19,880

Martha's Vineyard, MA Homes

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  • 229 Oak Ln, West Tisbury, MA 02575
    229 Oak Ln, West Tisbury, MA 02575
    229 Oak Ln, West Tisbury, MA 02575
    /39

    $2,500,000

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

    229 Oak Ln, West Tisbury, MA 02575

    A hidden gem in West Tisbury! Beautifully manicured, fenced in 2.2 - acre parcel with 100% privacy, and 84 evergreen trees. This modern, contemporary well maintained home is 3-bedroom, 3 bath with two levels of living and a partially finished basement. The first floor is a sunlight filled, open kitchen and dinning room, with hardwood floors throughout. There are multiple decks leading out to a

    Doug Burke Cronigs Real Estate

    229 Oak Ln, West Tisbury, MA 02575
  • 44 Music St Wt153, West Tisbury, MA 02575
    44 Music St Wt153, West Tisbury, MA 02575
    44 Music St Wt153, West Tisbury, MA 02575
    /12

    $6,180 total monthly price

    • 3 Beds
    • 3.5 Baths
    • 1,872 Sq Ft
    • House for Rent

    44 Music St Wt153, West Tisbury, MA 02575

    PLEASE TAKE NOTE!!!!!THIS IS A WEEKLY SUMMER RENTAL NOT A MONTHLY RENTAL. THE PRICE ON THIS LISTING IS A WEEkLY PRICE!!!!!!!

    Karen Overtoom Karen M. Overtoom R.E.

    44 Music St Wt153, West Tisbury, MA 02575
  • 31 9th St N, Edgartown, MA 02539
    31 9th St N, Edgartown, MA 02539
    31 9th St N, Edgartown, MA 02539
    /19

    $1,110,000 Sold May 08, 2025

    31 9th St N, Edgartown, MA 02539

    • 2 Beds
    • 1.5 Baths
    • 1,275 Sq Ft
    • Built 1972

    Last Sold Summary

    • 7% Below List Price
    • $871/SF
    • 45 Days On Market

    Current Estimated Value $1,170,058

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

    31 9th St N, Edgartown, MA 02539
    • 131 Shubael Weeks Path, Vineyard Haven, MA 02568
      131 Shubael Weeks Path, Vineyard Haven, MA 02568
      131 Shubael Weeks Path, Vineyard Haven, MA 02568
      /25

      Est $2,063,910 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

      • 3% Above List Price
      • $550/SF
      • 0 Days On Market

      Last Sold Price $2,000,000

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

  • 30 Sengekontacket Rd, Oak Bluffs, MA 02557
    30 Sengekontacket Rd, Oak Bluffs, MA 02557
    30 Sengekontacket Rd, Oak Bluffs, MA 02557
    /24

    $2,195,000 Pending

    • 4 Beds
    • 3 Baths
    • 2,262 Sq Ft

    30 Sengekontacket Rd, Oak Bluffs, MA 02557

    Secluded island retreat nestled above the trees! Located in the desirable Sengekontacket Association, this four-bedroom, three-bathroom home offers stunning views of acres of conservation land, Sengekontacket Pond, and Nantucket Sound. Perched on a hillside, the house provides utmost privacy from all rooms while being just a short walk from the Association boat ramp and kayak storage. The main

    Cassie Bradley Wallace & Co. Sotheby's International Realty

    30 Sengekontacket Rd, Oak Bluffs, MA 02557
  • 41 Naushon Rd Wt116, Aquinnah, MA 02575
    41 Naushon Rd Wt116, Aquinnah, MA 02575
    41 Naushon Rd Wt116, Aquinnah, MA 02575
    /12

    $15,000 total monthly price

    • 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
  • 87 Schoolhouse Rd, Edgartown, MA 02539
    87 Schoolhouse Rd, Edgartown, MA 02539
    87 Schoolhouse Rd, Edgartown, MA 02539
    /29

    $1,350,000 Sold Apr 18, 2025

    87 Schoolhouse Rd, Edgartown, MA 02539

    • 2 Beds
    • 2.5 Baths
    • 1,119 Sq Ft
    • Built 1983

    Last Sold Summary

    • 16% Below List Price
    • $1,206/SF
    • 123 Days On Market

    Current Estimated Value $1,438,132

    Last Listing Agent Stephanie Roache Donnelly + Co

    87 Schoolhouse Rd, Edgartown, MA 02539
    • 26 Old Coach Rd, Vineyard Haven, MA 02568
      26 Old Coach Rd, Vineyard Haven, MA 02568
      /2

      Est $1,725,306 Not Listed For Sale

      26 Old Coach Rd, Vineyard Haven, MA 02568

      • 3 Beds
      • 2.5 Baths
      • 2,102 Sq Ft
      • Built 1998
      26 Old Coach Rd, Vineyard Haven, MA 02568

      Last Sold Summary

      • 3% Above List Price
      • $795/SF
      • 26 Days On Market

      Last Sold Price $1,671,100

      Last Listing Agent Dawn Bellante Sandpiper Realty Inc

  • 23 Beetle Swamp Rd, Edgartown, MA 02539
    23 Beetle Swamp Rd, Edgartown, MA 02539
    23 Beetle Swamp Rd, Edgartown, MA 02539
    /40

    $3,995,000

    • 8 Beds
    • 6 Baths
    • 4,651 Sq Ft

    23 Beetle Swamp Rd, Edgartown, MA 02539

    Sweetened Water Farm ~ Just off the main road, past an idyllic horse barn and conserved association land, you’ll find this eight-bedroom residence that sits prominently on 2.4 acres. The sprawling main house, an expanded classic Cape featuring separate living areas, both inside and out, and six bedrooms, including two first-floor en-suites, overlooks the rolling pastures with grazing horses.

    Katie Donahue & Rachel Serwa Group Sandpiper Realty, Inc.

    23 Beetle Swamp Rd, Edgartown, MA 02539
  • 3 E Pasture Ln, Aquinnah, MA 02535
    3 E Pasture Ln, Aquinnah, MA 02535
    3 E Pasture Ln, Aquinnah, MA 02535
    /11

    $20,000 total monthly price

    • 4 Beds
    • 4.5 Baths
    • 2,306 Sq Ft
    • House for Rent

    3 E Pasture Ln, Aquinnah, MA 02535

    THIS PROPERTY IS A WEEKLY RENTAL PROPERTY!! Breathtaking water views from this contemporary home located on Menemsha Pond and recently renovated with new kitchen and baths. This four bedroom retreat offers the perfect place to come during the summer months or even enjoy during the shoulder season while sitting by the fire with a warm cup of your favorite hot beverage. PLEASE TAKE NOTE!!!!!THIS IS

    Karen Overtoom Karen M. Overtoom R.E.

    3 E Pasture Ln, Aquinnah, MA 02535
  • 48 Witchwood Ln, Edgartown, MA 02539
    48 Witchwood Ln, Edgartown, MA 02539
    48 Witchwood Ln, Edgartown, MA 02539
    /12

    $37,500,000 Sold Oct 30, 2025

    48 Witchwood Ln, Edgartown, MA 02539

    • 9 Beds
    • 9.5 Baths
    • 16,209 Sq Ft
    • Built 2000

    Last Sold Summary

    • $2,314/SF
    • 0 Days On Market

    Last Listing Agent Gerrett Conover Landvest MV

    48 Witchwood Ln, Edgartown, MA 02539
    • 38 Edgewood Dr, Edgartown, MA 02539
      38 Edgewood Dr, Edgartown, MA 02539
      38 Edgewood Dr, Edgartown, MA 02539
      /45

      Est $1,718,736 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

      • 1% Above List Price
      • $660/SF
      • 48 Days On Market

      Last Sold Price $1,700,000

      Last Listing Agent Jon Hartzband Martha's Vineyard Island-Wide Realty

  • 9 Moshup Trail, Aquinnah, MA 02535
    9 Moshup Trail, Aquinnah, MA 02535
    9 Moshup Trail, Aquinnah, MA 02535
    /29

    $2,275,000

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

    9 Moshup Trail, Aquinnah, MA 02535

    Spectacular property in Aquinnah, featuring a newly installed and town-approved 6-bedroom septic system, ready to support your vision for expansion and renovation. Located on 4.7 acres filled with rolling meadows and stone walls, this property boasts a truly remarkable barn that was transported from Maine, and rebuilt on the Island. The grandfathered-in barn spans approximately 61' by 45' with

    Patrick McCarthy Grace Hagerty Real Estate Inc

    9 Moshup Trail, Aquinnah, MA 02535
  • 227 S Gate Rd Wt120, West Tisbury, MA 02575
    227 S Gate Rd Wt120, West Tisbury, MA 02575
    227 S Gate Rd Wt120, West Tisbury, MA 02575
    /8

    $8,250 total monthly price

    • 7 Beds
    • 5 Baths
    • 3,528 Sq Ft
    • House for Rent

    227 S Gate Rd Wt120, West Tisbury, MA 02575

    THIS PROPERTY IS A WEEKLY PROPERTY!! Set on 12 acres of peaceful woods, meadows, stone walls and its own pond, this charming 18th century 4 bedroom farmhouse and 3 bedroom rustic barn sleeps 12 and is perfect for larger groups wanting peace and tranquility all within a short distance to private swimming beaches. The setting, on exclusive Seven Gates Farm, offers miles of sandy trails through open

    Karen Overtoom Karen M. Overtoom R.E.

    227 S Gate Rd Wt120, West Tisbury, MA 02575
  • 48 Edgartown - West Tisbury Rd, Edgartown, MA 02539
    48 Edgartown - West Tisbury Rd, Edgartown, MA 02539
    48 Edgartown - West Tisbury Rd, Edgartown, MA 02539
    /9

    $1,000,000 Sold Jan 13, 2026

    48 Edgartown - West Tisbury Rd, Edgartown, MA 02539

    • 3 Beds
    • 3 Baths
    • 1,959 Sq Ft
    • Built 1950

    Last Sold Summary

    • 29% Below List Price
    • $510/SF
    • 86 Days On Market

    Last Listing Agent Mavis Francis eXp Realty

    48 Edgartown - West Tisbury Rd, Edgartown, MA 02539
    • 53 Peases Point Way N, Edgartown, MA 02539
      53 Peases Point Way N, Edgartown, MA 02539
      53 Peases Point Way N, Edgartown, MA 02539
      /41

      Est $2,519,548 Not Listed For Sale

      53 Peases Point Way N, Edgartown, MA 02539

      • 4 Beds
      • 2 Baths
      • 1,704 Sq Ft
      • Built 1928
      53 Peases Point Way N, Edgartown, MA 02539

      Last Sold Summary

      • 1% Above List Price
      • $1,467/SF
      • 0 Days On Market

      Last Sold Price $2,500,000

      Last Listing Agent Jen O'Hanlon Compass | The O'Hanlon Group

  • 35 Mariners Way, Edgartown, MA 02539
    35 Mariners Way, Edgartown, MA 02539
    35 Mariners Way, Edgartown, MA 02539
    /32

    $2,095,000 Under Contract

    • 4 Beds
    • 2.5 Baths
    • 2,706 Sq Ft

    35 Mariners Way, Edgartown, MA 02539

    35 Mariner’s Way is sited on nearly a half acre lot and lies within walking distance to Edgartown Village shops, restaurants, galleries, and inns and Sheriff’s Meadow conservation land. This 4 bedroom, 2 1⁄2 bath home features a large living room and formal dining room, chef’s kitchen with two ovens and wine room/pantry, and a spacious family room with a gas fireplace. There are two ensuite

    Russell Maloney Russell Maloney Real Estate

    35 Mariners Way, Edgartown, MA 02539
  • 4 Windy Way Wt143, West Tisbury, MA 02575
    4 Windy Way Wt143, West Tisbury, MA 02575
    4 Windy Way Wt143, West Tisbury, MA 02575
    /8

    $18,500 total monthly price

    • 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
  • 191 Spring Hill Rd, Vineyard Haven, MA 02568
    191 Spring Hill Rd, Vineyard Haven, MA 02568
    191 Spring Hill Rd, Vineyard Haven, MA 02568
    /31

    $1,325,000 Sold Jun 30, 2025

    191 Spring Hill Rd, Vineyard Haven, MA 02568

    • 5 Beds
    • 4 Baths
    • 2,292 Sq Ft
    • Built 1992

    Last Sold Summary

    • 5% Below List Price
    • $578/SF
    • 10 Days On Market

    Current Estimated Value $1,259,725

    Last Listing Agent Madelyn Silvia Wallace & Co. Sotheby's

    191 Spring Hill Rd, Vineyard Haven, MA 02568
    • 56 Pinehurst Rd, Edgartown, MA 02539
      56 Pinehurst Rd, Edgartown, MA 02539
      56 Pinehurst Rd, Edgartown, MA 02539
      /38

      Not Listed For Sale

      56 Pinehurst Rd, Edgartown, MA 02539

      • 4 Beds
      • 2.5 Baths
      • 2,328 Sq Ft
      • Built 1973
      56 Pinehurst Rd, Edgartown, MA 02539

      Last Sold Summary

      • $1,108/SF
      • 141 Days On Market

      Last Sold Price $2,580,000

      Last Listing Agent Wendy Harman Compass

  • 6 Lauras Way, Edgartown, MA 02539
    6 Lauras Way, Edgartown, MA 02539
    6 Lauras Way, Edgartown, MA 02539
    /3

    $2,700,000

    • 4 Beds
    • 4.5 Baths
    • 2,750 Sq Ft

    6 Lauras Way, Edgartown, MA 02539

    Coastal Luxury Meets Versatility in EdgartownWelcome to a rare opportunity to own a brand-new, GORGEOUS, custom-built home in Edgartown, set on a sprawling one-acre plot with a stunning detached 900 sq ft accessory dwelling. The main residence opens to an inviting two-story foyer, leading to an expansive, sun-drenched living room featuring a wall of glass sliders that erase the boundary

    Michele Casavant Vineyard Village Realty

    6 Lauras Way, Edgartown, MA 02539
  • 33 Menemsha Inn Rd Ch223 3, Chilmark, MA 02535
    33 Menemsha Inn Rd Ch223 3, Chilmark, MA 02535
    33 Menemsha Inn Rd Ch223 3, Chilmark, MA 02535
    /8

    $4,500 total monthly price

    • 2 Beds
    • 2 Baths
    • 1,393 Sq Ft
    • House for Rent

    33 Menemsha Inn Rd Ch223 3, Chilmark, MA 02535

    THIS IS A WEEKLY RENTAL PROPERTY!! This spacious two bedroom home is filled with classic Vineyard charm. Each room features spectacular views overlooking Vineyard Sound, as well as stellar sunsets in the evening. Close to Menemsha Village and public beach as well as access to Lucy Vincent and Squibnocket beaches.

    Karen Overtoom Karen M. Overtoom R.E.

    33 Menemsha Inn Rd Ch223 3, Chilmark, MA 02535
  • 96 Pondview Dr, Oak Bluffs, MA 02536
    96 Pondview Dr, Oak Bluffs, MA 02536
    96 Pondview Dr, Oak Bluffs, MA 02536
    /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 Cronigs Real Estate

    96 Pondview Dr, Oak Bluffs, MA 02536
    • 260 South Rd, Chilmark, MA 02535
      260 South Rd, Chilmark, MA 02535
      260 South Rd, Chilmark, MA 02535
      /79

      Not Listed For Sale

      260 South Rd, Chilmark, MA 02535

      • 6 Beds
      • 2.5 Baths
      • 2,604 Sq Ft
      • Built 1688
      260 South Rd, Chilmark, MA 02535

      Last Sold Summary

      • $1,671/SF
      • 109 Days On Market

      Last Sold Price $4,350,000

      Last Listing Agent Jill Napior Tea Lane Associates

  • 34 Windemere Rd, Oak Bluffs, MA 02557
    34 Windemere Rd, Oak Bluffs, MA 02557
    34 Windemere Rd, Oak Bluffs, MA 02557
    /44

    $2,700,000

    • 4 Beds
    • 3 Baths
    • 1,399 Sq Ft

    34 Windemere Rd, Oak Bluffs, MA 02557

    Perfect opportunity to own a Beautiful Beach Cottage with access to Lagoon. Totally renovated in 2019. It has been designed for relaxed living and memorable entertaining. There are 3 seating areas on the deck, to enjoy dining outside, experiencing incredible waterviews and lovely sky reflections of sunsets. Beautifully landscaped, with seasonal flowers, and Butterfly flowering bushes. Easement to

    JoJo Lambert Island Home Realty Inc.

    34 Windemere Rd, Oak Bluffs, MA 02557
  • 19 Morse St, Edgartown, MA 02539
    19 Morse St, Edgartown, MA 02539
    19 Morse St, Edgartown, MA 02539
    /8

    $19,000 total monthly price

    • 5 Beds
    • 5 Baths
    • 3,137 Sq Ft
    • House for Rent

    19 Morse St, Edgartown, MA 02539

    THIS PROPERTY IS A WEEKLY RENTAL PROPERTY!! Newly renovated historical home in the heart of Edgartown Village, close to Fuller Street & Lighthouse Beaches. Beautifully designed interior with open gourmet kitchen and pickled hardwood floors, marble countertops, top of the line appliances and a large center island. Cozy family room with fireplace, formal living room, office/den and a full bath all

    Karen Overtoom Karen M. Overtoom R.E.

    19 Morse St, Edgartown, MA 02539
  • 345 Franklin St, Vineyard Haven, MA 02568
    345 Franklin St, Vineyard Haven, MA 02568
    345 Franklin St, Vineyard Haven, MA 02568
    /25

    $949,000 Sold Jun 23, 2025

    345 Franklin St, Vineyard Haven, MA 02568

    • 3 Beds
    • 1.5 Baths
    • 1,012 Sq Ft
    • Built 1986

    Last Sold Summary

    • $938/SF
    • 49 Days On Market

    Current Estimated Value $963,496

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

    345 Franklin St, Vineyard Haven, MA 02568
    • 100 Meetinghouse Way, Edgartown, MA 02539
      100 Meetinghouse Way, Edgartown, MA 02539
      100 Meetinghouse Way, Edgartown, MA 02539
      /14

      Est $5,865,611 Not Listed For Sale

      100 Meetinghouse Way, Edgartown, MA 02539

      • 4 Beds
      • 3 Baths
      • 3,193 Sq Ft
      • Built 1976
      100 Meetinghouse Way, Edgartown, MA 02539

      Last Sold Summary

      • 8% Below List Price
      • $1,988/SF
      • 5 Days On Market

      Last Sold Price $6,349,000

      Last Listing Agent Jennifer DaSilva Compass | Point B

  • 16 South Rd, Chilmark, MA 02535
    16 South Rd, Chilmark, MA 02535
    16 South Rd, Chilmark, MA 02535
    /36

    $2,500,000

    • 4 Beds
    • 3 Baths
    • 2,350 Sq Ft

    16 South Rd, Chilmark, MA 02535

    Where Vineyard history meets pastoral beauty.Classic, lovingly restored 1800’s Chilmark farmhouse with multiple outbuildings, which includes a large barn with second floor loft, a run-in barn with two horse stalls, both overlook an expansive, pastoral fenced pasture for horses to run or field games to be played. This historic farmhouse home offers four bedrooms, three baths and has been updated

    Michele Casavant Vineyard Village Realty

    16 South Rd, Chilmark, MA 02535
  • 165 Christiantown Rd, West Tisbury, MA 02575
    165 Christiantown Rd, West Tisbury, MA 02575
    165 Christiantown Rd, West Tisbury, MA 02575
    /8

    $4,800 total monthly price

    • 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
  • 160 Bernard Cir, Vineyard Haven, MA 02568
    160 Bernard Cir, Vineyard Haven, MA 02568
    160 Bernard Cir, Vineyard Haven, MA 02568
    /34

    $1,050,000 Sold Jun 30, 2025

    160 Bernard Cir, Vineyard Haven, MA 02568

    • 4 Beds
    • 2 Baths
    • 1,606 Sq Ft
    • Built 1977

    Last Sold Summary

    • 12% Below List Price
    • $654/SF
    • 45 Days On Market

    Current Estimated Value $1,116,442

    Last Listing Agent Dawn Bellante-Holand Sandpiper Realty

    160 Bernard Cir, Vineyard Haven, MA 02568
    • 45 Pine Tree Ln, Vineyard Haven, MA 02568
      45 Pine Tree Ln, Vineyard Haven, MA 02568
      /2

      Est $1,357,971 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

      Last Sold Summary

      • 10% Below List Price
      • $884/SF

      Last Sold Price $1,237,500

      Last Listing Agent Sheila Morse Island Real Estate

  • 35 Double Ox Rd, Oak Bluffs, MA 02557
    35 Double Ox Rd, Oak Bluffs, MA 02557
    35 Double Ox Rd, Oak Bluffs, MA 02557
    /9

    $2,250,000

    • 3 Beds
    • 3.5 Baths
    • 2,475 Sq Ft

    35 Double Ox Rd, Oak Bluffs, MA 02557

    Would you love to live or vacation in a brand-new home on Martha’s Vineyard?We have the LOCATION, REPUTABLE LONG-STANDING BUILDER & PROVEN TRACK RECORD!Come take a tour of the newest home under construction in the Lagoon Ridge neighborhood.Easy to show – Call now! To be built with lot purchase$700,000 and building contract $1,550,000.This 3-bedroom dream home is set in an elevated

    Marilyn Moses Ocean Park Realty Inc

    35 Double Ox Rd, Oak Bluffs, MA 02557
  • 6 Briar Path, Aquinnah, MA 02535
    6 Briar Path, Aquinnah, MA 02535
    6 Briar Path, Aquinnah, MA 02535
    /15

    $5,000 total monthly price

    • 4 Beds
    • 2.5 Baths
    • 2,300 Sq Ft
    • House for Rent

    6 Briar Path, Aquinnah, MA 02535

    THIS IS A WEEKLY SUMMER RENTAL ONLY. PRICES ARE WEEKLY NOT MONTHLY. Down a private country road, this bright and breezy post and beam home sits on a 3-acre rolling wooded parcel. With southern views of the Atlantic Ocean, it's just a short drive or bike to Philbin and Lobsterville beaches and Gay Head cliffs. This very Vineyard house offers three levels of living space, chef's kitchen, spacious

    Karen Overtoom Karen M. Overtoom R.E.

    6 Briar Path, Aquinnah, MA 02535
  • 37 Road To the Plains, Edgartown, MA 02539
    37 Road To the Plains, Edgartown, MA 02539
    37 Road To the Plains, Edgartown, MA 02539
    /42

    $3,695,000 Sold Nov 20, 2025

    37 Road To the Plains, Edgartown, MA 02539

    • 4 Beds
    • 2.5 Baths
    • 2,500 Sq Ft
    • Built 1986

    Last Sold Summary

    • $1,478/SF
    • 40 Days On Market

    Current Estimated Value $2,932,869

    Last Listing Agent Wendy Harman Compass

    37 Road To the Plains, Edgartown, MA 02539
    • 377 State Rd, Vineyard Haven, MA 02568
      377 State Rd, Vineyard Haven, MA 02568
      377 State Rd, Vineyard Haven, MA 02568
      /36

      Est $2,349,533 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

      • 7% Above List Price
      • $902/SF
      • 518 Days On Market

      Last Sold Price $2,197,000

      Last Listing Agent Jill Napior Tea Lane Associates

  • 43C Dark Woods Rd, Edgartown, MA 02539
    43C Dark Woods Rd, Edgartown, MA 02539
    43C Dark Woods Rd, Edgartown, MA 02539
    /40

    $2,095,000 Under Contract

    • 4 Beds
    • 3.5 Baths
    • 2,695 Sq Ft

    43C Dark Woods Rd, Edgartown, MA 02539

    Welcome to Dark Woods – A Quiet Retreat with Prime Convenience. Enjoy the ease and comfort of life in Dark Woods, a tranquil neighborhood ideally located just moments from the Village, scenic bike paths, pristine beaches, and 27 acres of Sheriff’s Meadow conservation land. This meticulously maintained property is being offered fully furnished and is ready for your immediate enjoyment. Sited on a

    Stephanie Roache Donnelly + Co

    43C Dark Woods Rd, Edgartown, MA 02539
  • 56 Chilmark Rd, Chilmark, MA 02535
    56 Chilmark Rd, Chilmark, MA 02535
    56 Chilmark Rd, Chilmark, MA 02535
    /8

    $8,000 total monthly price

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

    56 Chilmark Rd, Chilmark, MA 02535

    THIS PROPERTY IS A WEEKLY RENTAL PROPERTY!! This slice of paradise in the coveted Seven Gates Association gives you access to two miles of private beach just half a mile away, with tennis courts also nearby and 1000 acres of conservation land. The house is exquisitely crafted, well maintained and beautifully landscaped. Views of Harlock's pond are visible from the kitchen, living area and master

    Karen Overtoom Karen M. Overtoom R.E.

    56 Chilmark Rd, Chilmark, MA 02535
  • 25 Windy Hill Rd, Oak Bluffs, MA 02557
    25 Windy Hill Rd, Oak Bluffs, MA 02557
    25 Windy Hill Rd, Oak Bluffs, MA 02557
    /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 $969,547

    Last Listing Agent Rene Jackson Island Real Estate

    25 Windy Hill Rd, Oak Bluffs, MA 02557
    • 94 Marthas Rd, Edgartown, MA 02539
      94 Marthas Rd, Edgartown, MA 02539
      94 Marthas Rd, Edgartown, MA 02539
      /36

      Est $3,771,439 Not Listed For Sale

      94 Marthas Rd, Edgartown, MA 02539

      • 6 Beds
      • 4.5 Baths
      • 3,902 Sq Ft
      • Built 2009
      94 Marthas Rd, Edgartown, MA 02539

      Last Sold Summary

      • 13% Above List Price
      • $859/SF
      • 458 Days On Market

      Last Sold Price $3,350,000

      Last Listing Agent Bonnie Pierce Wallace & Co. Sotheby's International Realty

Showing Results 81 - 120, Page 3 of 18

Massachusetts Martha's Vineyard

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