Vineyard Haven, MA Homes

• 

  

  

  /24

  $3,050,000

  Sold Apr 15, 2026

  35 New York Ave, Oak Bluffs, MA 02568

  • 7 Beds
  • 5 Baths
  • 3,880 Sq Ft
  • Built 1884

  Last Sold Summary

  • 13% Below List Price
  • $786/SF
  • 23 Days On Market

  Last Listing Agent Emma Kennedy Sandpiper Realty, Inc.

  35 New York Ave, Oak Bluffs, MA 02568
• 

  

  

  /16

  Est $1,780,358

  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
• 

  

  

  /13

  $1,400,000

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

  318 Lamberts Cove Rd, Vineyard Haven, MA 02568

  Walk to the splendid sands of Lamberts Cove Beach for an afternoon dip followed by a romantic dinner at the nearby Inn. Fabulous location. The enchanting path to the white-rimmed cove is a mere 4-minute walk away. Main house with three bedrooms,large living room, many-windowed kitchen, artist's studio and upstairs sun room. The newer two story Guest House is bright and inviting nestled in the

  Holly Alaimo Tashmoo Realty

  318 Lamberts Cove Rd, Vineyard Haven, MA 02568
• 

  

  

  /22

  $1,100,000

  Sold Apr 30, 2026

  14 21st St N, Edgartown, MA 02539

  • 3 Beds
  • 1.5 Baths
  • 1,304 Sq Ft
  • Built 1978

  Last Sold Summary

  • 8% Below List Price
  • $844/SF
  • 141 Days On Market

  Current Estimated Value $1,157,876

  Last Listing Agent Fran Agnoli The Agency

  14 21st St N, Edgartown, MA 02539
• 

  

  

  /44

  Est $7,912,362

  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
• 

  

  /4

  $445,000

  $53K PRICE DROP

  • Land
  • 23,958 Sq Ft
  • $809,091 per Acre

  11 Boylston Dr Unit 1.314, Edgartown, MA 02539

  A picturesque half-acre lot in the desirable Edgartown neighborhood, perfect for building your Martha's Vineyard home. Bordered by more than 175 acres of pristine conservation land, this property offers peaceful surroundings with easy access to the island’s top attractions, including stunning beaches, scenic trails, vast state forests, and public transportation. In accordance with recent

  Alyssa Halisky Wallace & Co. Sotheby's

  11 Boylston Dr Unit 1.314, Edgartown, MA 02539
• 

  

  /16

  $970,000

  Sold Dec 08, 2025

  6 Sachem Way, Oak Bluffs, MA 02557

  • 3 Beds
  • 1 Bath
  • 1,546 Sq Ft
  • Built 1973

  Last Sold Summary

  • 8% Above List Price
  • $627/SF
  • 4 Days On Market

  Current Estimated Value $1,033,665

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

  6 Sachem Way, Oak Bluffs, MA 02557
• 

  

  /47

  Est $2,324,029

  Not Listed For Sale

  42 Hagerty Dr, Vineyard Haven, MA 02568

  • 4 Beds
  • 4.5 Baths
  • 2,569 Sq Ft
  • Built 1970

  42 Hagerty Dr, Vineyard Haven, MA 02568

  Last Sold Summary

  • 58 Days On Market
• 

  

  /36

  $2,250,000

  Under Contract

  • 4 Beds
  • 4 Baths
  • 2,340 Sq Ft

  11 Oak Ln, Vineyard Haven, MA 02568

  Welcome to 11 Oak Lane, a rare West Tisbury offering that lives as a true Martha's Vineyard family compound, an income-producing investment, or both. Set on 2.7 private acres, the property has been meticulously maintained and recently updated from the systems up, giving you the flexibility to gather generations under one address, live in one home and rent the other, or simply enjoy an exceptional

  Patrick McCarthy Grace Hagerty Real Estate Inc

  11 Oak Ln, Vineyard Haven, MA 02568
• 

  

  /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 $3,065,759

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

  78 Winemack St, Oak Bluffs, MA 02557
• 

  

  /16

  Est $1,360,285

  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
• 

  

  /40

  $1,395,000

  • 4 Beds
  • 3 Baths
  • 1,305 Sq Ft

  46 Kennebec Ave, Oak Bluffs, MA 02557

  This exquisite Victorian home, lovingly preserved by the same family for over a generation, stands in outstanding condition and is perfectly situated in the vibrant heart of Oak Bluffs Center. Enjoy the convenience of being just steps away from the Public Beach, Steamship Authority, Oak Bluffs Harbor, a supermarket, and a variety of charming restaurants and shops that contribute to Oak Bluffs'

  Michael Schweikert Ocean Park Realty Inc

  46 Kennebec Ave, Oak Bluffs, MA 02557
• 

  

  /20

  $1,295,000

  Sold Sep 05, 2025

  2 Upper Douglas Ln, Oak Bluffs, MA 02557

  • 4 Beds
  • 2 Baths
  • 1,584 Sq Ft
  • Built 1988

  Last Sold Summary

  • 3% Below List Price
  • $818/SF
  • 5 Days On Market

  Current Estimated Value $1,361,639

  Last Listing Agent Lynn Buder Sandpiper Realty

  2 Upper Douglas Ln, Oak Bluffs, MA 02557
• 

  

  /28

  Est $1,229,456

  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
• 

  

  /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
• 

  

  /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 $1,746,228

  Last Listing Agent Katherine Donahue Sandpiper Realty

  35 Tower Ridge Rd, Oak Bluffs, MA 02557
• 

  

  /86

  Est $1,581,571

  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
• 

  

  /33

  $3,750,000

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

  28 Beach Rd, Oak Bluffs, MA 02557

  Location, Location, location....This is rare opportunity to own a water front property with 240 degree views of the Harbor and Sound. The property is 5 minutes from either Ferry terminal and walking distance to East beach . The house is suitable for year round living , seasonal income and comfort through and through

  Scott Lewis Lewis Real Estate Services, LLC

  28 Beach Rd, Oak Bluffs, MA 02557
• 

  

  /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 $783,440

  Last Listing Agent Marilyn Moses Ocean Park Realty Inc

  17 Siloam Ave, Oak Bluffs, MA 02557
• 

  

  /19

  Est $1,320,995

  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
• 

  

  /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
• 

  /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 $4,543,714

  Last Listing Agent Jill Napior Tea Lane Associates

  662 Chappaquonsett Rd, Vineyard Haven, MA 02568
• 

  

  /29

  Est $1,483,009

  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
• 

  

  /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
• 

  

  /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 $1,326,953

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

  23 Laurel Ave, Oak Bluffs, MA 02557
• 

  /2

  Est $1,173,926

  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
• 

  

  /38

  $1,755,000

  $40K PRICE DROP

  • 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
• 

  

  /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 $1,641,964

  Last Listing Agent Lisa Da Silva Signal House Group at Compass

  105 Stoney Hill Rd, Vineyard Haven, MA 02568
• 

  

  /23

  Est $999,570

  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
• 

  

  /33

  $1,995,000

  • 3 Beds
  • 2.5 Baths
  • 1,431 Sq Ft

  33 Vineyard Ave, Oak Bluffs, MA 02557

  Welcome to 33 Vineyard Avenue in Oak Bluffs, Martha’s Vineyard. This fully renovated property features a 2BR/2BA primary home plus a separate 1BR/1BA suite—offering flexible, move-in ready living or investment potential in a prime in-town location. The main residence showcases a light-filled interior, wood floors, beamwork, and refined finishes throughout. Open living flows to a gourmet kitchen

  Allison Cameron Parry Douglas Elliman Real Estate - Nantucket

  33 Vineyard 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 $1,317,619

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

  32 MacHipscat Trail, Vineyard Haven, MA 02568
• 

  /2

  Est $972,084

  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
• 

  

  /21

  $2,150,000

  $100K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,867 Sq Ft

  237 Lagoon Pond Rd, Vineyard Haven, MA 02568

  Ideally located at the beginning of Hines Point, this light-filled, well-maintained home offers a central setting with easy access to the Lagoon, the MV Museum, and town. Public water access is just a short walk away, making it easy to enjoy all the benefits of this special area.Set on a gentle rise overlooking the Lagoon, the home is filled with natural light and offers beautiful water

  Alison Rich Carroll & Vincent R.E.

  237 Lagoon Pond 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
• 

  

  /44

  Est $1,402,287

  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
• 

  

  /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
• 

  

  /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 $2,218,495

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

  30 Sengekontacket Rd, Oak Bluffs, MA 02557
• 

  

  /19

  Est $1,069,013

  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
• 

  

  /35

  $1,369,000

  $26K PRICE DROP

  • 4 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 4-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
• 

  

  /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

Showing Results 281 - 320, Page 8 of 18