Vineyard Haven, MA Homes

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  /14

  $905,000

  Sold Sep 02, 2026

  22 Firehouse Ln, Oak Bluffs, MA 02557

  • 2 Beds
  • 1 Bath
  • 1,074 Sq Ft
  • Built 1980

  Last Sold Summary

  • 5% Below List Price
  • $843/SF
  • 64 Days On Market

  Last Listing Agent Jennifer O'hanlon Compass

  22 Firehouse Ln, Oak Bluffs, MA 02557
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  /8

  Not Listed For Sale

  0 Concord Ave, Oak Bluffs, MA 02568

  0 Concord Ave, Oak Bluffs, MA 02568

  Last Sold Summary

  • 83 Days On Market

  Last Listing Agent Leslie C. Floyd Portfolio Properties
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  /38

  $1,296,000

  Under Contract

  • 3 Beds
  • 2 Baths
  • 1,068 Sq Ft

  66 Hudson Ave, Oak Bluffs, MA 02557

  This warm and welcoming home with exceptional outdoor living space is sited on a beautifully landscaped lot just 1.5 miles from downtown Oak Bluffs. The private backyard, designed and cultivated by Donaroma’s, features a fenced lawn with irrigation, fire pit, outdoor dining area, and built-in grill—ideal for entertaining and relaxing. The open kitchen and living floor plan overlooks the backyard.

  Diana Gilmore Island Real Estate

  66 Hudson Ave, Oak Bluffs, MA 02557
• 

  

  /2

  $750,000

  Sold Oct 03, 2025

  35 Breakdown Ln, Oak Bluffs, MA 02557

  • 3 Beds
  • 2 Baths
  • 1,961 Sq Ft
  • Built 1983

  Last Sold Summary

  • $382/SF
  • 0 Days On Market

  Current Estimated Value $1,111,907

  Last Listing Agent LINK Email Cache LINK

  35 Breakdown Ln, Oak Bluffs, MA 02557
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  /6

  Not Listed For Sale

  0 Dudley St Unit 42584, Tisbury, MA 02568

  0 Dudley St Unit 42584, Tisbury, MA 02568

  Last Sold Summary

  • 0 Days On Market

  Last Listing Agent June Flake Viewpoints
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  /44

  $5,225,000

  $100K PRICE DROP

  • 6 Beds
  • 4 Baths
  • 2,890 Sq Ft

  4 Canonicus Ave, Oak Bluffs, MA 02557

  With a striking presence overlooking Nantucket Sound and just moments from the vibrant pulse of downtown, this distinctive compound is infused with a laid-back West Coast spirit while honoring the vintage charm of Oak Bluffs. Airy and effortlessly elegant, the four-bedroom main house has been masterfully updated, introducing refined, contemporary comforts, designed for every season. Tucked to the

  Katherine Donahue Sandpiper Realty

  4 Canonicus Ave, Oak Bluffs, MA 02557
• 

  

  /46

  $1,600,000

  Sold Jan 20, 2026

  5 Bayes Hill Cir, Vineyard Haven, MA 02568

  • 4 Beds
  • 2.5 Baths
  • 2,127 Sq Ft
  • Built 1997

  Last Sold Summary

  • 26% Below List Price
  • $752/SF
  • 182 Days On Market

  Current Estimated Value $1,730,027

  Last Listing Agent Rene Jackson Island Real Estate

  5 Bayes Hill Cir, Vineyard Haven, MA 02568
• 

  

  /9

  Not Listed For Sale

  21 Kennebec Ave Unit 6, Oak Bluffs, MA 02557

  • 1 Bed
  • 1 Bath
  • 985 Sq Ft
  • Built 2006

  21 Kennebec Ave Unit 6, Oak Bluffs, MA 02557

  Last Sold Summary

  • 0 Days On Market

  Last Listing Agent LINK Email Cache LINK
• 

  

  /24

  $925,000

  Pending Pre-Foreclosure

  • 2 Beds
  • 2 Baths
  • 1,000 Sq Ft

  67 Hudson Ave, Oak Bluffs, MA 02557

  ALL OFFERS REQUIRE COURT APPROVAL in multiple jurisdictions and may be somewhat lengthy. A straightforward offer is encouraged and may help expedite the required court approvals in multiple jurisdictions.Located in a convenient Oak Bluffs setting, this 2-bedroom, 2-bath home offers approximately 1,000 square feet of living space on a generous .69-acre lot. Built in 2014, the property presents

  Marilyn Moses Ocean Park Realty Inc

  67 Hudson Ave, Oak Bluffs, MA 02557
• 

  

  /32

  $1,475,000

  Sold Oct 10, 2025

  11 John Wesley Ave, Oak Bluffs, MA 02568

  • 4 Beds
  • 1.5 Baths
  • 1,304 Sq Ft
  • Built 1905

  Last Sold Summary

  • 5% Below List Price
  • $1,131/SF
  • 50 Days On Market

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

  11 John Wesley Ave, Oak Bluffs, MA 02568
• 

  

  /3

  Not Listed For Sale

  Baylis Woods Tashmoo Ave, Tisbury, MA 02568

  Baylis Woods Tashmoo Ave, Tisbury, MA 02568

  Last Sold Summary

  • 350 Days On Market

  Last Listing Agent Tom Zinno Vineyard Homes
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  /8

  $1,250,000

  • 1 Bed
  • 1 Bath
  • 855 Sq Ft

  0 Pennsylvania Ave Unit 43914, Oak Bluffs, MA 02568

  Unique new construction opportunity on Pennsylvania Ave in Oak Bluffs! Offered preconstruction so there is the ability to customize, this modern carriage house includes a spacious 1-bedroom apartment (855 sq ft with full kitchen, living room and bathroom) above a 2-car garage. Ideal for year round or seasonal residents, or businesses seeking to solve workforce housing needs along with secure

  Peyton Wallace Studio Realty

  0 Pennsylvania Ave Unit 43914, Oak Bluffs, MA 02568
• 

  

  /35

  $2,250,000

  Sold Dec 10, 2025

  10 Wood Duck Way, Oak Bluffs, MA 02557

  • 4 Beds
  • 3.5 Baths
  • 3,014 Sq Ft
  • Built 1980

  Last Sold Summary

  • 10% Below List Price
  • $747/SF
  • 119 Days On Market

  Current Estimated Value $2,390,178

  Last Listing Agent Marcia Sullivan Garvey Donnelly + Co.

  10 Wood Duck Way, Oak Bluffs, MA 02557
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  /66

  Not Listed For Sale

  95 Beach Rd Unit Residential & Commer, Vineyard Haven, MA 02568

  • 2 Beds
  • 3.5 Baths
  • 1,951 Sq Ft
  • Built 1935

  95 Beach Rd Unit Residential & Commer, Vineyard Haven, MA 02568

  Last Sold Summary

  • 81 Days On Market

  Last Listing Agent Alisan Lohan-Conway Alisan Lohan-Conway Properties
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  /27

  $2,695,000

  $130K PRICE DROP

  • 5 Beds
  • 2 Baths
  • 2,386 Sq Ft

  187 Lagoon Pond Rd, Vineyard Haven, MA 02568

  For the very first time, the historic Ben Luce Homestead (circa 1850) is being offered on the open market. This charming farmhouse blends rich Island history with timeless appeal.Once home to Benjamin Norton Luce (1840–1912) — Civil War veteran, blacksmith, and town constable — the property sits on 1.5 acres of pastoral land and offers 5 bedrooms, 2 full baths, solar panels, barn, and a newly

  Erin Leighton Compass

  187 Lagoon Pond Rd, Vineyard Haven, MA 02568
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  /2

  $500,000

  Sold Oct 02, 2025

  00 Tashmoo Ave Unit 19.3, Tisbury, MA 02568

  • Land
  • 14,422 Sq Ft
  • $1,510,118 per Acre

  Last Sold Summary

  • 0 Days On Market

  Last Listing Agent LINK Email Cache LINK

  00 Tashmoo Ave Unit 19.3, Tisbury, MA 02568
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  /3

  Not Listed For Sale

  2 Union St Unit A, Tisbury, MA 02568

  • 0.5 Baths
  • 1,100 Sq Ft
  • Built 2021

  2 Union St Unit A, Tisbury, MA 02568

  Last Sold Summary

  • 0 Days On Market

  Last Listing Agent LINK Email Cache LINK
• 

  

  /7

  $549,000

  $50K PRICE DROP

  • Land
  • 3,197 Sq Ft
  • $7,479,564 per Acre

  112 Dukes County Ave Unit 209, 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

  112 Dukes County Ave Unit 209, Oak Bluffs, MA 02557
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  /21

  $925,000

  Sold Mar 19, 2026

  95 Tashmoo Ave, Vineyard Haven, MA 02568

  • 3 Beds
  • 1 Bath
  • 1,380 Sq Ft
  • Built 1965

  Last Sold Summary

  • 7% Below List Price
  • $670/SF
  • 12 Days On Market

  Current Estimated Value $1,052,516

  Last Listing Agent Peter Cronig Cronigs Real Estate

  95 Tashmoo Ave, Vineyard Haven, MA 02568
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  /49

  Est $925,186

  Not Listed For Sale

  4 Quail Run Unit 17, Oak Bluffs, MA 02557

  • 2 Beds
  • 2 Baths
  • 1,208 Sq Ft
  • Built 1972

  4 Quail Run Unit 17, Oak Bluffs, MA 02557

  Last Sold Summary

  • 70 Days On Market

  Last Listing Agent Wendy Harman Compass | Point B
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  /27

  $1,299,000

  $100K PRICE DROP

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

  41 Edgartown Vineyard Haven 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

  41 Edgartown Vineyard Haven Rd, Vineyard Haven, MA 02568
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  /39

  $2,485,000

  Sold Apr 17, 2026

  63 Crowell Ln, Vineyard Haven, MA 02568

  • 6 Beds
  • 3.5 Baths
  • 3,000 Sq Ft
  • Built 1995

  Last Sold Summary

  • 8% Below List Price
  • $828/SF
  • 202 Days On Market

  Last Listing Agent Heather Dyas-Fried Tea Lane Associates

  63 Crowell Ln, Vineyard Haven, MA 02568
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  /56

  Not Listed For Sale

  9 Goode St, Oak Bluffs, MA 02557

  • 4 Beds
  • 4.5 Baths
  • 2,954 Sq Ft
  • Built 1900

  9 Goode St, Oak Bluffs, MA 02557

  Last Sold Summary

  • 314 Days On Market

  Last Listing Agent Grace Hagerty Grace Hagerty Real Estate Inc
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  /30

  $2,325,000

  $600K PRICE DROP

  • 5 Beds
  • 4 Baths
  • 3,704 Sq Ft

  21 Davis St, Vineyard Haven, MA 02568

  Ideally located just minutes from the heart of Vineyard Haven, 21 Davis Street offers exceptional island living in this beautifully crafted five-bedroom, four-bathroom home encompassing 3,704 square feet of thoughtfully designed living space. Rich hardwood flooring, custom cabinetry, elegant Restoration Hardware vanities, and custom tilework throughout the bathrooms reflect exceptional quality

  Valene Pires The Agency

  21 Davis St, Vineyard Haven, MA 02568
• 

  

  /59

  $4,500,000

  Sold Jun 11, 2026

  29 Majors Cove Ln, Edgartown, MA 02539

  • 5 Beds
  • 4 Baths
  • 3,518 Sq Ft
  • Built 1979

  Last Sold Summary

  • 4% Below List Price
  • $1,279/SF
  • 26 Days On Market

  Current Estimated Value $3,829,858

  Last Listing Agent Gerrett Conover Landvest MV

  29 Majors Cove Ln, Edgartown, MA 02539
• 

  

  /22

  Not Listed For Sale

  128 Manchester Ave, Oak Bluffs, MA 02568

  • 1 Bed
  • 2 Baths
  • 940 Sq Ft
  • Built 2025

  128 Manchester Ave, Oak Bluffs, MA 02568

  Last Sold Summary

  • 61 Days On Market

  Last Listing Agent Michele Moore Island Real Estate
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  /39

  $2,200,000

  $700K PRICE DROP Pending

  • 4 Beds
  • 3 Baths
  • 2,562 Sq Ft

  21 Woodlawn Ave, Vineyard Haven, MA 02568

  Thoughtfully designed with custom features throughout, this in-town Vineyard Haven home is the perfect blend of coastal charm and modern sophistication. The 4 bedroom 3 bath property offers a comfortable, easy flowing layout with gleaming hardwood floors and open sun-filled spaces.At the heart of the home is a chef-inspired gourmet kitchen with premium appliances, ample counter space, a

  Beth Welch Viewpoints

  21 Woodlawn Ave, Vineyard Haven, MA 02568
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  /4

  $435,000

  Sold Aug 18, 2026

  11 Boylston Dr, Edgartown, MA 02539

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

  Last Sold Summary

  • 2% Below List Price
  • 53 Days On Market

  Current Estimated Value $456,848

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

  11 Boylston Dr, Edgartown, MA 02539
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  /36

  Not Listed For Sale

  51 Black Brook Crossing Rd, West Tisbury, MA 02568

  • 4 Beds
  • 2.5 Baths
  • 2,691 Sq Ft
  • Built 1976

  51 Black Brook Crossing Rd, West Tisbury, MA 02568

  Last Sold Summary

  • 30 Days On Market

  Last Listing Agent Brenda Galligan Karen M. Overtoom R.E.
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  /7

  $850,000

  Under Contract

  • 2 Beds
  • 1 Bath
  • 992 Sq Ft

  61 Winemack St, Oak Bluffs, MA 02557

  Located in Oak Bluffs' desirable East Chop neighborhood, this 10,000± sq. ft. R2-zoned property offers an exceptional opportunity to renovate or build new (subject to applicable approvals). The existing two-bedroom, one-bath home is being sold as is.The level lot features a spacious yard and is ideally located just 0.9 miles from the East Chop Lighthouse, 1.3 miles from the East Chop

  Andrew McElhinney Compass LLC

  61 Winemack St, Oak Bluffs, MA 02557
• 

  

  /29

  $1,112,500

  Sold Dec 03, 2025

  324 Greenwood Ave, Vineyard Haven, MA 02568

  • 3 Beds
  • 2 Baths
  • 1,398 Sq Ft
  • Built 1983

  Last Sold Summary

  • 3% Below List Price
  • $796/SF
  • 38 Days On Market

  Current Estimated Value $1,239,625

  Last Listing Agent Emily Flake Viewpoints

  324 Greenwood Ave, Vineyard Haven, MA 02568
• 

  

  /29

  Est $1,122,420

  Not Listed For Sale

  10 Kims Way, Oak Bluffs, MA 02557

  • 4 Beds
  • 2.5 Baths
  • 1,976 Sq Ft
  • Built 1985

  10 Kims Way, Oak Bluffs, MA 02557

  Last Sold Summary

  • 9 Days On Market

  Last Listing Agent Michael Schweikert Ocean Park Realty Inc
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  /36

  $1,995,000

  • 5 Beds
  • 3 Baths
  • 3,480 Sq Ft

  135 Mayflower Ln, Vineyard Haven, MA 02568

  Ideally situated just minutes from the ferry, downtown Vineyard Haven, and West Tisbury, this charming, meticulously maintained property offers exceptional flexibility for year-round living, seasonal escape, or income potential. The main residence features three bedrooms and an inviting open-concept floor plan, seamlessly connecting an updated kitchen, living room, and dining area, perfect for

  Kathleen Dawson Donnelly + Co.

  135 Mayflower Ln, Vineyard Haven, MA 02568
• 

  

  /16

  $975,000

  Sold Mar 30, 2026

  12 Park Ave, Vineyard Haven, MA 02568

  • 3 Beds
  • 2 Baths
  • 1,469 Sq Ft
  • Built 1991

  Last Sold Summary

  • 25% Below List Price
  • $664/SF
  • 124 Days On Market

  Current Estimated Value $1,028,834

  Last Listing Agent Sheila Morse Island Real Estate

  12 Park Ave, Vineyard Haven, MA 02568
• 

  

  /23

  Est $1,548,618

  Not Listed For Sale

  12 Wing Rd, Oak Bluffs, MA 02557

  • 2 Beds
  • 2.5 Baths
  • 1,872 Sq Ft
  • Built 2014

  12 Wing Rd, Oak Bluffs, MA 02557

  Last Sold Summary

  • 9 Days On Market

  Last Listing Agent Barbara Twiss Laer Realty Partners
• 

  

  /25

  $6,500,000

  • 6 Beds
  • 7 Baths
  • 4,753 Sq Ft

  16 Red Coat Hill Rd, Vineyard Haven, MA 02568

  Private West Tisbury Oasis – Modern Luxury on 4.85 AcresBuilt by the highly regarded Novo Builds and designed by acclaimed architect Zander Auerbach, this newly constructed estate in the heart of West Tisbury offers the perfect blend of architectural sophistication, privacy, and resort-style amenities. Set on 4.85 acres, the main residence spans 3,806 square feet with an additional

  Joe & Nicole Holland Vineyard Dream Realty LLC

  16 Red Coat Hill Rd, Vineyard Haven, MA 02568
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  /34

  $2,850,000

  Sold Dec 16, 2025

  311 E Chop Dr, Oak Bluffs, MA 02557

  • 4 Beds
  • 2.5 Baths
  • 1,800 Sq Ft
  • Built 1900

  Last Sold Summary

  • 5% Below List Price
  • $1,583/SF
  • 19 Days On Market

  Current Estimated Value $3,269,860

  Last Listing Agent Dawn Bellante-Holand Sandpiper Realty

  311 E Chop Dr, Oak Bluffs, MA 02557
• 

  

  /18

  Est $1,011,315

  Not Listed For Sale

  41 Waterview Rd, Oak Bluffs, MA 02557

  • 3 Beds
  • 1.5 Baths
  • 869 Sq Ft
  • Built 1970

  41 Waterview Rd, Oak Bluffs, MA 02557

  Last Sold Summary

  • 22 Days On Market

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

  

  /23

  $849,000

  $50K PRICE DROP

  • 1 Bed
  • 1.5 Baths
  • 1,182 Sq Ft

  4 Quail Run Unit 1, Oak Bluffs, MA 02557

  Located in a desirable waterfront community, this newly painted end-unit condo offers 1 bedroom plus a versatile loft and 1.5 bathrooms, combining comfort with easy, low-maintenance ownership. Residents enjoy a community dock, pond access, kayak storage, boat launch, a clubhouse, and tennis courts. This year-round home is filled with natural light and features a spacious deck —perfect for

  Jarrett Hurwitz Keller Williams Realty

  4 Quail Run Unit 1, Oak Bluffs, MA 02557
• 

  

  /10

  $925,000

  Sold Sep 14, 2026

  15 Goah Way, Vineyard Haven, MA 02568

  • 3 Beds
  • 3 Baths
  • 1,581 Sq Ft
  • Built 1920

  Last Sold Summary

  • 23% Below List Price
  • $585/SF
  • 152 Days On Market

  Current Estimated Value $1,142,562

  Last Listing Agent Roy Cutrer Jr Laer Realty Partners

  15 Goah Way, Vineyard Haven, MA 02568

Showing Results 521 - 560, Page 14 of 18