Vineyard Haven, MA Homes

• 

  

  

  /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 $1,911,919

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

  126 Border Rd, Vineyard Haven, MA 02568
• 

  

  

  /19

  Est $1,170,101

  Not Listed For Sale

  31 9th St N, Edgartown, MA 02539

  • 2 Beds
  • 1.5 Baths
  • 1,275 Sq Ft
  • Built 1972

  31 9th St N, Edgartown, MA 02539

  Last Sold Summary

  • 45 Days On Market

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

  

  

  /25

  $1,599,000

  $26K PRICE DROP

  • 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. Also on

  Alyssa Halisky Wallace & Co. Sotheby's International Realty

  26 Union St Unit 7, Tisbury, MA 02568
• 

  

  /2

  $825,000

  Sold Dec 03, 2025

  69 Summit Ave, Vineyard Haven, MA 02568

  • 3 Beds
  • 2 Baths
  • 1,248 Sq Ft
  • Built 1998

  Last Sold Summary

  • $661/SF
  • 1 Day On Market

  Current Estimated Value $907,676

  Last Listing Agent Susie Wallo Compass

  69 Summit Ave, Vineyard Haven, MA 02568
• 

  

  

  /20

  Est $1,308,948

  Not Listed For Sale

  46 Old Coach Rd, Vineyard Haven, MA 02568

  • 3 Beds
  • 2 Baths
  • 1,374 Sq Ft
  • Built 1981

  46 Old Coach Rd, Vineyard Haven, MA 02568

  Last Sold Summary

  • 43 Days On Market

  Last Listing Agent Lisa Gilberto C McManus Realty Group
• 

  

  /48

  $839,000

  $60K PRICE DROP Under Contract

  • 1 Bed
  • 1 Bath
  • 804 Sq Ft

  26 Winthrop Ave, Oak Bluffs, MA 02557

  This little gem is waiting to be polished. Hidden behind a wall of vegetation on Winthrop Avenue, an 'oasis', with tons of potential. Existing one bedroom, two story house situated on a 1/3 Acre of land, a 14,810 sq.ft. level lot. Land is large enough for a house and guest house when meeting ZBA requirements, or build a new house and leave existing structure as an Accessory Dwelling Unit when in

  Alisan Lohan-Conway Alisan Lohan-Conway Properties

  26 Winthrop Ave, Oak Bluffs, MA 02557
• 

  /2

  $612,500

  Sold Jul 29, 2026

  77 Sixth Street N St, Edgartown, MA 02568

  • Land
  • 12,196 Sq Ft
  • $2,187,500 per Acre

  Last Sold Summary

  • 2% Below List Price
  • 13 Days On Market

  Last Listing Agent Sheila Morse Island Real Estate

  77 Sixth Street N St, Edgartown, MA 02568
• 

  

  /12

  Est $712,474

  Not Listed For Sale

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

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

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

  Last Sold Summary

  • 31 Days On Market

  Last Listing Agent Carleen Cordwell Anchor Realty of Martha's Vineyard
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  /36

  $2,260,000

  $335K PRICE DROP

  • 4 Beds
  • 3.5 Baths
  • 2,810 Sq Ft

  4 High Meadow Ln, Oak Bluffs, MA 02557

  Set within the coveted Meadow View Farms community, this exceptional post-and-beam residence offers timeless craftsmanship, generous living spaces, and nearly an acre of private beautifully landscaped grounds with significant potential for expansion.A full-length farmer’s porch creates a gracious arrival and provides the perfect setting to relax. Inside, the sun-drenched main level is defined

  Kate Burnside Portfolio Properties

  4 High Meadow Ln, Oak Bluffs, MA 02557
• 

  

  /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
• 

  

  /24

  Est $1,316,343

  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

  Last Listing Agent Neal Stiller Cronigs Real Estate
• 

  

  /26

  $1,299,000

  $100K PRICE DROP

  • 5 Beds
  • 2 Baths
  • 1,968 Sq Ft

  41 Edgartown Rd, Vineyard Haven, MA 02568

  Located on the edge of downtown Vineyard Haven, just steps from the ferry, harbor, shops, restaurants, and beaches, this two-family property presents a rare opportunity. With full-floor residences offering a combined five bedrooms, the home provides exceptional flexibility for owner occupancy with rental income, investment, employee housing, or multigenerational living. Ready for thoughtful

  Peyton Wallace Studio Realty LLC

  41 Edgartown Rd, Vineyard Haven, MA 02568
• 

  

  /28

  $2,401,000

  Sold Jan 06, 2026

  46 Bold Meadow Rd, Edgartown, MA 02539

  • 4 Beds
  • 3.5 Baths
  • 2,372 Sq Ft
  • Built 1992

  Last Sold Summary

  • $1,012/SF
  • 14 Days On Market

  Current Estimated Value $2,500,516

  Last Listing Agent Julianna Flanders Flanders Real Estate

  46 Bold Meadow Rd, Edgartown, MA 02539
• 

  

  /34

  Est $2,353,801

  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

  Last Listing Agent Emily Flake Viewpoints; Bobbi Flake Reed, Inc.
• 

  

  /15

  $725,000

  • 2 Beds
  • 1 Bath
  • 703 Sq Ft

  124 Skiff Ave Unit G-11, Vineyard Haven, MA 02568

  Vineyard Haven- Walk to the Ferry from this 2 bedroom condo with pool. Located near the downtown area a desirable place for a rental property or live there year-round. The property features common grounds, picnic tables, and seating by the pool to relax and enjoy the outdoors.

  Lisa Lucier Anchor Realty of MV

  124 Skiff Ave Unit G-11, 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 $2,874,197

  Last Listing Agent Joe & Nicole Holland Vineyard Dream Realty LLC

  64 Crowell Ln, Tisbury, MA 02568
• 

  

  /17

  Est $660,332

  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

  Last Listing Agent Candy DaRosa Feiner Real Estate
• 

  

  /17

  $849,000

  $146K PRICE DROP

  • 2 Beds
  • 0.5 Baths
  • 952 Sq Ft

  50 Canonicus Ave, Oak Bluffs, MA 02557

  Rare Opportunity to Be in a Special Location and Neighborhood! Loved by generations, this quintessential Vineyard cottage has been in the same family since its creation in 1900. Step back in time and enjoy easy cottage living of yesteryear with modern updates including newer windows and electrical. Nestled under mature trees and just .3 mile to Inkwell Beach, join this close-knit neighborhood and

  Michele Moore Island Real Estate

  50 Canonicus Ave, Oak Bluffs, MA 02557
• 

  

  /8

  $435,000

  Sold Apr 16, 2026

  36 Boylston Dr Unit 1.329, Edgartown, MA 02539

  • Land
  • 22,651 Sq Ft
  • $836,538 per Acre

  Last Sold Summary

  • 8% Below List Price
  • 131 Days On Market

  Last Listing Agent Mark Jenkins Wallace & Co. Sotheby's

  36 Boylston Dr Unit 1.329, Edgartown, MA 02539
• 

  

  /29

  Est $2,184,494

  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

  Last Listing Agent Laura Finney Wallace & Co. Sotheby's
• 

  

  /26

  $1,285,000

  $35K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 2,347 Sq Ft

  41 Cook Rd, Vineyard Haven, MA 02568

  Just moments from downtown Vineyard Haven, the ferry terminal, shops, restaurants, and harbor, this beautifully maintained three-bedroom home combines distinctive character with thoughtfully updated spaces, modern comforts, and a peaceful residential setting. The home offers over 2,300 square feet of living space with three bedrooms, 2.5 baths, central air, and wood flooring throughout. An

  Jennifer O'hanlon Compass

  41 Cook Rd, Vineyard Haven, MA 02568
• 

  

  /19

  $875,000

  Sold Jul 28, 2026

  15 Second Ave, Oak Bluffs, MA 02557

  • 2 Beds
  • 1 Bath
  • 520 Sq Ft
  • Built 1900

  Last Sold Summary

  • 5% Below List Price
  • $1,683/SF
  • 11 Days On Market

  Current Estimated Value $869,803

  Last Listing Agent Susie Wallo Compass LLC

  15 Second Ave, Oak Bluffs, MA 02557
• 

  

  /32

  Est $1,290,072

  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

  Last Listing Agent Neal Stiller Cronigs Real Estate
• 

  /2

  $399,000

  $26K PRICE DROP

  • Land
  • 7,840 Sq Ft
  • $2,216,667 per Acre

  0 Heather Ln Unit 56, Oak Bluffs, MA 02568

  Rare opportunity to build your dream retreat tucked away on a quiet lane just off Wing Road. This desirable vacant lot offers the perfect blank canvas to design a custom coastal home, seasonal sanctuary, or smart island investment. Enjoy the ideal balance of residential privacy and effortless convenience, located just minutes from iconic Circuit Avenue, Oak Bluffs Harbor, scenic biking trails,

  Jennifer DaSilva Compass | Point B

  0 Heather Ln Unit 56, Oak Bluffs, MA 02568
• 

  

  /55

  $2,100,000

  Sold Aug 11, 2026

  25 Pennacook Ave, Oak Bluffs, MA 02557

  • 4 Beds
  • 5 Baths
  • 2,516 Sq Ft
  • Built 1999

  Last Sold Summary

  • 4% Below List Price
  • $835/SF
  • 45 Days On Market

  Last Listing Agent Nya Clarke Martha's Vineyard Island-Wide Realty

  25 Pennacook Ave, Oak Bluffs, MA 02557
• 

  

  /22

  Est $1,033,127

  Not Listed For Sale

  10 Saddle Club Rd, Edgartown, MA 02539

  • 3 Beds
  • 2 Baths
  • 1,025 Sq Ft
  • Built 1985

  10 Saddle Club Rd, Edgartown, MA 02539

  Last Sold Summary

  • 102 Days On Market

  Last Listing Agent Jennifer B. DaSilva Compass
• 

  

  /33

  $1,400,000

  • 5 Beds
  • 2.5 Baths
  • 2,083 Sq Ft

  5 Paula Ave, Vineyard Haven, MA 02568

  Discover the opportunity to make this spacious Vineyard Haven home your own, ideally located on the desirable lower end of Lambert's Cove Road. Just across from Pilot Hill Road and approximately one mile from the pristine shores of Lambert's Cove Beach, this well-positioned property offers the perfect blend of convenience, privacy, and potential. Spanning three levels, this five-bedroom,

  Emma Bryant Studio Realty

  5 Paula Ave, Vineyard Haven, MA 02568
• 

  

  /29

  $1,075,000

  Sold Feb 26, 2026

  34 Pine Ln, Vineyard Haven, MA 02568

  • 3 Beds
  • 2 Baths
  • 1,120 Sq Ft
  • Built 1984

  Last Sold Summary

  • 14% Below List Price
  • $960/SF
  • 93 Days On Market

  Current Estimated Value $1,233,127

  Last Listing Agent Candy DaRosa Feiner Real Estate

  34 Pine Ln, Vineyard Haven, MA 02568
• 

  

  /32

  Est $1,194,521

  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

  Last Listing Agent Christine Rose Martha's Vineyard Island-Wide Realty
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  /37

  $3,750,000

  • 4 Beds
  • 3 Baths
  • 2,204 Sq Ft

  9 Weston Ave, Oak Bluffs, MA 02568

  This beautifully situated 4-bedroom, 3-bath home sits at the highest point of East Chop, offering sweeping views of Vineyard Sound. The property features a spacious clerestory living room with a fireplace, along with a combined family room and kitchen, also centered around a cozy fireplace. A large, screened porch opens onto an expansive deck, perfect for relaxing or entertaining. The first floor

  Gerrett Conover Landvest MV

  9 Weston Ave, Oak Bluffs, 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
• 

  

  /30

  Est $1,617,835

  Not Listed For Sale

  54 Lake St, Vineyard Haven, MA 02568

  • 4 Beds
  • 3 Baths
  • 2,016 Sq Ft
  • Built 1967

  54 Lake St, Vineyard Haven, MA 02568

  Last Sold Summary

  • 110 Days On Market

  Last Listing Agent Jon Hartzband Martha's Vineyard Island-Wide Realty
• 

  

  /13

  $1,575,000

  $70K PRICE DROP

  • Land
  • 3.32 Acres
  • $474,398 per Acre

  26 Flint Hill Rd, 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 no

  Dawn Bellante Sandpiper Realty, Inc.

  26 Flint Hill Rd, West Tisbury, MA 02575
• 

  

  /22

  $1,575,000

  Sold Nov 24, 2025

  60 Windsor Dr, Edgartown, MA 02539

  • 4 Beds
  • 2 Baths
  • 1,666 Sq Ft
  • Built 1996

  Last Sold Summary

  • 5% Below List Price
  • $945/SF
  • 204 Days On Market

  Current Estimated Value $1,459,173

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

  60 Windsor Dr, Edgartown, MA 02539
• 

  

  /20

  Est $1,354,941

  Not Listed For Sale

  225 Longview Rd, Vineyard Haven, MA 02568

  • 3 Beds
  • 2 Baths
  • 1,730 Sq Ft
  • Built 1977

  225 Longview Rd, Vineyard Haven, MA 02568

  Last Sold Summary

  • 18 Days On Market

  Last Listing Agent Michele Casavant Vineyard Village Realty
• 

  

  /33

  $1,499,000

  $100K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 1,645 Sq Ft

  7 Ploughshare Ln, Oak Bluffs, MA 02557

  Nestled in a quiet cul-de-sac within the coveted Hidden Cove neighborhood, this delightful property offers an exceptional Island lifestyle. The association delivers rare water access via a private dock on Sengekontacket Pond, plus newly resurfaced tennis and pickleball courts. The open-concept layout flows seamlessly from the fireplaced living room and kitchen through the dining area to an

  Emma Kennedy Sandpiper Realty, Inc.

  7 Ploughshare Ln, Oak Bluffs, MA 02557
• 

  

  /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 $2,447,880

  Last Listing Agent Stephanie Roache Donnelly + Co.

  61 Causeway Rd, Vineyard Haven, MA 02568
• 

  /2

  Est $2,295,585

  Not Listed For Sale

  59 Field View Ln, Vineyard Haven, MA 02568

  • 4 Beds
  • 4 Baths
  • 3,269 Sq Ft
  • Built 1975

  59 Field View Ln, Vineyard Haven, MA 02568
• 

  

  /42

  $3,225,000

  Pending

  • 3 Beds
  • 4.5 Baths
  • 3,219 Sq Ft

  8 Woodhaven Dr, Edgartown, MA 02539

  Hidden behind a veil of privacy on a generous coastal sanctuary, an extraordinary property waits to be discovered. This custom masterpiece blends timeless architecture with a modern, elusive sophistication, offering comfortable finished living space within an impressive total structure. Cross the threshold onto rich hardwood floors where light dances beneath a dramatic cathedral ceiling, drawing

  Jennifer B. DaSilva Compass

  8 Woodhaven Dr, Edgartown, MA 02539
• 

  

  /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

Showing Results 161 - 200, Page 5 of 18