Tisbury, MA Homes

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  /36

  $4,695,000

  • 3 Beds
  • 4 Baths
  • 2,606 Sq Ft

  95 Hines Point Rd, Vineyard Haven, MA 02568

  A rare opportunity, this Hines Point waterfront compound offers expansive views of the Lagoon and 100 feet of private beach. The home was built and has been enjoyed by the same family for gathering and summer recreation over generations. The main house offers an open first floor layout with high ceilings and large windows facing the water where you can watch sunrise over the water. A first floor

  Elissa Lash Tea Lane Associates

  95 Hines Point Rd, Vineyard Haven, MA 02568
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  /14

  $14,200 Per Month

  • 3 Beds
  • 2 Baths
  • 1,500 Sq Ft
  • House for Rent

  59 Prospect Ave Ob502, Oak Bluffs, MA 02557

  THIS IS A WEEKLY SUMMER RENTAL ONLY. SEE WEB SITE FOR WEEKLY PRICING. This immaculate home is located in a quiet neighborhood that is just a bike ride's distance from several lovely beaches as well as the center of Oak Bluffs. The home offers open living spaces, generously proportioned sunny bedrooms and is well equipped.

  Karen Overtoom Karen M. Overtoom R.E.

  59 Prospect Ave Ob502, Oak Bluffs, MA 02557
• 

  

  

  /19

  $980,000

  Sold Aug 11, 2025

  249 County Rd, Oak Bluffs, MA 02557

  • 1 Bed
  • 2 Baths
  • 1,401 Sq Ft
  • Built 2005

  Last Sold Summary

  • 7% Below List Price
  • $700/SF
  • 83 Days On Market

  Current Estimated Value $988,672

  Last Listing Agent Katherine Donahue Sandpiper Realty

  249 County Rd, Oak Bluffs, MA 02557
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  /32

  Est $1,818,777

  Not Listed For Sale

  11 Pine Tree Ln, Vineyard Haven, MA 02568

  • 4 Beds
  • 3 Baths
  • 1,240 Sq Ft
  • Built 1960

  11 Pine Tree Ln, Vineyard Haven, MA 02568

  Last Sold Summary

  • 179 Days On Market
• 

  

  

  /49

  $849,000

  $50K PRICE DROP

  • 1 Bed
  • 1 Bath
  • 803 Sq Ft

  26 Winthrop Ave, Oak Bluffs, MA 02557

  Hidden behind a wall of vegetation on Winthrop Avenue this is a little 'oasis' of a piece of land. One bedroom house situated on a 1/3 Acre, 14,810 sq.ft. level lot. One side of the property is lush with vegetation and the opposite side is clear. It is one lot in total and may not be subdivided. The existing house has been lived in year round. Only .6 of a mile to Oak Bluffs Harbor and .5 mile

  Alisan Lohan-Conway Alisan Lohan-Conway Properties

  26 Winthrop Ave, Oak Bluffs, MA 02557
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  /28

  $38,000 Per Month

  • 4 Beds
  • 3.5 Baths
  • 3,000 Sq Ft
  • House for Rent

  17 Otis Bassett Rd, West Tisbury, MA 02575

  THIS IS A WEEKLY RENTAL NOT MONTHLY. AUGUST WEEKLY IS $9,500. SEE OUR WEB SITE FOR WEEKLY PRICING!!!!!Are you looking for the perfect back yard Oasis? Well here it is!! Surrounding a large pool you will be able to relax on the expansive deck areas that include plenty of space for gathering. Inside is an amazing kitchen with every amenity you could want. Coffee lovers will appreciate a regular

  Karen Overtoom Karen M. Overtoom R.E.

  17 Otis Bassett Rd, West Tisbury, MA 02575
• 

  /2

  $825,000

  Sold Dec 03, 2025

  69 Summit Ave, Vineyard Haven, MA 02568

  • 3 Beds
  • 2 Baths
  • 1,248 Sq Ft
  • Built 1998

  Last Sold Summary

  • $661/SF
  • 1 Day On Market

  Current Estimated Value $849,324

  Last Listing Agent Susie Wallo Compass

  69 Summit Ave, Vineyard Haven, MA 02568
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  /2

  Est $946,919

  Not Listed For Sale

  84 Pine Tree Rd, Vineyard Haven, MA 02568

  • 3 Beds
  • 1 Bath
  • 1,116 Sq Ft
  • Built 1980

  84 Pine Tree Rd, Vineyard Haven, MA 02568

  Last Sold Summary
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  /26

  $1,299,000

  Under Contract

  • 3 Beds
  • 1 Bath
  • 1,150 Sq Ft

  9 Galway Rd, Vineyard Haven, MA 02568

  Tucked away off Old County Road in West Tisbury, this 3 bedroom 1 bath cape home has been owned by the same family for years. Sitting on 1.6 acres in a quiet area that is centrally located on the Island for easy access to up or down Island towns. Short walk to bike path and state forest. West Tisbury residents have access to the lovely Lambert's Cove Beach, with purchased sticker. Included on

  Julianna Flanders Flanders Real Estate

  9 Galway Rd, Vineyard Haven, MA 02568
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  /8

  $11,800 Per Month

  • 4 Beds
  • 4 Baths
  • 2,612 Sq Ft
  • House for Rent

  46 Buttonwood Farm Rd Unit 1, West Tisbury, MA 02575

  THIS IS A WEEKLY RENTAL PROPERTY!! Beautifully updated contemporary home with impeccably landscaped lawns and gardens, a swimming pond and hot tub with two outdoor showers - one enclosed and one open to the hot tub and patio area on the side of the house. Gorgeous back deck with outdoor dining accessible through sliding glass doors from the dining room. Inside, enjoy the fully equipped and

  Karen Overtoom Karen M. Overtoom R.E.

  46 Buttonwood Farm Rd Unit 1, West Tisbury, MA 02575
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  /40

  $650,000

  Sold Sep 10, 2025

  25 Oak Ave, Oak Bluffs, MA 02557

  • 2 Beds
  • 0.5 Baths
  • 759 Sq Ft
  • Built 1900

  Last Sold Summary

  • 4% Below List Price
  • $856/SF
  • 251 Days On Market

  Current Estimated Value $728,705

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

  25 Oak Ave, Oak Bluffs, MA 02557
• 

  

  /17

  Est $1,343,499

  Not Listed For Sale

  165 Weaver Ln, Vineyard Haven, MA 02568

  • 3 Beds
  • 2 Baths
  • 1,503 Sq Ft
  • Built 1974

  165 Weaver Ln, Vineyard Haven, MA 02568

  Last Sold Summary

  • 43 Days On Market
• 

  

  /13

  $1,645,000

  • Land
  • 3.32 Acres
  • $495,482 per Acre

  26 Flint Hill Rd, West Tisbury, MA 02575

  Stop Searching. Start Building. You've toured dozens of homes. Nothing feels right. What if your dream home on Martha's Vineyard simply hasn't been built yet? This rare 3.32-acre West Tisbury hilltop is the blank canvas you've been waiting for. Glacial boulders, open pasture, and cathedral oaks with Land Bank-preserved Arrowhead Farm and protected Rodgers Path land on two sides— a setting no

  Dawn Bellante Sandpiper Realty, Inc.

  26 Flint Hill Rd, West Tisbury, MA 02575
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  /8

  $4,800 Per Month

  • 3 Beds
  • 3 Baths
  • 3,279 Sq Ft
  • House for Rent

  165 Christiantown Rd, West Tisbury, MA 02575

  THIS PROPERTY IS A WEEKLY PROPERTY!! The home is set on six beautifully landscaped acres with original stone walls. It is located in private historic Christiantown on the North Shore, a short distance from both Lambert’s Cove Beach and Cedar Tree Neck Wildlife Reserve. Cedar Tree is a habitat with tumbling streams and freshwater ponds, sandy beaches and rocky cliffs, tall oaks and cool beech

  Karen Overtoom Karen M. Overtoom R.E.

  165 Christiantown Rd, West Tisbury, MA 02575
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  /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
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  /2

  Est $1,455,272

  Not Listed For Sale

  23 Anthiers Way, Edgartown, MA 02539

  • 4 Beds
  • 3 Baths
  • 2,066 Sq Ft
  • Built 1950

  23 Anthiers Way, Edgartown, MA 02539

  Last Sold Summary
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  /26

  $2,600,000

  Pending

  • 3 Beds
  • 1 Bath

  23 Circuit Avenue Extension, Oak Bluffs, MA 02557

  Rare Opportunity with Endless Possibilities - Unmatched Harbor & Vineyard Sound Views. Location, Location, Location! A truly rare offering in the heart of Oak Bluffs, where properties like this seldom become available. Positioned directly across from the iconic Oak Bluffs Harbor, this property boasts unobstructed harbor views and sweeping vistas of Vineyard Sound--a setting that captures the very

  Rene Ben David

  23 Circuit Avenue Extension, Oak Bluffs, MA 02557
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  /41

  $14,500 Per Month

  • 5 Beds
  • 5.5 Baths
  • 3,392 Sq Ft
  • House for Rent

  76 School House Lane Wt101, West Tisbury, MA 02575

  THIS IS A WEEKLY RENTAL NOT A MONTHLY!!!! An elegant, whimsical house full of color, quality and artistic touches. The grounds are sumptuous, nature at its apotheosis. There is gentle movement in the landscape with flowering trees and shrubs everywhere replete with a babbling brook flowing into a pond bordering the garden behind the house. The stonework is finely crafted with balanced proportions

  Karen Overtoom Karen M. Overtoom R.E.

  76 School House Lane Wt101, West Tisbury, MA 02575
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  /2

  $1,595,000

  Sold Jul 01, 2025

  10 Red Pony Rd, West Tisbury, MA 02568

  • 2 Beds
  • 1.5 Baths
  • 1,176 Sq Ft
  • Built 1998

  Last Sold Summary

  • $1,356/SF

  Current Estimated Value $1,686,926

  Last Listing Agent Lisa Da Silva Signal House Group at Compass

  10 Red Pony Rd, West Tisbury, MA 02568
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  /32

  Est $2,229,012

  Not Listed For Sale

  232 Lagoon Pond Rd, Vineyard Haven, MA 02568

  • 4 Beds
  • 4 Baths
  • 2,276 Sq Ft
  • Built 1970

  232 Lagoon Pond Rd, Vineyard Haven, MA 02568

  Last Sold Summary

  • 220 Days On Market
• 

  

  /31

  $5,995,000

  • 3 Beds
  • 3 Baths
  • 2,234 Sq Ft

  43 Sengekontacket Rd, Oak Bluffs, MA 02557

  Breathtaking property at the tip of a prominent peninsula on Sengekontacket Pond's western shoreline. Set beautifully at high elevation above the shore, this charming home and guest cottage includes jaw-dropping views of the pond, barrier dunes and Nantucket Sound. Direct from the property take your whaler or other watercraft out into the sound and beyond for endless recreational pursuits. Aside

  Peyton Wallace Studio Realty

  43 Sengekontacket Rd, Oak Bluffs, MA 02557
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  /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
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  /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 $2,337,575

  Last Listing Agent Julianna Flanders Flanders Real Estate

  46 Bold Meadow Rd, Edgartown, MA 02539
• 

  /2

  Est $1,663,812

  Not Listed For Sale

  323 Lamberts Cove Rd, Vineyard Haven, MA 02568

  • 4 Beds
  • 3 Baths
  • 1,144 Sq Ft
  • Built 1900

  323 Lamberts Cove Rd, Vineyard Haven, MA 02568

  Last Sold Summary
• 

  

  /9

  $1,395,000

  $600K PRICE DROP

  • 0.5 Baths
  • 1,283 Sq Ft

  4 Lagoon Pond Rd, Vineyard Haven, MA 02568

  Located at the five corners, this rare commercial property presents an opportunity to set your future business venture up for success. This prime location captures the attention of every single vehicle disembarking the Vineyard Haven Ferry! There are 2.5 parking spots included. Please note that the bike shop business is not for sale. This offering is solely for the real estate. The sellers

  Jarrett Hurwitz Keller Williams Realty

  4 Lagoon Pond Rd, Vineyard Haven, MA 02568
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  /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 $3,101,801

  Last Listing Agent Joe & Nicole Holland Vineyard Dream Realty LLC

  64 Crowell Ln, Tisbury, MA 02568
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  /44

  Est $1,683,089

  Not Listed For Sale

  30 Hillside Path, Vineyard Haven, MA 02568

  • 3 Beds
  • 4 Baths
  • 3,114 Sq Ft
  • Built 1999

  30 Hillside Path, Vineyard Haven, MA 02568

  Last Sold Summary

  • 39 Days On Market
• 

  

  /47

  $5,450,000

  • 4 Beds
  • 5.5 Baths
  • 3,300 Sq Ft

  8 Paddock Rd, Oak Bluffs, MA 02557

  Refined Vineyard Living in The Preserve - Set atop a knoll overlooking sweeping grassland and the pond, this exceptional residence embodies the perfect balance of classic coastal architecture and modern sophistication. Located within the prestigious enclave of The Preserve, the home offers a combination of privacy, elegance, and seamless indoor-outdoor living. At its core, an expansive great room

  Lesley Heidt Sandpiper Realty

  8 Paddock Rd, Oak Bluffs, MA 02557
• 

  /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 $768,672

  Last Listing Agent LINK Email Cache LINK

  84 12th St S, Edgartown, MA 02539
• 

  /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
• 

  

  /58

  $2,895,000

  • 5 Beds
  • 4 Baths
  • 2,300 Sq Ft

  27 Spring St, Vineyard Haven, MA 02568

  Located in the William Street Historic District, this elegant Greek Revival home, built in 1842, has stood the test of time and has been thoughtfully expanded and renovated in recent years. This five-bedroom, four-bath residence combines historic character with modern comforts. The home features a gracious living room, dining room, office, and an inviting kitchen/breakfast room. There are five

  Alexis Holden Tea Lane Associates

  27 Spring St, 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 $1,332,953

  Last Listing Agent Emma Bryant Studio Realty

  208 Irenes Way, Tisbury, MA 02568
• 

  

  /19

  Est $1,119,167

  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

  • 45 Days On Market
• 

  

  /10

  $3,995,000

  • Land
  • 1.92 Acres
  • $2,083,985 per Acre

  98 Farm Neck Way Unit 51, Oak Bluffs, MA 02568

  Farm Neck Golf Club – Undeveloped Water View Parcel with Membership A truly rare opportunity to acquire a 1.92-acre undeveloped parcel within the prestigious Farm Neck Golf Club community, one of the last remaining opportunities of its kind. This exceptional offering features sweeping water views over Sengekontacket Pond to the Vineyard Sound, creating a stunning backdrop for your future Martha’s

  Andrew McElhinney Compass LLC

  98 Farm Neck Way Unit 51, Oak Bluffs, MA 02568
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  /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
• 

  

  /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

  • 121 Days On Market
• 

  

  /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
• 

  

  /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 $1,257,168

  Last Listing Agent Lisa Gilberto C McManus Realty Group

  46 Old Coach Rd, Vineyard Haven, MA 02568
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  /34

  Est $2,243,149

  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

  • 68 Days On Market
• 

  

  /33

  $1,725,000

  • 3 Beds
  • 2.5 Baths
  • 1,588 Sq Ft

  225 Lamberts Cove Rd, Vineyard Haven, MA 02568

  This year-round home, situated less than half a mile from Lambert’s Cove Beach, boasts fine craftsmanship and character in a peaceful, wooded environment. Inside, the open living room features wide plank floors, cathedral ceilings with beams, and a central brick fireplace that connects seamlessly to the updated kitchen.

  Brenda Galligan Karen M. Overtoom R.E.

  225 Lamberts Cove Rd, Vineyard Haven, MA 02568

Showing Results 161 - 200, Page 5 of 18