11,335

Vineyard Haven, MA Homes

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  • /41

    $1,900,000 Sold May 01, 2026

    36 Smith Hollow Dr, Edgartown, MA 02539

    • 5 Beds
    • 2.5 Baths
    • 2,836 Sq Ft
    • Built 1985

    Last Sold Summary

    • 4% Below List Price
    • $670/SF
    • 172 Days On Market

    Current Estimated Value $1,947,965

    Last Listing Agent Katie Donahue Sandpiper Realty

    36 Smith Hollow Dr, Edgartown, MA 02539
    • /22

      Est $1,236,116 Not Listed For Sale

      41 Old County Rd, Vineyard Haven, MA 02568

      • 3 Beds
      • 1.5 Baths
      • 1,264 Sq Ft
      • Built 1983
      41 Old County Rd, Vineyard Haven, MA 02568

      Last Sold Summary

      • 7% Above List Price
      • $910/SF
      • 216 Days On Market
      • Last Sold Price $1,150,000
      • Apr 11, 2025

      Last Listing Agent Jared Bicknell Compass LLC

  • /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
  • /27

    $1,735,000 Sold Sep 29, 2025

    56 Bridle Path Rd, Vineyard Haven, MA 02568

    • 3 Beds
    • 4 Baths
    • 2,526 Sq Ft
    • Built 1996

    Last Sold Summary

    • 13% Below List Price
    • $687/SF
    • 2 Days On Market

    Current Estimated Value $1,854,798

    Last Listing Agent Tina Miller Donnelly + Co.

    56 Bridle Path Rd, Vineyard Haven, MA 02568
    • /17

      Est $1,217,993 Not Listed For Sale

      22 Briarwood Ln, Vineyard Haven, MA 02568

      • 2 Beds
      • 2 Baths
      • 1,241 Sq Ft
      • Built 2018
      22 Briarwood Ln, Vineyard Haven, MA 02568

      Last Sold Summary

      • 6% Below List Price
      • $1,048/SF
      • 4 Days On Market
      • Last Sold Price $1,300,000
      • Mar 03, 2025

      Last Listing Agent Carol Shore Donnelly + Co

  • /22

    $1,100,000

    • 2 Beds
    • 1 Bath
    • 1,118 Sq Ft

    4 5th St N, Edgartown, MA 02539

    An exciting rare find off the Edgartown / Tisbury road directly across from the bike path. The first floor open plan includes a fire place, family room and kitchen with a walk out to the wrap around porch. Two pleasant bedrooms and a full bath are on the first floor. The upper level loft opens to the living room visually expanding the living space. The house has the benefit of a full basement

    Doug Burke Signal House Group at Compass

    4 5th St N, Edgartown, MA 02539
  • /42

    $2,900,000 Sold Jul 03, 2025

    67 Hidden Village Rd, Vineyard Haven, MA 02568

    • 7 Beds
    • 5.5 Baths
    • 4,476 Sq Ft
    • Built 1997

    Last Sold Summary

    • 24% Below List Price
    • $648/SF
    • 347 Days On Market

    Last Listing Agent Stephanie Roache Donnelly + Co.

    67 Hidden Village Rd, Vineyard Haven, MA 02568
    • /25

      Est $5,531,270 Not Listed For Sale

      135 Capawock Rd, Vineyard Haven, MA 02568

      • 4 Beds
      • 3.5 Baths
      • 2,921 Sq Ft
      • Built 2001
      135 Capawock Rd, Vineyard Haven, MA 02568

      Last Sold Summary

      • 4% Below List Price
      • $1,969/SF
      • 7 Days On Market
      • Last Sold Price $5,750,000
      • Nov 19, 2024

      Last Listing Agent Jill Napior Tea Lane Associates

  • /28

    $2,495,000

    • 4 Beds
    • 3 Baths
    • 2,600 Sq Ft

    268 Tashmoo Ave, Vineyard Haven, MA 02568

    Welcome to this meticulously maintained home which features an attractive open kitchen with an island that seats four. The kitchen has a wall of built in appliances and a walk-in pantry for ease of cooking. The kitchen flows into the open dining area and lounge area with a wall of sliding glass doors that lead to the large outdoor entertaining area which features a lounge area and two eating

    Michele Casavant Vineyard Village Realty

    268 Tashmoo Ave, Vineyard Haven, MA 02568
  • /28

    $1,400,000 Sold Nov 26, 2025

    5 Scottys Ln, Vineyard Haven, MA 02568

    • 4 Beds
    • 1.5 Baths
    • 1,592 Sq Ft
    • Built 1968

    Last Sold Summary

    • 22% Below List Price
    • $879/SF
    • 126 Days On Market

    Current Estimated Value $1,455,768

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

    5 Scottys Ln, Vineyard Haven, MA 02568
    • /2

      Est $2,371,311 Not Listed For Sale

      84 Cuttyhunk Ave, Vineyard Haven, MA 02568

      • 3 Beds
      • 4 Baths
      • 2,396 Sq Ft
      • Built 2001
      84 Cuttyhunk Ave, Vineyard Haven, MA 02568

      Last Sold Summary

      • 3% Below List Price
      • $960/SF
      • Last Sold Price $2,300,000

      Last Listing Agent Rose Ryley Wallace & Co. Sotheby's

  • /65

    $2,690,000

    • 6 Beds
    • 4 Baths
    • 2,618 Sq Ft

    55 Old House Way, West Tisbury, MA 02575

    Lambert’s Cove/West Tisbury- custom-built contemporary farmhouse style. 4 bedrooms & 3 bathrooms in Main & 2 bedrooms & 1 bath Guest Cottage on 3 acres in a private neighborhood. Enter Main house from the covered porch -matching custom arch doors lead you to either the mudroom/laundry room-kitchen entry, or the living room. The kitchen has Mexican tiled floor & granite counters with stainless

    Leslie Graham Anchor Realty of Martha's Vineyard

    55 Old House Way, West Tisbury, MA 02575
  • /34

    $3,746,925 Sold Nov 14, 2025

    39 Sengekontacket Rd, Edgartown, MA 02539

    • 4 Beds
    • 3.5 Baths
    • 2,861 Sq Ft
    • Built 1974

    Last Sold Summary

    • 8% Below List Price
    • $1,310/SF
    • 114 Days On Market

    Current Estimated Value $3,615,189

    Last Listing Agent Jayne Isford Ocean Park Realty Inc

    39 Sengekontacket Rd, Edgartown, MA 02539
    • /24

      Est $985,700 Not Listed For Sale

      19 Speed Andrews Way, Vineyard Haven, MA 02568

      • 3 Beds
      • 1 Bath
      • 1,016 Sq Ft
      • Built 1972
      19 Speed Andrews Way, Vineyard Haven, MA 02568

      Last Sold Summary

      • 16% Above List Price
      • $837/SF
      • 20 Days On Market
      • Last Sold Price $850,000
      • Feb 29, 2024

      Last Listing Agent Grace Bishop Compass

  • /4

    $445,000

    • Land
    • 23,958 Sq Ft
    • $809,091 per Acre

    11 Boylston Dr Unit 1.314, Edgartown, MA 02539

    A picturesque half-acre lot in the desirable Edgartown neighborhood, perfect for building your Martha's Vineyard home. Bordered by more than 175 acres of pristine conservation land, this property offers peaceful surroundings with easy access to the island’s top attractions, including stunning beaches, scenic trails, vast state forests, and public transportation. In accordance with recent

    Alyssa Halisky Wallace & Co. Sotheby's

    11 Boylston Dr Unit 1.314, Edgartown, MA 02539
  • /17

    $700,000 Sold Jun 20, 2025

    2 Fisk Ave, Oak Bluffs, MA 02557

    • 3 Beds
    • 1 Bath
    • 725 Sq Ft
    • Built 1870

    Last Sold Summary

    • 7% Below List Price
    • $966/SF
    • 111 Days On Market

    Current Estimated Value $714,847

    Last Listing Agent Julie Walker Century 21 North East

    2 Fisk Ave, Oak Bluffs, MA 02557
    • /54

      Est $5,436,217 Not Listed For Sale

      14 E Sound Ln, Vineyard Haven, MA 02568

      • 4 Beds
      • 4 Baths
      • 2,470 Sq Ft
      • Built 1978
      14 E Sound Ln, Vineyard Haven, MA 02568

      Last Sold Summary

      • 19% Above List Price
      • $1,852/SF
      • 635 Days On Market
      • Last Sold Price $4,574,000
      • Jun 24, 2024

      Last Listing Agent Candy DaRosa Feiner Real Estate

  • /40

    $1,395,000

    • 4 Beds
    • 3 Baths
    • 1,305 Sq Ft

    46 Kennebec Ave, Oak Bluffs, MA 02557

    This exquisite Victorian home, lovingly preserved by the same family for over a generation, stands in outstanding condition and is perfectly situated in the vibrant heart of Oak Bluffs Center. Enjoy the convenience of being just steps away from the Public Beach, Steamship Authority, Oak Bluffs Harbor, a supermarket, and a variety of charming restaurants and shops that contribute to Oak Bluffs'

    Michael Schweikert Ocean Park Realty Inc

    46 Kennebec Ave, Oak Bluffs, MA 02557
  • /37

    $1,705,000 Sold Mar 24, 2026

    2 Farm Path, Oak Bluffs, MA 02557

    • 4 Beds
    • 3 Baths
    • 3,058 Sq Ft
    • Built 1992

    Last Sold Summary

    • 15% Below List Price
    • $558/SF
    • 347 Days On Market

    Current Estimated Value $1,670,124

    Last Listing Agent Sean Federowicz Landmarks at TODAY Real Estate

    2 Farm Path, Oak Bluffs, MA 02557
    • /35

      Est $1,895,268 Not Listed For Sale

      83 William Norton Rd, Vineyard Haven, MA 02568

      • 3 Beds
      • 3.5 Baths
      • 1,907 Sq Ft
      • Built 1999
      83 William Norton Rd, Vineyard Haven, MA 02568

      Last Sold Summary

      • 2% Above List Price
      • $970/SF
      • 62 Days On Market
      • Last Sold Price $1,850,000
      • Sep 20, 2023

      Last Listing Agent Alexis Holden Tea Lane Associates

  • /42

    $3,199,000

    • 3 Beds
    • 3.5 Baths
    • 3,082 Sq Ft

    53 Stoney Hill Rd, Vineyard Haven, MA 02568

    This custom-built residence is nestled in one of Martha’s Vineyard’s most coveted up-island towns. At the heart of the home lies a professionally designed chef’s kitchen, featuring bespoke cabinetry, honed Carrara marble countertops, Wolf stove and wall oven, Sub-Zero refrigerator, Miele dishwasher, Kohler farmhouse sink, and Rohl satin nickel gooseneck faucet. A custom bar is appointed with

    Jennifer B. DaSilva Compass

    53 Stoney Hill Rd, Vineyard Haven, MA 02568
  • /23

    $1,500,000 Sold Sep 25, 2025

    190 Longview Rd, Vineyard Haven, MA 02568

    • 3 Beds
    • 2 Baths
    • 1,400 Sq Ft
    • Built 1995

    Last Sold Summary

    • 15% Below List Price
    • $1,071/SF
    • 43 Days On Market

    Current Estimated Value $1,520,498

    Last Listing Agent Kathleen Kendrick Kendrick Real Estate

    190 Longview Rd, Vineyard Haven, MA 02568
    • /41

      Est $1,853,608 Not Listed For Sale

      93 Hvoslef Way, Vineyard Haven, MA 02568

      • 4 Beds
      • 2.5 Baths
      • 2,044 Sq Ft
      • Built 2007
      93 Hvoslef Way, Vineyard Haven, MA 02568

      Last Sold Summary

      • 3% Above List Price
      • $881/SF
      • 51 Days On Market
      • Last Sold Price $1,800,000
      • Jun 28, 2024

      Last Listing Agent Jennifer O'hanlon Compass

  • /45

    $6,395,000

    • 6 Beds
    • 5.5 Baths
    • 7,000 Sq Ft

    400 Barnes Rd, Vineyard Haven, MA 02568

    Experience the quiet elegance of this rare Asian-inspired contemporary estate set on 2.42 acres in a prime Oak Bluffs location. Tucked behind a long private drive and surrounded by 234 acres of Southern Woodlands conservation land offering biking and hiking, this expansive property offers unparalleled privacy just minutes from Featherstone Center for the Arts, Farm Neck Golf Club and the island’s

    Jennifer DaSilva Compass | Point B

    400 Barnes Rd, Vineyard Haven, MA 02568
  • /2

    $1,125,000 Sold Jan 23, 2026

    96 Manchester Ave, Oak Bluffs, MA 02557

    • 3 Beds
    • 2 Baths
    • 3,192 Sq Ft
    • Built 1999

    Last Sold Summary

    • 2% Below List Price
    • $352/SF
    • 7 Days On Market

    Current Estimated Value $1,114,225

    Last Listing Agent Michele Moore Island Real Estate

    96 Manchester Ave, Oak Bluffs, MA 02557
    • /16

      Est $1,783,044 Not Listed For Sale

      585 Herring Creek Rd, Vineyard Haven, MA 02568

      • 2 Beds
      • 1 Bath
      • 704 Sq Ft
      • Built 1950
      585 Herring Creek Rd, Vineyard Haven, MA 02568

      Last Sold Summary

      • 7% Below List Price
      • $2,734/SF
      • 10 Days On Market
      • Last Sold Price $1,925,000
      • Sep 13, 2024

      Last Listing Agent Cassie Courtney Wallace & Co. Sotheby's

  • /38

    $1,495,000

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

    20 Union St Unit C, Tisbury, MA 02568

    Welcome to 20 Union Court, Unit C at the Old Stone Bank Condominiums - a unique community in the heart of downtown Vineyard Haven. This two-level condo offers a truly special Vineyard lifestyle. Enter through the inviting porch into an open floor plan filled with character, thoughtful details, and sun-lit rooms that create a warm and welcoming atmosphere throughout. This home features a

    Michele Moore Island Real Estate

    20 Union St Unit C, Tisbury, MA 02568
  • /81

    $1,650,000 Sold Jan 09, 2026

    209 Cove Rd, Vineyard Haven, MA 02568

    • 4 Beds
    • 3.5 Baths
    • 2,194 Sq Ft
    • Built 1997

    Last Sold Summary

    • 15% Below List Price
    • $752/SF
    • 182 Days On Market

    Current Estimated Value $1,619,487

    Last Listing Agent Alisan Lohan-Conway Alisan Lohan-Conway Properties

    209 Cove Rd, Vineyard Haven, MA 02568
    • /44

      Est $7,197,993 Not Listed For Sale

      1115 Main St, Vineyard Haven, MA 02568

      • 11 Beds
      • 10 Baths
      • 7,026 Sq Ft
      • Built 1893
      1115 Main St, Vineyard Haven, MA 02568

      Last Sold Summary

      • 19% Below List Price
      • $1,263/SF
      • 280 Days On Market
      • Last Sold Price $8,875,000
      • Nov 09, 2023

      Last Listing Agent Gerrett Conover Landvest MV

  • /36

    $1,625,000

    • 4 Beds
    • 3 Baths
    • 1,514 Sq Ft

    26 Sea Glen Rd, Oak Bluffs, MA 02557

    Nestled in a desirable neighborhood, this beautifully maintained cape style home offers a rare blend of charm, flexibility and convenience in a serene island setting. Thoughtfully appointed throughout, the home welcomes you with an open living room that flows effortlessly into a bright dining area, where French doors open to a private stone patio—creating an inviting connection between indoor

    Jennifer DaSilva Compass | Point B

    26 Sea Glen Rd, Oak Bluffs, MA 02557
  • /24

    $3,050,000 Sold Apr 15, 2026

    35 New York Ave, Oak Bluffs, MA 02568

    • 7 Beds
    • 5 Baths
    • 3,880 Sq Ft
    • Built 1884

    Last Sold Summary

    • 13% Below List Price
    • $786/SF
    • 23 Days On Market

    Last Listing Agent Emma Kennedy Sandpiper Realty, Inc.

    35 New York Ave, Oak Bluffs, MA 02568
    • /47

      Est $2,363,943 Not Listed For Sale

      42 Hagerty Dr, Vineyard Haven, MA 02568

      • 4 Beds
      • 4.5 Baths
      • 2,569 Sq Ft
      • Built 1970
      42 Hagerty Dr, Vineyard Haven, MA 02568

      Last Sold Summary

      • 13% Above List Price
      • $817/SF
      • 58 Days On Market
      • Last Sold Price $2,100,000
      • Aug 22, 2023

      Last Listing Agent Bobbi Reed Viewpoints

  • /38

    $1,350,000

    • 4 Beds
    • 3 Baths
    • 1,714 Sq Ft

    116 Franklin Terrace, Vineyard Haven, MA 02568

    Nestled on a quiet street just moments from the heart of Vineyard Haven, this well-maintained 4 BR, 3 BA home offers a winning blend of comfort, privacy, and classic island appeal. The sun-filled main level features an open-concept living area flowing seamlessly into a bright, updated kitchen with center island, ideal for everyday living and casual entertaining. Two 1st floor bedrooms and a full

    Pricila Ray Keller Williams Realty

    116 Franklin Terrace, Vineyard Haven, MA 02568
  • /22

    $1,100,000 Sold Apr 30, 2026

    14 21st St N, Edgartown, MA 02539

    • 3 Beds
    • 1.5 Baths
    • 1,304 Sq Ft
    • Built 1978

    Last Sold Summary

    • 8% Below List Price
    • $844/SF
    • 141 Days On Market

    Current Estimated Value $1,127,849

    Last Listing Agent Fran Agnoli The Agency

    14 21st St N, Edgartown, MA 02539
    • /16

      Est $1,423,737 Not Listed For Sale

      222 Sandpiper Ln Unit 10, Vineyard Haven, MA 02568

      • 2 Beds
      • 3 Baths
      • 1,750 Sq Ft
      • Built 1988
      222 Sandpiper Ln Unit 10, Vineyard Haven, MA 02568

      Last Sold Summary

      • 12% Above List Price
      • $729/SF
      • 8 Days On Market
      • Last Sold Price $1,276,000
      • Jan 16, 2024

      Last Listing Agent Candy DaRosa Feiner Real Estate

  • /33

    $3,750,000

    • 4 Beds
    • 2.5 Baths
    • 1,800 Sq Ft

    28 Beach Rd, Oak Bluffs, MA 02557

    Location, Location, location....This is rare opportunity to own a water front property with 240 degree views of the Harbor and Sound. The property is 5 minutes from either Ferry terminal and walking distance to East beach . The house is suitable for year round living , seasonal income and comfort through and through

    Scott Lewis Lewis Real Estate Services, LLC

    28 Beach Rd, Oak Bluffs, MA 02557
  • /16

    $970,000 Sold Dec 08, 2025

    6 Sachem Way, Oak Bluffs, MA 02557

    • 3 Beds
    • 1 Bath
    • 1,546 Sq Ft
    • Built 1973

    Last Sold Summary

    • 8% Above List Price
    • $627/SF
    • 4 Days On Market

    Current Estimated Value $990,815

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

    6 Sachem Way, Oak Bluffs, MA 02557
    • /28

      Est $1,314,059 Not Listed For Sale

      208 Sandpiper Ln Unit 11, Vineyard Haven, MA 02568

      • 2 Beds
      • 2.5 Baths
      • 1,800 Sq Ft
      • Built 1988
      208 Sandpiper Ln Unit 11, Vineyard Haven, MA 02568

      Last Sold Summary

      • 1% Above List Price
      • $722/SF
      • 15 Days On Market
      • Last Sold Price $1,300,000
      • Apr 16, 2024

      Last Listing Agent Perry Patterson MV Luxury Homes

  • /31

    $1,575,000

    • 3 Beds
    • 4 Baths
    • 3,072 Sq Ft

    110 Clover Hill Dr, Vineyard Haven, MA 02568

    Minutes to downtown and the ferry, this updated year-round home checks every box buyers are asking for right now: space, flexibility, and a move-in ready setup in a highly convenient location. 3 bedrooms, 4 bathrooms, and over 3,000 sq ft of living space, including a private lower-level apartment ideal for guests, extended family, or income potential. The main level offers hardwood floors, a

    Jim Feiner Feiner Real Estate

    110 Clover Hill Dr, Vineyard Haven, MA 02568
  • /22

    $2,899,000 Sold Oct 01, 2025

    78 Winemack St, Oak Bluffs, MA 02557

    • 4 Beds
    • 2 Baths
    • 1,889 Sq Ft
    • Built 1956

    Last Sold Summary

    • $1,535/SF
    • 0 Days On Market

    Current Estimated Value $2,944,592

    Last Listing Agent Susan Austin Austin R.E. Properties of MV

    78 Winemack St, Oak Bluffs, MA 02557

Showing Results 241 - 280, Page 7 of 18

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