11,368

Vineyard Haven, MA Homes

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  • /75

    $3,750,000

    • 5 Beds
    • 6.5 Baths
    • 4,372 Sq Ft

    139 Main St, Vineyard Haven, MA 02568

    Nestled just two blocks from Vineyard Haven’s working harbor, 139 Main Street is a quietly grand in-town property with the feel of a private estate. Once two separate addresses—now gracefully combined into a single half-acre parcel—this home offers rare space, privacy, and timeless character in one of the island’s most approachable villages.From the moment you step through the welcoming

    Leslie C. Floyd Portfolio Properties

    139 Main St, 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 $943,219

    Last Listing Agent Helena Kirschenbaum Studio Realty

    22 Clark Ave, Vineyard Haven, MA 02568
    • /23

      Est $1,195,153

      Not Listed For Sale

      180 Main St Unit 30, Vineyard Haven, MA 02568

      • 2 Beds
      • 2 Baths
      • 1,300 Sq Ft
      • Built 1860
      180 Main St Unit 30, Vineyard Haven, MA 02568

      Last Sold Summary

      • 96 Days On Market

  • /4

    $439,500

    $6K PRICE DROP
    • Land
    • 24,393 Sq Ft
    • $784,821 per Acre

    5 Candle Maker Cir Unit 1.331, 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

    5 Candle Maker Cir Unit 1.331, Edgartown, MA 02539
  • /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 $1,208,482

    Last Listing Agent Candy DaRosa Feiner Real Estate

    185 Sandpiper Ln Unit 12, Vineyard Haven, MA 02568
    • /24

      Est $1,840,380

      Not Listed For Sale

      70 Tashmoo Ave, Vineyard Haven, MA 02568

      • 5 Beds
      • 4 Baths
      • 3,298 Sq Ft
      • Built 1920
      70 Tashmoo Ave, Vineyard Haven, MA 02568

      Last Sold Summary

      • 88 Days On Market

  • /37

    $3,600,000

    • 5 Beds
    • 3 Baths
    • 2,791 Sq Ft

    20 James Pond Way, Vineyard Haven, MA 02568

    Tucked away on 4.5 acres off Lambert’s Cove Road, this unique property offers privacy and peaceful views to James Pond. A private boardwalk leads to a boathouse with direct access to James Pond, perfect for paddling across to Lambert’s Cove and enjoying the nearby James Pond Preserve. The home features a spacious living room with cathedral ceilings and a wood burning fireplace, opening onto a

    Sheila Morse Island Real Estate

    20 James Pond Way, 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
    • /2

      Est $1,263,966

      Not Listed For Sale

      26 Daggett Ave, Vineyard Haven, MA 02568

      • 3 Beds
      • 2 Baths
      • 1,308 Sq Ft
      • Built 1904
      26 Daggett Ave, Vineyard Haven, MA 02568

  • /44

    $2,499,000

    $299K PRICE DROP
    • 6 Beds
    • 4 Baths
    • 2,400 Sq Ft

    111 Eastville Ave, Oak Bluffs, MA 02557

    LARGE PRICE DROP. THIS IS A PERFECT LOCATION FOR WEDDING PARTIES.Just steps from the beach and minutes to both Oak Bluffs and Vineyard Haven, this fully furnished, turnkey coastal retreat offers an exceptional location paired with a strong, proven rental history. Set on an oversized lot just two parcels from the shoreline, the home features six bedrooms and four bathrooms, providing generous

    Ed Charter Arrowhead Homes

    111 Eastville Ave, 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 $616,975

    Last Listing Agent Emma Kennedy Sandpiper Realty, Inc.

    124 Skiff Ave Unit D-10, Vineyard Haven, MA 02568
    • /2

      Not Listed For Sale

      301 Main St, Vineyard Haven, MA 02568

      • 4 Beds
      • 4 Baths
      • 1,632 Sq Ft
      • Built 1900
      301 Main St, Vineyard Haven, MA 02568

  • /21

    $1,999,000

    Pending
    • 4 Beds
    • 3 Baths
    • 2,730 Sq Ft

    5 Pine Tree Ln, Vineyard Haven, MA 02568

    Nestled at 5 Pinetree Lane, Vineyard Haven, MA, this single-family residence in Dukes County presents a unique opportunity to own a piece of classic American architecture. Built in 1927, this home offers a blend of vintage charm and comfortable living. The residence features three full bathrooms, providing convenience and privacy for all occupants. Imagine mornings where everyone can prepare for

    Kristin Francoeur Gibson Sotheby's International Realty

    5 Pine Tree Ln, Vineyard Haven, 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 $1,375,501

    Last Listing Agent Kristin Buck Donnelly + Co

    35 E Side Rd, Oak Bluffs, MA 02557
    • /2

      Est $2,192,643

      Not Listed For Sale

      51 Hatch Rd, Vineyard Haven, MA 02568

      • 4 Beds
      • 3 Baths
      • 2,066 Sq Ft
      • Built 1910
      51 Hatch Rd, Vineyard Haven, MA 02568

  • /26

    $1,595,000

    $55K PRICE DROP
    • 5 Beds
    • 3 Baths
    • 1,810 Sq Ft

    22 Old Lighthouse Rd, Vineyard Haven, MA 02568

    This spacious 5-bedroom, 3-bathroom home is located in a quiet enclave off Main Street, Vineyard Haven. Just half a mile to the vibrant restaurant and shopping scene in the village, and even closer to the library, Owen Little Beach, and Yacht Club. Thoughtfully designed across three finished levels featuring hardwood floors, a cozy fireplace, and a seamless layout, the home is ideal for

    Jessie Holtham Wallace & Co. Sotheby's International Realty

    22 Old Lighthouse Rd, Vineyard Haven, MA 02568
  • /2

    $660,000

    Sold May 26, 2026

    3 Elmwood Ave Unit 23, Oak Bluffs, MA 02568

    • Land
    • 6,534 Sq Ft
    • $4,400,000 per Acre

    Last Sold Summary

    • 0 Days On Market

    Last Listing Agent Eleanor Wilson LINK

    3 Elmwood Ave Unit 23, Oak Bluffs, MA 02568
    • /2

      Est $1,031,862

      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

  • /8

    $825,000

    $100K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 806 Sq Ft

    260 The Blvd, Edgartown, MA 02539

    Two-bedroom, one bath, renovated cottage in Ocean Heights, Edgartown, offering a classic island “camp” charm with a thoroughly modern interior. Over three phases of work (2001, 2021, 2025), the owners have rebuilt key exterior elements, upgraded major systems, and fully refreshed the living space to create a cozy move-in-ready home. The central living area features a cathedral ceiling and large

    Sean Federowicz Landmarks at TODAY Real Estate

    260 The Blvd, Edgartown, MA 02539
  • /38

    $2,450,000

    Sold Jun 02, 2026

    16 Atlantic Ave, Oak Bluffs, MA 02557

    • 6 Beds
    • 2.5 Baths
    • 2,577 Sq Ft
    • Built 1890

    Last Sold Summary

    • 2% Below List Price
    • $951/SF
    • 10 Days On Market

    Last Listing Agent Katherine Donahue Sandpiper Realty

    16 Atlantic Ave, Oak Bluffs, MA 02557
    • /27

      Est $2,519,250

      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

      • 14 Days On Market

  • /2

    $625,000

    Under Contract
    • Land
    • 11,996 Sq Ft
    • $2,269,426 per Acre

    77 Sixth St N Unit 160, Edgartown, MA 02539

    *All information should be confirmed with the town boards. From BOH - Lot can support a 2 bedroom system with a standard Title 5 or 3 bedrooms with an enhanced system.From Water Department - Town water runs down Sixth Street N. Buyer will need to hook up from the road.From Building/Zoning Department - Lot can support a house and an ADU, by right, with proper permitting.From Wastewater

    Sheila Morse Island Real Estate

    77 Sixth St N Unit 160, Edgartown, MA 02539
  • /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 $996,553

    Last Listing Agent Martha Smith C McManus Realty Group

    72 Washington Ave, Vineyard Haven, MA 02568
    • /26

      Est $3,877,354

      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

      • 437 Days On Market

  • /26

    $949,000

    • 3 Beds
    • 2 Baths
    • 1,328 Sq Ft

    96 Dunham Ave, Vineyard Haven, MA 02568

    NESTLED ON AN OVERSIZED LOT in a highly convenient Vineyard Haven location, this classic 1972 center-entrance Colonial offers timeless charm and exceptional potential. Inside, an inviting open-concept living space is anchored by a wood-burning fireplace, while soaring vaulted ceilings over the dining area and kitchen create an airy, light-filled atmosphere ideal for gathering with family and

    Leslie C. Floyd Portfolio Properties

    96 Dunham Ave, Vineyard Haven, MA 02568
  • /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 $1,348,463

    Last Listing Agent LINK Email Cache LINK

    1 Edgewood Dr, Edgartown, MA 02539
    • /24

      Est $2,086,381

      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

      • 1,036 Days On Market

  • /35

    $1,075,000

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

    21 Butler Ave, Oak Bluffs, MA 02557

    Located within the historic Martha’s Vineyard Camp Meeting Association, this rare double-lot property combines classic Campground charm with the comfort, privacy, and functionality of a thoughtfully modernized home. Two-car off-street parking—an exceptional Campground amenity—adds everyday convenience, while Oak Bluffs Harbor, beaches, ferries, shops, and restaurants are just moments away.

    Jennifer O'hanlon Compass LLC

    21 Butler Ave, Oak Bluffs, MA 02557
  • /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 $1,989,903

    Last Listing Agent Lynn Buder Sandpiper Realty

    1 Rowland Ave, Oak Bluffs, MA 02557
    • /18

      Est $1,279,685

      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

      • 2 Days On Market

  • /28

    $950,000

    Under Contract
    • 3 Beds
    • 1.5 Baths
    • 1,395 Sq Ft

    119 N William St, Vineyard Haven, MA 02568

    A rare opportunity to own a historic Martha’s Vineyard home just moments from town. Originally built in 1900, this charming 3-bedroom, 1.5 bath home in Vineyard Haven offers 1,395 sq ft of living space on a 0.20-acre lot, blending classic island character with an unbeatable location! Enjoy the ease of walk-to-town living in Vineyard Haven, with nearby access to shops, restaurants, the harbor and

    Kelly Mercier The Agency

    119 N William St, 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 $1,183,331

    Last Listing Agent LINK Email Cache LINK

    202 Lake St, Vineyard Haven, MA 02568
    • /2

      Est $1,325,397

      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

  • /2

    $899,000

    Pending
    • Land
    • 4.2 Acres
    • $214,048 per Acre

    5A2.12 State Rd, Tisbury, MA 02568

    This is a beautiful 3.5 acre piece of land! Stunning and Peaceful!

    Fred Mascolo Jane Brown Assoc.

    5A2.12 State Rd, Tisbury, MA 02568
  • /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 $1,681,888

    Last Listing Agent LINK Email Cache LINK

    63 Saddle Club Rd, Edgartown, MA 02539
    • /12

      Est $1,419,103

      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

      • 23 Days On Market

  • /44

    $5,225,000

    $100K PRICE DROP
    • 6 Beds
    • 4 Baths
    • 2,890 Sq Ft

    4 Canonicus Ave, Oak Bluffs, MA 02557

    With a striking presence overlooking Nantucket Sound and just moments from the vibrant pulse of downtown, this distinctive compound is infused with a laid-back West Coast spirit while honoring the vintage charm of Oak Bluffs. Airy and effortlessly elegant, the four-bedroom main house has been masterfully updated, introducing refined, contemporary comforts, designed for every season. Tucked to the

    Katherine Donahue Sandpiper Realty

    4 Canonicus Ave, Oak Bluffs, MA 02557
  • /11

    $585,000

    Sold Feb 05, 2026

    147 Red Buoy Ln Unit 2.1, Tisbury, MA 02568

    • Land
    • 26,462 Sq Ft
    • $962,963 per Acre

    Last Sold Summary

    • 20% Below List Price
    • 276 Days On Market

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

    147 Red Buoy Ln Unit 2.1, Tisbury, MA 02568
    • /22

      Est $1,174,739

      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

      • 11 Days On Market

  • /13

    $775,000

    $60K PRICE DROP Under Contract
    • 2 Beds
    • 1 Bath
    • 768 Sq Ft

    51 Lantern Ln, Vineyard Haven, MA 02568

    Find your sweet spot in this charming starter home, ideally located on a quiet street yet within an effortless walk of everything. Forget the car and get your steps in! You're a short jaunt to essentials like Cronig's Market and Shirley's Hardware, AND local favorites including The Maker, Black Dog Cafe, Island Fresh Pizza, Pie Chicks, and Island Adventures Mini Golf. Also within walking distance

    Idalyn Macchia Gilstad Wallace & Co. Sotheby's

    51 Lantern Ln, Vineyard Haven, MA 02568

Showing Results 361 - 400, Page 10 of 18

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