11,335

Vineyard Haven, MA Homes

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  • /7

    $600,000 Sold Jun 23, 2025

    27 7th St N Unit 198, Edgartown, MA 02539

    • Land
    • 21,780 Sq Ft
    • $1,200,000 per Acre

    Last Sold Summary

    • 4% Below List Price
    • 4 Days On Market

    Last Listing Agent Stephanie Roache Donnelly + Co

    27 7th St N Unit 198, Edgartown, MA 02539
    • /2

      Est $1,017,220 Not Listed For Sale

      50 Old Lighthouse Rd, Vineyard Haven, MA 02568

      • 2 Beds
      • 2 Baths
      • 961 Sq Ft
      • Built 1961
      50 Old Lighthouse Rd, Vineyard Haven, MA 02568

      Last Sold Summary

      • 7% Below List Price
      • $989/SF
      • Last Sold Price $950,000

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

  • /7

    $599,000

    • Land
    • 3,197 Sq Ft
    • $8,160,763 per Acre

    112 Dukes County Ave Unit 209, Oak Bluffs, MA 02557

    Downtown Oak Bluffs B1-zoned parcel offering a rare mixed-use development opportunity in one of Martha’s Vineyard’s most iconic and active locations. Conveniently located near Inkwell Beach, Oak Bluffs Harbor, the Steamship Authority, day-trip ferry services, Circuit Avenue, and Ocean Park. This level lot includes an existing poured concrete foundation and Martha’s Vineyard Commission–approved

    Rose Ryley Wallace & Co. Sotheby's

    112 Dukes County Ave Unit 209, 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 $1,304,688

    Last Listing Agent Candy DaRosa Feiner Real Estate

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

      Est $1,036,445 Not Listed For Sale

      90 Holly Tree Ln, Vineyard Haven, MA 02568

      • 2 Beds
      • 2 Baths
      • 1,081 Sq Ft
      • Built 1980
      90 Holly Tree Ln, Vineyard Haven, MA 02568

      Last Sold Summary

      • 12% Below List Price
      • $856/SF
      • Last Sold Price $925,000

      Last Listing Agent Stephanie Roache Donnelly + Co

  • /15

    $510,000

    • 1 Bed
    • 1.5 Baths
    • 591 Sq Ft

    21 39G Island Inn Rd Unit 39G, Oak Bluffs, MA 02557

    Own a piece of the Vineyard dream with a fully furnished, beautifully updated condo perfectly designed for comfort and vacation living at the Island Inn Country Club in Oak Bluffs. The location is just off Beach Road, a short distance to beaches, downtown Circuit Ave, and a lovely drive along Beach Road to Edgartown Village. The bike path, public transportation, and a popular restaurant with live

    Sheila Morse Island Real Estate

    21 39G Island Inn Rd Unit 39G, Oak Bluffs, MA 02557
  • /24

    $665,000 Sold May 23, 2025

    51 Rural Cir, Oak Bluffs, MA 02557

    • 3 Beds
    • 1.5 Baths
    • 806 Sq Ft
    • Built 1876

    Last Sold Summary

    • 8% Below List Price
    • $825/SF
    • 171 Days On Market

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

    51 Rural Cir, Oak Bluffs, MA 02557
    • /27

      Est $2,630,280 Not Listed For Sale

      484 Main St, Vineyard Haven, MA 02568

      • 4 Beds
      • 3 Baths
      • 3,310 Sq Ft
      • Built 1888
      484 Main St, Vineyard Haven, MA 02568

      Last Sold Summary

      • 2% Below List Price
      • $814/SF
      • 14 Days On Market
      • Last Sold Price $2,695,000
      • Dec 27, 2024

      Last Listing Agent Lenny Altieri Premier Properties

  • /20

    $2,295,000 Pending

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

    151 Tashmoo Ave, Vineyard Haven, MA 02568

    This Colonial Style home with wrap around porch is beautifully maintained and nicely sited on almost a half acre. The first floor is thoughtfully designed and offers an open floor plan that includes an ample mudroom with half bath and is just off the side porch that takes you into the well equipped kitchen with a center island, stainless appliances, custom cabinetry and dining room with sliders

    Brenda Galligan Karen M. Overtoom R.E.

    151 Tashmoo Ave, Vineyard Haven, MA 02568
  • /14

    $449,000 Sold Aug 14, 2025

    517 Edgartown Rd Unit 8.11, Tisbury, MA 02568

    • Land
    • 26,136 Sq Ft
    • $748,333 per Acre

    Last Sold Summary

    • 15% Below List Price
    • 89 Days On Market

    Last Listing Agent Meg Bodnar Tea Lane Associates

    517 Edgartown Rd Unit 8.11, Tisbury, MA 02568
    • /26

      Est $3,870,228 Not Listed For Sale

      137 Massasoit Ave, Vineyard Haven, MA 02568

      • 5 Beds
      • 3.5 Baths
      • 3,686 Sq Ft
      • Built 1988
      137 Massasoit Ave, Vineyard Haven, MA 02568

      Last Sold Summary

      • 11% Above List Price
      • $950/SF
      • 437 Days On Market
      • Last Sold Price $3,500,000
      • Oct 18, 2023

      Last Listing Agent Bobbi Reed Viewpoints

  • /58

    $2,495,000 Pending

    • 3 Beds
    • 3.5 Baths
    • 3,530 Sq Ft

    61 Causeway Rd, Vineyard Haven, MA 02568

    Welcome to this fabulous property nestled just a short stroll from all the best of Vineyard Haven. Easily accessible and within close proximity to the ferry, downtown shops, restaurants, galleries, Owen Park Beach, and the MV Playhouse, the location is ideal. This beautifully designed home has been lovingly maintained and offers a wonderful balance of Vineyard charm and modern convenience.

    Stephanie Roache Donnelly + Co

    61 Causeway Rd, Vineyard Haven, MA 02568
  • /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 $836,404

    Last Listing Agent Emma Kennedy Sandpiper Realty, Inc.

    124 Skiff Ave Unit D-10, Vineyard Haven, MA 02568
    • /24

      Est $2,116,697 Not Listed For Sale

      125 Massasoit Ave, Vineyard Haven, MA 02568

      • 5 Beds
      • 3 Baths
      • 1,830 Sq Ft
      • Built 1930
      125 Massasoit Ave, Vineyard Haven, MA 02568

      Last Sold Summary

      • 13% Above List Price
      • $1,025/SF
      • 1,036 Days On Market
      • Last Sold Price $1,875,000
      • Sep 01, 2023

      Last Listing Agent Emily Flake Viewpoints

  • /41

    $8,900,000

    • 8 Beds
    • 9 Baths
    • 8,170 Sq Ft

    150 E Chop Dr, Oak Bluffs, MA 02568

    BIG BLUFF- Recognized for its architectural significance and featured in leading design publications, this home stands as one of the Vineyard’s most notable coastal residences. Set along the prestigious shoreline of East Chop, this estate represents a rare convergence of architectural pedigree, craftsmanship, and irreplaceable setting. Designed by Hutker Architects, built by J.G. Early, and

    Andrew McElhinney Compass LLC

    150 E Chop Dr, Oak Bluffs, MA 02568
  • /41

    $1,310,000 Sold Aug 18, 2025

    35 E Side Rd, Oak Bluffs, MA 02557

    • 3 Beds
    • 2 Baths
    • 1,964 Sq Ft
    • Built 1965

    Last Sold Summary

    • 1% Above List Price
    • $667/SF
    • 0 Days On Market

    Current Estimated Value $1,319,615

    Last Listing Agent Kristin Buck Donnelly + Co

    35 E Side Rd, Oak Bluffs, MA 02557
    • /18

      Est $1,350,161 Not Listed For Sale

      46 Lake Ave, Edgartown, MA 02539

      • 3 Beds
      • 1.5 Baths
      • 1,764 Sq Ft
      • Built 1870
      46 Lake Ave, Edgartown, MA 02539

      Last Sold Summary

      • 13% Above List Price
      • $680/SF
      • 2 Days On Market
      • Last Sold Price $1,200,000
      • Jun 30, 2023

      Last Listing Agent Ed Charter Arrowhead Homes

  • /3

    $525,000

    • Land
    • 10,454 Sq Ft
    • $2,187,500 per Acre

    Lot 1 Dolan Ave, Tisbury, MA 02568

    A level parcel in a convenient Vineyard Haven location offering ease and opportunity. Set within an established neighborhood, it’s just a short stroll or bike ride to public beach access at the end of Owen Little Way. Only one mile from the vibrant shops and restaurants of Main Street, and less than two miles from the sandy shores of Lake Tashmoo beach, the setting provides the perfect balance of

    Katie Donahue & Rachel Serwa Group Sandpiper Realty, Inc.

    Lot 1 Dolan Ave, 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
    • /2

      Est $1,308,365 Not Listed For Sale

      4 Fowler Ave, Edgartown, MA 02539

      • 1 Bed
      • 1 Bath
      • 1,184 Sq Ft
      • Built 2002
      4 Fowler Ave, Edgartown, MA 02539

      Last Sold Summary

      • 1% Below List Price
      • $1,098/SF
      • Last Sold Price $1,300,000

      Last Listing Agent Nora Jardin Island Real Estate

  • /43

    $1,600,000

    • 3 Beds
    • 3 Baths
    • 1,737 Sq Ft

    150 Cove Rd Unit 10, Vineyard Haven, MA 02568

    The Premiere Townhouse at Tashmoo Wood. Elegantly renovated, this sun-filled end unit is fresh and modern with fine finish details. From the moment you step onto the expanded wrap-around deck, you will begin to see the fine craftsmanship of the property. Walk through the front entry and you will gain further appreciation for the meticulous attention to detail. Expansive windows fill the living

    Michele Moore Island Real Estate

    150 Cove Rd Unit 10, Vineyard Haven, MA 02568
  • /20

    $992,500 Sold Dec 22, 2025

    72 Washington Ave, Vineyard Haven, MA 02568

    • 1 Bed
    • 1.5 Baths
    • 1,152 Sq Ft
    • Built 2019

    Last Sold Summary

    • 4% Below List Price
    • $862/SF
    • 6 Days On Market

    Current Estimated Value $993,313

    Last Listing Agent Martha Smith C McManus Realty Group

    72 Washington Ave, Vineyard Haven, MA 02568
    • /12

      Est $1,368,561 Not Listed For Sale

      75 Anthiers Way, Edgartown, MA 02539

      • 3 Beds
      • 2.5 Baths
      • 1,624 Sq Ft
      • Built 1996
      75 Anthiers Way, Edgartown, MA 02539

      Last Sold Summary

      • 14% Above List Price
      • $739/SF
      • 23 Days On Market
      • Last Sold Price $1,200,000
      • Jul 24, 2023

      Last Listing Agent Michele Casavant Vineyard Village Realty

  • /27

    $2,400,000 Pending

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

    27 7th St N, Edgartown, MA 02539

    27 SEVENTH STREET NORTH, EDGARTOWN offers NEW CONSTRUCTION, with an anticipated completion date in MARCH of 2026; just in time to bring in the 2026 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 room is the open kitchen area which offers an island with

    Michele Casavant Vineyard Village Realty

    27 7th St N, Edgartown, MA 02539
  • /2

    $1,280,000 Sold Dec 12, 2025

    1 Edgewood Dr, Edgartown, MA 02539

    • 3 Beds
    • 2 Baths
    • 1,604 Sq Ft

    Last Sold Summary

    • $798/SF
    • 0 Days On Market

    Current Estimated Value $1,327,550

    Last Listing Agent LINK Email Cache LINK

    1 Edgewood Dr, Edgartown, MA 02539
    • /22

      Est $1,151,321 Not Listed For Sale

      5 12th St S, Edgartown, MA 02539

      • 3 Beds
      • 2 Baths
      • 1,296 Sq Ft
      • Built 1993
      5 12th St S, Edgartown, MA 02539

      Last Sold Summary

      • 12% Above List Price
      • $791/SF
      • 11 Days On Market
      • Last Sold Price $1,025,000
      • Jan 22, 2025

      Last Listing Agent Jared Bicknell Compass

  • /22

    $899,000

    • 2 Beds
    • 0.5 Baths
    • 953 Sq Ft

    50 Canonicus Ave, Oak Bluffs, MA 02557

    Rare Opportunity to Be in a Special Location and Neighborhood! Loved by generations, this quintessential Vineyard cottage has been in the same family since its creation in 1900. Step back in time and enjoy easy cottage living of yesteryear with modern updates including newer windows and electrical. Nestled under mature trees and just .3 mile to Inkwell Beach, join this close-knit neighborhood and

    Michele Moore Island Real Estate

    50 Canonicus Ave, Oak Bluffs, MA 02557
  • /31

    $1,750,000 Sold Jun 06, 2025

    97 Snake Hollow, Vineyard Haven, MA 02568

    • 3 Beds
    • 2 Baths
    • 1,850 Sq Ft
    • Built 1981

    Last Sold Summary

    • 11% Below List Price
    • $946/SF
    • 227 Days On Market

    Current Estimated Value $1,677,098

    Last Listing Agent Stephanie Roache Donnelly + Co

    97 Snake Hollow, Vineyard Haven, MA 02568
    • /27

      Est $1,701,947 Not Listed For Sale

      37 Weeks Ln, Edgartown, MA 02539

      • 3 Beds
      • 2 Baths
      • 2,066 Sq Ft
      • Built 1954
      37 Weeks Ln, Edgartown, MA 02539

      Last Sold Summary

      • 13% Above List Price
      • $726/SF
      • 154 Days On Market
      • Last Sold Price $1,500,000
      • Feb 13, 2025

      Last Listing Agent Michele Casavant Vineyard Village Realty

  • /68

    $2,300,000

    • 4 Beds
    • 3.5 Baths
    • 3,274 Sq Ft

    70 Spring St, Vineyard Haven, MA 02568

    Storybook setting in the quaint seaside village of Vineyard Haven, the commanding Captain Gilbert L. Smith House, c. 1854, affords an enchanting opportunity for space and privacy within the highly sought after William Street Historic District and just two blocks to all the shops, restaurants, galleries, town beach, tennis, and ferry. The property also has potential for an additional buildable

    June Flake Viewpoints

    70 Spring St, Vineyard Haven, MA 02568
  • /33

    $2,025,000 Sold Sep 30, 2025

    1 Rowland Ave, Oak Bluffs, MA 02557

    • 6 Beds
    • 3 Baths
    • 3,009 Sq Ft
    • Built 1853

    Last Sold Summary

    • 7% Above List Price
    • $673/SF
    • 6 Days On Market

    Current Estimated Value $1,956,920

    Last Listing Agent Lynn Buder Sandpiper Realty

    1 Rowland Ave, Oak Bluffs, MA 02557
    • /35

      Est $1,772,779 Not Listed For Sale

      15 Bold Meadow Ln, Edgartown, MA 02539

      • 3 Beds
      • 3.5 Baths
      • 1,715 Sq Ft
      • Built 1991
      15 Bold Meadow Ln, Edgartown, MA 02539

      Last Sold Summary

      • 1% Below List Price
      • $1,041/SF
      • 8 Days On Market
      • Last Sold Price $1,786,000
      • Dec 27, 2024

      Last Listing Agent Wendy Harman Compass

  • /39

    $2,400,000

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

    21 Woodlawn Ave, Vineyard Haven, MA 02568

    Experience the perfect blend of coastal charm and modern sophistication in this beautifully designed Vineyard Haven home. Ideally situated in-town, this 4-bedroom, 3-bath home offers a comfortable, easy flowing layout, complemented by gleaming hardwood floors and a warm, inviting atmosphere. Located just a short stroll from the ferry, vibrant shops, restaurants and the Vineyard Haven Yacht Club,

    Beth Welch Viewpoints; Bobbi Flake Reed, Inc.

    21 Woodlawn Ave, Vineyard Haven, MA 02568
  • /27

    $1,600,000 Sold May 22, 2025

    2 E Side Road & 60 Bay View Ave, Oak Bluffs, MA 02557

    • 3 Beds
    • 2 Baths
    • 1,594 Sq Ft
    • Built 1933

    Last Sold Summary

    • 43% Below List Price
    • $1,004/SF
    • 532 Days On Market

    Last Listing Agent Carol Shore Donnelly + Co

    2 E Side Road & 60 Bay View Ave, Oak Bluffs, MA 02557
    • /30

      Est $1,312,070 Not Listed For Sale

      23 Edgewood Dr, Edgartown, MA 02539

      • 3 Beds
      • 1.5 Baths
      • 1,439 Sq Ft
      • Built 1986
      23 Edgewood Dr, Edgartown, MA 02539

      Last Sold Summary

      • 5% Above List Price
      • $865/SF
      • 5 Days On Market
      • Last Sold Price $1,245,000
      • Jun 14, 2024

      Last Listing Agent Marilyn Moses Ocean Park Realty Inc

  • /34

    $1,250,000

    • 3 Beds
    • 3 Baths
    • 1,682 Sq Ft

    261 Sandpiper Ln Unit 12, Vineyard Haven, MA 02568

    END UNIT WITH PRIVATE DRIVEWAY IN TASHMOO WOODS. This well-maintained 3-bedroom, 3-bath end-unit condo offers a rare combination of privacy, space, and access to one of Vineyard Haven’s most sought-after communities. As an end unit with its own private driveway, this home offers added separation and a more single-family feel—along with a one-car garage and additional storage for bikes and beach

    Jennifer O'hanlon Compass LLC

    261 Sandpiper Ln Unit 12, Vineyard Haven, MA 02568
  • /4

    $1,130,000 Sold Apr 28, 2026

    202 Lake St, Vineyard Haven, MA 02568

    • 4 Beds
    • 2 Baths
    • 1,414 Sq Ft
    • Built 1988

    Last Sold Summary

    • $799/SF
    • 0 Days On Market

    Current Estimated Value $1,163,432

    Last Listing Agent LINK Email Cache LINK

    202 Lake St, Vineyard Haven, MA 02568
    • /26

      Est $1,366,727 Not Listed For Sale

      77 20th St S, Edgartown, MA 02539

      • 3 Beds
      • 2 Baths
      • 1,764 Sq Ft
      • Built 1998
      77 20th St S, Edgartown, MA 02539

      Last Sold Summary

      • 33% Above List Price
      • $581/SF
      • 18 Days On Market
      • Last Sold Price $1,025,000
      • Apr 27, 2023

      Last Listing Agent Leslie C. Floyd Portfolio Properties

  • /14

    $5,100,000

    • Land
    • 2.34 Acres
    • $2,182,285 per Acre

    7 Overview Ln Unit 47, Oak Bluffs, MA 02557

    A rare opportunity to own a 2.4-acre buildable lot within the prestigious Farm Neck Association. Perfectly situated overlooking the lush greens of Farm Neck Golf Club, this remarkable property also offers picturesque water views of Sengekontacket Pond and the distant Vineyard Sound. Design and build your dream home in this sought-after location. As a homeowner in Farm Neck, you'll enjoy exclusive

    Alyssa Halisky Wallace & Co. Sotheby's

    7 Overview Ln Unit 47, Oak Bluffs, MA 02557
  • /2

    $1,550,000 Sold Apr 09, 2026

    63 Saddle Club Rd, Edgartown, MA 02539

    • 4 Beds
    • 2.5 Baths
    • 2,291 Sq Ft
    • Built 1988

    Last Sold Summary

    • $677/SF
    • 0 Days On Market

    Current Estimated Value $1,693,478

    Last Listing Agent LINK Email Cache LINK

    63 Saddle Club Rd, Edgartown, MA 02539

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