11,368

Vineyard Haven, MA Homes

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  • /42

    $1,895,000

    Pending
    • 5 Beds
    • 3.5 Baths
    • 2,527 Sq Ft

    18 Puritan Dr, Vineyard Haven, MA 02568

    Craving the ultimate Martha's Vineyard escape? Discover a hidden architectural gem in the serene Tower Ridge community, across the street from Farm Neck Golf Club & Cafe! This striking contemporary home perfectly blends sophisticated design with the tranquil beauty of an expansive, private lot. Step inside to experience a breathtaking layout defined by soaring cathedral ceilings and an abundance

    Jennifer B. DaSilva Compass

    18 Puritan Dr, Vineyard Haven, MA 02568
  • /19

    $835,000

    Sold Nov 05, 2025

    1 Onondaga Ave, Oak Bluffs, MA 02557

    • 1 Bed
    • 1 Bath
    • 960 Sq Ft
    • Built 2000

    Last Sold Summary

    • 12% Below List Price
    • $870/SF
    • 119 Days On Market

    Last Listing Agent Leslie C. Floyd Portfolio Properties

    1 Onondaga Ave, Oak Bluffs, MA 02557
    • /19

      Not Listed For Sale

      37 Circuit Ave Unit 2, Oak Bluffs, MA 02557

      • 2 Beds
      • 1 Bath
      • 797 Sq Ft
      • Built 1900
      37 Circuit Ave Unit 2, Oak Bluffs, MA 02557

      Last Sold Summary

      • 7 Days On Market

  • /73

    $4,125,000

    $525K PRICE DROP
    • 7 Beds
    • 4.5 Baths
    • 3,312 Sq Ft

    31 Josiah Sachem Way, Vineyard Haven, MA 02568

    An Inspirational Oasis - Come unwind and experience a secluded multi-dwelling compound nestled along the gentle slopes of Indian Hill, where rural tranquility meets effortless island living on more than three acres of uncommon beauty. Centered around a heated saltwater pool reminiscent of a private resort, the main house, studio barn, and guesthouse with a total of 4,464 square feet of living

    Helena Kirschenbaum Studio Realty

    31 Josiah Sachem Way, Vineyard Haven, MA 02568
  • /33

    $839,000

    Sold Nov 14, 2025

    16 Cottage Park, Oak Bluffs, MA 02557

    • 2 Beds
    • 1 Bath
    • 939 Sq Ft
    • Built 1870

    Last Sold Summary

    • $894/SF
    • 12 Days On Market

    Current Estimated Value $833,903

    Last Listing Agent Marilyn Moses Ocean Park Realty Inc

    16 Cottage Park, Oak Bluffs, MA 02557
    • /56

      Not Listed For Sale

      5 & 7 Lyme St, Oak Bluffs, MA 02557

      • 5 Beds
      • 3 Baths
      • 1,999 Sq Ft
      • Built 1960
      5 & 7 Lyme St, Oak Bluffs, MA 02557

      Last Sold Summary

      • 26 Days On Market

  • /8

    $695,000

    $55K PRICE DROP
    • Land
    • 11,417 Sq Ft
    • $2,651,660 per Acre

    35 Double Ox Rd Unit 42, Oak Bluffs, MA 02557

    GOING, GOING... GONE!This is the LAST 3-bedroom lot available in Cluster C.12 lots SOLD 9 homes already built.Welcome to Lagoon Ridge Oak Bluffs’ newest and most sought-after neighborhood. This exceptional 3-bedroom building lot sits on a lofty setting approximately 95 feet above Lagoon Pond, offering sweeping sky views, vibrant sunsets, and refreshing sea breezes.The lot is ready

    Marilyn Moses Ocean Park Realty Inc

    35 Double Ox Rd Unit 42, Oak Bluffs, MA 02557
  • /27

    $4,583,000

    Sold Jun 23, 2026

    9 Fowler Ave, Edgartown, MA 02539

    • 4 Beds
    • 3.5 Baths
    • 3,018 Sq Ft
    • Built 1940

    Last Sold Summary

    • 13% Below List Price
    • $1,519/SF
    • 236 Days On Market

    Current Estimated Value $4,756,213

    Last Listing Agent Andrew McElhinney Compass LLC

    9 Fowler Ave, Edgartown, MA 02539
    • /34

      Est $1,552,386

      Not Listed For Sale

      18 Jesses Way, Tisbury, MA 02568

      • 4 Beds
      • 3 Baths
      • 2,484 Sq Ft
      • Built 2003
      18 Jesses Way, Tisbury, MA 02568

      Last Sold Summary

      • 85 Days On Market

  • /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
  • /40

    $2,300,000

    Sold Aug 21, 2025

    174 Tashmoo Ave, Vineyard Haven, MA 02568

    • 5 Beds
    • 4.5 Baths
    • 3,213 Sq Ft
    • Built 2011

    Last Sold Summary

    • 8% Below List Price
    • $716/SF
    • 75 Days On Market

    Current Estimated Value $2,298,818

    Last Listing Agent Lisa Lucier Anchor Realty of Martha's Vineyard

    174 Tashmoo Ave, Vineyard Haven, MA 02568
    • /5

      Not Listed For Sale

      45 Ice Pond Ln, Oak Bluffs, MA 02557

      • 1 Bed
      • 2.5 Baths
      • 1,560 Sq Ft
      • Built 1984
      45 Ice Pond Ln, Oak Bluffs, MA 02557

      Last Sold Summary

      • 0 Days On Market

  • /21

    $1,175,000

    $74K PRICE DROP
    • 3 Beds
    • 1 Bath
    • 998 Sq Ft

    299 Daggett Ave, Vineyard Haven, MA 02568

    This cheerful sun drenched three-bed & one bath home with cathedral ceilings sits on just over an acre of gently rolling land surrounded by mature pines, oaks and ornamental plantings. Inspired by Norwegian architecture, the current owner designed and built this home in 1999 with his wife who was an artist from Norway. It’s located about a mile to town in one direction and the beach in the other.

    Alyson Parker Karen M. Overtoom R.E.

    299 Daggett Ave, Vineyard Haven, MA 02568
  • /2

    $515,000

    Sold Jul 15, 2025

    64 Deer Run Rd, Oak Bluffs, MA 02568

    • Land
    • 20,124 Sq Ft
    • $1,114,719 per Acre

    Last Sold Summary

    • 0 Days On Market

    Last Listing Agent LINK Email Cache LINK

    64 Deer Run Rd, Oak Bluffs, MA 02568
    • /24

      Not Listed For Sale

      19 The Blvd, Edgartown, MA 02539

      • 4 Beds
      • 3.5 Baths
      • 2,073 Sq Ft
      • Built 1940
      19 The Blvd, Edgartown, MA 02539

      Last Sold Summary

      • 145 Days On Market

  • /4

    $445,000

    • Land
    • 23,958 Sq Ft
    • $809,091 per Acre

    11 Boylston Dr, Edgartown, MA 02539

    A picturesque half-acre lot in the desirable Edgartown neighborhood, perfect for building your Martha's Vineyard home. Bordered by more than 175 acres of pristine conservation land, this property offers peaceful surroundings with easy access to the island’s top attractions, including stunning beaches, scenic trails, vast state forests, and public transportation. In accordance with recent

    Alyssa Halisky Wallace & Co. Sotheby's International Realty

    11 Boylston Dr, Edgartown, MA 02539
  • /2

    $625,000

    Sold Dec 03, 2025

    0 Lyle Ln Unit 2B, Vineyard Haven, MA 02568

    • Land
    • 31,184 Acres
    • $20 per Acre

    Last Sold Summary

    • 0 Days On Market

    Last Listing Agent LINK Email Cache LINK

    0 Lyle Ln Unit 2B, Vineyard Haven, MA 02568
    • /19

      Not Listed For Sale

      2 Lagrange Ave, Oak Bluffs, MA 02557

      • 3 Beds
      • 2 Baths
      • 1,670 Sq Ft
      • Built 1996
      2 Lagrange Ave, Oak Bluffs, MA 02557

      Last Sold Summary

      • 4 Days On Market

  • /34

    $3,250,000

    • 4 Beds
    • 3 Baths
    • 1,728 Sq Ft

    6 Brewster Ave, Oak Bluffs, MA 02557

    Enjoy sweeping water views from this beautifully updated East Chop Victorian, featuring a charming guest cottage. Renovated in 2010, the main home effortlessly blends historic character with modern comfort. The kitchen and bathrooms have been thoughtfully updated, enhancing functionality while preserving the home’s original charm. Tucked privately at the rear of the property, the guest cottage

    Katie Donahue & Rachel Serwa Group Sandpiper Realty, Inc.

    6 Brewster Ave, Oak Bluffs, MA 02557
  • /3

    $3,067,050

    Sold Oct 22, 2025

    114 Park, Oak Bluffs, MA 02557

    • 4 Beds
    • 3.5 Baths
    • 1,872 Sq Ft
    • Built 1985

    Last Sold Summary

    • $1,638/SF
    • 0 Days On Market

    Current Estimated Value $2,969,498

    Last Listing Agent LINK Email Cache LINK

    114 Park, Oak Bluffs, MA 02557
    • /27

      Not Listed For Sale

      8 Circuit Avenue Extension Unit 14, Oak Bluffs, MA 02557

      • 1 Bath
      • 366 Sq Ft
      • Built 1989
      8 Circuit Avenue Extension Unit 14, Oak Bluffs, MA 02557

      Last Sold Summary

      • 12 Days On Market

  • /10

    $1,100,000

    $100K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 1,581 Sq Ft

    15 Goah Way, Vineyard Haven, MA 02568

    2 bedroom 2 bath cottage with 1 bedroom 1 bath ADU. Large 15,950 square foot lot, short distance to school and town. Second floor bedroom space is large and possibly convertable to 2 bedrooms. New windows and 2 mini split systems, ADU also has a mini split unit. ADU is beleived to have been built in 2017. Property is loacted in Tashmoo watershed district and will require an upgrade to an nitrogen

    Roy Cutrer Jr Laer Realty Partners

    15 Goah Way, Vineyard Haven, MA 02568
  • /20

    $2,000,000

    Sold May 28, 2026

    151 Tashmoo Ave, Vineyard Haven, MA 02568

    • 4 Beds
    • 3.5 Baths
    • 2,690 Sq Ft
    • Built 2022

    Last Sold Summary

    • 13% Below List Price
    • $743/SF
    • 128 Days On Market

    Current Estimated Value $2,192,688

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

    151 Tashmoo Ave, Vineyard Haven, MA 02568
    • /12

      Not Listed For Sale

      61 E Ocean Ave, Oak Bluffs, MA 02557

      • 1 Bed
      • 1 Bath
      • 512 Sq Ft
      • Built 1870
      61 E Ocean Ave, Oak Bluffs, MA 02557

      Last Sold Summary

      • 45 Days On Market

  • /46

    $2,750,000

    $650K PRICE DROP Pending
    • 5 Beds
    • 4 Baths
    • 3,361 Sq Ft

    735 Franklin St, Vineyard Haven, MA 02568

    Welcome to this stunning 4-bedroom, 3-bathroom primary residence along with a 1-bedroom studio apartment over the one-car garage, ideally located in West Chop! Together, they include approximately 3,871 square feet of beautifully renovated living space (an additional 510 sqft of living space on the 3rd floor in the main house is not included on the town assessment). Situated on a .99-acre lot,

    Emily Flake Viewpoints

    735 Franklin St, Vineyard Haven, MA 02568
  • /11

    $1,125,000

    Sold May 07, 2026

    52 Windsor Dr, Edgartown, MA 02539

    • 3 Beds
    • 2 Baths
    • 1,410 Sq Ft
    • Built 1985

    Last Sold Summary

    • 6% Below List Price
    • $798/SF
    • 22 Days On Market

    Current Estimated Value $1,184,232

    Last Listing Agent Emma Kennedy Sandpiper Realty, Inc.

    52 Windsor Dr, Edgartown, MA 02539
    • /14

      Est $709,548

      Not Listed For Sale

      56 Narragansett Ave Unit 3A, Oak Bluffs, MA 02557

      • 2 Beds
      • 1 Bath
      • 647 Sq Ft
      • Built 1880
      56 Narragansett Ave Unit 3A, Oak Bluffs, MA 02557

      Last Sold Summary

      • 178 Days On Market

  • /14

    $825,000

    • 2 Beds
    • 1 Bath
    • 985 Sq Ft

    19 Perkins Ave, Oak Bluffs, MA 02557

    Located under a mile from the heart of downtown Oak Bluffs, this charming property offers endless potential in a highly convenient location. Set on a level lot, the home is ready for its next chapter — whether as a summer getaway or year-round residence. Enjoy easy access to town, beaches, ferries, restaurants, and shops while creating your own vision in this classic Island setting.

    Katherine Donahue Sandpiper Realty

    19 Perkins Ave, Oak Bluffs, MA 02557
  • /39

    $1,290,020

    Sold Dec 05, 2025

    35 Stevens Ave, Oak Bluffs, MA 02557

    • 2 Beds
    • 3 Baths
    • 1,632 Sq Ft
    • Built 2008

    Last Sold Summary

    • 10% Below List Price
    • $790/SF
    • 130 Days On Market

    Current Estimated Value $1,351,211

    Last Listing Agent Paul Thoutsis Dockside Real Estate

    35 Stevens Ave, Oak Bluffs, MA 02557
    • /3

      Not Listed For Sale

      28 Chickawaukee St (Subdivided Lot #1), Oak Bluffs, MA 02557

      28 Chickawaukee St (Subdivided Lot #1), Oak Bluffs, MA 02557

      Last Sold Summary

      • 0 Days On Market

  • /19

    $1,300,000

    • 4 Beds
    • 2.5 Baths
    • 1,738 Sq Ft

    22 Oklahoma Ave, Vineyard Haven, MA 02568

    3 BEDROOM HOUSE + 1 BEDROOM APARTMENT! Discover a rare opportunity in a convenient Vineyard Haven neighborhood. This move-in ready property features a 3 BR, 1.5 BA main house plus a legal 1 BR, 1 BA accessory apartment, offering the perfect setup for multi-generational living or a high-demand rental to offset your mortgage. The main house features a stunning solarium or sunroom, a cheerful

    Idalyn Macchia Gilstad Wallace & Co. Sotheby's International Realty

    22 Oklahoma Ave, Vineyard Haven, MA 02568
  • /28

    $1,226,500

    Sold Oct 16, 2025

    9 Grovedale Rd, Oak Bluffs, MA 02557

    • 3 Beds
    • 2 Baths
    • 1,637 Sq Ft
    • Built 1988

    Last Sold Summary

    • 7% Above List Price
    • $749/SF
    • 6 Days On Market

    Current Estimated Value $1,273,737

    Last Listing Agent Bonnie Pierce Wallace & Co. Sotheby's

    9 Grovedale Rd, Oak Bluffs, MA 02557
    • /27

      Not Listed For Sale

      46 Towanticut Ave, Oak Bluffs, MA 02568

      • 3 Beds
      • 3 Baths
      • 1,642 Sq Ft
      • Built 1990
      46 Towanticut Ave, Oak Bluffs, MA 02568

      Last Sold Summary

      • 6 Days On Market

  • /30

    $1,245,000

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

    66 Barnes Rd, Vineyard Haven, MA 02568

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

    Marilyn Moses Ocean Park Realty Inc

    66 Barnes Rd, Vineyard Haven, MA 02568
  • /27

    $1,070,000

    Sold Apr 17, 2026

    70 Carol Ln, Oak Bluffs, MA 02557

    • 2 Beds
    • 2.5 Baths
    • 1,500 Sq Ft
    • Built 1971

    Last Sold Summary

    • 14% Below List Price
    • $713/SF
    • 463 Days On Market

    Current Estimated Value $1,141,016

    Last Listing Agent Lisa Lucier Anchor Realty of Martha's Vineyard

    70 Carol Ln, Oak Bluffs, MA 02557
    • /8

      Not Listed For Sale

      0 Concord Ave, Oak Bluffs, MA 02568

      0 Concord Ave, Oak Bluffs, MA 02568

      Last Sold Summary

      • 83 Days On Market

  • /25

    $4,695,000

    • 3 Beds
    • 2 Baths
    • 1,716 Sq Ft

    16 Frog Hollow, Vineyard Haven, MA 02568

    Downtown Vineyard Haven with Harbor Views. Positioned between the energy of Main Street and the quiet prestige of West Chop, this location delivers a rare balance of downtown access, privacy, and harbor frontage.Built in 2015, the three-bedroom, two-bath modern ranch is designed for easy first-floor living with expansive water views. Wide, harbor-facing windows showcase the meadow and water

    Rose Ryley Wallace & Co. Sotheby's International Realty

    16 Frog Hollow, Vineyard Haven, MA 02568
  • /36

    $1,765,000

    Sold Aug 18, 2025

    34 Tower Ridge Rd, Oak Bluffs, MA 02568

    • 4 Beds
    • 3.5 Baths
    • 2,450 Sq Ft
    • Built 1988

    Last Sold Summary

    • 5% Below List Price
    • $720/SF
    • 25 Days On Market

    Last Listing Agent Katherine Donahue Sandpiper Realty

    34 Tower Ridge Rd, Oak Bluffs, MA 02568
    • /6

      Not Listed For Sale

      0 Dudley St Unit 42584, Tisbury, MA 02568

      0 Dudley St Unit 42584, Tisbury, MA 02568

      Last Sold Summary

      • 0 Days On Market

  • /36

    $2,295,000

    • 3 Beds
    • 2 Baths
    • 1,425 Sq Ft

    312 E Chop Dr, Oak Bluffs, MA 02557

    “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 impeccably maintained, blending timeless Vineyard character with modern comfort. Surrounded by lush landscaping and beautiful hydrangea and perennial gardens, the property boasts

    Alyssa Halisky Wallace & Co. Sotheby's

    312 E Chop Dr, Oak Bluffs, MA 02557

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