11,368

Vineyard Haven, MA Homes

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  • /2

    $975,000

    Sold Jul 02, 2025

    28 Second Ave, Oak Bluffs, MA 02557

    • 3 Beds
    • 1 Bath
    • 1,056 Sq Ft
    • Built 1974

    Last Sold Summary

    • $923/SF
    • 0 Days On Market

    Current Estimated Value $1,024,517

    Last Listing Agent LINK Email Cache LINK

    28 Second Ave, Oak Bluffs, MA 02557
    • /27

      Est $1,648,597

      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

      • 154 Days On Market

  • /33

    $1,600,000

    Pending
    • 4 Beds
    • 2.5 Baths
    • 2,000 Sq Ft

    1 Red Arrow Rd, Vineyard Haven, MA 02568

    South Mountain designed and built, energy efficient home that takes excellent advantage of the 3-acre parcel's southerly orientation with both passive solar gain and solar panels. The sun-lit great room combines living room, dining and kitchen and opens out onto the lovely screened porch and patio beyond. The original 3-bedroom home was thoughtfully expanded by buiding out finished space in the

    Candy DaRosa Feiner Real Estate

    1 Red Arrow Rd, Vineyard Haven, MA 02568
  • /19

    $1,449,000

    Sold Aug 19, 2025

    14 High Meadow Ln, Oak Bluffs, MA 02557

    • 3 Beds
    • 3 Baths
    • 2,284 Sq Ft
    • Built 1987

    Last Sold Summary

    • 15% Below List Price
    • $634/SF
    • 263 Days On Market

    Current Estimated Value $1,534,375

    Last Listing Agent Michele Moore Island Real Estate

    14 High Meadow Ln, Oak Bluffs, MA 02557
    • /35

      Est $1,798,593

      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

      • 8 Days On Market

  • /24

    $925,000

    Under Contract Pre-Foreclosure
    • 2 Beds
    • 2 Baths
    • 1,000 Sq Ft

    67 Hudson Ave, Oak Bluffs, MA 02557

    Located in a convenient Oak Bluffs setting, this 2-bedroom, 2-bath home offers approximately 1,000 square feet of living space on a generous .69-acre lot. Built in 2014, the property presents an excellent opportunity for a year-round residence, vacation getaway, or investment.The property is being sold as is. Buyers and their agents are encouraged to perform their own due diligence and verify

    Marilyn Moses Ocean Park Realty Inc

    67 Hudson Ave, Oak Bluffs, MA 02557
  • /26

    $885,000

    Sold Jul 01, 2025

    1 Cottage Park, Oak Bluffs, MA 02557

    • 3 Beds
    • 2.5 Baths
    • 987 Sq Ft
    • Built 1869

    Last Sold Summary

    • 4% Below List Price
    • $897/SF
    • 29 Days On Market

    Current Estimated Value $921,520

    Last Listing Agent Diana Gilmore Island Real Estate

    1 Cottage Park, Oak Bluffs, MA 02557
    • /30

      Est $1,328,635

      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 Days On Market

  • /18

    $3,295,000

    Pending
    • 4 Beds
    • 3 Baths
    • 1,696 Sq Ft

    10 Fowler Ave, Edgartown, MA 02539

    Edgartown Waterfront - Enjoy sweeping water views and direct access to Sengekontacket Pond from this beautiful coastal retreat. Built in 2024, this four-bedroom, three-bath home blends classic Vineyard charm with modern coastal design and offers 95 feet of pond frontage with a private mooring. The open-concept living space is filled with natural light and features Thermador appliances, vaulted

    Andrew McElhinney Compass LLC

    10 Fowler Ave, Edgartown, MA 02539
  • /42

    $2,637,500

    Sold Dec 12, 2025

    36 Tashmoo Ave, Vineyard Haven, MA 02568

    • 4 Beds
    • 3 Baths
    • 2,770 Sq Ft
    • Built 1888

    Last Sold Summary

    • 20% Below List Price
    • $952/SF
    • 417 Days On Market

    Current Estimated Value $2,695,121

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

    36 Tashmoo Ave, Vineyard Haven, MA 02568
    • /2

      Not Listed For Sale

      10 Farm Way, Edgartown, MA 02539

      • 5 Beds
      • 4 Baths
      • 2,760 Sq Ft
      • Built 1984
      10 Farm Way, Edgartown, MA 02539

  • /25

    $1,155,000

    $40K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,164 Sq Ft

    3 Kims Way, Oak Bluffs, MA 02557

    Recently updated Oak Bluffs ranch-style home ideally located near Downtown and Oak Bluffs Harbor. Step inside to discover vaulted ceilings and an airy open floor plan that seamlessly connects the living room, dining area, and a spacious kitchen featuring granite countertops and updated appliances. The private primary suite is thoughtfully positioned off the main living area and offers a full bath

    Alyssa Halisky Wallace & Co. Sotheby's International Realty

    3 Kims Way, Oak Bluffs, MA 02557
  • /29

    $1,400,000

    Sold Jan 30, 2026

    67 New York Ave, Oak Bluffs, MA 02557

    • 3 Beds
    • 2 Baths
    • 1,629 Sq Ft
    • Built 1900

    Last Sold Summary

    • $859/SF
    • 0 Days On Market

    Current Estimated Value $1,385,360

    Last Listing Agent Erin Hegarty Donnelly + Co

    67 New York Ave, Oak Bluffs, MA 02557
    • /7

      Not Listed For Sale

      4 Lauras Way, Edgartown, MA 02539

      • 6 Beds
      • 4.5 Baths
      • 2,737 Sq Ft
      • Built 1985
      4 Lauras Way, Edgartown, MA 02539

      Last Sold Summary

      • 386 Days On Market

  • /28

    $550,000

    $49K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 725 Sq Ft

    124 Skiff Ave Unit A-11, Vineyard Haven, MA 02568

    JUST COMPLETED ~ fully renovated exterior including a new roof, siding, shutters, trim, all new windows, doors, stairways, and decks. Outstanding move-in-ready, year-round two-bedroom ground-level condo with dedicated parking in an ideal Vineyard Haven location close to the ferry, Main Street shops, and restaurants. The beautifully maintained common grounds feature colorful landscaping, picnic

    Stephanie Roache Donnelly + Co.

    124 Skiff Ave Unit A-11, Vineyard Haven, MA 02568
  • /35

    $1,295,000

    Sold Sep 02, 2025

    35 7th St N, Edgartown, MA 02539

    • 3 Beds
    • 2 Baths
    • 1,814 Sq Ft
    • Built 1980

    Last Sold Summary

    • 7% Below List Price
    • $714/SF
    • 3 Days On Market

    Last Listing Agent Stephanie Roache Donnelly + Co.

    35 7th St N, Edgartown, MA 02539
    • /29

      Est $1,614,115

      Not Listed For Sale

      41 Dodgers Hole Rd, Edgartown, MA 02539

      • 3 Beds
      • 2 Baths
      • 1,326 Sq Ft
      • Built 1997
      41 Dodgers Hole Rd, Edgartown, MA 02539

      Last Sold Summary

      • 38 Days On Market

  • /8

    $1,250,000

    • 1 Bed
    • 1 Bath
    • 855 Sq Ft

    0 Pennsylvania Ave Unit 43914, Oak Bluffs, MA 02568

    Unique new construction opportunity on Pennsylvania Ave in Oak Bluffs! Offered preconstruction so there is the ability to customize, this modern carriage house includes a spacious 1-bedroom apartment (855 sq ft with full kitchen, living room and bathroom) above a 2-car garage. Ideal for year round or seasonal residents, or businesses seeking to solve workforce housing needs along with secure

    Peyton Wallace Studio Realty

    0 Pennsylvania Ave Unit 43914, Oak Bluffs, MA 02568
  • /18

    $975,000

    Sold Mar 30, 2026

    12 Park Ave, Vineyard Haven, MA 02568

    • 3 Beds
    • 2 Baths
    • 1,469 Sq Ft
    • Built 1991

    Last Sold Summary

    • 25% Below List Price
    • $664/SF
    • 124 Days On Market

    Current Estimated Value $1,001,399

    Last Listing Agent Sheila Morse Island Real Estate

    12 Park Ave, Vineyard Haven, MA 02568
    • /2

      Est $1,415,654

      Not Listed For Sale

      12 Eagles Nest, Edgartown, MA 02539

      • 4 Beds
      • 2 Baths
      • 1,404 Sq Ft
      • Built 1990
      12 Eagles Nest, Edgartown, MA 02539

  • /27

    $2,695,000

    $130K PRICE DROP
    • 5 Beds
    • 2 Baths
    • 2,386 Sq Ft

    187 Lagoon Pond Rd, Vineyard Haven, MA 02568

    For the very first time, the historic Ben Luce Homestead (circa 1850) is being offered on the open market. This charming farmhouse blends rich Island history with timeless appeal.Once home to Benjamin Norton Luce (1840–1912) — Civil War veteran, blacksmith, and town constable — the property sits on 1.5 acres of pastoral land and offers 5 bedrooms, 2 full baths, solar panels, barn, and a newly

    Erin Leighton Compass

    187 Lagoon Pond Rd, Vineyard Haven, MA 02568
  • /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
    • /2

      Est $1,286,041

      Not Listed For Sale

      39 Flamingo Dr, Edgartown, MA 02539

      • 3 Beds
      • 2 Baths
      • 1,420 Sq Ft
      • Built 1986
      39 Flamingo Dr, Edgartown, MA 02539

  • /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
  • /21

    $500,000

    Sold Sep 12, 2025

    21 Rock Ave, Oak Bluffs, MA 02557

    • 1 Bed
    • 1 Bath
    • 604 Sq Ft
    • Built 1870

    Last Sold Summary

    • 17% Below List Price
    • $828/SF
    • 58 Days On Market

    Current Estimated Value $703,830

    Last Listing Agent Marilyn Moses Ocean Park Realty Inc

    21 Rock Ave, Oak Bluffs, MA 02557
    • /2

      Est $1,245,452

      Not Listed For Sale

      13 Flamingo Dr, Edgartown, MA 02539

      • 3 Beds
      • 2 Baths
      • 1,512 Sq Ft
      • Built 1994
      13 Flamingo Dr, Edgartown, MA 02539

  • /19

    $1,075,000

    $20K PRICE DROP Pending
    • 3 Beds
    • 1.5 Baths
    • 1,487 Sq Ft

    12 Wheelhouse Way, Oak Bluffs, MA 02557

    Charming, custom-built, 3-bedroom, 1.5-bath Oak Bluffs home on a quiet circle, offering a peaceful setting with convenient access to down-island attractions, year-round ferries, and miles of ancient way trails through acres of conservation land. Well-maintained with many decorative details, features include a large primary bedroom, a convenient first-floor bedroom, and an open kitchen dining area

    Dawn Bellante-Holand Sandpiper Realty

    12 Wheelhouse Way, Oak Bluffs, MA 02557
  • /32

    $2,875,000

    Sold Jun 15, 2026

    309 Barnes Rd, Oak Bluffs, MA 02557

    • 3 Beds
    • 2 Baths
    • 1,569 Sq Ft
    • Built 1988

    Last Sold Summary

    • 8% Below List Price
    • $1,832/SF
    • 62 Days On Market

    Current Estimated Value $3,069,525

    Last Listing Agent Dawn Bellante Sandpiper Realty, Inc.

    309 Barnes Rd, Oak Bluffs, MA 02557
    • /20

      Est $1,171,222

      Not Listed For Sale

      4 Mockingbird Dr, Edgartown, MA 02539

      • 3 Beds
      • 1.5 Baths
      • 1,200 Sq Ft
      • Built 1986
      4 Mockingbird Dr, Edgartown, MA 02539

      Last Sold Summary

      • 15 Days On Market

  • /35

    $2,825,000

    $100K PRICE DROP
    • 5 Beds
    • 4 Baths
    • 3,704 Sq Ft

    21 Davis St, Vineyard Haven, MA 02568

    Ideally located just minutes from the heart of Vineyard Haven, 21 Davis Street offers exceptional island living in this beautifully crafted five-bedroom, four-bathroom home with 3,704 square feet of thoughtfully designed living space. Rich hardwood flooring, custom cabinetry, elegant Restoration Hardware vanities, and custom tilework throughout the bathrooms reflect the care and craftsmanship the

    Valene Pires The Agency

    21 Davis St, Vineyard Haven, MA 02568
  • /26

    $1,900,000

    Sold Feb 09, 2026

    30 Franklin Ave, Oak Bluffs, MA 02568

    • 2 Beds
    • 2.5 Baths
    • 2,137 Sq Ft
    • Built 2024

    Last Sold Summary

    • 12% Below List Price
    • $889/SF
    • 195 Days On Market

    Current Estimated Value $1,939,239

    Last Listing Agent Stacy Ickes Donnelly + Co

    30 Franklin Ave, Oak Bluffs, MA 02568
    • /7

      Not Listed For Sale

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

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

      Last Sold Summary

      • 4 Days On Market

  • /39

    $2,200,000

    $700K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 2,562 Sq Ft

    21 Woodlawn Ave, Vineyard Haven, MA 02568

    Thoughtfully designed with custom features throughout, this in-town Vineyard Haven home is the perfect blend of coastal charm and modern sophistication. The 4 bedroom 3 bath property offers a comfortable, easy flowing layout with gleaming hardwood floors and open sun-filled spaces.At the heart of the home is a chef-inspired gourmet kitchen with premium appliances, ample counter space, a

    Beth Welch Viewpoints

    21 Woodlawn Ave, Vineyard Haven, MA 02568
  • /2

    $1,000,000

    Sold Dec 30, 2025

    22 Wing Rd, Oak Bluffs, MA 02557

    • 3 Beds
    • 1.5 Baths
    • 1,136 Sq Ft
    • Built 1900

    Last Sold Summary

    • $880/SF
    • 0 Days On Market

    Current Estimated Value $1,063,391

    Last Listing Agent LINK Email Cache LINK

    22 Wing Rd, Oak Bluffs, MA 02557
    • /6

      Not Listed For Sale

      72 Windsor Dr Unit 99.71, Edgartown, MA 02539

      72 Windsor Dr Unit 99.71, Edgartown, MA 02539

      Last Sold Summary

      • 0 Days On Market

  • /9

    $2,250,000

    • 3 Beds
    • 3.5 Baths
    • 2,475 Sq Ft

    35 Double Ox Rd, Oak Bluffs, MA 02557

    Would you love to live or vacation in a brand-new home on Martha’s Vineyard?We have the LOCATION, REPUTABLE LONG-STANDING BUILDER & PROVEN TRACK RECORD!Come take a tour of the newest home under construction in the Lagoon Ridge neighborhood.Easy to show – Call now! To be built with lot purchase $695,000 and building contract approximately $1,550,000.This 3-bedroom dream home is set

    Marilyn Moses Ocean Park Realty Inc

    35 Double Ox Rd, Oak Bluffs, MA 02557
  • /16

    $1,135,000

    Sold Oct 31, 2025

    30 Teaberry Ln, Edgartown, MA 02539

    • 3 Beds
    • 2 Baths
    • 1,344 Sq Ft
    • Built 2002

    Last Sold Summary

    • $844/SF
    • 10 Days On Market

    Current Estimated Value $1,139,147

    Last Listing Agent Dawn Bellante-Holand Sandpiper Realty

    30 Teaberry Ln, Edgartown, MA 02539
    • /27

      Not Listed For Sale

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

      • 3 Beds
      • 2 Baths
      • 1,594 Sq Ft
      • Built 1933
      2 E Side Road & 60 Bay View Ave, Oak Bluffs, MA 02557

      Last Sold Summary

      • 532 Days On Market

  • /15

    $510,000

    $50K PRICE DROP Pending
    • 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
  • /9

    $1,500,000

    Sold Mar 03, 2026

    515 Edgartown Rd, Vineyard Haven, MA 02568

    • 6 Beds
    • 3 Baths
    • 5,418 Sq Ft
    • Built 1997

    Last Sold Summary

    • $277/SF
    • 0 Days On Market

    Current Estimated Value $1,987,970

    Last Listing Agent LINK Email Cache LINK

    515 Edgartown Rd, Vineyard Haven, MA 02568

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