Vineyard Haven, MA Homes

• 

  

  

  /22

  $1,000,000

  $100K PRICE DROP Pending

  • 2 Beds
  • 1 Bath
  • 1,118 Sq Ft

  4 5th St N, Edgartown, MA 02539

  An exciting rare find off the Edgartown / Tisbury road directly across from the bike path. The first floor open plan includes a fire place, family room and kitchen with a walk out to the wrap around porch. Two pleasant bedrooms and a full bath are on the first floor. The upper level loft opens to the living room visually expanding the living space. The house has the benefit of a full basement

  Doug Burke Signal House Group at Compass

  4 5th St N, Edgartown, MA 02539
• 

  

  /2

  $660,000

  Sold May 26, 2026

  3 Elmwood Ave Unit 23, Oak Bluffs, MA 02568

  • Land
  • 6,534 Sq Ft
  • $4,400,000 per Acre

  Last Sold Summary

  • 0 Days On Market

  Last Listing Agent Eleanor Wilson LINK

  3 Elmwood Ave Unit 23, Oak Bluffs, MA 02568
• 

  

  

  /25

  Est $1,232,165

  Not Listed For Sale

  160 Causeway Rd, Vineyard Haven, MA 02568

  • 3 Beds
  • 2 Baths
  • 1,776 Sq Ft
  • Built 1948

  160 Causeway Rd, Vineyard Haven, MA 02568

  Last Sold Summary

  • 115 Days On Market

  Last Listing Agent Karen Overtoom Karen M. Overtoom R.E.
• 

  

  

  /42

  $2,590,000

  $360K PRICE DROP

  • 4 Beds
  • 8 Baths
  • 4,530 Sq Ft

  15 21st St N, Edgartown, MA 02539

  Located on a quiet street just minutes from Edgartown Village, this versatile compound offers privacy, flexibility, and close proximity to the Island’s best outdoor amenities. Set on over half an acre, the property includes a main house and detached guest house with separate driveways and mature landscaping.The main home features an open kitchen and dining area, sunken living room, and three

  Jennifer O'hanlon Compass

  15 21st St N, Edgartown, MA 02539
• 

  

  

  /38

  $2,450,000

  Sold Jun 02, 2026

  16 Atlantic Ave, Oak Bluffs, MA 02557

  • 6 Beds
  • 2.5 Baths
  • 2,577 Sq Ft
  • Built 1890

  Last Sold Summary

  • 2% Below List Price
  • $951/SF
  • 10 Days On Market

  Last Listing Agent Katherine Donahue Sandpiper Realty

  16 Atlantic Ave, Oak Bluffs, MA 02557
• 

  

  /19

  Est $987,622

  Not Listed For Sale

  238 State Rd, Vineyard Haven, MA 02568

  • 3 Beds
  • 1 Bath
  • 1,184 Sq Ft
  • Built 1920

  238 State Rd, Vineyard Haven, MA 02568

  Last Sold Summary

  • 83 Days On Market

  Last Listing Agent Elissa Lash Tea Lane Associates
• 

  

  /16

  $1,095,000

  $154K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 998 Sq Ft

  299 Daggett Ave Unit A, Vineyard Haven, MA 02568

  This cheerful sun drenched three-bed & one bath home with cathedral ceilings sits on just over an acre of gently rolling land surrounded by mature pines, oaks and ornamental plantings. Inspired by Norwegian architecture, the current owner designed and built this home in 1999 with his wife who was an artist from Norway. It’s located about a mile to town in one direction and the beach in the other.

  Karen Overtoom Karen M. Overtoom R.E.

  299 Daggett Ave Unit A, Vineyard Haven, MA 02568
• 

  

  /20

  $992,500

  Sold Dec 22, 2025

  72 Washington Ave, Vineyard Haven, MA 02568

  • 1 Bed
  • 1.5 Baths
  • 1,152 Sq Ft
  • Built 2019

  Last Sold Summary

  • 4% Below List Price
  • $862/SF
  • 6 Days On Market

  Current Estimated Value $1,081,521

  Last Listing Agent Martha Smith C McManus Realty Group

  72 Washington Ave, Vineyard Haven, MA 02568
• 

  

  /23

  Est $1,276,272

  Not Listed For Sale

  180 Main St Unit 30, Vineyard Haven, MA 02568

  • 2 Beds
  • 2 Baths
  • 1,300 Sq Ft
  • Built 1860

  180 Main St Unit 30, Vineyard Haven, MA 02568

  Last Sold Summary

  • 96 Days On Market

  Last Listing Agent Sean Federowicz Landmarks at TODAY Real Estate
• 

  

  /65

  $2,550,000

  $649K PRICE DROP

  • 6 Beds
  • 4 Baths
  • 2,618 Sq Ft

  55 Old House Way, West Tisbury, MA 02575

  Lambert’s Cove/West Tisbury- custom-built contemporary farmhouse style. 4 bedrooms & 3 bathrooms in Main & 2 bedrooms & 1 bath Guest Cottage on 3 acres in a private neighborhood. Enter Main house from the covered porch -matching custom arch doors lead you to either the mudroom/laundry room-kitchen entry, or the living room. The kitchen has Mexican tiled floor & granite counters with stainless

  Leslie Graham Anchor Realty of Martha's Vineyard

  55 Old House Way, West Tisbury, MA 02575
• 

  /2

  $1,280,000

  Sold Dec 12, 2025

  1 Edgewood Dr, Edgartown, MA 02539

  • 3 Beds
  • 2 Baths
  • 1,604 Sq Ft

  Last Sold Summary

  • $798/SF
  • 0 Days On Market

  Current Estimated Value $1,445,911

  Last Listing Agent LINK Email Cache LINK

  1 Edgewood Dr, Edgartown, MA 02539
• 

  

  /24

  Est $1,967,862

  Not Listed For Sale

  70 Tashmoo Ave, Vineyard Haven, MA 02568

  • 5 Beds
  • 4 Baths
  • 3,298 Sq Ft
  • Built 1920

  70 Tashmoo Ave, Vineyard Haven, MA 02568

  Last Sold Summary

  • 88 Days On Market

  Last Listing Agent Tina Miller Donnelly + Co.
• 

  

  /28

  $2,290,000

  $205K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 2,600 Sq Ft

  268 Tashmoo Ave, Vineyard Haven, MA 02568

  Welcome to this meticulously maintained home which features an attractive open kitchen with an island that seats four. The kitchen has a wall of built in appliances and a walk-in pantry for ease of cooking. The kitchen flows into the open dining area and lounge area with a wall of sliding glass doors that lead to the large outdoor entertaining area which features a lounge area and two eating

  Michele Casavant Vineyard Village Realty

  268 Tashmoo Ave, Vineyard Haven, MA 02568
• 

  

  /33

  $2,025,000

  Sold Sep 30, 2025

  1 Rowland Ave, Oak Bluffs, MA 02557

  • 6 Beds
  • 3 Baths
  • 3,009 Sq Ft
  • Built 1853

  Last Sold Summary

  • 7% Above List Price
  • $673/SF
  • 6 Days On Market

  Current Estimated Value $1,981,722

  Last Listing Agent Lynn Buder Sandpiper Realty

  1 Rowland Ave, Oak Bluffs, MA 02557
• 

  /2

  Est $1,032,845

  Not Listed For Sale

  299 Franklin St, Vineyard Haven, MA 02568

  • 3 Beds
  • 2 Baths
  • 1,286 Sq Ft
  • Built 1950

  299 Franklin St, Vineyard Haven, MA 02568
• 

  

  /36

  $2,250,000

  Pending

  • 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
• 

  

  /4

  $1,130,000

  Sold Apr 28, 2026

  202 Lake St, Vineyard Haven, MA 02568

  • 4 Beds
  • 2 Baths
  • 1,414 Sq Ft
  • Built 1988

  Last Sold Summary

  • $799/SF
  • 0 Days On Market

  Current Estimated Value $1,140,150

  Last Listing Agent LINK Email Cache LINK

  202 Lake St, Vineyard Haven, MA 02568
• 

  /2

  Est $1,293,933

  Not Listed For Sale

  26 Daggett Ave, Vineyard Haven, MA 02568

  • 3 Beds
  • 2 Baths
  • 1,308 Sq Ft
  • Built 1904

  26 Daggett Ave, Vineyard Haven, MA 02568
• 

  

  /40

  $1,350,000

  $45K PRICE DROP

  • 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'

  Cathy Gargiulo Ocean Park Realty Inc

  46 Kennebec Ave, Oak Bluffs, MA 02557
• 

  /2

  $1,550,000

  Sold Apr 09, 2026

  63 Saddle Club Rd, Edgartown, MA 02539

  • 4 Beds
  • 2.5 Baths
  • 2,291 Sq Ft
  • Built 1988

  Last Sold Summary

  • $677/SF
  • 0 Days On Market

  Current Estimated Value $1,803,120

  Last Listing Agent LINK Email Cache LINK

  63 Saddle Club Rd, Edgartown, MA 02539
• 

  

  /37

  Est $2,502,837

  Not Listed For Sale

  42 Daggett Ave, Vineyard Haven, MA 02568

  • 3 Beds
  • 3.5 Baths
  • 3,310 Sq Ft
  • Built 2009

  42 Daggett Ave, Vineyard Haven, MA 02568

  Last Sold Summary

  • 60 Days On Market

  Last Listing Agent Rene Jackson Island Real Estate
• 

  

  /9

  $1,600,000

  • Land
  • 5.15 Acres
  • $310,680 per Acre

  60A Davis Look Rd Unit 46, West Tisbury, MA 02575

  Over five acres of privacy in one of the Island's most sought-after settings. This 5.15-acre parcel offers a rare opportunity to build a primary residence and accessory structure on old farmland surrounded by large, mature trees. Idyllic stonewalls run along some of the property lines.Large parcel size and building envelope ensures that the character of the neighborhood endures. Adjacent Land

  Julianna Flanders Flanders Real Estate

  60A Davis Look Rd Unit 46, West Tisbury, MA 02575
• 

  

  /11

  $585,000

  Sold Feb 05, 2026

  147 Red Buoy Ln Unit 2.1, Tisbury, MA 02568

  • Land
  • 26,462 Sq Ft
  • $962,963 per Acre

  Last Sold Summary

  • 20% Below List Price
  • 276 Days On Market

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

  147 Red Buoy Ln Unit 2.1, Tisbury, MA 02568
• 

  /2

  Not Listed For Sale

  301 Main St, Vineyard Haven, MA 02568

  • 4 Beds
  • 4 Baths
  • 1,632 Sq Ft
  • Built 1900

  301 Main St, Vineyard Haven, MA 02568
• 

  

  /25

  $1,595,000

  $55K PRICE DROP

  • 5 Beds
  • 3 Baths
  • 1,810 Sq Ft

  22 Old Lighthouse Rd, Vineyard Haven, MA 02568

  This spacious 5-bedroom, 3-bathroom home is located in a quiet enclave off Main Street, Vineyard Haven. Just half a mile to the vibrant restaurant and shopping scene in the village, and even closer to the library, Owen Little Beach, and Yacht Club. Thoughtfully designed across three finished levels featuring hardwood floors, a cozy fireplace, and a seamless layout, the home is ideal for

  Jessie Holtham Wallace & Co. Sotheby's International Realty

  22 Old Lighthouse Rd, Vineyard Haven, MA 02568
• 

  

  /33

  $1,470,000

  Sold Aug 06, 2026

  150 Cove Rd Unit 10, Vineyard Haven, MA 02568

  • 3 Beds
  • 3 Baths
  • 1,737 Sq Ft
  • Built 1988

  Last Sold Summary

  • 8% Below List Price
  • $846/SF
  • 160 Days On Market

  Current Estimated Value $1,571,652

  Last Listing Agent Michele Moore Island Real Estate

  150 Cove Rd Unit 10, Vineyard Haven, MA 02568
• 

  /2

  Est $1,039,759

  Not Listed For Sale

  50 Old Lighthouse Rd, Vineyard Haven, MA 02568

  • 2 Beds
  • 2 Baths
  • 961 Sq Ft
  • Built 1961

  50 Old Lighthouse Rd, Vineyard Haven, MA 02568
• 

  

  /24

  $879,000

  $20K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 990 Sq Ft

  37 Circuit Ave Unit 4, Oak Bluffs, MA 02557

  Intown Oak Bluffs Condo with Panoramic Rooftop ViewsDiscover the charm of island living in this exceptional 2-bedroom, 1-bath condo in the heart of Oak Bluffs. Just under 1,000 square feet, this comfortable residence combines character, comfort, and an unbeatable in-town location.Step inside to an inviting custom wood interior that gives the home a distinctive coastal-island feel.

  Lisa Lucier Anchor Realty of Martha's Vineyard

  37 Circuit Ave Unit 4, Oak Bluffs, MA 02557
• 

  

  /42

  $2,637,500

  Sold Dec 12, 2025

  36 Tashmoo Ave, Vineyard Haven, MA 02568

  • 4 Beds
  • 3 Baths
  • 2,770 Sq Ft
  • Built 1888

  Last Sold Summary

  • 20% Below List Price
  • $952/SF
  • 417 Days On Market

  Current Estimated Value $2,621,625

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

  36 Tashmoo Ave, Vineyard Haven, MA 02568
• 

  

  /27

  Est $2,667,954

  Not Listed For Sale

  484 Main St, Vineyard Haven, MA 02568

  • 4 Beds
  • 3 Baths
  • 3,310 Sq Ft
  • Built 1888

  484 Main St, Vineyard Haven, MA 02568

  Last Sold Summary

  • 14 Days On Market

  Last Listing Agent Lenny Altieri Premier Properties
• 

  

  /31

  $2,595,000

  $650K PRICE DROP

  • 4 Beds
  • 4.5 Baths
  • 4,023 Sq Ft

  44 Tiffany Dr, Oak Bluffs, MA 02557

  Tucked away in a serene setting and set on 1.38 private acres, this beautifully renovated 4BR/4.5BA Cape offers over 4,000 sq. ft. of living space with plenty of room for a backyard pool. The main portion of the house includes a gourmet kitchen, multiple entertaining areas including living room, family room, game room, a screened porch, ensuite bedroom and powder room. An attached one-bedroom

  Perry Patterson MV Luxury Homes

  44 Tiffany Dr, Oak Bluffs, MA 02557
• 

  

  /29

  $1,400,000

  Sold Jan 30, 2026

  67 New York Ave, Oak Bluffs, MA 02557

  • 3 Beds
  • 2 Baths
  • 1,629 Sq Ft
  • Built 1900

  Last Sold Summary

  • $859/SF
  • 0 Days On Market

  Current Estimated Value $1,408,547

  Last Listing Agent Erin Hegarty Donnelly + Co

  67 New York Ave, Oak Bluffs, MA 02557
• 

  

  /26

  Est $4,292,681

  Not Listed For Sale

  137 Massasoit Ave, Vineyard Haven, MA 02568

  • 5 Beds
  • 3.5 Baths
  • 3,686 Sq Ft
  • Built 1988

  137 Massasoit Ave, Vineyard Haven, MA 02568

  Last Sold Summary

  • 437 Days On Market

  Last Listing Agent Bobbi Reed Viewpoints
• 

  

  /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
• 

  

  /32

  $2,875,000

  Sold Jun 15, 2026

  309 Barnes Rd, Oak Bluffs, MA 02557

  • 3 Beds
  • 2 Baths
  • 1,569 Sq Ft
  • Built 1988

  Last Sold Summary

  • 8% Below List Price
  • $1,832/SF
  • 62 Days On Market

  Current Estimated Value $2,976,926

  Last Listing Agent Dawn Bellante Sandpiper Realty, Inc.

  309 Barnes Rd, Oak Bluffs, MA 02557
• 

  

  /22

  Est $1,273,543

  Not Listed For Sale

  4 Fowler Ave, Edgartown, MA 02539

  • 1 Bed
  • 1 Bath
  • 1,184 Sq Ft
  • Built 2002

  4 Fowler Ave, Edgartown, MA 02539

  Last Sold Summary

  • 28 Days On Market

  Last Listing Agent Sheila Morse Island Real Estate
• 

  

  /31

  $1,495,000

  $80K PRICE DROP

  • 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
• 

  

  /26

  $1,900,000

  Sold Feb 09, 2026

  30 Franklin Ave, Oak Bluffs, MA 02568

  • 2 Beds
  • 2.5 Baths
  • 2,137 Sq Ft
  • Built 2024

  Last Sold Summary

  • 12% Below List Price
  • $889/SF
  • 195 Days On Market

  Current Estimated Value $2,068,665

  Last Listing Agent Stacy Ickes Donnelly + Co

  30 Franklin Ave, Oak Bluffs, MA 02568
• 

  

  /22

  Est $1,170,498

  Not Listed For Sale

  5 12th St S, Edgartown, MA 02539

  • 3 Beds
  • 2 Baths
  • 1,296 Sq Ft
  • Built 1993

  5 12th St S, Edgartown, MA 02539

  Last Sold Summary

  • 11 Days On Market

  Last Listing Agent Jared Bicknell Compass
• 

  

  /6

  $1,895,000

  • Land
  • 1.87 Acres
  • $1,014,997 per Acre

  22 Paddock Rd Unit 85, Oak Bluffs, MA 02568

  An exceptional offering—the final homesite available within The Preserve at The Woodlands, one of Oak Bluffs’ most coveted residential enclaves. Create a custom coastal retreat in an extraordinary setting where architecturally designed residences, protected conservation land, and the timeless beauty of Martha’s Vineyard converge.This 1.87-acre homesite represents the final opportunity to

  Marilyn Moses Ocean Park Realty Inc

  22 Paddock Rd Unit 85, Oak Bluffs, MA 02568

Showing Results 361 - 400, Page 10 of 18