12,001

Tisbury, MA Homes

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  • /39

    $1,495,000

    $130K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 1,514 Sq Ft

    26 Sea Glen Rd, Oak Bluffs, MA 02557

    Nestled in a desirable neighborhood, this beautifully maintained cape style home offers a rare blend of charm, flexibility and convenience in a serene island setting. Thoughtfully appointed throughout, the home welcomes you with an open living room that flows effortlessly into a bright dining area, where French doors open to a private stone patio—creating an inviting connection between indoor

    Jennifer B. DaSilva Compass

    26 Sea Glen Rd, Oak Bluffs, MA 02557
  • /28

    $32,000 Per Month

    • 4 Beds
    • 4 Baths
    • 3,200 Sq Ft
    • House for Rent

    37 Mempremagog Ave Vh410, Tisbury, MA 02568

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $8,200. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Fabulous custom designed and decorated four bedroom home is located in a wooded setting that offers total privacy and is with-in walking distance to a private association beach. And yet is only 3 miles from downtown Vineyard Haven. This lovely home offers a gourmet eat-in

    Karen Overtoom Karen M. Overtoom R.E.

    37 Mempremagog Ave Vh410, Tisbury, MA 02568
  • /2

    $1,700,000

    Sold Oct 20, 2025

    37 Vineyard Meadow Farms Rd, West Tisbury, MA 02568

    • 5 Beds
    • 3 Baths
    • 1,803 Sq Ft
    • Built 1982

    Last Sold Summary

    • $943/SF
    • 0 Days On Market

    Last Listing Agent LINK Email Cache LINK

    37 Vineyard Meadow Farms Rd, West Tisbury, MA 02568
    • /2

      Est $2,382,709

      Not Listed For Sale

      248 Pond Rd, Vineyard Haven, MA 02568

      • 5 Beds
      • 4 Baths
      • 3,208 Sq Ft
      • Built 1998
      248 Pond Rd, Vineyard Haven, MA 02568

  • /4

    $625,000

    • Land
    • 14,997 Sq Ft
    • $1,815,277 per Acre

    0-A California Ave Unit Part lot 79, Oak Bluffs, MA 02568

    Oak Bluffs Buildable Lot – Prime Location. This flat 2-bedroom building lot is ideally located just moments from the Hudson Avenue access to scenic Lagoon Pond, with easy access to both Farm Neck Golf Club and downtown Oak Bluffs. Situated in a neighborhood of newly constructed homes, this lot presents an excellent opportunity to become part of a growing community in Oak Bluffs. According to the

    Andrew McElhinney Compass LLC

    0-A California Ave Unit Part lot 79, Oak Bluffs, MA 02568
  • /27

    $18,840 Per Month

    • 3 Beds
    • 2.5 Baths
    • House for Rent

    21 William St Vh430, Tisbury, MA 02568

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $4,710. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Lovely elegant home with wonderful art and furnishings. Once you step in the front door you will fall in love with this lovely home. Each room is a delight. Large nicely appointed kitchen with easy access to a beautiful dining room. A formal living room is next to a less

    Karen Overtoom Karen M. Overtoom R.E.

    21 William St Vh430, Tisbury, MA 02568
  • /26

    $1,800,000

    Sold Oct 15, 2025

    82 Skiff Ave, Tisbury, MA 02568

    • 3 Beds
    • 3.5 Baths
    • 1,913 Sq Ft
    • Built 2020

    Last Sold Summary

    • 10% Below List Price
    • $941/SF
    • 128 Days On Market

    Current Estimated Value $2,165,409

    Last Listing Agent Lenny Altieri Premier Properties

    82 Skiff Ave, Tisbury, MA 02568
    • /25

      Est $2,009,090

      Not Listed For Sale

      131 Shubael Weeks Path, Vineyard Haven, MA 02568

      • 5 Beds
      • 3 Baths
      • 3,636 Sq Ft
      • Built 1985
      131 Shubael Weeks Path, Vineyard Haven, MA 02568

      Last Sold Summary

      • 0 Days On Market

  • /5

    $975,000

    • Land
    • 1.07 Acres
    • $912,921 per Acre

    68 Pond View Dr Unit 2, Oak Bluffs, MA 02557

    Create your ideal island retreat on this exceptional 1.068-acre parcel in Oak Bluffs. This desirable homesite comes with approved plans for a six-bedroom septic system, saving valuable time and expense as you begin the building process.The property also includes a topographic/boundary survey and soil test, providing a strong foundation for planning and development.Subject to the Town of

    Casandra Hyland Sandpiper Realty

    68 Pond View Dr Unit 2, Oak Bluffs, MA 02557
  • /9

    $19,000 Per Month

    • 6 Beds
    • 2.5 Baths
    • 2,155 Sq Ft
    • House for Rent

    17 Umbagog Ave Wt109, West Tisbury, MA 02575

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $4,750. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This three story home is located in a very desirable area off of Lambert's Cove Road, Makonikey, with access to a private association beach and walking trails. There are four plus bedrooms and bright and open living spaces that lead out to a deck and a screened-in porch.

    Karen Overtoom Karen M. Overtoom R.E.

    17 Umbagog Ave Wt109, West Tisbury, MA 02575
  • /19

    $750,000

    Sold Nov 07, 2025

    41 Trinity Park, Oak Bluffs, MA 02557

    • 4 Beds
    • 1 Bath
    • 1,154 Sq Ft
    • Built 1867

    Last Sold Summary

    • 6% Below List Price
    • $650/SF
    • 14 Days On Market

    Current Estimated Value $985,799

    Last Listing Agent Stacy Ickes Donnelly + Co.

    41 Trinity Park, Oak Bluffs, MA 02557
    • /2

      Est $1,723,455

      Not Listed For Sale

      26 Old Coach Rd, Vineyard Haven, MA 02568

      • 3 Beds
      • 2.5 Baths
      • 1,923 Sq Ft
      • Built 1998
      26 Old Coach Rd, Vineyard Haven, MA 02568

      Last Sold Summary

      • 0 Days On Market

  • /18

    $1,199,000

    • 3 Beds
    • 2 Baths
    • 1,302 Sq Ft

    47 Winemack St, Oak Bluffs, MA 02557

    Oak Bluffs -East Chop-Close to the beach. Two Year-round cottages on one lot. Stay in one and rent the other, the possibilities are great with this amazing opportunity to own close to the beach and just a mile to Oak Bluffs center. The front house is two bedrooms 1 bath: freshly painted with new flooring. The second home nestled in the back of the lot is an open floor plan with one bedroom, one

    Lisa Lucier Anchor Realty of MV

    47 Winemack St, Oak Bluffs, MA 02557
  • /34

    $25,000 Per Month

    • 4 Beds
    • 3.5 Baths
    • 2,334 Sq Ft
    • House for Rent

    100 Connie's Way Vh401, Tisbury, MA 02568

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $6,250. 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 Vh401, Tisbury, MA 02568
  • /26

    $1,600,000

    Sold Nov 07, 2025

    96 Pondview Dr, Oak Bluffs, MA 02536

    • 4 Beds
    • 2.5 Baths
    • 2,115 Sq Ft
    • Built 2004

    Last Sold Summary

    • 1% Below List Price
    • $757/SF
    • 35 Days On Market

    Last Listing Agent Doug Burke Signal House Group at Compass

    96 Pondview Dr, Oak Bluffs, MA 02536
    • /45

      Est $1,781,197

      Not Listed For Sale

      38 Edgewood Dr, Edgartown, MA 02539

      • 3 Beds
      • 2.5 Baths
      • 2,576 Sq Ft
      • Built 1987
      38 Edgewood Dr, Edgartown, MA 02539

      Last Sold Summary

      • 48 Days On Market

  • /35

    $1,225,000

    Open Sat 10AM - 12PM
    • 3 Beds
    • 2 Baths
    • 1,800 Sq Ft

    52 Oak Knoll Rd, Vineyard Haven, MA 02568

    Year-round living in the desirable Island Farms Road neighborhood of West Tisbury. This well-built three-bedroom, two-bath home offers a comfortable layout with a first-floor primary bedroom. While ready for your personal updates, it provides a solid foundation to create your forever home. The open kitchen and living area offer a welcoming space for everyday living while the screened porch

    Tina Miller Donnelly + Co.

    52 Oak Knoll Rd, Vineyard Haven, MA 02568
  • /30

    $20,000 Per Month

    • 4 Beds
    • 2 Baths
    • 1,920 Sq Ft
    • House for Rent

    291 Barnes Rd Ob516, Oak Bluffs, MA 02557

    THIS IS A WEEKLY SUMMER RENTAL ONLY.SEE WEB SITE FOR WEEKLY PRICING. Feel the ocean breezes from this classic waterfront home. There are four bedrooms, an open living room and dining room that open up to large deck overlooking beautiful views across the Lagoon. Walking path to private sandy beach. BOAT MOORING INCLUDED.

    Karen Overtoom Karen M. Overtoom R.E.

    291 Barnes Rd Ob516, Oak Bluffs, MA 02557
  • /27

    $1,625,000

    Sold May 12, 2026

    7 Upper Meadow Ln, Oak Bluffs, MA 02557

    • 4 Beds
    • 2.5 Baths
    • 3,268 Sq Ft
    • Built 1994

    Last Sold Summary

    • 10% Below List Price
    • $497/SF
    • 74 Days On Market

    Current Estimated Value $1,764,524

    Last Listing Agent Lesley Heidt Sandpiper Realty, Inc.

    7 Upper Meadow Ln, Oak Bluffs, MA 02557
    • /37

      Est $2,009,662

      Not Listed For Sale

      41 Smith Hollow Dr, Edgartown, MA 02539

      • 4 Beds
      • 3.5 Baths
      • 2,391 Sq Ft
      • Built 2001
      41 Smith Hollow Dr, Edgartown, MA 02539

      Last Sold Summary

      • 59 Days On Market

  • /21

    $4,695,000

    • 5 Beds
    • 4.5 Baths
    • 4,816 Sq Ft

    30 Water Gate Rd, Vineyard Haven, MA 02568

    Set privately in one of Vineyard Haven’s most tranquil enclaves, 30 Water Gate Road is a rare legacy offering defined by pastoral beauty and ready access to Lake Tashmoo. The nearly 5,000-square-foot residence offers five bedrooms and generous living spaces designed for both gathering and quiet retreat, with an effortless indoor-outdoor flow that embraces the surrounding landscape. Bedrooms are

    Peyton Wallace Studio Realty

    30 Water Gate Rd, Vineyard Haven, MA 02568
  • /12

    $7,500 Per Month

    • 3 Beds
    • 2 Baths
    • 1,435 Sq Ft
    • House for Rent

    43 Edgartown Rd, Vineyard Haven, MA 02568

    Located off of Edgartown-Vineyard Haven Road, close to down-town and bike path, this 3 bedroom, 2 bath property is being offered year round to the right tenants. The home has been completely renovated, is being offered fully furnished and features an open floor plan with wood floors on the first level, wall to wall carpet in the upstairs bedrooms and an in-ground pool in the backyard. Available

    Karen Overtoom Karen M. Overtoom R.E.

    43 Edgartown Rd, Vineyard Haven, MA 02568
  • /21

    $982,000

    Sold Dec 19, 2025

    25 Windy Hill Rd, Oak Bluffs, MA 02557

    • 3 Beds
    • 1 Bath
    • 980 Sq Ft
    • Built 1971

    Last Sold Summary

    • 1% Below List Price
    • $1,002/SF
    • 10 Days On Market

    Current Estimated Value $1,306,084

    Last Listing Agent Rene Jackson Island Real Estate

    25 Windy Hill Rd, Oak Bluffs, MA 02557
    • /2

      Est $1,352,807

      Not Listed For Sale

      45 Pine Tree Ln, Vineyard Haven, MA 02568

      • 3 Beds
      • 3 Baths
      • 1,400 Sq Ft
      • Built 1961
      45 Pine Tree Ln, Vineyard Haven, MA 02568

  • /37

    $3,999,999

    $500K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 2,715 Sq Ft

    94 Weaver Ln, Vineyard Haven, MA 02568

    Perched high above Lagoon Pond, this exceptional Martha's Vineyard estate offers a rare convergence of natural beauty, refined comfort, and Island living at its finest. Set on 2.25 secluded acres, panoramic views stretch across the shimmering waters, a private haven for kayaking, sailing, and peaceful exploration. Inside, four bedrooms and three full bathrooms are complemented by generous windows

    Emma Kennedy Sandpiper Realty, Inc.

    94 Weaver Ln, Vineyard Haven, MA 02568
  • /25

    $13,600 Per Month

    • 2 Beds
    • 2 Baths
    • 792 Sq Ft
    • House for Rent

    64 Bartimus Luce Road Wt125, West Tisbury, MA 02575

    THIS IS A WEEKLY RENTAL NOT A MONTHLY!!!!!!!!!!Idyllic location right above a sandy private beach on the North Shore. This beach cottage affords views of the Sound and the Elizabeth Islands with a front row seat on unrivaled sunsets. It is rustic and cozy with a large screened porch overlooking the view. Have a getaway like in days of yore when life was simple and the beach at your doorstep.Take

    Karen Overtoom Karen M. Overtoom R.E.

    64 Bartimus Luce Road Wt125, West Tisbury, MA 02575
  • /31

    $1,350,000

    Sold Aug 15, 2025

    35 Vineyard Avenue Extension, Oak Bluffs, MA 02568

    • 3 Beds
    • 2 Baths
    • 1,864 Sq Ft
    • Built 1970

    Last Sold Summary

    • 7% Below List Price
    • $724/SF
    • 9 Days On Market

    Last Listing Agent Lesley Heidt Sandpiper Realty

    35 Vineyard Avenue Extension, Oak Bluffs, MA 02568
    • /36

      Est $2,320,023

      Not Listed For Sale

      377 State Rd, Vineyard Haven, MA 02568

      • 4 Beds
      • 2.5 Baths
      • 2,436 Sq Ft
      • Built 1970
      377 State Rd, Vineyard Haven, MA 02568

      Last Sold Summary

      • 518 Days On Market

  • /66

    $2,675,000

    Open House 7/28 $275K PRICE DROP
    • 4 Beds
    • 8 Baths
    • 3,740 Sq Ft

    15 21st St N, Edgartown, MA 02539

    Located on a quiet street just moments from Edgartown Village, this versatile compound offers a rare combination of privacy, flexibility, and proximity to some of the Island’s most treasured outdoor amenities. Set on over a half-acre, the property features a main residence and a detached guest house, thoughtfully positioned with separate driveways and a natural buffer of mature trees. The main

    Jennifer O'hanlon Compass LLC

    15 21st St N, Edgartown, MA 02539
  • /8

    $18,500 Per Month

    • 4 Beds
    • 3.5 Baths
    • 1,714 Sq Ft
    • House for Rent

    4 Windy Way Wt143, West Tisbury, MA 02575

    THIS PROPERTY IS A WEEKLY RENTAL PROPERTY!! The 3.3 acre private setting is most picturesque with its positioning in private Upper Makonikey , the long circular driveway , its grassy lawn, and rolling landscape fields . Only a short distance away is over 3,000 feet of PRIVATE sandy association Beaches , directly below , with two nearby parking lot access-ways . Nestled onto this promontory is a

    Karen Overtoom Karen M. Overtoom R.E.

    4 Windy Way Wt143, West Tisbury, MA 02575
  • /19

    $1,865,000

    Sold Dec 04, 2025

    71 Netock Ave, Oak Bluffs, MA 02557

    • 4 Beds
    • 5 Baths
    • 2,820 Sq Ft
    • Built 1982

    Last Sold Summary

    • 7% Below List Price
    • $661/SF
    • 11 Days On Market

    Current Estimated Value $2,433,494

    Last Listing Agent Ellen Valentgas Sotheby's International Realty

    71 Netock Ave, Oak Bluffs, MA 02557
    • /5

      Est $2,516,506

      Not Listed For Sale

      21 Old Oklahoma Rd, Vineyard Haven, MA 02568

      • 3 Beds
      • 2.5 Baths
      • 1,657 Sq Ft
      • Built 1948
      21 Old Oklahoma Rd, Vineyard Haven, MA 02568

      Last Sold Summary

      • 0 Days On Market

  • /6

    $1,199,000

    Under Contract
    • Land
    • 22,498 Sq Ft
    • $2,321,394 per Acre

    66 Munroe Avenue and 17 Madison Ave Unit 180 &182, Oak Bluffs, MA 02557

    66 Munroe Avenue and 17 Madison Avenue Oak Bluffs East Chop~Build your custom island retreat in coveted East Chop on this over one-half acre parcel. Offering the potential for a 6 + bedroom residence, this exceptional homesite includes a topographic map and features expansive grounds that may accommodate a pool, subject to local approvals. Ideally located just minutes from the East Chop Beach

    Marilyn Moses Ocean Park Realty Inc

    66 Munroe Avenue and 17 Madison Ave Unit 180 &182, Oak Bluffs, MA 02557
  • /8

    $17,500 Per Month

    • 8 Beds
    • 4.5 Baths
    • 3,876 Sq Ft
    • House for Rent

    550 Chappaquonsett Rd Vh424 Unit 1, Tisbury, MA 02568

    THIS PROPERTY IS A WEEKLY RENTAL PROPERTY!!!!!! Classic vineyard cottage with large open indoor and outdoor spaces to choose from while you and your family create memories to last a lifetime. Enjoy creating appetizers or three course meals in the newly renovated kitchen, bask in the light filled sun room or one of several covered porches while you take in the smell of fresh ocean air and relaxing

    Karen Overtoom Karen M. Overtoom R.E.

    550 Chappaquonsett Rd Vh424 Unit 1, Tisbury, MA 02568
  • /25

    $1,125,000

    Sold Oct 28, 2025

    140 Longview Rd, Vineyard Haven, MA 02568

    • 3 Beds
    • 1.5 Baths
    • 1,432 Sq Ft
    • Built 1964

    Last Sold Summary

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

    Current Estimated Value $1,471,455

    Last Listing Agent Candy DaRosa Feiner Real Estate

    140 Longview Rd, Vineyard Haven, MA 02568
    • /14

      Est $2,541,898

      Not Listed For Sale

      30 Pond Ln, Vineyard Haven, MA 02568

      • 3 Beds
      • 2.5 Baths
      • 2,926 Sq Ft
      • Built 2004
      30 Pond Ln, Vineyard Haven, MA 02568

      Last Sold Summary

      • 5 Days On Market

  • /45

    $1,395,000

    • 2 Beds
    • 1.5 Baths
    • 1,126 Sq Ft

    29 Jernegan Ave, Edgartown, MA 02539

    Set on a generous .72-acre parcel just two miles from Edgartown Village and near the bike path, this thoughtfully renovated cottage offers comfortable living today with expansion potential. The property is move-in ready and provides easy access to beaches, boating, dining, and nearby conservation trails. The bright interior features an open floor plan with a spacious kitchen that flows into the

    Stephanie Roache Donnelly + Co

    29 Jernegan Ave, Edgartown, MA 02539
  • /8

    $18,000 Per Month

    • 3 Beds
    • 2.5 Baths
    • House for Rent

    71 Bartmus Luce Road Wt154, West Tisbury, MA 02575

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $5,000. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Finest Views on the Island!! This house is set high on a hill surrounded by nature. The expansive views from the front of this house are spectacular. Enjoy the large deck or the screened porch and gaze upon one of the most amazing Vineyard Views available. It is a short

    Karen Overtoom Karen M. Overtoom R.E.

    71 Bartmus Luce Road Wt154, West Tisbury, MA 02575
  • /37

    $1,175,000

    Sold Apr 22, 2026

    112 3rd St N, Edgartown, MA 02568

    • 3 Beds
    • 2 Baths
    • 1,196 Sq Ft
    • Built 1980

    Last Sold Summary

    • 8% Below List Price
    • $982/SF
    • 139 Days On Market

    Last Listing Agent Kristin Buck Donnelly + Co.

    112 3rd St N, Edgartown, MA 02568
    • /47

      Est $1,799,363

      Not Listed For Sale

      179 Main St, Vineyard Haven, MA 02568

      • 5 Beds
      • 2.5 Baths
      • 2,134 Sq Ft
      • Built 1840
      179 Main St, Vineyard Haven, MA 02568

      Last Sold Summary

      • 24 Days On Market

Showing Results 41 - 80, Page 2 of 18

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