12,001

Tisbury, MA Homes

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  • /36

    $2,260,000

    $335K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 2,810 Sq Ft

    4 High Meadow Ln, Oak Bluffs, MA 02557

    Set within the coveted Meadow View Farms community, this exceptional post-and-beam residence offers timeless craftsmanship, generous living spaces, and nearly an acre of private beautifully landscaped grounds with significant potential for expansion. A full-length farmer’s porch creates a gracious arrival and provides the perfect setting to relax. Inside, the sun-drenched main level is defined by

    Kate Burnside Portfolio Properties

    4 High Meadow Ln, Oak Bluffs, MA 02557
  • /18

    $10,000 Per Month

    • 3 Beds
    • 2 Baths
    • 1,439 Sq Ft
    • House for Rent

    24 Nat's Farm Lane Wt113, West Tisbury, MA 02575

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $2,500. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Charming three bedroom home located in a private neighborhood close to bike path, walking trails and public tennis courts. Just a short drive to Lambert's Cove Beach, West Tisbury Village and down island restaurants and shops.Amenities include High definition TV, wifi

    Karen Overtoom Karen M. Overtoom R.E.

    24 Nat's Farm Lane Wt113, West Tisbury, MA 02575
  • /3

    $665,000

    Sold Mar 06, 2026

    2 Hope's Way Unit 31, Oak Bluffs, MA 02557

    • Land
    • 11,133 Sq Ft
    • $2,601,721 per Acre

    Last Sold Summary

    • 5% Below List Price
    • 37 Days On Market

    Last Listing Agent Marilyn Moses Ocean Park Realty Inc

    2 Hope's Way Unit 31, Oak Bluffs, MA 02557
    • /34

      Est $1,507,739

      Not Listed For Sale

      84 Christiantown Rd, Vineyard Haven, MA 02568

      • 3 Beds
      • 2 Baths
      • 1,452 Sq Ft
      • Built 2018
      84 Christiantown Rd, Vineyard Haven, MA 02568

      Last Sold Summary

      • 59 Days On Market

  • /27

    $1,800,000

    Pending
    • 3 Beds
    • 3 Baths
    • 2,293 Sq Ft

    10 Trotters Ln, West Tisbury, MA 02575

    Centrally located and surrounded by lush landscaping, this inviting cape offers three bedrooms and three full baths. Warm, mellow wood floors, tiled bathrooms and a spacious living area anchored by a cozy fireplace. The full basement provides ample storage or expansion potential, while a versatile bonus room on the second level is perfect as an art studio, home office or guest overflow.

    Rebecca V Conroy Conroy & Company R.E., Inc.

    10 Trotters Ln, West Tisbury, MA 02575
  • /10

    $8,500 Per Month

    • 3 Beds
    • 2 Baths
    • House for Rent

    29 Bea Lane Wt160 Unit 1, West Tisbury, MA 02575

    THIS IS A WEEKLY RENTAL PROPERTY!! Red Farm, Off Lambert's Cove Road West Tisbury. This newly built Contemporary Home is privately sited overlooking a peaceful meadow and wooded setting. The spacious floor plan features an open living, dining and a well equipped chef's kitchen, cathedral ceilings, wood floors and sliders that lead to a nicely landscaped yard. Three spacious bedrooms, the primary

    Karen Overtoom Karen M. Overtoom R.E.

    29 Bea Lane Wt160 Unit 1, West Tisbury, MA 02575
  • /2

    $880,000

    Sold Oct 17, 2025

    5 Johns Way, Oak Bluffs, MA 02557

    • 3 Beds
    • 2 Baths
    • 1,365 Sq Ft
    • Built 1987

    Last Sold Summary

    • $645/SF
    • 0 Days On Market

    Current Estimated Value $1,273,903

    Last Listing Agent LINK Email Cache LINK

    5 Johns Way, Oak Bluffs, MA 02557
    • /19

      Not Listed For Sale

      43 Look St, Vineyard Haven, MA 02568

      • 4 Beds
      • 2.5 Baths
      • 1,714 Sq Ft
      • Built 1900
      43 Look St, Vineyard Haven, MA 02568

      Last Sold Summary

      • 19 Days On Market

  • /26

    $1,299,000

    Pending
    • 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
  • /41

    $13,500 Per Month

    • 5 Beds
    • 5.5 Baths
    • 3,000 Sq Ft
    • House for Rent

    14 Bernard Cir, Vineyard Haven, MA 02568

    ** SUMMER WEEKLY RATE ** Private and luxurious BRAND NEW contemporary chic 5 BED 5.5 BATH home perfectly situated close to downtown Vineyard Haven yet set amongst a rural and peaceful WEST CHOP adjacent neighborhood. Indulge and unwind in the PRIVATE HEATED SALTWATER IN-GROUND POOL surrounded by opulent outdoor living and dining area highlighted by covered al-fresco kitchen, BBQ grill and bar -

    Allison Cameron Parry Douglas Elliman Real Estate - Nantucket

    14 Bernard Cir, Vineyard Haven, MA 02568
  • /2

    $1,390,000

    Sold Jul 22, 2025

    57 Colonial Dr, Vineyard Haven, MA 02568

    • 3 Beds
    • 2 Baths
    • 1,299 Sq Ft
    • Built 1984

    Last Sold Summary

    • $1,070/SF
    • 0 Days On Market

    Current Estimated Value $1,504,131

    Last Listing Agent LINK Email Cache LINK

    57 Colonial Dr, Vineyard Haven, MA 02568
    • /18

      Est $1,776,976

      Not Listed For Sale

      29 Brook Hollow Rd, Vineyard Haven, MA 02568

      • 4 Beds
      • 2.5 Baths
      • 2,461 Sq Ft
      • Built 1994
      29 Brook Hollow Rd, Vineyard Haven, MA 02568

      Last Sold Summary

      • 52 Days On Market

  • /27

    $1,365,000

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

    51 Davis St, Vineyard Haven, MA 02568

    Discover the charm of Vineyard Haven in this delightful two-bedroom, 3 bath cottage, ideally located just moments from downtown, the Steamship Authority, and the picturesque Lagoon. Whether you're looking for a year-round residence, vacation retreat, or investment property, this home offers the perfect blend of comfort and convenience. Inside you'll find a bright and welcoming floor plan with

    Casandra Hyland Sandpiper Realty, Inc.

    51 Davis St, Vineyard Haven, MA 02568
  • /16

    $5,000 Per Month

    • 1 Bath
    • 400 Sq Ft
    • House for Rent

    90 Edgartown Rd, Vineyard Haven, MA 02568

    *Summer Weekly Rate** Inquire For Long-term Off-Season Rates. Renovated Studio Cottage on Martha's Vineyard w/private feel. Within walking distance to shops, dining, and the ferry. Lots of trees for year-round enjoyment. Open floor plan with Murphy bed for additional space and a large comfortable sofa, galley kitchen with granite countertops, stainless steel appliances, amazing tiled bathroom

    Kim Seawright Generations Realty Group

    90 Edgartown Rd, Vineyard Haven, MA 02568
  • /30

    $1,050,000

    Sold Oct 06, 2025

    4 Quail Run Unit 2, Oak Bluffs, MA 02557

    • 2 Beds
    • 1.5 Baths
    • 1,323 Sq Ft
    • Built 1972

    Last Sold Summary

    • 11% Below List Price
    • $794/SF
    • 62 Days On Market

    Current Estimated Value $1,348,422

    Last Listing Agent Marilyn Moses Ocean Park Realty Inc

    4 Quail Run Unit 2, Oak Bluffs, MA 02557
    • /10

      Est $1,215,283

      Not Listed For Sale

      345 Franklin St, Vineyard Haven, MA 02568

      • 3 Beds
      • 1.5 Baths
      • 1,012 Sq Ft
      • Built 1986
      345 Franklin St, Vineyard Haven, MA 02568

      Last Sold Summary

      • 29 Days On Market

  • /20

    $1,150,000

    $125K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,110 Sq Ft

    34 10th St S, Edgartown, MA 02539

    Welcome to easy Edgartown living in this charming 3-bedroom, 2-bath ranch offering comfort, convenience, and classic Vineyard appeal. Designed for effortless single-level living, the home features a spacious living room, an open kitchen and dining area, and a thoughtful layout ideal for both everyday life and entertaining. The private primary suite includes its own bath, while two additional

    Michael McGuire Insight Realty Group, Inc

    34 10th St S, Edgartown, MA 02539
  • /19

    $30,000 Per Month

    • 5 Beds
    • 4 Baths
    • 3,600 Sq Ft
    • House for Rent

    37 Sachem Cir, West Tisbury, MA 02575

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $7,500. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Lovely pastoral setting with an elegant farm house and guest house. Abutting Land Bank property on two sides. Quiet privacy, yet just minutes to Lambert’s Cove Beach. The four bedroom house and separate guest house are impeccably decorated and the floor plan lends itself

    Karen Overtoom Karen M. Overtoom R.E.

    37 Sachem Cir, West Tisbury, MA 02575
  • /36

    $2,900,000

    Sold Mar 30, 2026

    63 Bayes Hill Rd, Oak Bluffs, MA 02557

    • 4 Beds
    • 5 Baths
    • 5,165 Sq Ft
    • Built 1988

    Last Sold Summary

    • $561/SF
    • 35 Days On Market

    Current Estimated Value $3,833,462

    Last Listing Agent Casandra Hyland Sandpiper Realty, Inc.

    63 Bayes Hill Rd, Oak Bluffs, MA 02557
    • /38

      Est $2,078,601

      Not Listed For Sale

      83 Dolan Ave, Vineyard Haven, MA 02568

      • 5 Beds
      • 4.5 Baths
      • 3,841 Sq Ft
      • Built 1994
      83 Dolan Ave, Vineyard Haven, MA 02568

      Last Sold Summary

      • 24 Days On Market

  • /37

    $3,750,000

    • 4 Beds
    • 3 Baths
    • 2,204 Sq Ft

    9 Weston Ave, Oak Bluffs, MA 02557

    This beautifully situated 4-bedroom, 3-bath home sits at the highest point of East Chop, offering sweeping views of Vineyard Sound. The property features a spacious clerestory living room with a fireplace, along with a combined family room and kitchen, also centered around a cozy fireplace. A large, screened porch opens onto an expansive deck, perfect for relaxing or entertaining. The first floor

    Gerrett Conover Landvest MV

    9 Weston Ave, Oak Bluffs, MA 02557
  • /39

    $46,000 Per Month

    • 6 Beds
    • 4.5 Baths
    • 3,800 Sq Ft
    • House for Rent

    99 Pond Road Wt104, West Tisbury, MA 02575

    THIS IS A WEEKLY RENTAL NOT A MONTHLY!!!!! Beautiful bright sunny home with open concept living. Main floor features a gourmet kitchen with stainless appliances, breakfast bar and formal dining table to seat 10. Large glass sliders open up to expansive views of the deck, pool and pasture beyond. Also on the main level is a separate living area with large screen TV, powder room, and den with twin

    Karen Overtoom Karen M. Overtoom R.E.

    99 Pond Road Wt104, West Tisbury, MA 02575
  • /23

    $1,800,000

    Sold Aug 26, 2025

    12 Martha's Park Rd, Oak Bluffs, MA 02557

    • 4 Beds
    • 1.5 Baths
    • 1,351 Sq Ft
    • Built 1910

    Last Sold Summary

    • 1% Below List Price
    • $1,332/SF
    • 0 Days On Market

    Current Estimated Value $2,281,072

    Last Listing Agent Michele Moore Island Real Estate

    12 Martha's Park Rd, Oak Bluffs, MA 02557
    • /2

      Est $2,629,023

      Not Listed For Sale

      89 Main St, Vineyard Haven, MA 02568

      • 4 Beds
      • 5 Baths
      • 2,728 Sq Ft
      • Built 1830
      89 Main St, Vineyard Haven, MA 02568

  • /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
  • /34

    $12,000 Per Month

    • 3 Beds
    • 2.5 Baths
    • 2,240 Sq Ft
    • House for Rent

    267 Great Plains Road Wt117, West Tisbury, MA 02575

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $4,000. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Large spacious home with open concept living and dining area. This house has gorgeous hardwood floors throughout, separate media room, and loads of natural sunlight. It also features an exceptionally large master bedroom with en-suite bath, and private deck. There is

    Karen Overtoom Karen M. Overtoom R.E.

    267 Great Plains Road Wt117, West Tisbury, MA 02575
  • /12

    $860,000

    Sold Feb 09, 2026

    8 Hitchings Cir, Oak Bluffs, MA 02557

    • 2 Beds
    • 2 Baths
    • 1,232 Sq Ft
    • Built 1985

    Last Sold Summary

    • 6% Below List Price
    • $698/SF
    • 22 Days On Market

    Last Listing Agent Peyton Wallace Studio Realty

    8 Hitchings Cir, Oak Bluffs, MA 02557
    • /31

      Est $1,419,170

      Not Listed For Sale

      48 Puritan Dr, Vineyard Haven, MA 02568

      • 3 Beds
      • 2 Baths
      • 1,999 Sq Ft
      • Built 1985
      48 Puritan Dr, Vineyard Haven, MA 02568

      Last Sold Summary

      • 25 Days On Market

  • /33

    $1,599,000

    • 3 Beds
    • 2.5 Baths
    • 1,645 Sq Ft

    7 Ploughshare Ln, Oak Bluffs, MA 02557

    Nestled in a quiet cul-de-sac within the coveted Hidden Cove neighborhood, this delightful property offers an exceptional Island lifestyle. The association delivers rare water access via a private dock on Sengekontacket Pond, plus newly resurfaced tennis and pickleball courts. The open-concept layout flows seamlessly from the fireplaced living room and kitchen through the dining area to an

    Emma Kennedy Sandpiper Realty, Inc.

    7 Ploughshare Ln, Oak Bluffs, MA 02557
  • /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
  • /31

    $1,685,000

    Sold Oct 09, 2025

    126 Border Rd, Vineyard Haven, MA 02568

    • 3 Beds
    • 3 Baths
    • 2,251 Sq Ft
    • Built 1979

    Last Sold Summary

    • 16% Below List Price
    • $749/SF
    • 337 Days On Market

    Current Estimated Value $2,207,204

    Last Listing Agent Natalie Conroy Conroy & Company R.E., Inc.

    126 Border Rd, Vineyard Haven, MA 02568
    • /14

      Est $1,541,594

      Not Listed For Sale

      13 Saddle Club Rd, Edgartown, MA 02539

      • 3 Beds
      • 2 Baths
      • 2,717 Sq Ft
      • Built 1988
      13 Saddle Club Rd, Edgartown, MA 02539

      Last Sold Summary

      • 43 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
  • /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
  • /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 $1,310,646

    Last Listing Agent Katherine Donahue Sandpiper Realty

    249 County Rd, Oak Bluffs, MA 02557
    • /2

      Est $970,045

      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

  • /42

    $4,600,000

    $350K PRICE DROP
    • 6 Beds
    • 5.5 Baths
    • 3,998 Sq Ft

    15 Tamarack Ln, Oak Bluffs, MA 02557

    Nestled within the idyllic and highly coveted setting of Farm Neck Golf Club, 15 Tamarack Lane offers a rare opportunity to own a stunning 3.7 acres in one of Martha’s Vineyard’s most exclusive communities. The property enjoys picturesque views over the 7th fairway and 8th tee box, across to Sengekontacket Pond, creating a peaceful backdrop of lush greens and distant water. The historic

    Stephanie Roache Donnelly + Co.

    15 Tamarack Ln, Oak Bluffs, MA 02557
  • /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
  • /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 $1,093,126

    Last Listing Agent Susie Wallo Compass

    69 Summit Ave, Vineyard Haven, MA 02568
    • /42

      Not Listed For Sale

      67 Hidden Village Rd, Vineyard Haven, MA 02568

      • 7 Beds
      • 5.5 Baths
      • 4,476 Sq Ft
      • Built 1997
      67 Hidden Village Rd, Vineyard Haven, MA 02568

      Last Sold Summary

      • 347 Days On Market

Showing Results 121 - 160, Page 4 of 18

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