Tisbury, MA Homes

• 

  

  /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 $4,643,458

  Last Listing Agent Jill Napior Tea Lane Associates

  662 Chappaquonsett Rd, Vineyard Haven, MA 02568
• 

  

  

  /29

  Est $1,471,213

  Not Listed For Sale

  140 Tashmoo Ave, Vineyard Haven, MA 02568

  • 3 Beds
  • 2.5 Baths
  • 1,528 Sq Ft
  • Built 1993

  140 Tashmoo Ave, Vineyard Haven, MA 02568

  Last Sold Summary

  • 122 Days On Market
• 

  

  

  /30

  $3,245,000

  • 4 Beds
  • 4.5 Baths
  • 3,927 Sq Ft

  44 Tiffany Dr, Oak Bluffs, MA 02557

  This handsome, newly renovated classic Cape, is nestled on a private 1.38 acre lot in the sought after Lagoon Estates community. The property has been thoughtfully renovated with two new kitchens, 5 new bathrooms, 4-bedrooms (two ensuite), all new windows and new flooring on first floor. It's seamless floor plan is great for entertaining and flows family and guests from an oversized living room

  Perry Patterson MV Luxury Homes

  44 Tiffany Dr, Oak Bluffs, MA 02557
• 

  

  

  /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 $1,273,195

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

  23 Laurel Ave, Oak Bluffs, MA 02557
• 

  

  /2

  Est $1,211,607

  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

  Last Sold Summary
• 

  

  /4

  $809,000

  • Land
  • 16,901 Sq Ft
  • $2,085,052 per Acre

  7 Highland Ave Unit 119, Vineyard Haven, MA 02568

  Rare opportunity in East Chop. Beautiful lot in a serene, wooded area, walking distance to town, beach, and ferries. Secluded yet accessible. This is a pre-existing nonconforming lot, with a legal opinion letter attached stating buildability. Buyer to perform all due diligence regarding town building requirements. Opportunity for buyer to design to their own specifications.

  Shera Toledo eXp Realty

  7 Highland Ave Unit 119, 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 $1,622,178

  Last Listing Agent Lisa Da Silva Signal House Group at Compass

  105 Stoney Hill Rd, Vineyard Haven, MA 02568
• 

  

  /23

  Est $980,902

  Not Listed For Sale

  95 Summer St, Vineyard Haven, MA 02568

  • 3 Beds
  • 2 Baths
  • 836 Sq Ft
  • Built 1973

  95 Summer St, Vineyard Haven, MA 02568

  Last Sold Summary

  • 25 Days On Market
• 

  

  /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
• 

  

  /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 $1,294,419

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

  32 MacHipscat Trail, Vineyard Haven, MA 02568
• 

  /2

  Est $992,645

  Not Listed For Sale

  26 Midland Ave, Vineyard Haven, MA 02568

  • 3 Beds
  • 1 Bath
  • 1,186 Sq Ft
  • Built 1940

  26 Midland Ave, Vineyard Haven, MA 02568

  Last Sold Summary
• 

  

  /38

  $1,795,000

  • 3 Beds
  • 3 Baths
  • 2,695 Sq Ft

  68 Front St, Oak Bluffs, MA 02557

  Nestled at the end of a quiet street, this charming and spacious Cape-style home offers both privacy and convenience, just a short distance from the Oak Bluffs School and town center, and walking distance to the Lagoon. Thoughtfully maintained, the sun-filled main level boasts an open floor plan with large windows that frame views of the surrounding property. The generously sized kitchen features

  Jayne Isford Ocean Park Realty Inc

  68 Front St, Oak Bluffs, MA 02557
• 

  

  /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
• 

  

  /44

  Est $1,447,752

  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
• 

  

  /48

  $1,495,000

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

  651 State Rd, Vineyard Haven, MA 02568

  Fabulous four-building farmhouse compound offered in the heart of West Tisbury. This cherished property features a well-maintained classic 1880 main house with 4 bedrooms and 3 baths, plus a fully separate guest cottage with 1 bedroom and 1 bath — offering immediate income potential through seasonal or year-round rental. A bunkhouse/office building provides flexible space ideal for a home office

  Jim Feiner Feiner Real Estate

  651 State Rd, Vineyard Haven, 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 $2,132,986

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

  30 Sengekontacket Rd, Oak Bluffs, MA 02557
• 

  

  /19

  Est $1,042,987

  Not Listed For Sale

  160 Spring Hill Rd, Vineyard Haven, MA 02568

  • 3 Beds
  • 2 Baths
  • 1,235 Sq Ft
  • Built 1983

  160 Spring Hill Rd, Vineyard Haven, MA 02568

  Last Sold Summary

  • 2 Days On Market
• 

  

  /36

  $2,400,000

  • 5 Beds
  • 4 Baths
  • 3,328 Sq Ft

  159 Lake St, Vineyard Haven, MA 02568

  Tucked back from the road on scenic Lake Street, this one-of-a-kind home offers privacy and charm on a beautifully landscaped 0.7 acre lot accented by mature trees and a classic stone wall. Inside, rich wood detailing, exposed beams, and high ceilings create a warm and inviting atmosphere. The home’s four-level design provides exceptional character and flexibility. The main level features a

  Alyssa Halisky Wallace & Co. Sotheby's

  159 Lake St, Vineyard Haven, MA 02568
• 

  

  /22

  $975,000

  Sold Jul 07, 2025

  128 Manchester Ave, Oak Bluffs, MA 02568

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

  Last Sold Summary

  • $1,037/SF
  • 61 Days On Market

  Last Listing Agent Michele Moore Island Real Estate

  128 Manchester Ave, Oak Bluffs, MA 02568
• 

  

  /72

  Est $1,177,658

  Not Listed For Sale

  18 Goah Way, Vineyard Haven, MA 02568

  • 4 Beds
  • 2 Baths
  • 1,861 Sq Ft
  • Built 1998

  18 Goah Way, Vineyard Haven, MA 02568

  Last Sold Summary

  • 135 Days On Market
• 

  

  /32

  $1,395,000

  • 3 Beds
  • 2.5 Baths
  • 1,783 Sq Ft

  51 Summer St, Vineyard Haven, MA 02568

  Rare under-$1.4M value story in Vineyard Haven. In a Martha’s Vineyard price range where buyers are often choosing between smaller homes, dated interiors, limited bath count, or properties needing immediate improvements, 51 Summer Street offers a cleaner path. This updated 3-bedroom, 2.5-bath home features 1,783 square feet of well-planned living space in a convenient Vineyard Haven setting near

  Janet Scott eXp Realty

  51 Summer St, Vineyard Haven, MA 02568
• 

  

  /24

  $1,200,180

  Sold Aug 12, 2025

  110 Otis Bassett Rd, Vineyard Haven, MA 02568

  • 3 Beds
  • 1 Bath
  • 1,144 Sq Ft
  • Built 1972

  Last Sold Summary

  • $1,049/SF
  • 13 Days On Market

  Current Estimated Value $1,161,646

  Last Listing Agent Jennifer O'hanlon Compass LLC

  110 Otis Bassett Rd, Vineyard Haven, MA 02568
• 

  

  /35

  Est $1,368,170

  Not Listed For Sale

  26 Heath Hen Ln, Vineyard Haven, MA 02568

  • 3 Beds
  • 2.5 Baths
  • 2,076 Sq Ft
  • Built 1983

  26 Heath Hen Ln, Vineyard Haven, MA 02568

  Last Sold Summary

  • 84 Days On Market
• 

  

  /31

  $4,695,000

  • 3 Beds
  • 2 Baths
  • 1,716 Sq Ft

  16 Frog Hollow, Vineyard Haven, MA 02568

  Downtown Vineyard Haven with Harbor Views. Positioned between the energy of Main Street and the quiet prestige of West Chop, this location delivers a rare balance of downtown access, privacy, and harbor frontage.Built in 2015, the three-bedroom, two-bath modern ranch is designed for easy first-floor living with expansive water views. Wide, harbor-facing windows showcase the meadow and water

  Rose Ryley Wallace & Co. Sotheby's

  16 Frog Hollow, Vineyard Haven, 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 $159,170

  Last Listing Agent Nantucket CompLINK LINK

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

  

  /28

  Est $1,028,837

  Not Listed For Sale

  280 State Rd, Vineyard Haven, MA 02568

  • 4 Beds
  • 2 Baths
  • 1,387 Sq Ft
  • Built 1920

  280 State Rd, Vineyard Haven, MA 02568

  Last Sold Summary

  • 3 Days On Market
• 

  

  /42

  $1,275,000

  $520K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,033 Sq Ft

  9 Brunswick Ave, Oak Bluffs, MA 02557

  PRIME LOCATION! Beautifully Renovated in Oak Bluffs! This move-in ready home at 9 Brunswick Ave has been thoughtfully and extensively UPDATED inside and out. Enjoy peace of mind with a NEW septic system, siding, windows, water line from the street, and upgraded electrical and plumbing. The interior boasts NEW flooring, insulation, fresh paint, a stylishly renovated kitchen, and efficient new

  Alice Pierce Coldwell Banker Realty - Martha's Vineyard

  9 Brunswick Ave, 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 $1,172,363

  Last Listing Agent Kathleen Kendrick Kathleen Kendrick

  52 Old Coach Rd, Vineyard Haven, MA 02568
• 

  

  /45

  Not Listed For Sale

  15 Canterbury Ln, Vineyard Haven, MA 02568

  • 6 Beds
  • 3 Baths
  • 3,394 Sq Ft
  • Built 1987

  15 Canterbury Ln, Vineyard Haven, MA 02568

  Last Sold Summary

  • 14 Days On Market
• 

  

  /21

  $799,900

  • Land
  • 1.4 Acres
  • $571,357 per Acre

  90 Charles Neck Way, West Tisbury, MA 02568

  Spacious 1.4-acre corner lot in Vineyard Meadow Farms. This private parcel sits on a paved road with no unwanted through traffic and is centrally located to all Island towns. Enjoy a peaceful neighborhood and easy access to Long Point Wild Refuge Beach and the Nature Preserve conservation land, featuring 632 acres of Trustees of the Reservations beach and trails. Pack a lunch and spend a relaxing

  Kimberly Rocci Keller Williams Realty Colonial Partners

  90 Charles Neck Way, West Tisbury, MA 02568
• 

  

  /37

  $2,495,000

  Sold Nov 20, 2025

  16 Mockingbird Dr, Edgartown, MA 02539

  • 4 Beds
  • 6 Baths
  • 2,694 Sq Ft
  • Built 2016

  Last Sold Summary

  • 6% Below List Price
  • $926/SF
  • 146 Days On Market

  Current Estimated Value $2,432,604

  Last Listing Agent Emma Kennedy Sandpiper Realty

  16 Mockingbird Dr, Edgartown, MA 02539
• 

  

  /30

  Est $898,639

  Not Listed For Sale

  7 Elm St, Vineyard Haven, MA 02568

  • 2 Beds
  • 1 Bath
  • 962 Sq Ft
  • Built 1969

  7 Elm St, Vineyard Haven, MA 02568

  Last Sold Summary

  • 213 Days On Market
• 

  

  /38

  $2,495,000

  Under Contract

  • 6 Beds
  • 2.5 Baths
  • 2,577 Sq Ft

  16 Atlantic Ave, Oak Bluffs, MA 02557

  Oak Bluffs | East Chop - Tucked away on a quiet lane just moments from the iconic East Chop Lighthouse and breathtaking bluff views, this timeless retreat invites you to embrace the slower pace of island life. The stately five-bedroom main residence is rich in character and nostalgic charm, thoughtfully updated to enhance comfort for year-round living. Tucked privately at the rear of the

  Katherine Donahue Sandpiper Realty

  16 Atlantic Ave, Oak Bluffs, MA 02557
• 

  /2

  $1,775,000

  Sold Mar 02, 2026

  14 Chapman Ave, Oak Bluffs, MA 02557

  • 5 Beds
  • 2 Baths
  • 1,469 Sq Ft
  • Built 1890

  Last Sold Summary

  • $1,208/SF
  • 0 Days On Market

  Current Estimated Value $1,691,485

  Last Listing Agent LINK Email Cache LINK

  14 Chapman Ave, Oak Bluffs, MA 02557
• 

  

  /22

  Not Listed For Sale

  189 Winyah Ln, Vineyard Haven, MA 02568

  • 3 Beds
  • 1.5 Baths
  • 576 Sq Ft
  • Built 1974

  189 Winyah Ln, Vineyard Haven, MA 02568

  Last Sold Summary

  • 50 Days On Market
• 

  

  /39

  $3,250,000

  • 5 Beds
  • 3.5 Baths
  • 4,068 Sq Ft

  241 Daggett Ave, Vineyard Haven, MA 02568

  Built in 2016 by Squash Meadow Builders, this exceptional five bedroom Colonial sits moments from the sandy shores of Tashmoo Beach on Vineyard Sound. Spanning four levels, it blends timeless architecture with modern comfort. The main floor offers open living with gas fireplace, a gourmet kitchen with custom built-ins and bench seating, and a sunlit sunroom for relaxed coastal living. A private

  Alyssa Halisky Wallace & Co. Sotheby's International Realty

  241 Daggett Ave, Vineyard Haven, MA 02568
• 

  

  /16

  $800,000

  Sold Sep 04, 2025

  21 Norris Ave, Vineyard Haven, MA 02568

  • 2 Beds
  • 1 Bath
  • 1,086 Sq Ft
  • Built 1948

  Last Sold Summary

  • $737/SF
  • 16 Days On Market

  Current Estimated Value $820,277

  Last Listing Agent Rene Ben David Ocean Park Realty Inc

  21 Norris Ave, Vineyard Haven, MA 02568
• 

  

  /20

  Est $1,015,566

  Not Listed For Sale

  33 Renear St, Vineyard Haven, MA 02568

  • 3 Beds
  • 1.5 Baths
  • 1,200 Sq Ft
  • Built 1950

  33 Renear St, Vineyard Haven, MA 02568

  Last Sold Summary

  • 7 Days On Market
• 

  

  /73

  $3,200,000

  $600K PRICE DROP

  • 4 Beds
  • 3.5 Baths
  • 3,274 Sq Ft

  70 Spring St, Vineyard Haven, MA 02568

  NOW INCLUDING RARE 12,527 S.F. TOWN APPROVED BUILDING LOT ON WILLIAM STREET! Storybook setting in the quaint seaside village of Vineyard Haven, the commanding Captain Gilbert L. Smith House*, c. 1854, affords an enchanting opportunity for space and privacy within the highly sought after William Street Historic District, just two blocks to all the shops, restaurants, galleries, town beach, tennis,

  June Flake Viewpoints

  70 Spring St, Vineyard Haven, MA 02568
• 

  

  /31

  $941,000

  Sold Oct 03, 2025

  4 Quail Run Unit 7, Oak Bluffs, MA 02557

  • 2 Beds
  • 1.5 Baths
  • 1,323 Sq Ft
  • Built 1972

  Last Sold Summary

  • $711/SF
  • 52 Days On Market

  Current Estimated Value $928,859

  Last Listing Agent Janna O'Loughlin Portfolio Properties

  4 Quail Run Unit 7, Oak Bluffs, MA 02557

Showing Results 321 - 360, Page 9 of 18