3,458

Vineyard Haven Homes

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  • /58

    $2,895,000

    • 5 Beds
    • 4 Baths
    • 2,300 Sq Ft

    27 Spring St, Vineyard Haven, MA 02568

    Located in the William Street Historic District, this elegant Greek Revival home, built in 1842, has stood the test of time and has been thoughtfully expanded and renovated in recent years. This five-bedroom, four-bath residence combines historic character with modern comforts. The home features a gracious living room, dining room, office, and an inviting kitchen/breakfast room. There are five

    Alexis Holden Tea Lane Associates

    27 Spring St, Vineyard Haven, MA 02568
  • /41

    $13,500 Per Month

    • 5 Beds
    • 5.5 Baths
    • 3,000 Sq Ft
    • House for Rent

    14 Bernard Cir, Vineyard Haven, MA 02568

    ** SUMMER WEEKLY RATE ** Private and luxurious BRAND NEW contemporary chic 5 BED 5.5 BATH home perfectly situated close to downtown Vineyard Haven yet set amongst a rural and peaceful WEST CHOP adjacent neighborhood. Indulge and unwind in the PRIVATE HEATED SALTWATER IN-GROUND POOL surrounded by opulent outdoor living and dining area highlighted by covered al-fresco kitchen, BBQ grill and bar -

    Allison Cameron Parry Douglas Elliman Real Estate - Nantucket

    14 Bernard Cir, Vineyard Haven, MA 02568
  • /2

    $1,390,000

    Sold Jul 22, 2025

    57 Colonial Dr, Vineyard Haven, MA 02568

    • 3 Beds
    • 2 Baths
    • 1,299 Sq Ft
    • Built 1984

    Last Sold Summary

    • $1,070/SF
    • 0 Days On Market

    Current Estimated Value $1,504,131

    Last Listing Agent LINK Email Cache LINK

    57 Colonial Dr, Vineyard Haven, MA 02568
    • /38

      Est $2,078,601

      Not Listed For Sale

      83 Dolan Ave, Vineyard Haven, MA 02568

      • 5 Beds
      • 4.5 Baths
      • 3,841 Sq Ft
      • Built 1994
      83 Dolan Ave, Vineyard Haven, MA 02568

      Last Sold Summary

      • 24 Days On Market

  • /5

    $639,000

    • Land
    • 12,998 Sq Ft
    • $2,141,421 per Acre

    52 Heath Hen Ln Unit 5, Vineyard Haven, MA 02568

    GOOD TO GO! This sunny 13,000-square-foot lot is ready for your Vineyard home. The property comes with a complete six-bedroom septic design prepared by Vineyard Land Surveying, allowing for both a main house and guest house. With key planning work already completed, this is an outstanding opportunity to move forward with confidence and begin the building process. Conveniently located just off

    Tina Miller Donnelly + Co

    52 Heath Hen Ln Unit 5, Vineyard Haven, MA 02568
  • /16

    $5,000 Per Month

    • 1 Bath
    • 400 Sq Ft
    • House for Rent

    90 Edgartown Rd, Vineyard Haven, MA 02568

    *Summer Weekly Rate** Inquire For Long-term Off-Season Rates. Renovated Studio Cottage on Martha's Vineyard w/private feel. Within walking distance to shops, dining, and the ferry. Lots of trees for year-round enjoyment. Open floor plan with Murphy bed for additional space and a large comfortable sofa, galley kitchen with granite countertops, stainless steel appliances, amazing tiled bathroom

    Kim Seawright Generations Realty Group

    90 Edgartown Rd, Vineyard Haven, MA 02568
  • /31

    $1,685,000

    Sold Oct 09, 2025

    126 Border Rd, Vineyard Haven, MA 02568

    • 3 Beds
    • 3 Baths
    • 2,251 Sq Ft
    • Built 1979

    Last Sold Summary

    • 16% Below List Price
    • $749/SF
    • 337 Days On Market

    Current Estimated Value $2,207,204

    Last Listing Agent Natalie Conroy Conroy & Company R.E., Inc.

    126 Border Rd, Vineyard Haven, MA 02568
    • /2

      Est $2,759,984

      Not Listed For Sale

      89 Main St, Vineyard Haven, MA 02568

      • 4 Beds
      • 5 Baths
      • 2,728 Sq Ft
      • Built 1830
      89 Main St, Vineyard Haven, MA 02568

  • /20

    $1,149,000

    • 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
  • /40

    $32,500 Per Month

    • 6 Beds
    • 4.5 Baths
    • 3,222 Sq Ft
    • House for Rent

    100 Connie's Way &83 Ashtonw Vh408, Tisbury, MA 02568

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $5,000. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Located in Mink Meadows Association, this wonderful four bedroom, three full and one half bath home has many nice features that include a large eat-in kitchen/family room, a more formal living room with fireplace, dining room and den. Televisions in every bedroom, living

    Karen Overtoom Karen M. Overtoom R.E.

    100 Connie's Way &83 Ashtonw Vh408, Tisbury, MA 02568
  • /31

    $1,000,000

    Sold Jun 01, 2026

    73 & 0 Old Country Ln, Vineyard Haven, MA 02568

    • 2 Beds
    • 1 Bath
    • 1,040 Sq Ft
    • Built 1978

    Last Sold Summary

    • 13% Below List Price
    • $962/SF
    • 217 Days On Market

    Last Listing Agent Julianna Flanders Flanders Real Estate

    73 & 0 Old Country Ln, Vineyard Haven, MA 02568
    • /2

      Est $970,045

      Not Listed For Sale

      84 Pine Tree Rd, Vineyard Haven, MA 02568

      • 3 Beds
      • 1 Bath
      • 1,116 Sq Ft
      • Built 1980
      84 Pine Tree Rd, Vineyard Haven, MA 02568

  • /12

    $1,395,000

    $100K PRICE DROP
    • 4 Beds
    • 4 Baths
    • 2,304 Sq Ft

    33 Alyssa Ln, Vineyard Haven, MA 02568

    Country Living so close to Town! Lovely 4 Bedroom 2,304sq ft. Colonial Cape perched on a rise on Alyssa Lane off West Spring Street. Open Kitchen with handcrafted side cabinets and Island with stool seating. Dining, sitting, entertainment area with sliders open to a generous front to back side deck. Living room with propane fired wood stove and half bath also on the first floor. Interior stairs

    Stephanie Burke Portfolio Properties

    33 Alyssa Ln, Vineyard Haven, MA 02568
  • /10

    $4,895,000

    Sold Feb 13, 2026

    64 Crowell Ln, Tisbury, MA 02568

    • 5 Beds
    • 6.5 Baths
    • 4,216 Sq Ft
    • Built 2025

    Last Sold Summary

    • 2% Below List Price
    • $1,161/SF
    • 307 Days On Market

    Current Estimated Value $3,285,841

    Last Listing Agent Joe & Nicole Holland Vineyard Dream Realty LLC

    64 Crowell Ln, Tisbury, MA 02568
    • /46

      Est $6,414,246

      Not Listed For Sale

      79 Rachels Way, Vineyard Haven, MA 02568

      • 4 Beds
      • 4 Baths
      • 3,278 Sq Ft
      • Built 1983
      79 Rachels Way, Vineyard Haven, MA 02568

      Last Sold Summary

      • 0 Days On Market

  • /7

    $2,000,000

    • Land
    • 21,801 Sq Ft
    • $3,996,004 per Acre

    0 State Rd Unit 29.3, Vineyard Haven, MA 02568

    1/2 acre of commercial land in the State Road B-2 district. Possibilities are endless for the right business. Also available, next door, is a commercial building that currently has 10 rental units. $6,000,000.

    Peter Cronig Cronigs Real Estate

    0 State Rd Unit 29.3, Vineyard Haven, MA 02568
  • /69

    $1,160,000

    Sold Jan 05, 2026

    208 Irenes Way, Tisbury, MA 02568

    • 4 Beds
    • 3 Baths
    • 2,961 Sq Ft
    • Built 2005

    Last Sold Summary

    • 24% Below List Price
    • $392/SF
    • 168 Days On Market

    Current Estimated Value $1,302,062

    Last Listing Agent Emma Bryant Studio Realty

    208 Irenes Way, Tisbury, MA 02568
    • /32

      Est $2,261,413

      Not Listed For Sale

      232 Lagoon Pond Rd, Vineyard Haven, MA 02568

      • 4 Beds
      • 4 Baths
      • 2,276 Sq Ft
      • Built 1970
      232 Lagoon Pond Rd, Vineyard Haven, MA 02568

      Last Sold Summary

      • 220 Days On Market

  • /32

    $1,625,000

    • 2 Beds
    • 2.5 Baths
    • 1,532 Sq Ft

    26 Union St Unit 7, Tisbury, MA 02568

    Waterview Condo in the Heart of Downtown Vineyard Haven. Experience the best of in-town living with this newly built, thoughtfully designed 2-bedroom condo offering beautiful harbor views and luxurious modern finishes. The first level welcomes you with a primary suite featuring a full bath with a tub/shower combination and direct access to a private deck complete with an outdoor shower, perfect

    Alyssa Halisky Wallace & Co. Sotheby's

    26 Union St Unit 7, Tisbury, MA 02568
  • /37

    $2,100,000

    Sold Aug 27, 2025

    42 Daggett Ave, Vineyard Haven, MA 02568

    • 3 Beds
    • 3.5 Baths
    • 3,310 Sq Ft
    • Built 2009

    Last Sold Summary

    • 4% Below List Price
    • $634/SF
    • 60 Days On Market

    Current Estimated Value $2,996,401

    Last Listing Agent Rene Jackson Island Real Estate

    42 Daggett Ave, Vineyard Haven, MA 02568
    • /44

      Est $1,725,906

      Not Listed For Sale

      30 Hillside Path, Vineyard Haven, MA 02568

      • 3 Beds
      • 4 Baths
      • 3,114 Sq Ft
      • Built 1999
      30 Hillside Path, Vineyard Haven, MA 02568

      Last Sold Summary

      • 39 Days On Market

  • /110

    $2,000,000

    • 4 Beds
    • 6 Baths
    • 2,972 Sq Ft

    398 Main St, Vineyard Haven, MA 02568

    Ideally situated on Main Street in Vineyard Haven, just moments from the Yacht Club and West Chop, this charming four-bedroom, six-bathroom home offers the perfect blend of convenience, comfort, and Island living. Set on a quarter-acre lot, the property features a private and inviting backyard—ideal for entertaining, gardening, or simply enjoying warm summer evenings. Inside, generous living

    Peter Cronig Cronigs Real Estate

    398 Main St, Vineyard Haven, MA 02568
  • /12

    $686,000

    Sold Jul 23, 2025

    124 Skiff Ave Unit A-10, Vineyard Haven, MA 02568

    • 2 Beds
    • 1 Bath
    • 725 Sq Ft
    • Built 1953

    Last Sold Summary

    • $946/SF
    • 31 Days On Market

    Current Estimated Value $854,208

    Last Listing Agent Carleen Cordwell Anchor Realty of Martha's Vineyard

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

      Est $1,306,083

      Not Listed For Sale

      19 Renear St, Vineyard Haven, MA 02568

      • 4 Beds
      • 3 Baths
      • 1,736 Sq Ft
      • Built 1985
      19 Renear St, Vineyard Haven, MA 02568

      Last Sold Summary

      • 121 Days On Market

  • /3

    $639,000

    • Land
    • 13,068 Sq Ft
    • $2,130,000 per Acre

    52 Heath Hen Ln, Vineyard Haven, MA 02568

    GOOD TO GO! This sunny 13,000-square-foot sunny lot is ready for your Vineyard home. The property comes with a complete six bedroom septic design prepared by Vineyard Land Surveying, allowing for both a main house and guest house. With key planning work already completed, this is an outstanding opportunity to move forward with confidence and begin the building process.Conveniently located just

    Tina Miller Donnelly + Co.

    52 Heath Hen Ln, Vineyard Haven, MA 02568
  • /2

    $3,500,000

    Sold Oct 07, 2025

    339 Lake St, Vineyard Haven, MA 02568

    • 3 Beds
    • 3.5 Baths
    • 2,448 Sq Ft
    • Built 2001

    Last Sold Summary

    • $1,430/SF
    • 0 Days On Market

    Last Listing Agent LINK Email Cache LINK

    339 Lake St, Vineyard Haven, MA 02568
    • /34

      Est $2,340,864

      Not Listed For Sale

      338 Bigelow Rd, Vineyard Haven, MA 02568

      • 3 Beds
      • 2.5 Baths
      • 1,783 Sq Ft
      • Built 1978
      338 Bigelow Rd, Vineyard Haven, MA 02568

      Last Sold Summary

      • 68 Days On Market

  • /4

    $2,995,000

    Pending
    • 4 Beds
    • 4.5 Baths
    • 3,024 Sq Ft

    9 Hagerty Dr, Tisbury, MA 02568

    West Chop Dream Home in the Making! Experience the charm of this brand-new Shingle Style Colonial, currently under construction. Featuring 4 spacious bedrooms, 4 full and one half bath. This thoughtfully designed home offers generous space. Venture outside into your private oasis, complete with an in-ground pool (36' x18') — perfect for sun-soaked afternoons and evening gatherings. Situated in a

    Lisa Gilberto C McManus Realty Group

    9 Hagerty Dr, Tisbury, MA 02568
  • /42

    $2,448,000

    Sold May 22, 2026

    61 Causeway Rd, Vineyard Haven, MA 02568

    • 3 Beds
    • 3.5 Baths
    • 3,530 Sq Ft
    • Built 2008

    Last Sold Summary

    • 2% Below List Price
    • $693/SF
    • 51 Days On Market

    Current Estimated Value $2,464,000

    Last Listing Agent Stephanie Roache Donnelly + Co.

    61 Causeway Rd, Vineyard Haven, MA 02568
    • /17

      Est $643,282

      Not Listed For Sale

      15 Walker Way, Vineyard Haven, MA 02568

      • 1 Bed
      • 1 Bath
      • 432 Sq Ft
      • Built 1940
      15 Walker Way, Vineyard Haven, MA 02568

      Last Sold Summary

      • 30 Days On Market

  • /50

    $1,770,000

    • 4 Beds
    • 2.5 Baths
    • 2,329 Sq Ft

    37 Old Hedge Row, Vineyard Haven, MA 02568

    Move in ready and easy to show! Just atop a modest knoll sits this well cared for, light filled, privately sited, four bedroom custom home. A six bedroom septic offers further spatial enhancement, or ADU potential with proper Town permitting. Convenient to downtown, public library, shopping, eateries, and ferries, the youthful home has an open floor plan, thoughtful built-ins and attractive

    Sean Federowicz Landmarks at TODAY Real Estate

    37 Old Hedge Row, Vineyard Haven, MA 02568
  • /13

    $2,237,500

    Sold Nov 19, 2025

    26 Chappaquiddick Avenue and Passamaquoddy Ave, West Tisbury, MA 02575

    • 4 Beds
    • 3 Baths
    • 2,299 Sq Ft
    • Built 1974

    Last Sold Summary

    • 16% Below List Price
    • $973/SF
    • 120 Days On Market

    Last Listing Agent Jill Napior Tea Lane Associates

    26 Chappaquiddick Avenue and Passamaquoddy Ave, West Tisbury, MA 02575
    • /29

      Est $2,486,709

      Not Listed For Sale

      21 William St, Vineyard Haven, MA 02568

      • 3 Beds
      • 2.5 Baths
      • 2,378 Sq Ft
      • Built 1928
      21 William St, Vineyard Haven, MA 02568

      Last Sold Summary

      • 0 Days On Market

  • /16

    $1,175,000

    $74K PRICE DROP
    • 3 Beds
    • 1 Bath
    • 998 Sq Ft

    299 Daggett Ave Unit A, Vineyard Haven, MA 02568

    This cheerful sun drenched three-bed & one bath home with cathedral ceilings sits on just over an acre of gently rolling land surrounded by mature pines, oaks and ornamental plantings. Inspired by Norwegian architecture, the current owner designed and built this home in 1999 with his wife who was an artist from Norway. It’s located about a mile to town in one direction and the beach in the other.

    Karen Overtoom Karen M. Overtoom R.E.

    299 Daggett Ave Unit A, Vineyard Haven, MA 02568
  • /61

    $1,910,000

    Sold Apr 03, 2026

    28 Pine Tree Ln, Vineyard Haven, MA 02568

    • 5 Beds
    • 3.5 Baths
    • 3,250 Sq Ft
    • Built 1974

    Last Sold Summary

    • 15% Below List Price
    • $588/SF
    • 132 Days On Market

    Current Estimated Value $2,115,133

    Last Listing Agent Wendy Harman Compass | Point B

    28 Pine Tree Ln, Vineyard Haven, MA 02568
    • /32

      Est $1,295,220

      Not Listed For Sale

      58 Hagerty Dr, Vineyard Haven, MA 02568

      • 3 Beds
      • 1 Bath
      • 1,118 Sq Ft
      • Built 1983
      58 Hagerty Dr, Vineyard Haven, MA 02568

      Last Sold Summary

      • 167 Days On Market

  • /28

    $2,290,000

    $205K PRICE DROP
    • 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
  • /7

    $600,000

    Sold Nov 04, 2025

    10 Putnam Way, Vineyard Haven, MA 02568

    • 3 Beds
    • 1 Bath
    • 1,168 Sq Ft
    • Built 1972

    Last Sold Summary

    • 22% Below List Price
    • $514/SF
    • 39 Days On Market

    Current Estimated Value $823,389

    Last Listing Agent Kathleen Dawson Donnelly + Co.

    10 Putnam Way, Vineyard Haven, MA 02568
    • /32

      Est $1,163,101

      Not Listed For Sale

      10 Elm St, Vineyard Haven, MA 02568

      • 3 Beds
      • 2 Baths
      • 1,429 Sq Ft
      • Built 1970
      10 Elm St, Vineyard Haven, MA 02568

      Last Sold Summary

      • 35 Days On Market

  • /38

    $1,495,000

    Pending
    • 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

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