Sound Views. Location, Location, Location! A truly rare offering in the heart of Oak Bluffs, where properties like this seldom become available. Positioned directly across from the iconic Oak Bluffs Harbor, this property boasts unobstructed harbor views and sweeping vistas of Vineyard Sound--a setting that captures the very

    Rene Ben David Ocean Park Realty, Inc.

    23 Circuit Avenue Extension, Oak Bluffs, MA 02557
  • 79 Circuit Ave, Oak Bluffs, MA 02557
    79 Circuit Ave, Oak Bluffs, MA 02557
    79 Circuit Ave, Oak Bluffs, MA 02557
    /64

    $2,250,000 Open Wed 10AM - 12PM

    • 4 Beds
    • 4 Baths
    • 3,076 Sq Ft

    79 Circuit Ave, Oak Bluffs, MA 02557

    Wonderful opportunity to reimagine this historic classic Victorian home located at the gateway to the Oak Bluffs Business district with a gorgeous, secluded garden and 5 off street parking spaces the property lends itself to a single-family home or conversion to a multi-family. The home has been both of these configurations in previous years. The current layout offers incredible opportunities

    kyle Neyer Tea Lane Associates

    79 Circuit Ave, Oak Bluffs, MA 02557
  • 2 Farm Path, Oak Bluffs, MA 02557
    2 Farm Path, Oak Bluffs, MA 02557
    2 Farm Path, Oak Bluffs, MA 02557
    /37

    $1,995,000

    • 4 Beds
    • 3 Baths
    • 3,058 Sq Ft

    2 Farm Path, Oak Bluffs, MA 02557

    "Turn-key" offering! This custom cape design with a delightful farmer's porch provides ample opportunities to entertain. Set upon nearly an acre of level and landscaped land with irrigation, it abuts the State Forrest, has an open floor plan with cathedral ceilings and skylights. The three bedroom main, has A/C, a finished basement rec room, a large rear deck that spills forth onto a large yard

    Sean Federowicz Landmarks at TODAY Real Estate

    2 Farm Path, Oak Bluffs, MA 02557
  • 30 Sengekontacket Rd, Oak Bluffs, MA 02557
    30 Sengekontacket Rd, Oak Bluffs, MA 02557
    30 Sengekontacket Rd, Oak Bluffs, MA 02557
    /24

    $2,195,000

    • 4 Beds
    • 3 Baths
    • 2,262 Sq Ft

    30 Sengekontacket Rd, Oak Bluffs, MA 02557

    Secluded island retreat nestled above the trees! Located in the desirable Sengekontacket Association, this four-bedroom, three-bathroom home offers stunning views of acres of conservation land, Sengekontacket Pond, and Nantucket Sound. Perched on a hillside, the house provides utmost privacy from all rooms while being just a short walk from the Association boat ramp and kayak storage. The main

    Cassie Bradley Wallace & Co. Sotheby's International Realty

    30 Sengekontacket Rd, Oak Bluffs, MA 02557
  • 30 Franklin Ave, Oak Bluffs, MA 02568
    30 Franklin Ave, Oak Bluffs, MA 02568
    30 Franklin Ave, Oak Bluffs, MA 02568
    /24

    $2,150,000

    • 2 Beds
    • 2.5 Baths
    • 2,137 Sq Ft

    30 Franklin Ave, Oak Bluffs, MA 02568

    Welcome to your dream home! This stunning new construction boasts a coastal feel throughout and is situated on a spacious corner lot. Inside, you'll find luxurious finishes, including Thermador appliances and quartz countertops in the gourmet kitchen including a large pantry with beverage refrigerator. The elegance continues with white oak floors throughout the home. With 2 bedrooms and 2.5

    Stacy Ickes Donnelly + Co.

    30 Franklin Ave, Oak Bluffs, MA 02568
  • 30 Franklin Ave, Oak Bluffs, MA 02568
    30 Franklin Ave, Oak Bluffs, MA 02568
    30 Franklin Ave, Oak Bluffs, MA 02568
    /26

    $2,150,000 New Construction

    • 2 Beds
    • 3 Baths
    • 2,137 Sq Ft

    30 Franklin Ave, Oak Bluffs, MA 02568

    Welcome to your dream home! This stunning new construction boasts a coastal feel throughout and is situated on a spacious corner lot. Inside, you'll find luxurious finishes, including Thermador appliances and quartz countertops in the gourmet kitchen including a large pantry with beverage refrigerator. The elegance continues with white oak floors throughout the home. With 2 bedrooms and 2.5

    Stacy Ickes Donnelly + Co

    30 Franklin Ave, Oak Bluffs, MA 02568
  • 112 County Rd, Oak Bluffs, MA 02557
    112 County Rd, Oak Bluffs, MA 02557
    112 County Rd, Oak Bluffs, MA 02557
    /11

    $575,000

    • Land
    • 0.29 Acre
    • $1,982,759 per Acre

    112 County Rd, Oak Bluffs, MA 02557

    Discover the perfect opportunity to build your dream home on this desirable parcel located at 112 County Road, Oak Bluffs. This spacious lot offers convenient access to local amenities, beaches, ferry terminals, and town attractions. With its central location and natural surroundings, this property is ideal for those seeking both privacy and convenience. Bring your vision to life on Martha’s

    Kiet Bordley Fort Hill Brokerage Group

    112 County Rd, Oak Bluffs, MA 02557
  • 12 & 14 Maple Ave, Oak Bluffs, MA 02557
    12 & 14 Maple Ave, Oak Bluffs, MA 02557
    12 & 14 Maple Ave, Oak Bluffs, MA 02557
    /54

    $1,830,000

    • 4 Beds
    • 4 Baths
    • 1,600 Sq Ft

    12 & 14 Maple Ave, Oak Bluffs, MA 02557

    Two Historic Oak Bluffs Cottages - Prime Location - Deeded Separately Perched atop a gentle hill, surrounded by lush, established gardens in one of the island's most storied neighborhoods, these two charming 1909 twin cottages offer a rare opportunity to own a piece of local history--just a short distance to the harbor, downtown, and the beloved Winston's takeout. Built at a time when automobiles

    Leslie Floyd Portfolio Properties

    12 & 14 Maple Ave, Oak Bluffs, MA 02557
  • 13 County Rd, Oak Bluffs, MA 02557
    13 County Rd, Oak Bluffs, MA 02557
    13 County Rd, Oak Bluffs, MA 02557
    /7

    $1,199,000

    • 3 Beds
    • 1 Bath
    • 1,176 Sq Ft

    13 County Rd, Oak Bluffs, MA 02557

    Welcome to an inviting single-story ranch nestled in the heart of Oak Bluffs. This cozy and charming home offers a comfortable living space and is set on a generous, water view landscaped lot with mature trees and natural privacy.Inside, the home features a functional layout with a mix of wood and carpet flooring, a cozy wood-burning fireplace, and abundant natural light throughout. The

    Jennifer DaSilva Compass | Point B

    13 County Rd, Oak Bluffs, MA 02557
  • 400 Barnes Rd, Vineyard Haven, MA 02568
    400 Barnes Rd, Vineyard Haven, MA 02568
    400 Barnes Rd, Vineyard Haven, MA 02568
    /44

    $6,395,000

    • 6 Beds
    • 6 Baths
    • 7,000 Sq Ft

    400 Barnes Rd, Vineyard Haven, MA 02568

    Experience the quiet elegance of this rare Asian-inspired contemporary estate set on 2.42 acres in a prime Oak Bluffs location. Tucked behind a long private drive and surrounded by 234 acres of Southern Woodlands conservation land offering biking and hiking, this expansive property offers unparalleled privacy just minutes from Featherstone Center for the Arts, Farm Neck Golf Club and the island’s

    Jennifer DaSilva Compass | Point B

    400 Barnes Rd, Vineyard Haven, MA 02568
  • 46 Kennebec Ave, Oak Bluffs, MA 02557
    46 Kennebec Ave, Oak Bluffs, MA 02557
    46 Kennebec Ave, Oak Bluffs, MA 02557
    /34

    $1,590,000

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

    46 Kennebec Ave, Oak Bluffs, MA 02557

    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' allure as a premier summer destination on Martha's Vineyard. This delightful three-season cottage has been carefully modernized over the years, offering a rare investment opportunity. Located

    Michael Schweikert Ocean Park Realty, Inc.

    46 Kennebec Ave, 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
    /59

    $6,495,000

    • 6 Beds
    • 6 Baths
    • 3,998 Sq Ft

    15 Tamarack Ln, Oak Bluffs, MA 02557

    FARM NECK: The original 1780 Farm House was tastefully restored in 1985 to honor the land and legacy of Farm Neck. This serene 3.7 acre oasis of rolling greenery with a variety of mature trees and lots of natural privacy has an up Island feel with the down Island convenience to fine dining, shopping, ferry, airport, bike paths and includes Stockholder Membership in the popular Farm Neck Golf

    Alan Schweikert Ocean Park Realty Inc

    15 Tamarack Ln, 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
    • 0.22 Acre
    • $3,068,182 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
  • 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
    • 0.34 Acre
    • $1,838,235 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
  • 44 Iron Hill Rd Unit 1.7, Oak Bluffs, MA 02557
    44 Iron Hill Rd Unit 1.7, Oak Bluffs, MA 02557
    44 Iron Hill Rd Unit 1.7, Oak Bluffs, MA 02557
    /8

    $1,350,000

    • Land
    • 1.62 Acres
    • $833,333 per Acre

    44 Iron Hill Rd Unit 1.7, Oak Bluffs, MA 02557

    Drive past bucolic horse pastures and Duartes Pond to a sweet neighborhood near the Alpaca Farm. This property at the end of a cul-de-sac on Iron Hill Road is filled with possibilities. This 1.6-acre lot has 60,000 sq ft+ and can therefore accommodate up to 6 bedrooms with the 10,000 sq ft per bedroom rule. There is a current home on the property is in need of renovations or start fresh and build

    Cheri Mason Landvest MV

    44 Iron Hill Rd Unit 1.7, Oak Bluffs, MA 02557
  • 44 Iron Hill Rd, Oak Bluffs, MA 02557
    44 Iron Hill Rd, Oak Bluffs, MA 02557
    44 Iron Hill Rd, Oak Bluffs, MA 02557
    /11

    $1,350,000

    • 2 Beds
    • 1.5 Baths
    • 1,496 Sq Ft

    44 Iron Hill Rd, Oak Bluffs, MA 02557

    Drive past bucolic horse pastures and Duartes Pond to a sweet neighborhood near the Alpaca Farm. This property at the end of a cul de sac on Iron Hill Road is filled with possibilities. This 1.6-acre has 60,000 sq ft+ and can therefore accommodate up to 6 bedrooms with the 10,000 sq ft per bedroom rule. Intended to be a guest house to a future-built main house, the current home is 3-bedrooms

    Cheri Mason LandVest MV

    44 Iron Hill Rd, Oak Bluffs, MA 02557
  • 44 Iron Hill Rd, Vineyard Haven, MA 02568
    44 Iron Hill Rd, Vineyard Haven, MA 02568
    44 Iron Hill Rd, Vineyard Haven, MA 02568
    /16

    $1,350,000

    • 3 Beds
    • 2 Baths
    • 1,496 Sq Ft

    44 Iron Hill Rd, Vineyard Haven, MA 02568

    Drive past bucolic horse pastures and Duartes Pond to a sweet neighborhood near the Alpaca Farm. This property at the end of a cul de sac on Iron Hill Road is filled with possibilities. This 1.6-acre has 60,000 sq ft+ and can therefore accommodate up to 6 bedrooms with the 10,000 sq ft per bedroom rule. Intended to be a guest house to a future-built main house, the current home is 3-bedrooms

    Cheri Mason Landvest MV

    44 Iron Hill Rd, Vineyard Haven, MA 02568
  • 17 John Wesley Ave, Vineyard Haven, MA 02568
    17 John Wesley Ave, Vineyard Haven, MA 02568
    17 John Wesley Ave, Vineyard Haven, MA 02568
    /91

    $1,895,000

    • 3 Beds
    • 3 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

    kyle Neyer Tea Lane Associates

    17 John Wesley Ave, Vineyard Haven, MA 02568
  • 4 Quail Run Unit 2, Oak Bluffs, MA 02557
    4 Quail Run Unit 2, Oak Bluffs, MA 02557
    4 Quail Run Unit 2, Oak Bluffs, MA 02557
    /30

    $1,175,000 Open Wed 10AM - 12PM

    • 2 Beds
    • 2 Baths
    • 1,323 Sq Ft

    4 Quail Run Unit 2, Oak Bluffs, MA 02557

    FULLY FURNISHED Ready to live in or rent~ COASTAL CHIC CONDO in a TERRIFIC LOCATION with WATERFRONT ACCESS ~Meticulously crafted and exceptionally appointed, this end unit condo/townhouse has been architecturally designed with style. Featuring 2 bedrooms, a flexible third-floor loft flex room, and 1.5 bathrooms, this stylish 1,323 sq. ft. residence blends designer touches with top-tier appliances

    Marilyn Moses Ocean Park Realty Inc

    4 Quail Run Unit 2, 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
    /39

    $5,325,000

    • 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 Inc

    4 Canonicus Ave, Oak Bluffs, MA 02557

Showing Results 1 - 40, Page 1 of 3

Massachusetts 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 and historical significance as a summer haven for Black Americans. 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. Oak Bluffs is a neighborhood with a crime score of 2, 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 2 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 $475,000. If you put a 20% down payment of $95,000 and had a 30-year fixed mortgage with an interest rate of 6.74%, your estimated principal and interest payment would be $2,460 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $105K a year to afford the median home price in Oak Bluffs. The average household income in Oak Bluffs is $134K.
What are the best public schools in Oak Bluffs?
The best public schools that serve Oak Bluffs are:
What are the best private schools in Oak Bluffs?
The best private schools that serve Oak Bluffs are:
What are the most popular zip codes in Oak Bluffs, Marthas Vineyard, MA?
The most popular zip codes in Oak Bluffs, Marthas Vineyard, MA include 02568, 02536, 02539, 02575 and 02535.
What are the most popular neighborhoods near Oak Bluffs, Marthas Vineyard, MA?
The most popular neighborhoods near Oak Bluffs, Marthas Vineyard, MA are Vineyard Haven, Edgartown, West Tisbury, Chilmark and Falmouth Village.

Home Trends in Oak Bluffs, MA

On average, homes in Oak Bluffs, Marthas Vineyard sell after 67 days on the market compared to the national average of 70 days. The median sale price for homes in Oak Bluffs, Marthas Vineyard over the last 12 months is $612,247, up 32% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$612,247
Median Single Family Sale Price
$545,000
Median Townhouse Sale Price
$284,990
Median 2 Bedroom Sale Price
$287,500
Average Price Per Sq Ft
$248
Number of Homes for Sale
5
Last 12 months Home Sales
16
Months of Supply
3.80
Median List Price
$475,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
32%
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