4,261

Oak Bluffs, MA Homes

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  • /20

    $821,000 Sold Jun 17, 2025

    168 Charles Neck Way Unit 49, Vineyard Haven, MA 02568

    • Land
    • 1.4 Acres
    • $586,429 per Acre

    Last Sold Summary

    • 2% Below List Price
    • 0 Days On Market

    Last Listing Agent Janna O'Loughlin Portfolio Properties

    168 Charles Neck Way Unit 49, Vineyard Haven, MA 02568
    • /30

      Est $1,568,627 Not Listed For Sale

      12 Lily Farm Rd, Vineyard Haven, MA 02568

      • 3 Beds
      • 1 Bath
      • 1,560 Sq Ft
      • Built 1991
      12 Lily Farm Rd, Vineyard Haven, MA 02568

      Last Sold Summary

      • 3% Below List Price
      • $1,042/SF
      • 198 Days On Market
      • Last Sold Price $1,625,000
      • Jul 03, 2023

      Last Listing Agent Richard Rooney Rooney & Company

  • /21

    $1,599,000

    • 3 Beds
    • 2 Baths
    • 1,562 Sq Ft

    111 Charles Neck Way, Vineyard Haven, MA 02568

    Tucked away on 1.6 wooded acres in West Tisbury, this classic Cape-style home offers both privacy and convenience, with easy access to the charm of Up-Island and the amenities of Down-Island. Located on a paved road near Long Point Beach, it also includes coveted access to Lambert's Cove Beach. The bright, open interior features a living and dining area with a wood-burning fireplace, a kitchen

    Emma Kennedy Sandpiper Realty, Inc.

    111 Charles Neck Way, Vineyard Haven, MA 02568
  • /48

    $1,775,000 Sold Nov 07, 2025

    3 Fulling Mill Rd, Chilmark, MA 02535

    • 3 Beds
    • 2 Baths
    • 1,728 Sq Ft
    • Built 1976

    Last Sold Summary

    • 5% Below List Price
    • $1,027/SF
    • 170 Days On Market

    Current Estimated Value $1,814,136

    Last Listing Agent Jill Napior Tea Lane Associates

    3 Fulling Mill Rd, Chilmark, MA 02535
    • /22

      Est $1,236,116 Not Listed For Sale

      41 Old County Rd, Vineyard Haven, MA 02568

      • 3 Beds
      • 1.5 Baths
      • 1,264 Sq Ft
      • Built 1983
      41 Old County Rd, Vineyard Haven, MA 02568

      Last Sold Summary

      • 7% Above List Price
      • $910/SF
      • 216 Days On Market
      • Last Sold Price $1,150,000
      • Apr 11, 2025

      Last Listing Agent Jared Bicknell Compass LLC

  • /40

    $7,350,000

    • 4 Beds
    • 4.5 Baths
    • 3,490 Sq Ft

    308 South Rd, Chilmark, MA 02535

    Waterfront South Shore Retreat with Private Dock and Water Views. Set on the edge of Chilmark Pond, this exceptional waterfront residence offers rare privacy, refined design, generous water views and easy pond access. Thoughtfully renovated in 2018, the home blends contemporary sophistication with the beauty of its natural environment. A private dock on the property provides direct pond access.

    Rose Ryley Wallace & Co. Sotheby's International Realty

    308 South Rd, Chilmark, MA 02535
  • /36

    $1,950,000 Sold Jul 02, 2025

    51 Black Brook Crossing Rd, West Tisbury, MA 02568

    • 4 Beds
    • 2.5 Baths
    • 2,691 Sq Ft
    • Built 1976

    Last Sold Summary

    • 6% Below List Price
    • $725/SF
    • 30 Days On Market

    Last Listing Agent Brenda Galligan Karen M. Overtoom R.E.

    51 Black Brook Crossing Rd, West Tisbury, MA 02568
    • /17

      Est $1,217,993 Not Listed For Sale

      22 Briarwood Ln, Vineyard Haven, MA 02568

      • 2 Beds
      • 2 Baths
      • 1,241 Sq Ft
      • Built 2018
      22 Briarwood Ln, Vineyard Haven, MA 02568

      Last Sold Summary

      • 6% Below List Price
      • $1,048/SF
      • 4 Days On Market
      • Last Sold Price $1,300,000
      • Mar 03, 2025

      Last Listing Agent Carol Shore Donnelly + Co

  • /39

    $3,995,000

    • 3 Beds
    • 4 Baths
    • 3,426 Sq Ft

    96 Hammett Ln, Chilmark, MA 02535

    Beautifully designed and built Post & Beam style home is tastefully thought out and meticulously maintained. The open living, dining and kitchen feature custom built-ins, a wood burning fireplace and a fabulous gourmet kitchen with Wolfe 8 burner professional style stove, Sub Zero refrigerator, Boshe dishwasher, soapstone counters and a butlers pantry with extra cupboards, shelving and a wine

    Brenda Galligan Karen M. Overtoom R.E.

    96 Hammett Ln, Chilmark, MA 02535
  • /13

    $2,050,000 Sold May 01, 2025

    16 Red Coat Hill Rd, Vineyard Haven, MA 02568

    • 2 Beds
    • 1 Bath
    • 1,007 Sq Ft
    • Built 2016

    Last Sold Summary

    • 2% Below List Price
    • $2,036/SF
    • 0 Days On Market

    Current Estimated Value $1,588,789

    Last Listing Agent Joe & Nicole Holland Vineyard Dream Realty LLC

    16 Red Coat Hill Rd, Vineyard Haven, MA 02568
    • /5

      Est $655,458 Not Listed For Sale

      1 Carroll Ln, Chilmark, MA 02535

      • 2 Beds
      • 1 Bath
      • 708 Sq Ft
      • Built 1920
      1 Carroll Ln, Chilmark, MA 02535

      Last Sold Summary

      • 46% Above List Price
      • $636/SF
      • 21 Days On Market
      • Last Sold Price $450,000
      • Dec 12, 2024

      Last Listing Agent Nicholas Korba Landmarks at TODAY Real Estate

  • /2

    $799,000

    • Land
    • 39,639 Sq Ft
    • $878,022 per Acre

    22 Bramble Path, West Tisbury, MA 02568

    Flat building lot centrally located in West Tisbury. A perc test has been done that supports a four bedroom title five system. It is the buyers responsibility to install utilities, well and septic.

    Michele Casavant Vineyard Village Realty

    22 Bramble Path, West Tisbury, MA 02568
  • /24

    $4,325,000 Sold Dec 05, 2025

    18 Homeward Way, Chilmark, MA 02535

    • 5 Beds
    • 2.5 Baths
    • 3,885 Sq Ft
    • Built 1986

    Last Sold Summary

    • 8% Below List Price
    • $1,113/SF
    • 8 Days On Market

    Current Estimated Value $4,550,558

    Last Listing Agent Bill Rossi Studio Realty

    18 Homeward Way, Chilmark, MA 02535
    • /29

      Est $1,694,033 Not Listed For Sale

      7 Flanders Ln, Chilmark, MA 02535

      • 3 Beds
      • 2 Baths
      • 1,200 Sq Ft
      • Built 1954
      7 Flanders Ln, Chilmark, MA 02535

      Last Sold Summary

      • 1% Above List Price
      • $1,400/SF
      • 4 Days On Market
      • Last Sold Price $1,680,000
      • Oct 09, 2024

      Last Listing Agent Meg Bodnar Tea Lane Associates

  • /33

    $2,300,000

    • 4 Beds
    • 3.5 Baths
    • 2,428 Sq Ft

    35 Nat's Farm Ln, West Tisbury, MA 02568

    Nestled within the prestigious Nats Farm Association, this beautifully crafted West Tisbury home offers a quintessential Martha’s Vineyard retreat. The first floor features a bright, open layout with a well-appointed kitchen, dining area, and inviting living room, ideal for gatherings. The spacious primary suite is located on the main level and includes a private office and a spa-like bath with

    Alyssa Halisky Wallace & Co. Sotheby's International Realty

    35 Nat's Farm Ln, West Tisbury, MA 02568
  • /15

    $1,150,000 Sold May 30, 2025

    14 Galway Rd, Vineyard Haven, MA 02568

    • 4 Beds
    • 1.5 Baths
    • 1,338 Sq Ft
    • Built 1966

    Last Sold Summary

    • 8% Below List Price
    • $859/SF
    • 48 Days On Market

    Current Estimated Value $1,215,978

    Last Listing Agent Michele Casavant Vineyard Village Realty

    14 Galway Rd, Vineyard Haven, MA 02568
    • /13

      Est $1,576,691 Not Listed For Sale

      12 Harbor Hill Rd, Chilmark, MA 02535

      • 1 Bed
      • 1 Bath
      • 640 Sq Ft
      • Built 1955
      12 Harbor Hill Rd, Chilmark, MA 02535

      Last Sold Summary

      • 13% Above List Price
      • $2,188/SF
      • 0 Days On Market
      • Last Sold Price $1,400,000
      • Sep 13, 2023

      Last Listing Agent Deb Hancock Hancock Real Estate

  • /3

    $1,325,000

    • Land
    • 4.28 Acres
    • $309,579 per Acre

    0/15 N Way, Chilmark, MA 02535

    Set just off North Road, this exceptional parcel offers a rare opportunity to build in a setting rich with natural beauty. Recently subdivided, this land combines privacy, character and thoughtful positioning. The lot is perfectly sited capturing serene woodland views and the natural contours of Middle Line Ridge. A 600ft stonewall lines the western property line, creating a timeless sense of

    Stacy Ickes Donnelly + Co.

    0/15 N Way, Chilmark, MA 02535
  • /37

    $4,350,000 Sold Jan 07, 2026

    146 Quansoo Rd, Chilmark, MA 02535

    • 5 Beds
    • 3 Baths
    • 3,440 Sq Ft
    • Built 1988

    Last Sold Summary

    • 21% Below List Price
    • $1,265/SF
    • 155 Days On Market

    Current Estimated Value $4,333,864

    Last Listing Agent Meg Bodnar Tea Lane Associates

    146 Quansoo Rd, Chilmark, MA 02535
    • /18

      Est $3,991,443 Not Listed For Sale

      1 Pond Mark, Chilmark, MA 02535

      • 3 Beds
      • 2 Baths
      • 1,316 Sq Ft
      • Built 1955
      1 Pond Mark, Chilmark, MA 02535

      Last Sold Summary

      • 1% Above List Price
      • $3,002/SF
      • 466 Days On Market
      • Last Sold Price $3,950,000
      • Jan 19, 2024

      Last Listing Agent Mark Jenkins Wallace & Co. Sotheby's International Realty

  • /42

    $7,950,000

    • 5 Beds
    • 7 Baths
    • 4,531 Sq Ft

    85 Reservoir Rd, Vineyard Haven, MA 02568

    Nestled within Seven Gates Farm, one of Martha's Vineyard's most storied and scenic communities, this 26.5-acre estate offers a beautifully renovated farmhouse that seamlessly blends modern comforts with historic charm. Surrounded by ancient stone walls, mature trees, and lush gardens, the property includes a charming guest house, scenic walking paths, and a peaceful hilltop retreat with a stone

    Alyssa Halisky Wallace & Co. Sotheby's

    85 Reservoir Rd, Vineyard Haven, MA 02568
  • /17

    $1,790,000 Sold Sep 23, 2025

    32 Stonewall Rd Unit 2.1, Chilmark, MA 02535

    • Land
    • 3.3 Acres
    • $542,424 per Acre

    Last Sold Summary

    • 15% Below List Price
    • 77 Days On Market

    Last Listing Agent Jill Napior Tea Lane Associates

    32 Stonewall Rd Unit 2.1, Chilmark, MA 02535
    • /12

      Est $2,495,155 Not Listed For Sale

      5 Ocean View Farm Rd, Chilmark, MA 02535

      • 3 Beds
      • 1.5 Baths
      • 1,342 Sq Ft
      • Built 1971
      5 Ocean View Farm Rd, Chilmark, MA 02535

      Last Sold Summary

      • 4% Above List Price
      • $1,796/SF
      • 3 Days On Market
      • Last Sold Price $2,410,000
      • Aug 02, 2023

      Last Listing Agent Russell Maloney Russel Maloney Real Estate

  • /55

    $4,450,000

    • 6 Beds
    • 4.5 Baths
    • 2,960 Sq Ft

    104 Pond View Farm Rd, Vineyard Haven, MA 02568

    Two homes on over 3 flat acres of waterfront on the Tisbury Great Pond. This remarkable waterfront property offers a rare opportunity to own a serene compound with two homes and a private permitted dock—ideal for boating to the Atlantic barrier beach, fishing, kayaking, and enjoying the peaceful beauty of the pond.Both the main house and guest house boast unobstructed water views, creating a

    Alexis Holden Tea Lane Associates

    104 Pond View Farm Rd, Vineyard Haven, MA 02568
  • /3

    $3,100,000 Sold Jul 03, 2025

    10 Basin Rd, Chilmark, MA 02535

    • 6 Beds
    • 3 Baths
    • 1,500 Sq Ft
    • Built 1975

    Last Sold Summary

    • $2,067/SF

    Current Estimated Value $3,030,376

    Last Listing Agent Julianna Flanders Flanders Real Estate

    10 Basin Rd, Chilmark, MA 02535
    • /19

      Est $2,722,278 Not Listed For Sale

      27 Ocean View Farm Rd, Chilmark, MA 02535

      • 4 Beds
      • 3 Baths
      • 2,450 Sq Ft
      • Built 1964
      27 Ocean View Farm Rd, Chilmark, MA 02535

      Last Sold Summary

      • 24% Above List Price
      • $898/SF
      • 182 Days On Market
      • Last Sold Price $2,200,000
      • Oct 25, 2024

      Last Listing Agent Russell Maloney Russel Maloney Real Estate

  • /18

    $1,425,000

    • Land
    • 3.01 Acres
    • $473,422 per Acre

    38 Fire Tower Rd Unit 40.2, West Tisbury, MA 02568

    The Tower Hill land, once known as the Dancing Hills, is considered by many a sacred Island space. Standing on the ridge top, you're at one of the highest points on Martha's Vineyard. This 3.01 acre parcel looks out over the trees of Red Farm and the dramatic blue expanse of Vineyard Sound. It's easy to understand why this property is so special. There's a generous designated building envelope of

    Elissa Lash Tea Lane Associates

    38 Fire Tower Rd Unit 40.2, West Tisbury, MA 02568
  • /32

    $2,278,000 Sold Aug 01, 2025

    35 Woody Bottom Rd, West Tisbury, MA 02575

    • 5 Beds
    • 3.5 Baths
    • 2,685 Sq Ft
    • Built 1998

    Last Sold Summary

    • 9% Below List Price
    • $848/SF
    • 139 Days On Market

    Current Estimated Value $2,351,579

    Last Listing Agent Brenda Galligan Karen M. Overtoom R.E.

    35 Woody Bottom Rd, West Tisbury, MA 02575
    • /69

      Est $2,566,601 Not Listed For Sale

      276 South Rd, Chilmark, MA 02535

      • 4 Beds
      • 2 Baths
      • 2,034 Sq Ft
      • Built 1981
      276 South Rd, Chilmark, MA 02535

      Last Sold Summary

      • 32% Above List Price
      • $959/SF
      • 122 Days On Market
      • Last Sold Price $1,950,000
      • Aug 15, 2023

      Last Listing Agent Julianna Flanders Flanders Real Estate

  • /13

    $1,645,000

    • Land
    • 3.32 Acres
    • $495,482 per Acre

    26 Flint Hill Rd Unit 3B, West Tisbury, MA 02575

    Stop Searching. Start Building. You've toured dozens of homes. Nothing feels right. What if your dream home on Martha's Vineyard simply hasn't been built yet? This rare 3.32-acre West Tisbury hilltop is the blank canvas you've been waiting for. Glacial boulders, open pasture, and cathedral oaks with Land Bank-preserved Arrowhead Farm and protected Rodgers Path land on two sides - a setting unlike

    Dawn Bellante-Holand Sandpiper Realty

    26 Flint Hill Rd Unit 3B, West Tisbury, MA 02575
  • /50

    $3,000,000 Sold Apr 29, 2025

    34 S Pond Rd, Vineyard Haven, MA 02568

    • 3 Beds
    • 2.5 Baths
    • 3,311 Sq Ft
    • Built 2000

    Last Sold Summary

    • 1% Above List Price
    • $906/SF

    Current Estimated Value $2,974,820

    Last Listing Agent Stephanie Roache Donnelly + Co

    34 S Pond Rd, Vineyard Haven, MA 02568
    • /37

      Est $2,261,629 Not Listed For Sale

      2 Rockrose Path, Chilmark, MA 02535

      • 4 Beds
      • 3 Baths
      • 1,900 Sq Ft
      • Built 1978
      2 Rockrose Path, Chilmark, MA 02535

      Last Sold Summary

      • 46% Above List Price
      • $816/SF
      • 414 Days On Market
      • Last Sold Price $1,550,000
      • Sep 05, 2024

      Last Listing Agent Jill Napior Tea Lane Associates

  • /16

    $3,200,000

    • 4 Beds
    • 3 Baths
    • 2,346 Sq Ft

    6 Trails End, Chilmark, MA 02535

    Step into timeless mid-century modern style and comfort in this single-level, 4-bedroom, 3-bathroom home located in the heart of Chilmark. This home features an open layout with large glass panel doors that lead to a sun-drenched deck, heated in-ground pool, and grassy lawn. This home is offered completely furnished with a well-equipped kitchen, large living room with wood burning fireplace,

    Russell Maloney Russell Maloney Real Estate

    6 Trails End, Chilmark, MA 02535
  • /32

    $3,925,000 Sold Jul 01, 2025

    140 Merry Farm Rd, Vineyard Haven, MA 02568

    • 6 Beds
    • 7 Baths
    • 5,603 Sq Ft
    • Built 1995

    Last Sold Summary

    • 8% Below List Price
    • $701/SF
    • 238 Days On Market

    Last Listing Agent Mark Jenkins Wallace & Co. Sotheby's

    140 Merry Farm Rd, Vineyard Haven, MA 02568
    • /53

      Est $12,341,145 Not Listed For Sale

      8 Snail Rd, Chilmark, MA 02535

      • 6 Beds
      • 8 Baths
      • 6,967 Sq Ft
      • Built 2006
      8 Snail Rd, Chilmark, MA 02535

      Last Sold Summary

      • 18% Below List Price
      • $2,153/SF
      • 25 Days On Market
      • Last Sold Price $15,000,000
      • Apr 08, 2025

      Last Listing Agent Alyssa Halisky Wallace & Co. Sotheby's International Realty

  • /37

    $1,195,000

    • 4 Beds
    • 2 Baths
    • 2,059 Sq Ft

    4 Rock Pond Rd, Vineyard Haven, MA 02568

    4 Bedroom ++ home, has room for your family and your in-home business. This is the home that has it all. An abundance of light, space and potential. A large Atrium off the living room invites in the light and warmth of outside, creating an oasis of possibilities-The expansive open living-kitchen-dining area has space for all to gather, the wood stove and kitchen bringing warmth and sunlight

    Kerry Quinlan-Potter Breakwater MV

    4 Rock Pond Rd, Vineyard Haven, MA 02568
  • /28

    $2,550,000 Sold Oct 02, 2025

    10 Mollys Way, Chilmark, MA 02535

    • 3 Beds
    • 2 Baths
    • 1,524 Sq Ft
    • Built 1926

    Last Sold Summary

    • 14% Below List Price
    • $1,673/SF
    • 130 Days On Market

    Current Estimated Value $2,466,710

    Last Listing Agent Peyton Wallace Studio Realty

    10 Mollys Way, Chilmark, MA 02535
    • /20

      Est $2,855,269 Not Listed For Sale

      23 Black Point Rd, Chilmark, MA 02535

      • 2 Beds
      • 2 Baths
      • 1,164 Sq Ft
      • Built 2004
      23 Black Point Rd, Chilmark, MA 02535

      Last Sold Summary

      • 13% Below List Price
      • $2,835/SF
      • 13 Days On Market
      • Last Sold Price $3,300,000
      • Jul 10, 2023

      Last Listing Agent Jill Napior Tea Lane Associates

  • /59

    $2,250,000 Pending

    • 4 Beds
    • 2.5 Baths
    • 2,983 Sq Ft

    157 Ben Chase Rd, West Tisbury, MA 02575

    You will find this outstanding property at the end of a quiet country lane in West Tisbury nestled alongside hundreds of acres of conservation land and walking trails that extend all the way to Lamberts Cove Road. The setting is magical - 4 acres of rolling lawns with specimen trees and ponds. There are multiple structures to allow you to customize this compound to your personal needs. The main

    Madelyn Silvia Wallace & Co. Sotheby's

    157 Ben Chase Rd, West Tisbury, MA 02575
  • /47

    $1,595,500 Sold Jun 23, 2025

    21 Coffins Field Rd, Edgartown, MA 02539

    • 5 Beds
    • 3 Baths
    • 1,822 Sq Ft
    • Built 2003

    Last Sold Summary

    • 6% Below List Price
    • $876/SF
    • 73 Days On Market

    Current Estimated Value $1,666,077

    Last Listing Agent Helena Kirschenbaum Studio Realty

    21 Coffins Field Rd, Edgartown, MA 02539

Showing Results 161 - 200, Page 5 of 18

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