11,971

Tisbury, MA Homes

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  • /37

    $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

    Agent Photo

    Lisa Lucier

    Anchor Realty of Martha's Vineyard

    (508) 905-5649

    47 Winemack St, Oak Bluffs, MA 02557
  • /20

    $11,845

    Total Monthly Price

    • 4 Beds
    • 3 Baths
    • 2,281 Sq Ft
    • Condo for Rent

    13 N Meadow Ln Unit SI ID1514673P, Oak Bluffs, MA 02568

    The advertised rate of $11,846/month is the lowest available price, based on a 1 month(s) stay with a move-in date of November 16, 2026.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can

    (508) 594-3463

    13 N Meadow Ln Unit SI ID1514673P, Oak Bluffs, MA 02568
  • /27

    $1,070,000

    Sold Apr 17, 2026

    70 Carol Ln, Oak Bluffs, MA 02557

    • 2 Beds
    • 2.5 Baths
    • 1,500 Sq Ft
    • Built 1971

    Last Sold Summary

    • 14% Below List Price
    • $713/SF
    • 463 Days On Market

    Current Estimated Value $1,131,267

    Last Listing Agent Lisa Lucier Anchor Realty of Martha's Vineyard

    70 Carol Ln, Oak Bluffs, MA 02557
    • /19

      Est $1,312,407

      Not Listed For Sale

      193 Franklin Terrace, Vineyard Haven, MA 02568

      • 3 Beds
      • 2 Baths
      • 2,080 Sq Ft
      • Built 1972
      193 Franklin Terrace, Vineyard Haven, MA 02568

      Last Sold Summary

      • 487 Days On Market

  • /53

    $2,295,000

    • 4 Beds
    • 3.5 Baths
    • 3,015 Sq Ft

    3 Hidden Cove Rd, Oak Bluffs, MA 02557

    HIDDEN COVE GEM WITH SERENE POND VIEWS AND COVETED WATER ACCESS. Located in the desirable Hidden Cove enclave, a 65+ acre water-access community with direct access to Sengekontacket Pond and Nantucket Sound, this inviting contemporary home offers privacy, comfort, and high-end finishes throughout. Community amenities include a private boat dock, walking trails, pickleball and tennis, all

    Agent Photo

    Wendy Harman

    Compass | Point B

    (508) 456-9911

    3 Hidden Cove Rd, Oak Bluffs, MA 02557
  • /29

    $64,000 Per Month

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

    385 Barnes Rd Ob534, Oak Bluffs, MA 02557

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $18,000. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This is a beautiful waterfront home with a pool on the Lagoon. Enter through the impressive foyer with water views over the pool and lawn. There is a large living room with cathedral ceilings and dining area on the main level. There is a gourmet kitchen with eat-in

    Karen Overtoom Karen M. Overtoom R.E.

    385 Barnes Rd Ob534, Oak Bluffs, MA 02557
  • /6

    $600,000

    Sold Jun 23, 2025

    27 7th St N, Edgartown, MA 02539

    • Land
    • 21,780 Sq Ft
    • $1,200,000 per Acre

    Last Sold Summary

    • 4% Below List Price
    • 4 Days On Market

    Last Listing Agent Stephanie Roache Donnelly + Co.

    27 7th St N, Edgartown, MA 02539
    • /3

      Est $1,558,471

      Not Listed For Sale

      18 Towanticut Ave, Oak Bluffs, MA 02557

      • 4 Beds
      • 2.5 Baths
      • 2,329 Sq Ft
      • Built 1989
      18 Towanticut Ave, Oak Bluffs, MA 02557

      Last Sold Summary

      • 13 Days On Market

  • /35

    $2,595,000

    • 4 Beds
    • 4.5 Baths
    • 2,288 Sq Ft

    54 Amelia's Crossing, Tisbury, MA 02568

    COASTAL CHIC RETREAT IN VINEYARD HAVEN. Located less than five blocks from Main Street in Vineyard Haven, this classically styled home is perfectly positioned for easy access to restaurants, shops, the harbor, and the ferry, offering the ideal blend of in-town convenience, relaxed island living, and timeless Vineyard appeal. The open-designed living area flows seamlessly to the outdoor living

    Agent Photo

    Wendy Harman

    Compass | Point B

    (508) 290-8910

    54 Amelia's Crossing, Tisbury, MA 02568
  • /21

    $10,338

    Total Monthly Price

    • 3 Beds
    • 2 Baths
    • 1,022 Sq Ft
    • Condo for Rent

    25 Simpson Ave Unit SI ID1514679P, Oak Bluffs, MA 02568

    The advertised rate of $10,339/month is the lowest available price, based on a 1 month(s) stay with a move-in date of November 16, 2026.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can

    25 Simpson Ave Unit SI ID1514679P, Oak Bluffs, MA 02568
  • /42

    $1,300,000

    Sold Feb 13, 2026

    169 Clover Hill Dr, Vineyard Haven, MA 02568

    • 3 Beds
    • 2 Baths
    • 1,809 Sq Ft
    • Built 1977

    Last Sold Summary

    • 4% Below List Price
    • $719/SF
    • 9 Days On Market

    Current Estimated Value $1,321,749

    Last Listing Agent Stephanie Roache Donnelly + Co

    169 Clover Hill Dr, Vineyard Haven, MA 02568
    • /2

      Est $2,575,443

      Not Listed For Sale

      28 Woodhaven Dr, Edgartown, MA 02539

      • 3 Beds
      • Built 2013
      28 Woodhaven Dr, Edgartown, MA 02539

      Last Sold Summary

      • 6,292 Days On Market

  • /24

    $899,000

    • 2 Beds
    • 1 Bath
    • 990 Sq Ft

    37 Circuit Ave Unit 4, Oak Bluffs, MA 02557

    In the heart of Downtown Oak Bluffs- Restless Winds Condominium Unit #4 comes with an amazing roof top deck that is only shared with one other condo (#5). This spacious unit just under 1,000 sq. ft. has a ships feel with custom wood features and a ships ladder leading to the roof top deck. This condo packs a lot in with a full kitchen, living and dining area, a guest bedroom, a tiled bathroom

    Agent Photo

    Lisa Lucier

    Anchor Realty of Martha's Vineyard

    (508) 546-9282

    37 Circuit Ave Unit 4, Oak Bluffs, MA 02557
  • /12

    $15,000 Per Month

    • 5 Beds
    • 6.5 Baths
    • 4,137 Sq Ft
    • House for Rent

    41 Naushon Rd Wt116, Aquinnah, MA 02575

    Stunning water views from this expansive beachfront estate in Makonikey off Lambert's Cove Rd. Enjoy the large living area with comfortable couches, floor to ceiling windows and french doors for seamless indoor to outdoor living and dining. There is a fully equipped kitchen. Some folks will enjoy the treadmill and elliptical while watching boats pass by or even play squash in the indoor squash

    Karen Overtoom Karen M. Overtoom R.E.

    41 Naushon Rd Wt116, Aquinnah, MA 02575
  • /30

    $1,550,000

    Sold Oct 16, 2025

    251 State Rd, Vineyard Haven, MA 02568

    • 3 Beds
    • 2 Baths
    • 1,986 Sq Ft
    • Built 1986

    Last Sold Summary

    • 9% Below List Price
    • $780/SF
    • 114 Days On Market

    Current Estimated Value $1,608,294

    Last Listing Agent Meg Bodnar Tea Lane Associates

    251 State Rd, Vineyard Haven, MA 02568
    • /10

      Not Listed For Sale

      0 Bridle Path Rd, Vineyard Haven, MA 02568

      0 Bridle Path Rd, Vineyard Haven, MA 02568

      Last Sold Summary

      • 17 Days On Market

  • /9

    $1,495,000

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

    33 Alyssa Ln, Vineyard Haven, MA 02568

    Country Living so close to Town! Lovely 4 Bedroom 2,304 sq ft Colonial Cape with Garage and lower level living space . Open kitchen, dining & entertainment area. Sliders open to Large side deck. High Ceilings Wood floors Living Room with additional nook. Half bath. Interior stairs to lower level with office/bedroom, half bath, private exterior entrance and garage. 2nd floor has large primary

    Agent Photo

    Stephanie Burke

    Portfolio Properties

    (508) 719-7391

    33 Alyssa Ln, Vineyard Haven, MA 02568
  • /20

    $20,000 Per Month

    • 3 Beds
    • 3 Baths
    • House for Rent

    40 Hidden Cove Rd, Oak Bluffs, MA 02557

    THIS IS A WEEKLY SUMMER RENTAL ONLY.SEE WEB SITE FOR WEEKLY PRICING. Welcome to "Shangri-la" A beautiful townhouse condominium end unit with magnificent views. Located midway between Oak Bluffs and Edgartown. You can enjoy the beautiful pool or one of the close local beaches. You will want to sit and enjoy the water views on the deck. The townhouse has a great living room with views and bedrooms

    Karen Overtoom Karen M. Overtoom R.E.

    40 Hidden Cove Rd, Oak Bluffs, MA 02557
  • /28

    $1,350,000

    Sold Nov 20, 2025

    16 Majors Cove Ln, Edgartown, MA 02539

    • 3 Beds
    • 2 Baths
    • 1,965 Sq Ft
    • Built 1986

    Last Sold Summary

    • 26% Below List Price
    • $687/SF
    • 156 Days On Market

    Current Estimated Value $1,436,329

    Last Listing Agent Stephanie Roache Donnelly + Co

    16 Majors Cove Ln, Edgartown, MA 02539
    • /15

      Est $1,164,649

      Not Listed For Sale

      15 14th St N, Edgartown, MA 02539

      • 2 Beds
      • 2 Baths
      • 1,056 Sq Ft
      • Built 2018
      15 14th St N, Edgartown, MA 02539

      Last Sold Summary

      • 55 Days On Market

  • /21

    $869,000

    • 1 Bed
    • 1 Bath
    • 797 Sq Ft

    37 Circuit Ave Unit 5, Oak Bluffs, MA 02557

    In the heart of Downtown Oak Bluffs Restless Winds Unit #5 comes with an amazing roof top deck shared with only one other condo (unit #4). You're in the middle of it all with this great location, yet you have easy access to a private and peaceful deck overlooking the town of Oak Bluffs and the surrounding waters. This incredible space takes you to another level of relaxation and a birds eye view

    Agent Photo

    Lisa Lucier

    Anchor Realty of Martha's Vineyard

    (508) 544-0253

    37 Circuit Ave Unit 5, Oak Bluffs, MA 02557
  • /26

    $50,000 Per Month

    • 4 Beds
    • 3 Baths
    • 3,237 Sq Ft
    • House for Rent

    29 Naushon Rd Wt142, West Tisbury, MA 02575

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $12,500. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Waterfront home in spectacular location overlooking the Vineyard Sound and the Elizabeth Islands. This casual and comfortable single level 4 BR 3 bath home has central air and heat. Enjoy summer star-studded skies from your patio or through skylights in each bedroom.

    Karen Overtoom Karen M. Overtoom R.E.

    29 Naushon Rd Wt142, West Tisbury, MA 02575
  • /26

    $1,500,000

    Sold Mar 30, 2026

    68 20th St S, Edgartown, MA 02539

    • 4 Beds
    • 3 Baths
    • 1,975 Sq Ft
    • Built 1997

    Last Sold Summary

    • 6% Below List Price
    • $759/SF
    • 28 Days On Market

    Current Estimated Value $1,610,146

    Last Listing Agent Carol Shore Donnelly + Co

    68 20th St S, Edgartown, MA 02539
    • /38

      Est $1,020,600

      Not Listed For Sale

      287 County Rd, Vineyard Haven, MA 02568

      • 3 Beds
      • 1 Bath
      • 1,120 Sq Ft
      • Built 1998
      287 County Rd, Vineyard Haven, MA 02568

      Last Sold Summary

      • 10 Days On Market

  • /34

    $3,350,000

    • 3 Beds
    • 4.5 Baths
    • 2,912 Sq Ft

    40 Edgewood Dr, Edgartown, MA 02539

    This is an excellent opportunity to own a beautiful crafted custom home set on over half an acre in a peaceful neighborhood just minutes from downtown Edgartown. The property offers striking curb appeal with stone walls, granite steps, professional landscaping, and ample parking, and it borders protected association land that will remain undeveloped. Inside, the home features three spacious

    Carol McManus C McManus Realty Group

    40 Edgewood Dr, Edgartown, MA 02539
  • /22

    $20,000 Per Month

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

    55 Samoset Ave, Oak Bluffs, MA 02557

    Modernized 5 bed, 3 full bath Victorian in the heart of Downtown Oak Bluffs. Steps to restaurants, shopping, harbor, ferries and beaches. Accommodates 10 guests. Easy breezy outdoor living, dining, bluestone patio and BBQ grill. Relax on the covered porch surrounded by a lush flower garden or unwind in the outdoor shower. Updated stone and stainless kitchen. Formal dining for eight. A/C, WIFI and

    Allison Cameron Parry Douglas Elliman Real Estate - Nantucket

    55 Samoset Ave, Oak Bluffs, MA 02557
  • /26

    $1,935,000

    Sold May 06, 2026

    34 Davis St, Tisbury, MA 02568

    • 3 Beds
    • 3.5 Baths
    • 2,453 Sq Ft
    • Built 2025

    Last Sold Summary

    • 19% Below List Price
    • $789/SF
    • 160 Days On Market

    Last Listing Agent Andrew McElhinney Compass LLC

    34 Davis St, Tisbury, MA 02568
    • /26

      Est $1,529,549

      Not Listed For Sale

      19 Quantapog Rd, Vineyard Haven, MA 02568

      • 3 Beds
      • 3 Baths
      • 1,822 Sq Ft
      • Built 1988
      19 Quantapog Rd, Vineyard Haven, MA 02568

      Last Sold Summary

      • 177 Days On Market

  • /66

    $2,950,000

    • 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
  • /21

    $9,500 Per Month

    • 4 Beds
    • 2 Baths
    • 1,579 Sq Ft
    • House for Rent

    155 Skiff Ave, Vineyard Haven, MA 02568

    **SUMMER RENTAL ONLY** PRICE IS WEEKLY** Enjoy the serenity of a four bedroom, two full bathroom peaceful oasis complete with private in-ground pool. Close to lively dining and boutiques of downtown Vineyard Haven. Unwind at neighborhood beaches; Eastville, Owen Park, Tashmoo beaches all just a few minutes drive from your vacation retreat.This lovely home spread over 1600ft of living area

    Allison Cameron Parry Douglas Elliman Real Estate - Nantucket

    155 Skiff Ave, Vineyard Haven, MA 02568
  • /2

    $1,850,000

    Sold Mar 31, 2026

    7 S Meadow Ln, Oak Bluffs, MA 02557

    • 4 Beds
    • 3 Baths
    • 3,142 Sq Ft
    • Built 1987

    Last Sold Summary

    • 1% Above List Price
    • $589/SF
    • 74 Days On Market

    Current Estimated Value $2,021,820

    Last Listing Agent Katie Donahue & Rachel Serwa Group Sandpiper Realty, Inc.

    7 S Meadow Ln, Oak Bluffs, MA 02557
    • /12

      Est $1,192,024

      Not Listed For Sale

      3 Carole Ave, Vineyard Haven, MA 02568

      • 4 Beds
      • 2 Baths
      • 1,997 Sq Ft
      • Built 1985
      3 Carole Ave, Vineyard Haven, MA 02568

      Last Sold Summary

      • 209 Days On Market

  • /46

    $2,400,000

    Under Contract
    • 5 Beds
    • 3.5 Baths
    • 3,873 Sq Ft

    50 Hidden Cove Rd, Edgartown, MA 02539

    Sengekontacket–Walk into a “turn-key” opportunity located within the desirable Hidden Cove community, centrally located to the down-Island villages, ferries, shopping and dininig, and just steps (.3 miles) from Sengekontacket Pond with access to State Beach and Nantucket Sound beyond. The lovingly-maintained 4 bedroom, 2.5 bath, 2 car garage main home sits high on the 1.5 acre property offering

    Sean Federowicz Landmarks at TODAY Real Estate

    50 Hidden Cove Rd, Edgartown, MA 02539
  • /25

    $24,000 Per Month

    • 3 Beds
    • 2 Baths
    • 1,257 Sq Ft
    • House for Rent

    5 Laurel Ave, Oak Bluffs, MA 02557

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $6,500. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Wonderful, fully redecorated Gingerbread house on East Chop, just minutes from the excitement of Oak Bluffs. There are three bedrooms and two full baths. The interior is clean and crisp, with beach cottage décor and beautiful bamboo floors. Entertainment options include

    Karen Overtoom Karen M. Overtoom R.E.

    5 Laurel Ave, Oak Bluffs, MA 02557
  • /27

    $1,560,000

    Sold Jan 15, 2026

    36 Ferro Way, Tisbury, MA 02568

    • 5 Beds
    • 3.5 Baths
    • 4,032 Sq Ft
    • Built 2020

    Last Sold Summary

    • 4% Below List Price
    • $387/SF
    • 37 Days On Market

    Current Estimated Value $1,568,044

    Last Listing Agent Hope O'Brien Compass LLC

    36 Ferro Way, Tisbury, MA 02568
    • /29

      Est $1,248,599

      Not Listed For Sale

      33 Menahan St, Vineyard Haven, MA 02568

      • 3 Beds
      • 2 Baths
      • 1,428 Sq Ft
      • Built 1993
      33 Menahan St, Vineyard Haven, MA 02568

      Last Sold Summary

      • 30 Days On Market

  • /54

    $2,000,000

    • 5 Beds
    • 3.5 Baths
    • 2,075 Sq Ft

    63 Vineyard Meadow Farms Rd, West Tisbury, MA 02575

    Set within the coveted Vineyard Meadow Farms community, this West Tisbury property presents a rare opportunity to own a thoughtfully configured compound in one of the island’s most peaceful and sought-after settings. Privately sited on a generous parcel, the property is surrounded by natural beauty and offers a sense of calm that defines up-island living.The three-bedroom main residence is

    Valene Pires The Agency

    63 Vineyard Meadow Farms Rd, West Tisbury, MA 02575
  • /8

    $6,000 Per Month

    • 4 Beds
    • 2.5 Baths
    • 2,000 Sq Ft
    • House for Rent

    33 Kennebago Ave Vh414, Tisbury, MA 02568

    THIS PROPERTY IS A WEEKLY RENTAL PROPERTY!! This beautiful home has lots of open space for cooking, yard activities or just plain relaxing. Private association beach overlooking the Elizabethan Islands. Plan a sunset picnic on the beach or plan in the morning to see the rays of sun break on the water.

    Karen Overtoom Karen M. Overtoom R.E.

    33 Kennebago Ave Vh414, 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
    • /14

      Est $981,636

      Not Listed For Sale

      51 Manchester Ave, Vineyard Haven, MA 02568

      • 2 Beds
      • 1 Bath
      • 1,024 Sq Ft
      • Built 1978
      51 Manchester Ave, Vineyard Haven, MA 02568

      Last Sold Summary

      • 22 Days On Market

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