Vineyard Haven, MA Homes

• 

  

  

  /24

  $2,925,000

  • 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 with 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 the care and craftsmanship the

  Paul Pertile The Agency

  21 Davis St, Vineyard Haven, MA 02568
• 

  

  

  /40

  $32,500 Per Month

  • 6 Beds
  • 4.5 Baths
  • 3,222 Sq Ft
  • House for Rent

  100 Connie's Way &83 Ashtonw Vh408, Tisbury, MA 02568

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $5,000. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Located in Mink Meadows Association, this wonderful four bedroom, three full and one half bath home has many nice features that include a large eat-in kitchen/family room, a more formal living room with fireplace, dining room and den. Televisions in every bedroom, living

  Karen Overtoom Karen M. Overtoom R.E.

  100 Connie's Way &83 Ashtonw Vh408, Tisbury, MA 02568
• 

  

  

  /40

  $1,600,000 Sold Jan 06, 2026

  44 Tiffany Dr, Oak Bluffs, MA 02557

  • 4 Beds
  • 4 Baths
  • 3,927 Sq Ft
  • Built 1987

  Last Sold Summary

  • 24% Below List Price
  • $407/SF
  • 115 Days On Market

  Current Estimated Value $1,626,271

  Last Listing Agent Sheila Morse Island Real Estate

  44 Tiffany Dr, Oak Bluffs, MA 02557
• 

  

  /2

  Est $1,921,257 Not Listed For Sale

  54 Bold Meadow Rd, Edgartown, MA 02539

  • 3 Beds
  • 3 Baths
  • 2,026 Sq Ft
  • Built 1993

  54 Bold Meadow Rd, Edgartown, MA 02539

  Last Sold Summary

  • 13% Below List Price
  • $839/SF

  • Last Sold Price $1,700,000

  Last Listing Agent Dawn Bellante-Holand Sandpiper Realty
• 

  

  

  /4

  $809,000

  • Land
  • 16,988 Sq Ft
  • $2,074,359 per Acre

  7 Highland Ave, 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, LLC

  7 Highland Ave, Vineyard Haven, MA 02568
• 

  /2

  $965,000 Sold Sep 04, 2025

  62 Jernegan Ave, Edgartown, MA 02539

  • 3 Beds
  • 1 Bath
  • 1,886 Sq Ft
  • Built 1998

  Last Sold Summary

  • $512/SF
  • 0 Days On Market

  Current Estimated Value $1,048,459

  Last Listing Agent LINK Email Cache LINK

  62 Jernegan Ave, Edgartown, MA 02539
• 

  

  /19

  Est $1,121,247 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

  • 1% Above List Price
  • $871/SF
  • 45 Days On Market

  • Last Sold Price $1,110,000
  • May 08, 2025

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

  

  /31

  $1,050,000 Under Contract

  • 2 Beds
  • 1 Bath
  • 1,040 Sq Ft

  73 & 0 Old Country Ln, Vineyard Haven, MA 02568

  Charming 2-bedroom, 1-bath ranch house in Vineyard Haven, in town—just minutes from shops, restaurants, and schools. This well-maintained property offers a functional layout with a bright living area, a cozy kitchen overlooking the backyard, two comfortable bedrooms, and a full bathroom. The house has a full basement with ample room for storage and projects. This home is situated on two lots,

  Julianna Flanders Flanders Real Estate

  73 & 0 Old Country Ln, 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 $2,398,926

  Last Listing Agent Julianna Flanders Flanders Real Estate

  46 Bold Meadow Rd, Edgartown, MA 02539
• 

  

  /24

  Est $1,265,419 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

  • 12% Above List Price
  • $648/SF
  • 121 Days On Market

  • Last Sold Price $1,125,000
  • Dec 17, 2018

  Last Listing Agent Michael Schweikert Ocean Park Realty Inc
• 

  

  /21

  $1,295,000 Pending

  • 4 Beds
  • 2 Baths
  • 1,764 Sq Ft

  54 Columbian Ave, Oak Bluffs, MA 02557

  Nestled in a quiet Oak Bluffs neighborhood, this charming, sun-filled four-bedroom, two-bath home sits on a spacious corner lot and offers an ideal opportunity for both seasonal and year-round living. The home features a functional layout with a cozy wood burning stove and abundant natural light throughout. The main level offers a spacious living area open to a kitchen, both with wide plank

  Marcia Sullivan Garvey Donnelly + Co.

  54 Columbian Ave, Oak Bluffs, MA 02557
• 

  

  /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 $1,675,000

  Last Listing Agent Joe & Nicole Holland Vineyard Dream Realty LLC

  64 Crowell Ln, Tisbury, MA 02568
• 

  

  /34

  Est $2,354,063 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

  • 5% Above List Price
  • $1,262/SF
  • 68 Days On Market

  • Last Sold Price $2,250,000
  • Aug 08, 2024

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

  

  /21

  $1,445,000

  • 4 Beds
  • 2.5 Baths
  • 1,738 Sq Ft

  22 Oklahoma Ave, Vineyard Haven, MA 02568

  3 BEDROOM HOUSE + 1 BEDROOM APARTMENT! A rare opportunity in a convenient Vineyard Haven neighborhood. This move-in ready property features a 3 BR, 1.5 BA main house plus a legal 1 BR, 1 BA accessory apartment, offering the perfect setup for multi-generational living or a high-demand rental to offset your mortgage. The main house features a stunning sun-room, a cheerful efficient kitchen, and a

  Idalyn Macchia Gilstad Wallace & Co. Sotheby's International Realty

  22 Oklahoma Ave, Vineyard Haven, MA 02568
• 

  /2

  $600,000 Sold Jul 23, 2025

  84 12th St S, Edgartown, MA 02539

  • 3 Beds
  • 2 Baths
  • 1,568 Sq Ft
  • Built 1978

  Last Sold Summary

  • $383/SF
  • 0 Days On Market

  Current Estimated Value $644,019

  Last Listing Agent LINK Email Cache LINK

  84 12th St S, Edgartown, MA 02539
• 

  

  /17

  Est $678,459 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

  • 29% Above List Price
  • $1,215/SF
  • 30 Days On Market

  • Last Sold Price $525,000
  • Feb 10, 2025

  Last Listing Agent Candy DaRosa Feiner Real Estate
• 

  

  /25

  $599,000

  • 2 Beds
  • 1 Bath
  • 725 Sq Ft

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

  JUST COMPLETED ~ fully renovated exterior including a new roof, siding, shutters, trim, all new windows, doors, stairways, and decks. Outstanding move-in-ready, year-round two-bedroom ground-level condo with dedicated parking in an ideal Vineyard Haven location close to the ferry, Main Street shops, and restaurants.The beautifully maintained common grounds feature colorful landscaping, picnic

  Stephanie Roache Donnelly + Co

  124 Skiff Ave Unit A-11, Vineyard Haven, MA 02568
• 

  

  /69

  $1,160,000 Sold Jan 05, 2026

  208 Irenes Way, Tisbury, MA 02568

  • 4 Beds
  • 3 Baths
  • 2,961 Sq Ft
  • Built 2005

  Last Sold Summary

  • 24% Below List Price
  • $392/SF
  • 168 Days On Market

  Current Estimated Value $1,298,778

  Last Listing Agent Emma Kiley Bryant Landmarks at TODAY Real Estate

  208 Irenes Way, Tisbury, MA 02568
• 

  

  /32

  Est $1,320,066 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

  • 22% Above List Price
  • $970/SF
  • 167 Days On Market

  • Last Sold Price $1,085,000
  • Sep 29, 2023

  Last Listing Agent Neal Stiller Cronigs Real Estate
• 

  

  /3

  $857,000

  • Land
  • 16,892 Sq Ft
  • $2,209,902 per Acre

  24 Towanticut Ave Unit 188, Oak Bluffs, MA 02568

  OAK BLUFFS - A Rare Opportunity to purchase an Eight (8) Bedroom lot. This already cleared, oversized lot, 16,895sq.ft., (more than 1/3 acre) comes with an Approved Eight (8) Bedroom Septic Design, ready to build. Exceptional potential for a spacious custom home, family compound, or a rental property. Utilities are available by the lot, which significantly reduces development costs and time.

  Alisan Lohan-Conway Alisan Lohan-Conway Properties

  24 Towanticut Ave Unit 188, Oak Bluffs, MA 02568
• 

  

  /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
• 

  

  /22

  Est $1,072,777 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

  • 18% Above List Price
  • $888/SF
  • 102 Days On Market

  • Last Sold Price $910,000
  • Dec 15, 2023

  Last Listing Agent Jennifer B. DaSilva Compass
• 

  

  /12

  $1,495,000 Open Sat 11AM - 2PM

  • 4 Beds
  • 4 Baths
  • 2,304 Sq Ft

  33 Alyssa Ln, Vineyard Haven, MA 02568

  Country Living so close to Town! Lovely 4 Bedroom 2,304sq ft. Colonial Cape perched on a rise on Alyssa Lane off West Spring Street. Open Kitchen with handcrafted side cabinets and Island with stool seating. Dining, sitting, entertainment area with sliders open to a generous front to back side deck. Living room with propane fired wood stove and half bath also on the first floor. Interior stairs

  Stephanie Burke Portfolio Properties

  33 Alyssa Ln, Vineyard Haven, MA 02568
• 

  

  /20

  $1,150,000 Sold Jun 13, 2025

  46 Old Coach Rd, Vineyard Haven, MA 02568

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

  Last Sold Summary

  • 10% Below List Price
  • $837/SF
  • 43 Days On Market

  Current Estimated Value $1,283,412

  Last Listing Agent Lisa Gilberto C McManus Realty Group

  46 Old Coach Rd, Vineyard Haven, MA 02568
• 

  

  /32

  Est $1,184,034 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

  • 6% Above List Price
  • $784/SF
  • 35 Days On Market

  • Last Sold Price $1,120,000
  • Jun 20, 2024

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

  

  /7

  $2,000,000

  • Land
  • 21,801 Sq Ft
  • $3,996,004 per Acre

  0 State Rd Unit 29.3, Vineyard Haven, MA 02568

  1/2 acre of commercial land in the State Road B-2 district. Possibilities are endless for the right business. Also available, next door, is a commercial building that currently has 10 rental units. $6,000,000.

  Peter Cronig Cronigs Real Estate

  0 State Rd Unit 29.3, Vineyard Haven, MA 02568
• 

  

  /22

  $4,250,000 Sold Sep 09, 2025

  420 Lamberts Cove Rd, Vineyard Haven, MA 02568

  • 7 Beds
  • 6 Baths
  • 4,125 Sq Ft
  • Built 1900

  Last Sold Summary

  • 5% Below List Price
  • $1,030/SF
  • 21 Days On Market

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

  420 Lamberts Cove Rd, Vineyard Haven, MA 02568
• 

  /2

  Est $1,406,986 Not Listed For Sale

  88 Hopps Farm Rd, Vineyard Haven, MA 02568

  • 3 Beds
  • 2 Baths
  • 1,464 Sq Ft
  • Built 1992

  88 Hopps Farm Rd, Vineyard Haven, MA 02568

  Last Sold Summary

  • 6% Below List Price
  • $908/SF

  • Last Sold Price $1,330,000

  Last Listing Agent Emma Kiley Bryant Landmarks at TODAY Real Estate
• 

  

  /32

  $1,625,000

  • 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, perfect

  Alyssa Halisky Wallace & Co. Sotheby's

  26 Union St Unit 7, Tisbury, MA 02568
• 

  

  /22

  $1,299,000 Sold Jun 25, 2025

  2 Boylston Dr, Edgartown, MA 02539

  • 3 Beds
  • 2 Baths
  • 1,512 Sq Ft
  • Built 1984

  Last Sold Summary

  • 13% Below List Price
  • $859/SF
  • 77 Days On Market

  Current Estimated Value $1,310,252

  Last Listing Agent Martha Smith C McManus Realty Group

  2 Boylston Dr, Edgartown, MA 02539
• 

  

  /29

  Not Listed For Sale

  33 Summer St, Vineyard Haven, MA 02568

  • 4 Beds
  • 3 Baths
  • 1,558 Sq Ft
  • Built 1924

  33 Summer St, Vineyard Haven, MA 02568

  Last Sold Summary

  • $720/SF
  • 192 Days On Market

  • Last Sold Price $1,122,000
  • Mar 15, 2018

  Last Listing Agent Emma Kennedy Sandpiper Realty
• 

  

  /30

  $999,000 Under Contract

  • 2 Beds
  • 1 Bath
  • 1,232 Sq Ft

  28 Barling Ave, Vineyard Haven, MA 02568

  Oak Bluffs: Home Sweet HomeSituated on over a quarter acre of beautifully landscaped, level grounds with colorful perennial plantings and mature trees, this sun-filled ranch offers a perfect blend of comfort and charm. The open kitchen, dining, and living areas feature cathedral ceilings, classic vertical knotty pine walls, and a cozy brick fireplace. Enjoy a convenient first-floor bedroom

  Michael Schweikert Ocean Park Realty Inc

  28 Barling Ave, Vineyard Haven, MA 02568
• 

  

  /28

  $1,320,000 Sold Aug 29, 2025

  10 Eagles Nest, Edgartown, MA 02539

  • 3 Beds
  • 2 Baths
  • 1,450 Sq Ft
  • Built 1987

  Last Sold Summary

  • 5% Below List Price
  • $910/SF
  • 6 Days On Market

  Current Estimated Value $1,269,620

  Last Listing Agent Jennifer B. DaSilva Compass

  10 Eagles Nest, Edgartown, MA 02539
• 

  /2

  Est $1,039,258 Not Listed For Sale

  73 Leonard Cir, Vineyard Haven, MA 02568

  • 3 Beds
  • 2 Baths
  • 1,140 Sq Ft
  • Built 1980

  73 Leonard Cir, Vineyard Haven, MA 02568

  Last Sold Summary

  • 1% Below List Price
  • $921/SF

  • Last Sold Price $1,050,000

  Last Listing Agent Leslie C. Floyd Portfolio Properties
• 

  

  /26

  $1,750,000 Pending

  • 3 Beds
  • 2.5 Baths
  • 2,862 Sq Ft

  103 Meadow View Rd, Oak Bluffs, MA 02557

  Nestled on a rare, oversized 1.5-acre lot, this spacious 3-bed/2 1/2 bath contemporary home offers a perfect blend of privacy and coastal convenience. Perched elegantly upon a gentle rise, the residence is bathed in natural light and framed by a beautifully landscaped lawn with mature plantings. The interior is designed for both comfort and scale. An expansive front living room has soaring

  Alyson Parker Karen M. Overtoom R.E.

  103 Meadow View Rd, Oak Bluffs, MA 02557
• 

  

  /37

  $2,100,000 Sold Aug 27, 2025

  42 Daggett Ave, Vineyard Haven, MA 02568

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

  Last Sold Summary

  • 4% Below List Price
  • $634/SF
  • 60 Days On Market

  Current Estimated Value $2,296,727

  Last Listing Agent Rene Jackson Island Real Estate

  42 Daggett Ave, Vineyard Haven, MA 02568
• 

  

  /20

  Est $1,358,504 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

  • 1% Above List Price
  • $780/SF
  • 18 Days On Market

  • Last Sold Price $1,350,000
  • Nov 20, 2023

  Last Listing Agent Michele Casavant Vineyard Village Realty
• 

  

  /60

  $5,495,000

  • 3 Beds
  • 7 Baths
  • 3,608 Sq Ft

  385 Barnes Rd, Vineyard Haven, MA 02568

  SPECTACULAR WATERFRONT ESCAPE WITH POOL AND UNFORGETTABLE SUNSETS. Set along a coveted stretch of Lagoon frontage, this beautifully designed waterfront home captures the essence of relaxed luxury on Martha’s Vineyard. With 125 feet of private sandy beachfront and over 5,400 square feet of living space across three levels, the property is thoughtfully oriented to maximize light, views, and

  Stephanie Roache Donnelly + Co

  385 Barnes Rd, Vineyard Haven, MA 02568
• 

  

  /12

  $686,000 Sold Jul 23, 2025

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

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

  Last Sold Summary

  • $946/SF
  • 31 Days On Market

  Current Estimated Value $677,134

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

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

  /2

  Est $2,260,316 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

  Last Sold Summary

  • 3% Below List Price
  • $673/SF

  • Last Sold Price $2,200,000

  Last Listing Agent Emma Kennedy Sandpiper Realty

Showing Results 161 - 200, Page 5 of 18