Vineyard Haven, MA Homes

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  /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 $3,206,924

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

  78 Winemack St, Oak Bluffs, MA 02557
• 

  

  

  /31

  Est $1,764,363

  Not Listed For Sale

  97 Snake Hollow, Vineyard Haven, MA 02568

  • 3 Beds
  • 2 Baths
  • 1,822 Sq Ft
  • Built 1981

  97 Snake Hollow, Vineyard Haven, MA 02568

  Last Sold Summary

  • 6 Days On Market

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

  

  

  /18

  $1,255,000

  • 3 Beds
  • 1.5 Baths
  • 912 Sq Ft

  11 Stanley St, Oak Bluffs, MA 02557

  Charming Oak Bluffs Ranch on a Peaceful Cul-de-SacWelcome to this inviting 3-bedroom, 1.5-bath ranch-style home nestled on a generous .35-acre lot at the end of a peaceful cul-de-sac in Oak Bluffs, Massachusetts. Ideally located near the beach and town center, this property offers a wonderful blend of privacy, convenience, and classic island living.The comfortable single-level layout

  Lisa Lucier Anchor Realty of Martha's Vineyard

  11 Stanley St, Oak Bluffs, MA 02557
• 

  

  

  /50

  $1,680,000

  Sold Sep 16, 2026

  37 Old Hedge Row, Vineyard Haven, MA 02568

  • 4 Beds
  • 2.5 Baths
  • 2,329 Sq Ft
  • Built 2003

  Last Sold Summary

  • 5% Below List Price
  • $721/SF
  • 32 Days On Market

  Current Estimated Value $1,728,126

  Last Listing Agent Sean Federowicz Landmarks at TODAY Real Estate

  37 Old Hedge Row, Vineyard Haven, MA 02568
• 

  

  

  /41

  Est $1,906,649

  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

  • 51 Days On Market

  Last Listing Agent Jennifer O'hanlon Compass
• 

  

  /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
• 

  

  /42

  $1,700,000

  Sold Nov 03, 2025

  35 Tower Ridge Rd, Oak Bluffs, MA 02557

  • 3 Beds
  • 4 Baths
  • 2,558 Sq Ft
  • Built 1986

  Last Sold Summary

  • 20% Below List Price
  • $665/SF
  • 106 Days On Market

  Current Estimated Value $1,845,380

  Last Listing Agent Katherine Donahue Sandpiper Realty

  35 Tower Ridge Rd, Oak Bluffs, MA 02557
• 

  

  /16

  Est $1,792,713

  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

  • 10 Days On Market

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

  

  /41

  $2,500,000

  Pending

  • 4 Beds
  • 2.5 Baths
  • 3,225 Sq Ft

  272 Bigelow Rd, Vineyard Haven, MA 02568

  Welcome to Mink Meadows, a picturesque neighborhood in the West Chop section of Vineyard Haven. This sought-after enclave offers a private, rural feel while keeping residents conveniently close to town. Set on a lush 2.2-acre lot, 272 Bigelow Road offers more than 3,200 square feet of living space designed for comfort, gathering, and easy indoor-outdoor living. The first-floor features cathedral

  Elissa Lash Tea Lane Associates

  272 Bigelow Rd, Vineyard Haven, MA 02568
• 

  

  /30

  $815,000

  Sold Nov 14, 2025

  17 Siloam Ave, Oak Bluffs, MA 02557

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

  Last Sold Summary

  • 2% Below List Price
  • $899/SF
  • 100 Days On Market

  Current Estimated Value $870,780

  Last Listing Agent Marilyn Moses Ocean Park Realty Inc

  17 Siloam Ave, Oak Bluffs, MA 02557
• 

  

  /44

  Est $8,279,616

  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

  • 280 Days On Market

  Last Listing Agent Gerrett Conover Landvest MV
• 

  

  /25

  $1,850,000

  Pending

  • 4 Beds
  • 2 Baths
  • 1,833 Sq Ft

  22 Old Harbor Ln, Oak Bluffs, MA 02557

  Quintessential Waterview Farm! Built as a year-round home with the charm of the original cottages, this well-loved retreat awaits its next chapter. The sunny, open floor plan offers two bedrooms and a full bath on each level, with generous gathering spaces throughout. A skylit kitchen is tucked into a corner of the main living area, where a curved wall of glass opens to a deck and private yard.

  Lisa Stewart Sandpiper Realty, Inc.

  22 Old Harbor Ln, Oak Bluffs, MA 02557
• 

  /2

  $6,825,000

  Sold Jan 05, 2026

  662 Chappaquonsett Rd, Vineyard Haven, MA 02568

  • 3 Beds
  • 3 Baths
  • 1,914 Sq Ft
  • Built 1973

  Last Sold Summary

  • 2% Below List Price
  • $3,566/SF
  • 0 Days On Market

  Current Estimated Value $5,303,543

  Last Listing Agent Jill Napior Tea Lane Associates

  662 Chappaquonsett Rd, Vineyard Haven, MA 02568
• 

  

  /16

  Est $1,363,746

  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

  • 8 Days On Market

  Last Listing Agent Candy DaRosa Feiner Real Estate
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  /4

  $1,800,000

  • Land
  • 1.1 Acres
  • $1,635,026 per Acre

  0 Weaver Lane (Lot 5) Unit 5, Vineyard Haven, MA 02568

  This 1.1-acre waterfront lot is located at the end of a quiet lane abutting 20+ acres of conservation land. The level and heavily wooded lot sits high on a bluff overlooking the Lagoon. The lot has been engineered, and the bounds have been staked. A buyer would be able to connect to Town water nearby, and an enhanced septic system should allow at least four bedrooms. This quiet, beautiful

  Gerrett Conover Landvest MV

  0 Weaver Lane (Lot 5) Unit 5, Vineyard Haven, MA 02568
• 

  

  /25

  $1,300,000

  Sold Dec 18, 2025

  23 Laurel Ave, Oak Bluffs, MA 02557

  • 4 Beds
  • 2 Baths
  • 1,248 Sq Ft
  • Built 1900

  Last Sold Summary

  • 13% Below List Price
  • $1,042/SF
  • 64 Days On Market

  Current Estimated Value $1,376,058

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

  23 Laurel Ave, Oak Bluffs, MA 02557
• 

  

  /28

  Est $1,277,864

  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

  • 15 Days On Market

  Last Listing Agent Perry Patterson MV Luxury Homes
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  /70

  $5,295,000

  $200K PRICE DROP Pending

  • 3 Beds
  • 7 Baths
  • 3,608 Sq Ft

  385 Barnes Rd, Vineyard Haven, MA 02568

  SPECTACULAR WATERFRONT ESCAPE WITH POOL AND UNFORGETTABLE SUNSETS. Set along a coveted stretch of Lagoon frontage, this beautifully designed waterfront home captures the essence of relaxed luxury on Martha’s Vineyard. With 125 feet of private sandy beachfront and over 5,400 square feet of living space across three levels, the property is thoughtfully oriented to maximize light, views, and

  Stephanie Roache Donnelly + Co

  385 Barnes Rd, Vineyard Haven, MA 02568
• 

  

  /44

  $1,525,000

  Sold Feb 03, 2026

  105 Stoney Hill Rd, Vineyard Haven, MA 02568

  • 4 Beds
  • 2.5 Baths
  • 1,815 Sq Ft
  • Built 1986

  Last Sold Summary

  • 8% Below List Price
  • $840/SF
  • 60 Days On Market

  Current Estimated Value $1,737,716

  Last Listing Agent Lisa Da Silva Signal House Group at Compass

  105 Stoney Hill Rd, Vineyard Haven, MA 02568
• 

  

  /86

  Est $1,638,930

  Not Listed For Sale

  176 Sandpiper Ln Unit 11, Vineyard Haven, MA 02568

  • 3 Beds
  • 3.5 Baths
  • 2,455 Sq Ft
  • Built 1988

  176 Sandpiper Ln Unit 11, Vineyard Haven, MA 02568

  Last Sold Summary

  • 187 Days On Market

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

  

  /14

  $685,000

  Pending

  • 2 Beds
  • 1.5 Baths
  • 782 Sq Ft

  10 Siloam Ave, Oak Bluffs, MA 02557

  The cottage has been maintained throughout the years, with a new roof in 2015, at which time it was insulated. The original Campground charm has been preserved thoughtfully. New mahogany boards are on front porch and a new paint job on the exterior of the cottage was done last year. The kitchen cabinets have been crafted by a master wood worker and there is a new kitchen floor and appliances.

  Elise LeBovit Gay Head Realty

  10 Siloam Ave, Oak Bluffs, MA 02557
• 

  

  /19

  $1,330,000

  Sold Oct 17, 2025

  32 MacHipscat Trail, Vineyard Haven, MA 02568

  • 3 Beds
  • 1.5 Baths
  • 1,404 Sq Ft
  • Built 1983

  Last Sold Summary

  • 11% Below List Price
  • $947/SF
  • 112 Days On Market

  Current Estimated Value $1,417,863

  Last Listing Agent Brenda Galligan Karen M. Overtoom R.E.

  32 MacHipscat Trail, Vineyard Haven, MA 02568
• 

  

  /19

  Est $1,423,546

  Not Listed For Sale

  193 Franklin Terrace, Vineyard Haven, MA 02568

  • 3 Beds
  • 2 Baths
  • 2,080 Sq Ft
  • Built 1972

  193 Franklin Terrace, Vineyard Haven, MA 02568

  Last Sold Summary

  • 487 Days On Market

  Last Listing Agent Claire Callagy Wallace & Co. Sotheby's
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  /33

  $1,325,000

  $575K PRICE DROP Under Contract

  • 4 Beds
  • 3 Baths
  • 2,056 Sq Ft

  20 Brook Hollow Rd, Vineyard Haven, MA 02568

  Fantastic opportunity for a great locationb and a spacious custom designed home! This house is well sited to offer maximum privacy in the lush area of Long View, a short bike ride to Lambert's Cove beach. It's also about a 20-minute walk down a quiet private road. The home lays out well for family and extended guests with a roomy living room boasting vaulted ceilings and large windows. The house

  Jim Feiner Feiner Real Estate

  20 Brook Hollow Rd, Vineyard Haven, MA 02568
• 

  

  /17

  $1,200,000

  Sold Oct 28, 2025

  211 Edgartown Vineyard Haven Rd, Tisbury, MA 02568

  • 4 Beds
  • 2 Baths
  • 1,680 Sq Ft
  • Built 1987

  Last Sold Summary

  • 25% Below List Price
  • $714/SF
  • 209 Days On Market

  Last Listing Agent Jim Feiner Feiner Real Estate

  211 Edgartown Vineyard Haven Rd, Tisbury, MA 02568
• 

  

  /45

  Est $1,526,935

  Not Listed For Sale

  140 Tashmoo Ave, Vineyard Haven, MA 02568

  • 3 Beds
  • 2.5 Baths
  • 2,096 Sq Ft
  • Built 1993

  140 Tashmoo Ave, Vineyard Haven, MA 02568

  Last Sold Summary

  • 61 Days On Market

  Last Listing Agent Emma Bryant Landmarks at TODAY Real Estate
• 

  

  /45

  $1,765,000

  • 2 Beds
  • 2 Baths
  • 890 Sq Ft

  2 Great Rock Rd, Oak Bluffs, MA 02568

  Ready - Set - Go! This gorgeous centrally located private 1.5 acre wooded property is ready for you to complete. The Town approved this property to accommodate a 9 bedroom septic system, 20' x 40' in-ground pool, a 7 bedroom main house, garage and a 2 bedroom accessory dwelling unit. The town building and board of health departments approved the house and and septic plans attached. The property

  Susan Lemoie-Zarba Premier Properties

  2 Great Rock Rd, Oak Bluffs, MA 02568
• 

  

  /24

  $2,125,000

  Sold Oct 30, 2025

  30 Sengekontacket Rd, Oak Bluffs, MA 02557

  • 4 Beds
  • 3 Baths
  • 2,262 Sq Ft
  • Built 1978

  Last Sold Summary

  • 11% Below List Price
  • $939/SF
  • 265 Days On Market

  Current Estimated Value $2,314,985

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

  30 Sengekontacket Rd, Oak Bluffs, MA 02557
• 

  

  /22

  Est $1,256,505

  Not Listed For Sale

  110 Daggett Ave, Vineyard Haven, MA 02568

  • 3 Beds
  • 2 Baths
  • 1,650 Sq Ft
  • Built 1921

  110 Daggett Ave, Vineyard Haven, MA 02568

  Last Sold Summary

  • 106 Days On Market

  Last Listing Agent Kate Burnside Portfolio Properties
• 

  

  /20

  $1,745,000

  • 2 Beds
  • 1 Bath
  • 560 Sq Ft

  11 Beach Rd, Oak Bluffs, MA 02568

  Wake up to breathtaking ocean views and the soothing rhythm of waves from this charming two-bedroom oceanfront cottage on East Chop. Set on approximately .21 acres of waterfront property with more than 50 feet of shoreline, this special retreat offers a rare opportunity to own a true piece of the island's coastline. Positioned directly on the water, the cottage captures the beauty of the

  Carleen Cordwell Anchor Realty of Martha's Vineyard

  11 Beach Rd, Oak Bluffs, MA 02568
• 

  

  /9

  $160,000

  Sold Nov 14, 2025

  60 Beach Rd Unit 105, Vineyard Haven, MA 02568

  • 1 Bed
  • 1 Bath
  • 381 Sq Ft
  • Built 1958

  Last Sold Summary

  • $420/SF
  • 0 Days On Market

  Current Estimated Value $165,210

  Last Listing Agent Nantucket CompLINK LINK

  60 Beach Rd Unit 105, Vineyard Haven, MA 02568
• 

  /2

  Est $1,198,771

  Not Listed For Sale

  284 Daggett Ave, Vineyard Haven, MA 02568

  • 3 Beds
  • 2 Baths
  • 1,416 Sq Ft
  • Built 1970

  284 Daggett Ave, Vineyard Haven, MA 02568
• 

  

  /31

  $2,995,000

  • 5 Beds
  • 1.5 Baths
  • 1,731 Sq Ft

  27 Beach Rd, Oak Bluffs, MA 02557

  WATERFRONT WITH DOCK - Nestled along the sparkling shores of Vineyard Haven Harbor, this waterfront cottage presents a rare opportunity to own a piece of Martha's Vineyard history. Originally part of the iconic Mary Guerin Inn, the home blends timeless Vineyard charm with an exceptional setting featuring a private sandy beach, deep-water dock, and sweeping views of the harbor, the Cape, and

  Bonnie Pierce Wallace & Co. Sotheby's International Realty

  27 Beach Rd, Oak Bluffs, MA 02557
• 

  

  /29

  $1,150,000

  Sold Dec 16, 2025

  52 Old Coach Rd, Vineyard Haven, MA 02568

  • 3 Beds
  • 2 Baths
  • 1,296 Sq Ft
  • Built 1988

  Last Sold Summary

  • 8% Below List Price
  • $887/SF
  • 18 Days On Market

  Current Estimated Value $1,285,685

  Last Listing Agent Kathleen Kendrick Kathleen Kendrick

  52 Old Coach Rd, Vineyard Haven, MA 02568
• 

  

  /44

  Est $1,411,081

  Not Listed For Sale

  4 Lady Slipper Way, Vineyard Haven, MA 02568

  • 5 Beds
  • 3 Baths
  • 1,781 Sq Ft
  • Built 1997

  4 Lady Slipper Way, Vineyard Haven, MA 02568

  Last Sold Summary

  • 101 Days On Market

  Last Listing Agent June Flake Viewpoints
• 

  

  /48

  $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

  Peter Cronig Cronigs Real Estate

  398 Main St, Vineyard Haven, MA 02568
• 

  

  /13

  $1,205,000

  Sold Aug 07, 2026

  318 Lamberts Cove Rd, Vineyard Haven, MA 02568

  • 4 Beds
  • 3 Baths
  • 2,345 Sq Ft
  • Built 1970

  Last Sold Summary

  • 14% Below List Price
  • $514/SF
  • 63 Days On Market

  Current Estimated Value $1,752,572

  Last Listing Agent Holly Alaimo Tashmoo Realty

  318 Lamberts Cove Rd, Vineyard Haven, MA 02568
• 

  

  /31

  Est $1,338,607

  Not Listed For Sale

  191 Spring Hill Rd, Vineyard Haven, MA 02568

  • 5 Beds
  • 4 Baths
  • 2,292 Sq Ft
  • Built 1992

  191 Spring Hill Rd, Vineyard Haven, MA 02568

  Last Sold Summary

  • 10 Days On Market

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

  

  /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
• 

  

  /4

  $435,000

  Sold Aug 18, 2026

  11 Boylston Dr Unit 1.314, Edgartown, MA 02539

  • Land
  • 23,958 Sq Ft
  • $790,909 per Acre

  Last Sold Summary

  • 13% Below List Price
  • 433 Days On Market

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

  11 Boylston Dr Unit 1.314, Edgartown, MA 02539

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