4,282

Oak Bluffs, MA Homes

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  • /24

    $4,695,000 Pending

    • 5 Beds
    • 2.5 Baths
    • 3,885 Sq Ft

    18 Homeward Way, Chilmark, MA 02535

    Welcome to 18 Homeward Way — a peaceful Chilmark retreat tucked off scenic North Road, just minutes from the storied fishing village of Menemsha. This rare 15-acre offering includes two buildable parcels, creating an extraordinary opportunity for a Vineyard compound. The impeccably maintained residence, built in 1986, radiates classic Vineyard charm. Its thoughtful single-level layout fosters

    Bill Rossi Studio Realty

    18 Homeward Way, Chilmark, MA 02535
  • /26

    $1,850,000 Sold May 14, 2025

    • 2,610 Sq Ft
    • $709/SF
    • 8 Days On Market
    • 5 Beds
    • 4 Baths
    • Built 1986

    137 Charles Neck Way, Vineyard Haven, MA 02568

    Fantastic opportunity to buy a two house compound in West Tisbury close to Long Point Beach access. A perfect investment, rental income generator or to host extended family and guests.Two well built houses on 1.6 acres, that have been impeccably maintained by the original owner. Offering a total of 5 bedrooms, 4 bathrooms, 2 outdoor showers and 2 garages. There is a charming garden shed and

    Rebecca V Conroy Conroy & Company R.E., Inc.

    137 Charles Neck Way, Vineyard Haven, MA 02568
    • /20

      Est $2,623,653 Not Listed For Sale

      • 2 Beds
      • 2 Baths
      • 1,164 Sq Ft

      23 Black Point Rd, Chilmark, MA 02535

      23 Black Point Rd, Chilmark, MA 02535
  • /37

    $4,850,000 Pending

    • 5 Beds
    • 3 Baths
    • 3,440 Sq Ft

    146 Quansoo Rd, Chilmark, MA 02535

    Nestled along the beautiful and tranquil shoreline of Tisbury Great Pond and surrounded by a stunning natural environment of water, sand and sky, this is an unparallelled beach house experience on the south shore of Chilmark. The five-bedroom home consists of a three-bedroom main house connected by walkways to a two-bedroom guest wing with studio space above, all with spectacular water views

    Meg Bodnar Tea Lane Associates

    146 Quansoo Rd, Chilmark, MA 02535
  • /50

    $3,000,000 Sold Apr 29, 2025

    • 3,311 Sq Ft
    • $906/SF
    • 3 Beds
    • 2.5 Baths
    • Built 2000

    34 S Pond Rd, Vineyard Haven, MA 02568

    Stunning Deep Bottom Pond property with an oversized 3.77-acre lot surrounded by Mother Nature’s beauty, with exclusive association access to Tisbury Great Pond and private tennis courts. This beautiful home is lovingly maintained and ready for immediate occupancy. Through the welcoming grand foyer, a cathedral-ceiling living room with a fabulous wood-burning fireplace, and slider doors leading

    Stephanie Roache Donnelly + Co

    34 S Pond Rd, Vineyard Haven, MA 02568
    • /21

      Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 2,686 Sq Ft

      3 Pepperbush Ln, Chilmark, MA 02535

      3 Pepperbush Ln, Chilmark, MA 02535
  • /51

    $4,950,000 Pending

    • 5 Beds
    • 3.5 Baths
    • 4,044 Sq Ft

    49 Gosnold's Way, Chilmark, MA 02535

    Perched high on the north shore with sweeping views of the Vineyard Sound, this expansive and private property is surrounded by Menemsha Hills conservation land and trails and offers broad water views, even from ground floor of house. The house is large and well maintained with an upside down floor plan allowing for high ceilings and bright spaces in the open plan kitchen/dining/living room, as

    Meg Bodnar Tea Lane Associates

    49 Gosnold's Way, Chilmark, MA 02535
  • /35

    $1,837,500 Sold Apr 18, 2025

    • 1,654 Sq Ft
    • $1,111/SF
    • 182 Days On Market
    • 4 Beds
    • 3 Baths
    • Built 1984

    55 Charles Neck Way, Vineyard Haven, MA 02568

    LONG POINT BEACH RETREAT. Privately set on 1.6 acres in the highly-coveted Long Point area of West Tisbury, this reverse style beach house is an idyllic island retreat. The open-designed Great Room features vaulted ceilings and a wall of sliding glass doors that open out to an expansive deck, perfect for indoor-outdoor summer living and entertaining. There are also screened porches on both

    Wendy Harman Compass | Point B

    55 Charles Neck Way, Vineyard Haven, MA 02568
    • /29

      Est $2,271,694 Not Listed For Sale

      • 5 Beds
      • 3 Baths
      • 2,427 Sq Ft

      50 South Rd, Chilmark, MA 02535

      50 South Rd, Chilmark, MA 02535
  • /4

    $1,449,000 Pending

    • Land
    • 3.9 Acres
    • $371,538 per Acre

    34 Ebens Ln, Chilmark, MA 02535

    Settled high on a peaceful ridge this 3.9-acre property is being offered with a long-term lease for 2.5 acres of prime restricted agricultural farmland abutting the property and the Tiasquam River. With the river running along the edge of the property this area is ideal for growing flowers, vegetables, and/or arbors. The land may also be used for grazing and housing livestock along with any

    Thomas Wallace Wallace & Co. Sotheby's

    34 Ebens Ln, Chilmark, MA 02535
  • /22

    $1,150,000 Sold Apr 11, 2025

    • 1,264 Sq Ft
    • $910/SF
    • 216 Days On Market
    • 3 Beds
    • 1.5 Baths
    • Built 1983

    41 Old County Rd, Vineyard Haven, MA 02568

    Let your imagination run wild with this peaceful, pastoral property centrally located between down and up-island. This home is perfectly sited on just over 2 acres and is ready for your vision. The cape-style main house features a spacious wrap around deck and an open floor plan on the first level. The entire home is outfitted with hardwood floors. According to the West Tisbury Board of Health,

    Jared Bicknell Compass | The O'Hanlon Group

    41 Old County Rd, Vineyard Haven, MA 02568
    • /24

      Est $2,467,460 Not Listed For Sale

      • 4 Beds
      • 5.5 Baths
      • 2,405 Sq Ft

      99 Hammett Rd, Chilmark, MA 02535

      99 Hammett Rd, Chilmark, MA 02535
  • /30

    $1,175,000 Sold Mar 20, 2025

    • 1,389 Sq Ft
    • $846/SF
    • 173 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1988

    12 W Farm Rd, West Tisbury, MA 02575

    Welcome to 12 West Farm Road, a delightful classic cape nestled among beautiful mature evergreens in the Coffins Field neighborhood of West Tisbury. This well-kept home features 3 bedrooms and 2 bathrooms, offering 1,389 square feet of cozy and inviting living space. Skylighted ceilings and an open first-floor living/cooking/dining area combination provide a spacious feeling for everyday

    Carson Crissman Compass | Point B

    12 W Farm Rd, West Tisbury, MA 02575
    • /48

      Not Listed For Sale

      • 6 Beds
      • 5 Baths
      • 3,834 Sq Ft

      49 Tilton Rd, Chilmark, MA 02535

      49 Tilton Rd, Chilmark, MA 02535
  • /22

    $1,115,000 Sold Mar 14, 2025

    • 1,286 Sq Ft
    • $867/SF
    • 212 Days On Market
    • 2 Beds
    • 1 Bath
    • Built 1955

    496 Lamberts Cove Rd, Vineyard Haven, MA 02568

    Two peaceful acres on coveted Lamberts Cove Road with access to Lamberts Cove Beach and proximity to West Tisbury Center and Conservation Land. This property boasts mature plantings, various trees, and much Mother Nature offers, including a small pond. The home has been completely renovated and enjoys hardwood floors, skylights, a wood stove, and other special features such as antique

    Stephanie Roache Donnelly + Co

    496 Lamberts Cove Rd, Vineyard Haven, MA 02568
    • /7

      Not Listed For Sale

      419 Lamberts Cove Rd, West Tisbury, MA 02568

      419 Lamberts Cove Rd, West Tisbury, MA 02568
  • /17

    $1,300,000 Sold Mar 03, 2025

    • 1,241 Sq Ft
    • $1,048/SF
    • 4 Days On Market
    • 2 Beds
    • 2 Baths
    • Built 2018

    22 Briarwood Ln, Vineyard Haven, MA 02568

    This Recently Constructed Carriage House in Vineyard Haven is the epitome of thoughtful planning with custom details and exceptional finishes throughout. The sunny second level has an open floor living and kitchen area with vaulted ceilings. Highlights include a farmer’s sink, quartz countertops, pull out kitchen cabinets and self-closing drawers. There are two bedrooms, one is ensuite and

    Carol Shore Donnelly + Co

    22 Briarwood Ln, Vineyard Haven, MA 02568
    • /3

      Not Listed For Sale

      25 Plum Bush Point Rd, West Tisbury, MA 02568

      25 Plum Bush Point Rd, West Tisbury, MA 02568
  • /45

    $990,000 Sold Feb 19, 2025

    • 1,618 Sq Ft
    • $612/SF
    • 145 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1999

    5 Rock Pond Rd, Vineyard Haven, MA 02568

    Fantastic opportunity to own a South Mountain designed and built home in the coveted Island Co-Housing community. House #5 sits back from the community road with a great side yard, patio and outdoor shower.3 Large Bedrooms include a downstairs master w/ensuite bath off the living room area with a mid-way access leading to a private patio. The entryway opens on the kitchen, with thick shaker

    Kerry Quinlan-Potter Breakwater MV

    5 Rock Pond Rd, Vineyard Haven, MA 02568
    • /26

      Not Listed For Sale

      • 8 Beds
      • 4 Baths
      • 4,800 Sq Ft

      48 Forest Road Sgf Site 37, West Tisbury, MA 02575

      48 Forest Road Sgf Site 37, West Tisbury, MA 02575
  • /2

    $1,600,000 Sold Feb 04, 2025

    • Land
    • 3.6 Acres
    • $444,444 per Acre
    • 0 Days On Market

    493 South Rd, Chilmark, MA 02535

    Lovely pastoral lot within walking distance of beach and center of town.Perc test completed, septic being designed and well to be drilled shortly.Includes conservation restricted lot which consists of 10.6 acres.Build the home of your dreams in this amazing location.

    Julianna Flanders Flanders Real Estate

    493 South Rd, Chilmark, MA 02535
    • /55

      Not Listed For Sale

      • 11 Beds
      • 9.5 Baths
      • 4,985 Sq Ft

      28 & 18 Hillbrook Ln, West Tisbury, MA 02575

      28 & 18 Hillbrook Ln, West Tisbury, MA 02575
  • /49

    $1,750,000 Sold Jan 31, 2025

    • 2,548 Sq Ft
    • $687/SF
    • 186 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 1984

    75 Skiffs Ln, Vineyard Haven, MA 02568

    Located on a beautiful, private 2.6 acre lot, this well-maintained home is move-in ready and awaiting your personal touch! Pool, manicured yard, plentiful parking, attached garage, large basement, outdoor shower and many more features make this spacious family home versatile and accommodating to your needs. You're able to enjoy the patio and pool with a built in fire pit during the summer months

    Kelly Mercier The Agency

    75 Skiffs Ln, Vineyard Haven, MA 02568
    • /31

      Not Listed For Sale

      • 3 Beds
      • 3 Baths
      • 4,591 Sq Ft

      8 Vineyard Meadow Farms Rd, West Tisbury, MA 02575

      8 Vineyard Meadow Farms Rd, West Tisbury, MA 02575
  • /31

    $2,525,000 Sold Jan 17, 2025

    • 3,310 Sq Ft
    • $763/SF
    • 80 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 1991

    106 Panhandle Rd, Vineyard Haven, MA 02568

    With easy access to the West Tisbury Village, this lovely 4 bedroom, 3.5 bath home is privately sited on 1.4 acres overlooking a protected pasture. Many nice features include open living spaces, a well equipped kitchen with stainless steel appliances, a center island and granite. The sun-filled great room with oversized windows offer peaceful views of the meadow, a cathedral ceiling and sliders

    Brenda Galligan Karen M. Overtoom R.E.

    106 Panhandle Rd, Vineyard Haven, MA 02568
    • /21

      Not Listed For Sale

      • 6 Beds
      • 4 Baths
      • 4,967 Sq Ft

      27, 30, 31 Tower Lane; 34 Eben's Ln, Chilmark, MA 02535

      27, 30, 31 Tower Lane; 34 Eben's Ln, Chilmark, MA 02535
  • /39

    $2,895,000 Sold Jan 10, 2025

    • 4,239 Sq Ft
    • $683/SF
    • 341 Days On Market
    • 5 Beds
    • 4.5 Baths
    • Built 1999

    18 S Pond Rd, Vineyard Haven, MA 02568

    DEEP BOTTOM POND: 5-bedroom custom home with heated Pebbletec pool and exclusive association access to Tisbury Great Pond. This spacious layout features two primary suites, two guest rooms, and a third private guest suite. Perfect for entertaining, the open floor plan centers around the kitchen, dining, and living areas. The dramatic living room has cathedral ceilings, floor-to-ceiling windows, a

    Rose Ryley Wallace & Co. Sotheby's

    18 S Pond Rd, Vineyard Haven, MA 02568
    • /7

      Not Listed For Sale

      609 State Rd, West Tisbury, MA 02575

      609 State Rd, West Tisbury, MA 02575
  • /32

    $3,000,000 Sold Jan 09, 2025

    • 3,500 Sq Ft
    • $857/SF
    • 194 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 2023

    4 Bartlett Woods, Chilmark, MA 02535

    NEW BRIGHT & AIRY CONTEMPORARY OFF SOUTH ROAD! The house newly completed in 2023 & the one car garage in 2024 are nicely situated on a 4.56 acre lot. The 4 bedroom residence offers 3500 sf of finished living on two levels. On the first level are 2 primary bedrooms, each with en suite bathrooms, and a spacious open floor plan for living, dining and kitchen. An office off the kitchen allows you to

    Kathryn Tate Kathryn Tate Gothard

    4 Bartlett Woods, Chilmark, MA 02535
    • /33

      Not Listed For Sale

      • 3 Beds
      • 3 Baths
      • 2,123 Sq Ft

      74 Waldrons Bottom Rd, West Tisbury, MA 02575

      74 Waldrons Bottom Rd, West Tisbury, MA 02575
  • /39

    $1,650,000 Sold Jan 07, 2025

    • 2,146 Sq Ft
    • $769/SF
    • 202 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1982

    3 Danls Way, Vineyard Haven, MA 02568

    Discover a unique opportunity to own 4.5 acres in the picturesque heart of West Tisbury, complete with the potential for a guest house of up to 1,000 square feet. This property, cherished and maintained by the same family for over two centuries, offers a serene pastoral setting that invites you to embrace the beauty of nature. Enjoy sweeping views of lush meadows adorned with a diverse array

    Marilyn Moses Ocean Park Realty Inc

    3 Danls Way, Vineyard Haven, MA 02568
    • /14

      Not Listed For Sale

      34 Ebens Lane & 31 Tower Ln, Chilmark, MA 02535

      34 Ebens Lane & 31 Tower Ln, Chilmark, MA 02535
  • /29

    $2,250,000 Sold Dec 27, 2024

    • 1,705 Sq Ft
    • $1,320/SF
    • 5 Days On Market
    • 4 Beds
    • 3 Baths
    • Built 1976

    47 Stonebridge Rd, West Tisbury, MA 02568

    Lamberts Cove Beach access, first and second floor water views, and a warm and inviting home in a private West Tisbury location - that is what is on offer here. The home was recently upgraded with a new kitchen and bathrooms. The primary bedroom suite has even better views than those from the first floor. The walkout lower level is a two bedroom suite with full bath, sitting area, kitchenette,

    Mark Jenkins Wallace & Co. Sotheby's International Realty

    47 Stonebridge Rd, West Tisbury, MA 02568
    • /13

      Not Listed For Sale

      • 1 Bed
      • 1 Bath
      • 816 Sq Ft

      70 State Rd, Aquinnah, MA 02535

      70 State Rd, Aquinnah, MA 02535
  • /5

    $450,000 Sold Dec 12, 2024

    • 708 Sq Ft
    • $636/SF
    • 21 Days On Market
    • 2 Beds
    • 1 Bath
    • Built 1920

    1 Carroll Ln, Chilmark, MA 02535

    Discover the perfect blend of comfort and character in this delightful bungalow nestled in the heart of historic Chilmark. Surrounded by scenic landscapes and the serene beauty of Martha's Vineyard. This home will require substantial renovations and improvements or explore possibilities of a complete renovation. This property could be your idyllic escape and is less than a mile from Menemsha

    Nicholas Korba Landmarks at TODAY Real Estate

    1 Carroll Ln, Chilmark, MA 02535
    • /5

      Not Listed For Sale

      80 Watcha Club Rd, West Tisbury, MA 02568

      80 Watcha Club Rd, West Tisbury, MA 02568
  • /26

    $1,830,000 Sold Dec 05, 2024

    • 1,862 Sq Ft
    • $983/SF
    • 10 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1960

    82 South Rd, Chilmark, MA 02535

    This charming Chilmark home sits on over 3 acres and features an updated, move-in ready home, expansive outdoor living space with deck, lawn and firepit area, and a six-bedroom septic system for future expansion. The welcoming foyer opens into the dining room, kitchen and a large airy living room with vaulted ceiling and stone fireplace. Beyond the kitchen there are two bedrooms and a shared

    Meg Bodnar Tea Lane Associates

    82 South Rd, Chilmark, MA 02535
    • /6

      Not Listed For Sale

      0 Beach Lot Quansoo #136, Chilmark, MA 02535

      0 Beach Lot Quansoo #136, Chilmark, MA 02535
  • /2

    $440,000 Sold Sep 22, 2025

    • Land
    • 0 Acre
    • 0 Days On Market

    0 Quansoo Beach Lot Unit 49 43779, Chilmark, MA 02535

    Beach lot at Quansoo. Not Listed in LINK> Not a buildable lot.

    LINK Email Cache LINK

    0 Quansoo Beach Lot Unit 49 43779, Chilmark, MA 02535
    • /13

      Not Listed For Sale

      0 Gosnold's Way, Chilmark, MA 02535

      0 Gosnold's Way, Chilmark, MA 02535

Showing Results 201 - 240, Page 6 of 18

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