10,865

Vineyard Haven, MA Homes

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  • /14

    $625,000

    Sold Sep 01, 2026

    10 Forest Cir, Oak Bluffs, MA 02557

    • 2 Beds
    • 1 Bath
    • 814 Sq Ft
    • Built 1872

    Last Sold Summary

    • 14% Below List Price
    • $768/SF
    • 21 Days On Market

    Last Listing Agent Neal Stiller Cronigs Real Estate

    10 Forest Cir, Oak Bluffs, MA 02557
    • /47

      Est $1,560,926

      Not Listed For Sale

      15 Beech Tree Landing, Oak Bluffs, MA 02557

      • 3 Beds
      • 3 Baths
      • 1,923 Sq Ft
      • Built 1999
      15 Beech Tree Landing, Oak Bluffs, MA 02557

      Last Sold Summary

      • 26 Days On Market

      Last Listing Agent Marilyn Moses Ocean Park Realty Inc

  • /56

    $1,250,000

    $185K PRICE DROP Pending
    • 3 Beds
    • 1.5 Baths
    • 1,456 Sq Ft

    101 Tradewinds Rd, Oak Bluffs, MA 02557

    Motivated sellers - a great opportunity for a savvy buyer! Set on just over half an acre near downtown Oak Bluffs abutting permanently preserved acres by Land Bank - a rare find in central Oak Bluffs! This home blends classic Midcentury architectural character with abundant natural light from floor-to-ceiling windows and soaring post-and-beam ceilings creating a warm and inviting space. The

    Nya Clarke Martha's Vineyard Island-Wide Realty

    101 Tradewinds Rd, Oak Bluffs, MA 02557
  • /38

    $2,195,000

    Sold Aug 19, 2026

    30 Daggett Ave, Vineyard Haven, MA 02568

    • 4 Beds
    • 2.5 Baths
    • 2,390 Sq Ft
    • Built 1900

    Last Sold Summary

    • $918/SF
    • 0 Days On Market

    Current Estimated Value $2,056,544

    Last Listing Agent Dawn Bellante-Holand Sandpiper Realty

    30 Daggett Ave, Vineyard Haven, MA 02568
    • /4

      Est $1,125,224

      Not Listed For Sale

      28 Vineyard Ave, Oak Bluffs, MA 02557

      • 2 Beds
      • 1.5 Baths
      • 1,525 Sq Ft
      • Built 1900
      28 Vineyard Ave, Oak Bluffs, MA 02557

      Last Sold Summary

      • 0 Days On Market

      Last Listing Agent LINK Foreclosure Resale LINK

  • /25

    $5,495,000

    $500K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 2,234 Sq Ft

    43 Sengekontacket Rd, Oak Bluffs, MA 02557

    Breathtaking property at the tip of a prominent peninsula on Sengekontacket Pond's western shoreline. Set beautifully at high elevation above the shore, this charming home and guest cottage includes jaw-dropping views of the pond, barrier dunes and Nantucket Sound. Direct from the property take your whaler or other watercraft out into the sound and beyond for endless recreational pursuits. Aside

    Peyton Wallace Studio Realty LLC

    43 Sengekontacket Rd, Oak Bluffs, MA 02557
  • /58

    $4,450,000

    Sold Feb 13, 2026

    41 Crowell Ln, Tisbury, MA 02568

    • 5 Beds
    • 5 Baths
    • 4,185 Sq Ft
    • Built 2025

    Last Sold Summary

    • 11% Below List Price
    • $1,063/SF
    • 257 Days On Market

    Current Estimated Value $3,820,603

    Last Listing Agent Joe & Nicole Holland Vineyard Dream Realty LLC

    41 Crowell Ln, Tisbury, MA 02568
    • /10

      Est $1,196,396

      Not Listed For Sale

      55 Tuckernuck Ave, Oak Bluffs, MA 02557

      • 3 Beds
      • 1 Bath
      • 1,093 Sq Ft
      • Built 1900
      55 Tuckernuck Ave, Oak Bluffs, MA 02557

      Last Sold Summary

      • 34 Days On Market

      Last Listing Agent Sean Federowicz Landmarks at TODAY Real Estate

  • /24

    $935,000

    • 2 Beds
    • 1 Bath
    • 763 Sq Ft

    3 Dukes County Ave, Oak Bluffs, MA 02557

    A Gem of a Marthas Vineyard Camp Meeting House Association Home, 3 Dukes County Ave. Located down from the Oak Bluffs Harbor. A couple house from Sunset Pond.Convenient to Beaches,Harbor, Resturants, Shopping, Dancing Music and walk to and from the Steamship Authority.2 bedroom,1 queen bedroom 1 full bed and twin bunk room with built in wardrobe and desk bathroom. Bathroom shower bath

    Karen Trotier Laer Realty Partners

    3 Dukes County Ave, Oak Bluffs, MA 02557
  • /18

    $750,000

    Sold Jun 08, 2026

    1 Pease Ave, Oak Bluffs, MA 02557

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

    Last Sold Summary

    • 6% Below List Price
    • $1,204/SF
    • 21 Days On Market

    Current Estimated Value $749,602

    Last Listing Agent Katie Donahue & Rachel Serwa Group Sandpiper Realty, Inc.

    1 Pease Ave, Oak Bluffs, MA 02557
    • /29

      Est $1,559,256

      Not Listed For Sale

      21 Pheasant Ln, Oak Bluffs, MA 02557

      • 3 Beds
      • 2 Baths
      • 2,235 Sq Ft
      • Built 1971
      21 Pheasant Ln, Oak Bluffs, MA 02557

      Last Sold Summary

      • 4 Days On Market

      Last Listing Agent Stephanie Roache Donnelly + Co

  • /20

    $1,149,000

    Pending
    • 3 Beds
    • 2 Baths
    • 1,373 Sq Ft

    72 Moonstone Way, Vineyard Haven, MA 02568

    Nestled in a quiet neighborhood just a short stroll from Lake Tashmoo and less than a mile from Main Street, Owen Park Beach, and the Steamship Authority, this lovingly maintained Colonial Saltbox offers the perfect blend of comfort, convenience, and island charm. With a strong rental history, the home is ideally suited as a vacation getaway, year-round residence, or investment property. The

    Carol Shore Donnelly + Co.

    72 Moonstone Way, Vineyard Haven, MA 02568
  • /59

    $2,225,000

    Sold Jun 10, 2026

    157 Ben Chase Rd, West Tisbury, MA 02575

    • 4 Beds
    • 2.5 Baths
    • 2,983 Sq Ft
    • Built 1980

    Last Sold Summary

    • 13% Below List Price
    • $746/SF
    • 465 Days On Market

    Last Listing Agent Madelyn Silvia Wallace & Co. Sotheby's

    157 Ben Chase Rd, West Tisbury, MA 02575
    • /41

      Est $1,398,235

      Not Listed For Sale

      35 E Side Rd, Oak Bluffs, MA 02557

      • 3 Beds
      • 2 Baths
      • 1,964 Sq Ft
      • Built 1965
      35 E Side Rd, Oak Bluffs, MA 02557

      Last Sold Summary

      • 0 Days On Market

      Last Listing Agent Kristin Buck Donnelly + Co

  • /7

    $549,000

    $50K PRICE DROP
    • Land
    • 3,049 Sq Ft
    • $7,842,857 per Acre

    112 Dukes County Ave, 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 International Realty

    112 Dukes County Ave, Oak Bluffs, MA 02557
  • /21

    $1,090,000

    Sold Jan 16, 2026

    9 Bayview Ave, Oak Bluffs, MA 02568

    • 3 Beds
    • 2 Baths
    • 1,428 Sq Ft
    • Built 1997

    Last Sold Summary

    • 16% Below List Price
    • $763/SF
    • 72 Days On Market

    Last Listing Agent Andrew McElhinney Compass LLC

    9 Bayview Ave, Oak Bluffs, MA 02568
    • /2

      Not Listed For Sale

      47 Stonebridge Rd, West Tisbury, MA 02568

      • 4 Beds
      • 3 Baths
      • 2,500 Sq Ft
      • Built 1983
      47 Stonebridge Rd, West Tisbury, MA 02568

  • /12

    $865,000

    Under Contract
    • 3 Beds
    • 2 Baths
    • 1,116 Sq Ft

    51 Daggett Ave, Vineyard Haven, MA 02568

    A fabulous location and a treasured historic home on Daggett Avenue in Tisbury. Ideally situated, the property is just 0.8 miles from Main Street in downtown Vineyard Haven, 0.9 miles from the public beach at Owen Park, and 1.2 miles from Tisbury Town Beach at the end of Owen Little Way.Filled with warmth, charm, and period character, the home is served by a four-bedroom Title 5 septic

    Michele Casavant Vineyard Village Realty

    51 Daggett Ave, Vineyard Haven, MA 02568
  • /7

    $1,000,000

    Sold Oct 02, 2025

    13 County Rd, Oak Bluffs, MA 02557

    • 2 Beds
    • 1 Bath
    • 1,176 Sq Ft
    • Built 1948

    Last Sold Summary

    • 17% Below List Price
    • $850/SF
    • 9 Days On Market

    Current Estimated Value $1,101,005

    Last Listing Agent Jennifer B. DaSilva Compass

    13 County Rd, Oak Bluffs, MA 02557
    • /17

      Est $1,490,636

      Not Listed For Sale

      16 Gamba Rd, Oak Bluffs, MA 02557

      • 4 Beds
      • 2.5 Baths
      • 2,693 Sq Ft
      • Built 1980
      16 Gamba Rd, Oak Bluffs, MA 02557

      Last Sold Summary

      • 10 Days On Market

      Last Listing Agent Michele Casavant Vineyard Village Realty

  • /36

    $2,195,000

    $100K PRICE DROP Pending
    • 3 Beds
    • 2 Baths
    • 1,425 Sq Ft

    312 E Chop Dr, Vineyard Haven, MA 02568

    ''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 meticulously maintained, blending timeless Vineyard character with modern comfort. Surrounded by lush hydrangea and perennial gardens, the property boasts nearly 150 feet of

    Alyssa Halisky Wallace & Co. Sotheby's International Realty

    312 E Chop Dr, Vineyard Haven, MA 02568
    • /17

      Est $1,004,612

      Not Listed For Sale

      27 Hitchings Cir, Vineyard Haven, MA 02568

      • 2 Beds
      • 1.5 Baths
      • 986 Sq Ft
      • Built 1986
      27 Hitchings Cir, Vineyard Haven, MA 02568

      Last Sold Summary

      • 88 Days On Market

      Last Listing Agent Andrew McElhinney Compass LLC

  • /33

    $1,225,000

    $25K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,338 Sq Ft

    37 Dodgers Hole Rd, Edgartown, MA 02539

    This split-level home in the highly desirable Dodger’s Hole neighborhood offers a central location with easy access to VTA bus routes, the bike path, all down-island towns and both South Beach and State Beach. The main level features a bright and open living room, dining area, and kitchen designed for comfortable island living. A hallway leads to the primary bedroom with private bath, along with

    Beth Welch Viewpoints

    37 Dodgers Hole Rd, Edgartown, MA 02539
    • /34

      Est $2,472,604

      Not Listed For Sale

      41 Bold Meadow Rd, Edgartown, MA 02539

      • 4 Beds
      • 3 Baths
      • 2,770 Sq Ft
      • Built 2011
      41 Bold Meadow Rd, Edgartown, MA 02539

      Last Sold Summary

      • 43 Days On Market

      Last Listing Agent Emma Kennedy Sandpiper Realty

  • /10

    $1,375,000

    • 5 Beds
    • 2 Baths
    • 1,952 Sq Ft

    234 County Rd, Oak Bluffs, MA 02557

    Surprisingly roomy Cape-style home, centrally located in Oak Bluffs and right across from the bike path. This five-bedroom house offers generously scaled living spaces throughout, including a large living room filled with natural light, an open stairway, a spacious dining room, and an updated kitchen. The first floor features a primary bedroom, a full bath with laundry, and a separate

    Emma Kennedy Sandpiper Realty, Inc.

    234 County Rd, Oak Bluffs, MA 02557
    • /34

      Est $1,057,387

      Not Listed For Sale

      11 Fairway Dr, Oak Bluffs, MA 02557

      • 2 Beds
      • 1 Bath
      • 1,608 Sq Ft
      • Built 1969
      11 Fairway Dr, Oak Bluffs, MA 02557

      Last Sold Summary

      • 191 Days On Market

      Last Listing Agent Sandra Grymes Martha's Vineyard Island-Wide Realty

  • /10

    $1,350,000

    $75K PRICE DROP
    • Land
    • 3.01 Acres
    • $448,505 per Acre

    38 Fire Tower Rd Unit 40.2, West Tisbury, MA 02568

    The Tower Hill land, once known as the Dancing Hills, is considered by many a sacred Island space. Standing on the ridge top, you're at one of the highest points on Martha's Vineyard. This 3.01 acre parcel looks out over the trees of Red Farm and the dramatic blue expanse of Vineyard Sound. It's easy to understand why this property is so special. There's a generous designated building envelope of

    Elissa Lash Tea Lane Associates

    38 Fire Tower Rd Unit 40.2, West Tisbury, MA 02568
    • /24

      Est $2,049,081

      Not Listed For Sale

      142 Lake St, Vineyard Haven, MA 02568

      • 4 Beds
      • 3.5 Baths
      • 2,672 Sq Ft
      • Built 2016
      142 Lake St, Vineyard Haven, MA 02568

      Last Sold Summary

      • 211 Days On Market

      Last Listing Agent Kathryn Tate Kathryn Tate Gothard

  • /75

    $5,500,000

    • 6 Beds
    • 6 Baths
    • 5,706 Sq Ft

    53 Circuit Ave, Oak Bluffs, MA 02557

    This exceptional mixed-use property occupies a premier location in the heart of Oak Bluffs thriving Circuit Avenue business district. Meticulously renovated and designed by architect Chuck Sullivan, the building offers a distinctive combination of commercial and residential spaces in one of Martha's Vineyard's most sought-after high-foot-traffic downtown locations. The Union Chapel, across the

    Stephanie Roache Donnelly + Co

    53 Circuit Ave, Oak Bluffs, MA 02557
    • /27

      Est $1,232,999

      Not Listed For Sale

      4 Combra Way, Oak Bluffs, MA 02557

      • 3 Beds
      • 2 Baths
      • 1,428 Sq Ft
      • Built 2002
      4 Combra Way, Oak Bluffs, MA 02557

      Last Sold Summary

      • 84 Days On Market

      Last Listing Agent Marilyn Moses Ocean Park Realty Inc

  • /45

    $1,595,000

    Open Sat 12PM - 2PM $30K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 1,898 Sq Ft

    20 Hidden Cove Rd, Oak Bluffs, MA 02557

    Nestled in this desirable Hidden Cove community, this contemporary residence offers a quintessential retreat centered on outdoor recreation and coastal living. Residents enjoy premier neighborhood amenities, including direct water access to Sengekontacket Pond for seamless kayaking and paddleboarding, as well as community tennis courts just steps from your front door. Set on a private, wooded

    Jennifer DaSilva Compass | Point B

    20 Hidden Cove Rd, Oak Bluffs, MA 02557
    • /34

      Est $1,135,841

      Not Listed For Sale

      41 Towanticut Ave, Oak Bluffs, MA 02557

      • 3 Beds
      • 2 Baths
      • 1,152 Sq Ft
      • Built 1999
      41 Towanticut Ave, Oak Bluffs, MA 02557

      Last Sold Summary

      • 239 Days On Market

      Last Listing Agent JoJo Lambert Island Home Realty Inc.

  • /7

    $1,150,000

    • Land
    • 1.09 Acres
    • $1,055,046 per Acre

    30 Double Ox Rd Unit 33, Oak Bluffs, MA 02557

    Create an extraordinary Martha's Vineyard estate in the exclusive Lagoon Ridge community of Oak Bluffs. This mostly wooded estate parcel of over one acre features gently rolling topography, providing an exceptional canvas for a custom-designed luxury residence. Privately situated within an intimate enclave of just four estate parcels, the property is accessed by a welcoming paved approach. This

    Marilyn Moses Ocean Park Realty Inc

    30 Double Ox Rd Unit 33, Oak Bluffs, MA 02557
    • /41

      Est $1,166,551

      Not Listed For Sale

      123 Manchester Ave, Oak Bluffs, MA 02557

      • 2 Beds
      • 2 Baths
      • 1,620 Sq Ft
      • Built 1997
      123 Manchester Ave, Oak Bluffs, MA 02557

      Last Sold Summary

      • 30 Days On Market

      Last Listing Agent Marilyn Moses Ocean Park Realty Inc

  • /37

    $11,400,000

    • 4 Beds
    • 3.5 Baths
    • 2,480 Sq Ft

    104 Old Herring Creek Rd, Vineyard Haven, MA 02568

    An extraordinary opportunity to own one of the Cape’s most distinctive waterfront properties, this exceptional 5.3-acre estate parcel combines remarkable natural beauty, complete privacy, and an unparalleled coastal setting. At its heart is a beautifully renovated four-bedroom beach cottage, thoughtfully updated with modern amenities while preserving the character and intimacy of a classic

    Thomas Leclair Landvest MV

    104 Old Herring Creek Rd, Vineyard Haven, MA 02568
    • /32

      Est $1,207,174

      Not Listed For Sale

      10 Nunes Way, Oak Bluffs, MA 02557

      • 2 Beds
      • 3.5 Baths
      • 1,680 Sq Ft
      • Built 2003
      10 Nunes Way, Oak Bluffs, MA 02557

      Last Sold Summary

      • 172 Days On Market

      Last Listing Agent Neal Stiller Cronigs Real Estate

  • /13

    $1,575,000

    $70K PRICE DROP
    • Land
    • 3.32 Acres
    • $474,398 per Acre

    26 Flint Hill Rd Unit 3B, West Tisbury, MA 02575

    Stop Searching. Start Building. You've toured dozens of homes. Nothing feels right. What if your dream home on Martha's Vineyard simply hasn't been built yet? This rare 3.32-acre West Tisbury hilltop is the blank canvas you've been waiting for. Glacial boulders, open pasture, and cathedral oaks with Land Bank-preserved Arrowhead Farm and protected Rodgers Path land on two sides - a setting unlike

    Dawn Bellante-Holand Sandpiper Realty

    26 Flint Hill Rd Unit 3B, West Tisbury, MA 02575
    • /16

      Est $758,527

      Not Listed For Sale

      14 Pacific Ave, Oak Bluffs, MA 02557

      • 2 Beds
      • 1 Bath
      • 426 Sq Ft
      • Built 1960
      14 Pacific Ave, Oak Bluffs, MA 02557

      Last Sold Summary

      • 85 Days On Market

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

  • /48

    $4,695,000

    • 7 Beds
    • 4.5 Baths
    • 5,320 Sq Ft

    8 Fresh Pond Rd, Oak Bluffs, MA 02557

    The Ultimate Oak Bluffs Compound: A rare opportunity to own a stunning seven-bedroom estate, thoughtfully designed for both luxurious living and exceptional rental potential. This expansive property features a newly built pool, lush landscaping, and direct access to Fresh Pond—ideal for kayaking, paddleboarding, and swimming. Perfect for entertaining, the home showcases a dramatic great room, an

    Jarrett Hurwitz Keller Williams Realty

    8 Fresh Pond Rd, Oak Bluffs, MA 02557
    • /17

      Est $1,495,979

      Not Listed For Sale

      11 Strawberry Ln, Oak Bluffs, MA 02557

      • 3 Beds
      • 2.5 Baths
      • 1,800 Sq Ft
      • Built 1995
      11 Strawberry Ln, Oak Bluffs, MA 02557

      Last Sold Summary

      • 102 Days On Market

      Last Listing Agent Jim Feiner Feiner Real Estate

Showing Results 641 - 680, Page 17 of 18

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