10,865

Vineyard Haven, MA Homes

Section Image
    • /19

      Est $1,081,585

      Not Listed For Sale

      160 Spring Hill Rd, Vineyard Haven, MA 02568

      • 3 Beds
      • 2 Baths
      • 1,235 Sq Ft
      • Built 1983
      160 Spring Hill Rd, Vineyard Haven, MA 02568

      Last Sold Summary

      • 2 Days On Market

      Last Listing Agent Rene Jackson Island Real Estate

  • /28

    $839,000

    Pending
    • 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 lots 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
  • /37

    $2,495,000

    Sold Nov 20, 2025

    16 Mockingbird Dr, Edgartown, MA 02539

    • 4 Beds
    • 6 Baths
    • 2,694 Sq Ft
    • Built 2016

    Last Sold Summary

    • 6% Below List Price
    • $926/SF
    • 146 Days On Market

    Current Estimated Value $2,635,198

    Last Listing Agent Emma Kennedy Sandpiper Realty

    16 Mockingbird Dr, Edgartown, MA 02539
    • /72

      Est $1,198,382

      Not Listed For Sale

      18 Goah Way, Vineyard Haven, MA 02568

      • 4 Beds
      • 2 Baths
      • 1,861 Sq Ft
      • Built 1998
      18 Goah Way, Vineyard Haven, MA 02568

      Last Sold Summary

      • 135 Days On Market

      Last Listing Agent Stephanie Burke Portfolio Properties

  • /40

    $1,750,000

    Pending
    • 3 Beds
    • 3.5 Baths
    • 2,376 Sq Ft

    28 Grovedale Rd, Oak Bluffs, MA 02557

    GORGEOUS NEWER CONSTRUCTION (2023), contemporary farmhouse style home w/ classic wrap around porch & designed w/ Vineyard charm & modern comfort. And yet still there is opportunity to add value to this open concept home, w/ high ceilings, 3 en-suite BRs, laundry on each level, hardwoods throughout. Well designed, fully poured unfinished basement w/ high ceilings, wide open & w/ a separate

    David White OwnerEntry.com

    28 Grovedale Rd, Oak Bluffs, MA 02557
  • /2

    $1,775,000

    Sold Mar 02, 2026

    14 Chapman Ave, Oak Bluffs, MA 02557

    • 5 Beds
    • 2 Baths
    • 1,469 Sq Ft
    • Built 1890

    Last Sold Summary

    • $1,208/SF
    • 0 Days On Market

    Current Estimated Value $1,853,266

    Last Listing Agent LINK Email Cache LINK

    14 Chapman Ave, Oak Bluffs, MA 02557
    • /35

      Est $1,431,817

      Not Listed For Sale

      26 Heath Hen Ln, Vineyard Haven, MA 02568

      • 3 Beds
      • 2.5 Baths
      • 2,076 Sq Ft
      • Built 1983
      26 Heath Hen Ln, Vineyard Haven, MA 02568

      Last Sold Summary

      • 84 Days On Market

      Last Listing Agent Candy DaRosa Feiner Real Estate

  • /6

    $2,700,000

    • 4 Beds
    • 4.5 Baths
    • 2,750 Sq Ft

    6 Laura's Way, Edgartown, MA 02568

    Welcome to the opportunity to own a brand-new, GORGEOUS, custom-built home in Edgartown, set on a one-acre plot with a detached 900 sq ft accessory dwelling. The main residence opens to an inviting two-story foyer, leading to an expansive, living room featuring a wall of glass sliders. The gourmet kitchen is a chef’s dream, boasting Bosch appliances, a large quartz-topped island with seating for

    Michele Casavant Vineyard Village Realty

    6 Laura's Way, Edgartown, MA 02568
  • /31

    $941,000

    Sold Oct 03, 2025

    4 Quail Run Unit 7, Oak Bluffs, MA 02557

    • 2 Beds
    • 1.5 Baths
    • 1,323 Sq Ft
    • Built 1972

    Last Sold Summary

    • $711/SF
    • 52 Days On Market

    Current Estimated Value $971,484

    Last Listing Agent Janna O'Loughlin Portfolio Properties

    4 Quail Run Unit 7, Oak Bluffs, MA 02557
    • /28

      Est $1,010,024

      Not Listed For Sale

      280 State Rd, Vineyard Haven, MA 02568

      • 4 Beds
      • 2 Baths
      • 1,387 Sq Ft
      • Built 1920
      280 State Rd, Vineyard Haven, MA 02568

      Last Sold Summary

      • 3 Days On Market

      Last Listing Agent Marilyn Moses Ocean Park Realty Inc

  • /2

    $749,000

    $50K PRICE DROP
    • Land
    • 39,996 Sq Ft
    • $815,726 per Acre

    22 Bramble Path Unit 214, West Tisbury, MA 02568

    Flat building lot centrally located in West Tisbury. A perc test has been completed which supports a four bedroom Title Five septic system. It is the Buyers responsibility to install utilities, well and septic.

    Michele Casavant Vineyard Village Realty

    22 Bramble Path Unit 214, West Tisbury, MA 02568
  • /38

    $1,400,000

    Sold Sep 18, 2026

    20 Union St Unit C, Tisbury, MA 02568

    • 1 Bed
    • 2.5 Baths
    • 1,254 Sq Ft
    • Built 2021

    Last Sold Summary

    • 6% Below List Price
    • $1,116/SF
    • 34 Days On Market

    Last Listing Agent Michele Moore Island Real Estate

    20 Union St Unit C, Tisbury, MA 02568
    • /36

      Not Listed For Sale

      15 Canterbury Ln, Vineyard Haven, MA 02568

      • 6 Beds
      • 3.5 Baths
      • 3,394 Sq Ft
      • Built 1987
      15 Canterbury Ln, Vineyard Haven, MA 02568

      Last Sold Summary

      • 16 Days On Market

      Last Listing Agent Sheila Morse Island Real Estate

  • /36

    $1,755,000

    • 3 Beds
    • 3 Baths
    • 2,815 Sq Ft

    68 Front St, Oak Bluffs, MA 02557

    Located on a quiet street in Oak Bluffs, this beautifully expanded Cape offers generous living spaces, along with an additional 700+ square feet of newly finished recreation space above the two-car garage, complete with a private entrance and second-floor deck. The inviting first floor is designed for comfortable living and entertaining, featuring a spacious kitchen with a center island and

    Alyssa Halisky Wallace & Co. Sotheby's International Realty

    68 Front St, Oak Bluffs, MA 02557
  • /26

    $782,000

    Sold Mar 06, 2026

    24 School St, Oak Bluffs, MA 02557

    • 2 Beds
    • 1 Bath
    • 861 Sq Ft
    • Built 1925

    Last Sold Summary

    • 11% Below List Price
    • $908/SF
    • 86 Days On Market

    Current Estimated Value $808,156

    Last Listing Agent Stephanie Roache Donnelly + Co.

    24 School St, Oak Bluffs, MA 02557
    • /30

      Est $923,972

      Not Listed For Sale

      7 Elm St, Vineyard Haven, MA 02568

      • 2 Beds
      • 1 Bath
      • 962 Sq Ft
      • Built 1969
      7 Elm St, Vineyard Haven, MA 02568

      Last Sold Summary

      • 213 Days On Market

      Last Listing Agent Jennifer O'hanlon Compass

  • /4

    $2,995,000

    Pending
    • 4 Beds
    • 4.5 Baths
    • 3,024 Sq Ft

    9 Hagerty Dr, Tisbury, MA 02568

    West Chop Dream Home in the Making! Experience the charm of this brand-new Shingle Style Colonial, currently under construction. Featuring 4 spacious bedrooms, 4 full and one half bath. This thoughtfully designed home offers generous space. Venture outside into your private oasis, complete with an in-ground pool (36' x18') — perfect for sun-soaked afternoons and evening gatherings. Situated in a

    Lisa Gilberto C McManus Realty Group

    9 Hagerty Dr, Tisbury, MA 02568
  • /49

    $1,650,000

    Sold Apr 28, 2026

    39 Iron Hill Rd, Oak Bluffs, MA 02557

    • 5 Beds
    • 5.5 Baths
    • 4,334 Sq Ft
    • Built 1987

    Last Sold Summary

    • 6% Below List Price
    • $381/SF
    • 2 Days On Market

    Current Estimated Value $1,513,528

    Last Listing Agent Wendy Harman Compass | Point B

    39 Iron Hill Rd, Oak Bluffs, MA 02557
    • /22

      Not Listed For Sale

      189 Winyah Ln, Vineyard Haven, MA 02568

      • 3 Beds
      • 1.5 Baths
      • 576 Sq Ft
      • Built 1974
      189 Winyah Ln, Vineyard Haven, MA 02568

      Last Sold Summary

      • 52 Days On Market

      Last Listing Agent Sheila Morse Island Real Estate

  • /2

    $595,000

    $55K PRICE DROP Pending
    • Land
    • 11,630 Sq Ft
    • $2,228,464 per Acre

    5 Temahigan Ave Unit 4-139-0, Oak Bluffs, MA 02568

    Serious Seller.......Price will be discounted for cash sale................A perfect Vineyard location that is convenient to beaches, a bike path and both downtown Oak Bluffs and Vineyard Haven. This is a unique location in an area of very substantial homes. Per an island engineer, your future house can possibly have up to seven bedrooms and have up to three floors. Include on the property

    Ed Charter Arrowhead Homes

    5 Temahigan Ave Unit 4-139-0, Oak Bluffs, MA 02568
  • /35

    $1,035,000

    Sold Aug 13, 2026

    21 Butler Ave Unit 1, Oak Bluffs, MA 02557

    • 3 Beds
    • 2 Baths
    • 1,135 Sq Ft
    • Built 1870

    Last Sold Summary

    • 4% Below List Price
    • $912/SF
    • 21 Days On Market

    Last Listing Agent Jennifer O'hanlon Compass

    21 Butler Ave Unit 1, Oak Bluffs, MA 02557
    • /20

      Est $1,064,739

      Not Listed For Sale

      33 Renear St, Vineyard Haven, MA 02568

      • 3 Beds
      • 1.5 Baths
      • 1,200 Sq Ft
      • Built 1950
      33 Renear St, Vineyard Haven, MA 02568

      Last Sold Summary

      • 7 Days On Market

      Last Listing Agent Tina Miller Donnelly + Co.

  • /18

    $2,500,000

    • 3 Beds
    • 3.5 Baths
    • 1,884 Sq Ft

    77 Sixth St N, Edgartown, MA 02539

    WATERVIEWS of Sengenotacket when you pull out of the driveway at 77 SIXTH STREET NORTH, EDGARTOWN. NEW CONSTRUCTION, with an anticipated completion date in MARCH of 2027; just in time to bring in the 2027 SPRING/SUMMER SEASON! The first floor entry offers an inviting two story foyer which opens to the living room which has a gas fireplace and wall of glass slider doors. Flowing from the living

    Michele Casavant Vineyard Village Realty

    77 Sixth St N, Edgartown, MA 02539
  • /20

    $975,000

    Sold Sep 30, 2025

    32 Beach Rd, Oak Bluffs, MA 02557

    • 3 Beds
    • 2 Baths
    • 836 Sq Ft
    • Built 1920

    Last Sold Summary

    • 7% Below List Price
    • $1,166/SF
    • 29 Days On Market

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

    32 Beach Rd, Oak Bluffs, MA 02557
    • /2

      Est $1,011,713

      Not Listed For Sale

      146 Edgartown Rd, Vineyard Haven, MA 02568

      • 2 Beds
      • 2 Baths
      • 1,214 Sq Ft
      • Built 1958
      146 Edgartown Rd, Vineyard Haven, MA 02568

  • /5

    $439,500

    Pending
    • Land
    • 24,393 Sq Ft
    • $784,821 per Acre

    5 Candle Maker Cir, Edgartown, MA 02539

    Located on a quiet cul-de-sac in a private Edgartown neighborhood, this half-acre parcel offers the perfect setting for your Martha's Vineyard home. Centrally located, the property provides easy access to the bike path and State Forest walking trails. With the recent Massachusetts Affordable Homes Act, this lot is now buildable and will include an approved 3-bedroom septic plan. The site allows

    Alyssa Halisky Wallace & Co. Sotheby's International Realty

    5 Candle Maker Cir, Edgartown, MA 02539
  • /29

    $2,000,000

    Sold Feb 11, 2026

    34 Massasoit Ave, Oak Bluffs, MA 02557

    • 6 Beds
    • 3.5 Baths
    • 1,616 Sq Ft
    • Built 1900

    Last Sold Summary

    • $1,238/SF
    • 0 Days On Market

    Current Estimated Value $1,613,456

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

    34 Massasoit Ave, Oak Bluffs, MA 02557
    • /19

      Est $1,308,623

      Not Listed For Sale

      31 Davis St, Vineyard Haven, MA 02568

      • 3 Beds
      • 2 Baths
      • 1,945 Sq Ft
      • Built 1966
      31 Davis St, Vineyard Haven, MA 02568

      Last Sold Summary

      • 5 Days On Market

      Last Listing Agent Sheila Morse Island Real Estate

  • /30

    $2,095,000

    • 4 Beds
    • 4 Baths
    • 2,876 Sq Ft

    18 Sylvan Ave, Vineyard Haven, MA 02568

    COMING SOON! Welcome to 18 Sylvan Avenue, a delightful, custom-crafted four-bedroom, four-bath, contemporary-style home set at the end of a quiet neighborhood road in Vineyard Haven. Surrounded by eight acres of conservation land, the property offers a peaceful setting with a spacious wraparound deck overlooking the natural landscape. It truly feels like its own private enclave, both inside and

    Madelyn Silvia Wallace & Co. Sotheby's International Realty

    18 Sylvan Ave, Vineyard Haven, MA 02568
  • /30

    $946,500

    Sold Mar 11, 2026

    22 Clark Ave, Vineyard Haven, MA 02568

    • 3 Beds
    • 1 Bath
    • 1,008 Sq Ft
    • Built 1967

    Last Sold Summary

    • 4% Below List Price
    • $939/SF
    • 82 Days On Market

    Current Estimated Value $1,011,338

    Last Listing Agent Helena Kirschenbaum Studio Realty

    22 Clark Ave, Vineyard Haven, MA 02568
    • /25

      Est $4,298,577

      Not Listed For Sale

      36 Burts Way, Vineyard Haven, MA 02568

      • 4 Beds
      • 7 Baths
      • 4,000 Sq Ft
      • Built 2004
      36 Burts Way, Vineyard Haven, MA 02568

      Last Sold Summary

      • 19 Days On Market

      Last Listing Agent Elaine Miller & Partners Realty, EMPR Sandpiper Realty

  • /54

    $1,150,000

    • 3 Beds
    • 1.5 Baths
    • 1,284 Sq Ft

    41 Renear St, Vineyard Haven, MA 02568

    Some properties you visit, and some properties you experience. Tucked behind mature gardens and a lush natural landscape, 41 Renear Street is a hidden Vineyard treasure — a classic 1927 cottage where timeless character, village convenience, and the beauty of the outdoors come together.Set on a generous .26-acre R10 parcel, this three-bedroom home offers the warmth and craftsmanship of an

    Leslie C. Floyd Portfolio Properties

    41 Renear St, Vineyard Haven, MA 02568
  • /14

    $775,000

    Sold Aug 06, 2026

    51 Lantern Ln, Vineyard Haven, MA 02568

    • 2 Beds
    • 1 Bath
    • 768 Sq Ft
    • Built 1968

    Last Sold Summary

    • $1,009/SF
    • 14 Days On Market

    Current Estimated Value $780,395

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

    51 Lantern Ln, Vineyard Haven, MA 02568
    • /2

      Est $1,921,014

      Not Listed For Sale

      39 Burts Way, Vineyard Haven, MA 02568

      • 3 Beds
      • 3 Baths
      • 2,068 Sq Ft
      • Built 1965
      39 Burts Way, Vineyard Haven, MA 02568

      Last Sold Summary

      • 0 Days On Market

      Last Listing Agent LINK Email Cache LINK

  • /16

    $710,000

    Pending
    • 1 Bed
    • 1 Bath
    • 542 Sq Ft

    66 Canonicus Ave, Oak Bluffs, MA 02557

    The Pinkletink Could be Yours!!!This unspoiled 1950's cottage is named for the Island's tiny frogs who "sing" the announcement of spring. The location is sublime, just 5 blocks from Inkwell Beach and only a few more to the top of Circuit Avenue, while feeling miles away in this quiet location near Farm Pond. Cherished by its owners for decades, the cottage has been lovingly maintained

    Candy DaRosa Feiner Real Estate

    66 Canonicus Ave, Oak Bluffs, MA 02557
  • /46

    $1,150,000

    Sold Apr 14, 2026

    185 Sandpiper Ln Unit 12, Vineyard Haven, MA 02568

    • 3 Beds
    • 3 Baths
    • 1,750 Sq Ft
    • Built 1988

    Last Sold Summary

    • 11% Below List Price
    • $657/SF
    • 85 Days On Market

    Current Estimated Value $1,269,041

    Last Listing Agent Candy DaRosa Feiner Real Estate

    185 Sandpiper Ln Unit 12, Vineyard Haven, MA 02568
    • /2

      Est $1,913,810

      Not Listed For Sale

      201 Lagoon Pond Rd, Vineyard Haven, MA 02568

      • 4 Beds
      • 2 Baths
      • 1,676 Sq Ft
      • Built 1870
      201 Lagoon Pond Rd, Vineyard Haven, MA 02568

  • /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
  • /7

    $550,000

    Sold Apr 15, 2026

    124 Skiff Ave Unit D-10, Vineyard Haven, MA 02568

    • 3 Beds
    • 2 Baths
    • 1,356 Sq Ft
    • Built 1953

    Last Sold Summary

    • 8% Below List Price
    • $406/SF
    • 5 Days On Market

    Current Estimated Value $609,509

    Last Listing Agent Emma Kennedy Sandpiper Realty, Inc.

    124 Skiff Ave Unit D-10, Vineyard Haven, MA 02568
    • /21

      Est $1,938,242

      Not Listed For Sale

      61 Hines Point Rd, Vineyard Haven, MA 02568

      • 1 Bed
      • 1 Bath
      • 524 Sq Ft
      • Built 1915
      61 Hines Point Rd, Vineyard Haven, MA 02568

      Last Sold Summary

      • 591 Days On Market

      Last Listing Agent Wendy Harman Compass | Point B

Showing Results 321 - 360, Page 9 of 18

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