4,289

West Tisbury, MA Homes

Section Image
  • 6 Trails End, Chilmark, MA 02535
    6 Trails End, Chilmark, MA 02535
    6 Trails End, Chilmark, MA 02535
    /16

    $3,200,000

    • 4 Beds
    • 3 Baths
    • 2,346 Sq Ft

    6 Trails End, Chilmark, MA 02535

    Step into timeless mid-century modern style and comfort in this single-level, 4-bedroom, 3-bathroom home located in the heart of Chilmark. This home features an open layout with large glass panel doors that lead to a sun-drenched deck, heated in-ground pool, and grassy lawn. This home is offered completely furnished with a well-equipped kitchen, large living room with wood burning fireplace,

    Russell Maloney Russell Maloney Real Estate

    6 Trails End, Chilmark, MA 02535
  • 27 Beach Plum Ln, Chilmark, MA 02535
    27 Beach Plum Ln, Chilmark, MA 02535
    27 Beach Plum Ln, Chilmark, MA 02535
    /21

    $7,000 total monthly price

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

    27 Beach Plum Ln, Chilmark, MA 02535

    weekly rental rate negotiable, cost $400-$975 per night depending on season and month 3 night min stay The "Grapevine" is located on a private road next door to the Beach Plum Inn, It was completely rebuilt . it has 3 generous size bedrooms all with private baths, 2 of the bedrooms are located on the second floor, 1 bedroom is located on the first floor as well as the Open concept living with a

    Bryan Hummel Commonwealth Realty Group

    27 Beach Plum Ln, Chilmark, MA 02535
  • 140 Longview Rd, Vineyard Haven, MA 02568
    140 Longview Rd, Vineyard Haven, MA 02568
    140 Longview Rd, Vineyard Haven, MA 02568
    /25

    $1,125,000 Sold Oct 28, 2025

    • 1,432 Sq Ft
    • $786/SF
    • 97 Days On Market
    • 3 Beds
    • 1.5 Baths
    • Built 1964

    140 Longview Rd, Vineyard Haven, MA 02568

    Nestled in the hills of Longview, less than 1 mile from beautiful Lambert's Cove Beach, this 3-bedroom retreat is a cozy year-round home or an airy summer getaway - whatever your needs might be. The vaulted ceilings throughout the home allow it to live much larger than its square footage - and the expansive front deck stretches the living space all through the spring, summer and even fall

    Candy DaRosa Feiner Real Estate

    140 Longview Rd, Vineyard Haven, MA 02568
    • 10 Crow Hollow Rd, Vineyard Haven, MA 02568
      10 Crow Hollow Rd, Vineyard Haven, MA 02568
      10 Crow Hollow Rd, Vineyard Haven, MA 02568
      /30

      Est $2,449,577 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 2,555 Sq Ft

      10 Crow Hollow Rd, Vineyard Haven, MA 02568

      10 Crow Hollow Rd, Vineyard Haven, MA 02568
  • 229 Oak Ln, West Tisbury, MA 02575
    229 Oak Ln, West Tisbury, MA 02575
    229 Oak Ln, West Tisbury, MA 02575
    /39

    $2,650,000

    • 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

    Doug Burke Cronigs Real Estate

    229 Oak Ln, West Tisbury, MA 02575
  • 11 Hammett Ln, Chilmark, MA 02535
    11 Hammett Ln, Chilmark, MA 02535
    11 Hammett Ln, Chilmark, MA 02535
    /20

    $4,250 total monthly price

    • 2 Beds
    • 2 Baths
    • 1,152 Sq Ft
    • House for Rent

    11 Hammett Ln, Chilmark, MA 02535

    ** WEEKLY SUMMER RATE** Welcome to 11 Hammett Lane in Chilmark, up-island on beautiful Martha's Vineyard. This sweet private cottage is designer done with gorgeous furnishings, comfortable touches, and a nod to all things local. Affectionately named 'The Blueberry House' by the original owners, this 2 bedroom, 2 bath, 2 story home with outdoor shower will quickly find a place in your heart.

    Allison Cameron Parry Douglas Elliman Real Estate - Nantucket

    11 Hammett Ln, Chilmark, MA 02535
  • 9 Beetlebung Grove Way, Chilmark, MA 02535
    9 Beetlebung Grove Way, Chilmark, MA 02535
    9 Beetlebung Grove Way, Chilmark, MA 02535
    /39

    $2,225,000 Sold Oct 24, 2025

    • 2,968 Sq Ft
    • $750/SF
    • 98 Days On Market
    • 4 Beds
    • 3 Baths
    • Built 1994

    9 Beetlebung Grove Way, Chilmark, MA 02535

    Beautifully sited on 3.4 acres, this distinctive Chilmark home offers a rare blend of privacy, comfort, and expansive living space, ideal for entertaining, both inside and outside. From the welcoming foyer, step into the dramatic vaulted living room, where wood-paneled ceilings, a gas fireplace, and abundant natural light from skylights and picture windows create a warm and inviting atmosphere.

    Stephanie Roache Donnelly + Co.

    9 Beetlebung Grove Way, Chilmark, MA 02535
    • 230 Pond Rd, Vineyard Haven, MA 02568
      230 Pond Rd, Vineyard Haven, MA 02568
      /2

      Est $2,469,488 Not Listed For Sale

      • 4 Beds
      • 4 Baths
      • 3,527 Sq Ft

      230 Pond Rd, Vineyard Haven, MA 02568

      230 Pond Rd, Vineyard Haven, MA 02568
  • 97 Longview Rd, Vineyard Haven, MA 02568
    97 Longview Rd, Vineyard Haven, MA 02568
    97 Longview Rd, Vineyard Haven, MA 02568
    /42

    $4,695,000

    • 5 Beds
    • 5.5 Baths
    • 4,003 Sq Ft

    97 Longview Rd, Vineyard Haven, MA 02568

    This beautifully designed post-and-beam home features stunning views of the Vineyard Sound, Elizabeth Islands, and unforgettable sunsets. Surrounded by beautiful stone walls, sited on 2.2 acres, this serene property offers luxury and comfort, exuding tranquility and timeless charm. The main home spans three spacious levels with generous decks ideal for outdoor living and entertaining. The upper

    Stephanie Roache Donnelly + Co.

    97 Longview Rd, Vineyard Haven, MA 02568
  • 29 Bea Lane Wt160 Unit 1, West Tisbury, MA 02575
    29 Bea Lane Wt160 Unit 1, West Tisbury, MA 02575
    29 Bea Lane Wt160 Unit 1, West Tisbury, MA 02575
    /10

    $8,500 total monthly price

    • 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
  • 25 Plum Bush Point Rd Unit 6, West Tisbury, MA 02568
    25 Plum Bush Point Rd Unit 6, West Tisbury, MA 02568
    25 Plum Bush Point Rd Unit 6, West Tisbury, MA 02568
    /12

    $1,250,000 Sold Oct 23, 2025

    • Land
    • 4.12 Acres
    • $303,398 per Acre
    • 127 Days On Market

    25 Plum Bush Point Rd Unit 6, West Tisbury, MA 02568

    This beautiful wooded 4.12 acre parcel of land is peaceful, serene and ready to build. The well is installed, boundaries staked, perc test approved for a five-bedroom home and a septic plan designed. This is an opportunity to realize your vision and build a home that reflects your lifestyle. The large, flat building envelope offers many siting possibilities and, should you choose, the property is

    Abby Rabinovitz Tea Lane Associates

    25 Plum Bush Point Rd Unit 6, West Tisbury, MA 02568
    • 188 Pond Rd, Vineyard Haven, MA 02568
      188 Pond Rd, Vineyard Haven, MA 02568
      188 Pond Rd, Vineyard Haven, MA 02568
      /4

      Est $2,880,204 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 2,789 Sq Ft

      188 Pond Rd, Vineyard Haven, MA 02568

      188 Pond Rd, Vineyard Haven, MA 02568
  • 15 Old Farm Rd, Chilmark, MA 02535
    15 Old Farm Rd, Chilmark, MA 02535
    15 Old Farm Rd, Chilmark, MA 02535
    /42

    $4,250,000

    • 3 Beds
    • 6 Baths
    • 3,171 Sq Ft

    15 Old Farm Rd, Chilmark, MA 02535

    CHILMARK BLISS – Refined Retreat | 15 Old Farm Road. Set on 3+ acres of manicured grounds, this 2020 Peter Breese–redesigned home blends elegance and tranquility. A serene pond, stream, and custom hardscape set the tone. Inside, a dramatic open kitchen/living area boasts high-end appliances, stone countertops, and a striking fireplace, with a pantry leading to a screened porch. The main-level

    Tina Miller Donnelly + Co.

    15 Old Farm Rd, Chilmark, MA 02535
  • 46 Buttonwood Farm Rd Unit 1, West Tisbury, MA 02575
    46 Buttonwood Farm Rd Unit 1, West Tisbury, MA 02575
    46 Buttonwood Farm Rd Unit 1, West Tisbury, MA 02575
    /8

    $11,800 total monthly price

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

    $1,700,000 Sold Oct 20, 2025

    • 1,803 Sq Ft
    • $943/SF
    • 0 Days On Market
    • 5 Beds
    • 3 Baths
    • Built 1982

    37 Vineyard Meadow Farms Rd, West Tisbury, MA 02568

    Not Listed in LINK

    LINK Email Cache LINK

    37 Vineyard Meadow Farms Rd, West Tisbury, MA 02568
    • 248 Pond Rd, Vineyard Haven, MA 02568
      248 Pond Rd, Vineyard Haven, MA 02568
      248 Pond Rd, Vineyard Haven, MA 02568
      /34

      Est $2,309,824 Not Listed For Sale

      • 5 Beds
      • 3.5 Baths
      • 1 Sq Ft

      248 Pond Rd, Vineyard Haven, MA 02568

      248 Pond Rd, Vineyard Haven, MA 02568
  • 96 Hammett Ln, Chilmark, MA 02535
    96 Hammett Ln, Chilmark, MA 02535
    96 Hammett Ln, Chilmark, MA 02535
    /42

    $3,995,000

    • 3 Beds
    • 4 Baths
    • 3,426 Sq Ft

    96 Hammett Ln, Chilmark, MA 02535

    Beautifully designed and built Post & Beam style home is tastefully thought out and meticulously maintained. The open living, dining and kitchen feature custom built-ins, a wood burning fireplace and a fabulous gourmet kitchen with Wolfe 8 burner professional style stove, Sub Zero refrigerator, Boshe dishwasher, soapstone counters and a butlers pantry with extra cupboards, shelving and a wine

    Brenda Galligan Karen M. Overtoom R.E.

    96 Hammett Ln, Chilmark, MA 02535
  • 5 Wauwompauque Trail Unit 1 CH213, Chilmark, MA 02535
    5 Wauwompauque Trail Unit 1 CH213, Chilmark, MA 02535
    5 Wauwompauque Trail Unit 1 CH213, Chilmark, MA 02535
    /8

    $16,000 total monthly price

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

    5 Wauwompauque Trail Unit 1 CH213, Chilmark, MA 02535

    THIS PROPERTY IS A WEEKLY RENTAL PROPERTY!! Expansive home in North Abels Hill association with water views, private association beach and tennis. Centrally air conditioned, this family home has been well appointed with a large living room featuring fireplaces at both ends, a formal dining room, a first floor primary bedroom with en suite as well as a second floor primary bedroom with en suite.

    Karen Overtoom Karen M. Overtoom R.E.

    5 Wauwompauque Trail Unit 1 CH213, Chilmark, MA 02535
  • 49 Cobbs Hill Rd Unit 24.3, Chilmark, MA 02535
    49 Cobbs Hill Rd Unit 24.3, Chilmark, MA 02535
    49 Cobbs Hill Rd Unit 24.3, Chilmark, MA 02535
    /9

    $1,500,000 Sold Oct 20, 2025

    • Land
    • 3.9 Acres
    • $384,615 per Acre

    49 Cobbs Hill Rd Unit 24.3, Chilmark, MA 02535

    3.9-acre parcel in a very distinguished Chilmark neighborhood. The property comes with deeded access to Tisbury Great Pond via the boat landing just 1/3 of a mile away. From there the Atlantic Ocean is just a boat ride away.

    Mark Jenkins Wallace & Co. Sotheby's

    49 Cobbs Hill Rd Unit 24.3, Chilmark, MA 02535
    • 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 $1,984,778 Not Listed For Sale

      • 5 Beds
      • 3 Baths
      • 3,636 Sq Ft

      131 Shubael Weeks Path, Vineyard Haven, MA 02568

      131 Shubael Weeks Path, Vineyard Haven, MA 02568
  • 27 Clambelly Rd, Chilmark, MA 02535
    27 Clambelly Rd, Chilmark, MA 02535
    27 Clambelly Rd, Chilmark, MA 02535
    /39

    $3,500,000

    • 3 Beds
    • 4 Baths
    • 2,500 Sq Ft

    27 Clambelly Rd, Chilmark, MA 02535

    A place of serenity tucked in the woods of Chilmark. Complete renovation 2017/2018, large fenced in back yard with exquisite fish pond with waterfall and lighting. Kitchen has concrete countertops, sub zero refrigerator, Wolf Oven & Speed Oven. Large open formal dining area and open formal sitting area with fireplace. Beautiful reclaimed wood flooring. LED lighting throughout house, Media

    Julianna Flanders Flanders Real Estate

    27 Clambelly Rd, Chilmark, MA 02535
  • 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
  • 0 Quansoo Beach Lot Unit 50 43710, Chilmark, MA 02535
    0 Quansoo Beach Lot Unit 50 43710, Chilmark, MA 02535
    0 Quansoo Beach Lot Unit 50 43710, Chilmark, MA 02535
    /16

    $475,000 Sold Oct 20, 2025

    • Land
    • 0 Acre
    • 11 Days On Market

    0 Quansoo Beach Lot Unit 50 43710, Chilmark, MA 02535

    Spectacular beach lot at Quansoo. This is the ultimate amenity. Ownership provides access to one of the most stunning beaches on the entire eastern seaboard. On one side is the majestic Atlantic Ocean and on the other the calm waters of Tisbury Great Pond where kids can catch crabs and play safely as you watch. Skip the lines and crowds at other beaches - come and go as you please for sun, sand,

    Mark Jenkins Wallace & Co. Sotheby's

    0 Quansoo Beach Lot Unit 50 43710, Chilmark, MA 02535
    • 26 Old Coach Rd, Vineyard Haven, MA 02568
      26 Old Coach Rd, Vineyard Haven, MA 02568
      /2

      Est $1,698,838 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 2,102 Sq Ft

      26 Old Coach Rd, Vineyard Haven, MA 02568

      26 Old Coach Rd, Vineyard Haven, MA 02568
  • 5 Ocean View Farm Rd, Chilmark, MA 02535
    5 Ocean View Farm Rd, Chilmark, MA 02535
    5 Ocean View Farm Rd, Chilmark, MA 02535
    /19

    $2,675,000

    • 3 Beds
    • 1.5 Baths
    • 1,540 Sq Ft

    5 Ocean View Farm Rd, Chilmark, MA 02535

    Designed by the famous mid century architect Andrew Geller, this contemporary home is situated at the top of the parcel with ocean views and a glimpse of Chilmark pond. There is ample open space to accommodate family and friends and overlooks the large meadow which follows the stone wall to South Road. Access to walking trails, and Lucy Vincent Beach is a short distance away.

    Natalie Conroy Conroy & Company R.E., Inc.

    5 Ocean View Farm Rd, Chilmark, 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

    Karen Overtoom Karen M. Overtoom R.E.

    227 S Gate Rd Wt120, West Tisbury, MA 02575
  • 32 MacHipscat Trail, Vineyard Haven, MA 02568
    32 MacHipscat Trail, Vineyard Haven, MA 02568
    32 MacHipscat Trail, Vineyard Haven, MA 02568
    /19

    $1,330,000 Sold Oct 17, 2025

    • 1,404 Sq Ft
    • $947/SF
    • 112 Days On Market
    • 3 Beds
    • 1.5 Baths
    • Built 1983

    32 MacHipscat Trail, Vineyard Haven, MA 02568

    This Cape Style home privately sited on 1.89 acres at the end of a cul-de-sac abutting conservation land with many walking trails. Nice features include spacious living spaces that include a well equipped kitchen with custom cherry cabinets, dining room, living room with fireplace, wood stove and french doors that lead you out to a private patio and backyard. Second floor offers two guest

    Brenda Galligan Karen M. Overtoom R.E.

    32 MacHipscat Trail, Vineyard Haven, MA 02568
    • 260 South Rd, Chilmark, MA 02535
      260 South Rd, Chilmark, MA 02535
      260 South Rd, Chilmark, MA 02535
      /79

      Not Listed For Sale

      • 6 Beds
      • 2.5 Baths
      • 2,604 Sq Ft

      260 South Rd, Chilmark, MA 02535

      260 South Rd, Chilmark, MA 02535
  • 300 North Rd, Chilmark, MA 02535
    300 North Rd, Chilmark, MA 02535
    300 North Rd, Chilmark, MA 02535
    /36

    $2,995,000

    • 4 Beds
    • 3.5 Baths
    • 2,515 Sq Ft

    300 North Rd, Chilmark, MA 02535

    Winding tree lined driveway off North Rd brings you to this commanding, custom designed residence built by a top tier island builder. This home is set on over 4 private acres of rolling meadows and big sky views. Main living space is all on one level which includes primary bedroom with en-suite bath, large living area with fireplace, bright sunroom or second living room, custom kitchen and two

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

    300 North 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
  • 251 State Rd, Vineyard Haven, MA 02568
    251 State Rd, Vineyard Haven, MA 02568
    251 State Rd, Vineyard Haven, MA 02568
    /30

    $1,550,000 Sold Oct 16, 2025

    • 1,986 Sq Ft
    • $780/SF
    • 114 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1986

    251 State Rd, Vineyard Haven, MA 02568

    This private and pastoral year-round home with fine craftsmanship and loads of character is a classic up-island refuge, yet in a location that is central on the island and convenient to town. Abutting Land Bank property, the charming home features an open living and dining room with wide plank floors and beams flowing into the kitchen, all surrounding a central brick fireplace. An expansive

    Meg Bodnar Tea Lane Associates

    251 State Rd, Vineyard Haven, MA 02568
    • 377 State Rd, Vineyard Haven, MA 02568
      377 State Rd, Vineyard Haven, MA 02568
      377 State Rd, Vineyard Haven, MA 02568
      /36

      Est $2,328,792 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 2,436 Sq Ft

      377 State Rd, Vineyard Haven, MA 02568

      377 State Rd, Vineyard Haven, MA 02568
  • 53 Stoney Hill Rd, Vineyard Haven, MA 02568
    53 Stoney Hill Rd, Vineyard Haven, MA 02568
    53 Stoney Hill Rd, Vineyard Haven, MA 02568
    /39

    $3,299,000

    • 3 Beds
    • 3.5 Baths
    • 3,082 Sq Ft

    53 Stoney Hill Rd, Vineyard Haven, MA 02568

    This custom-built residence is nestled in one of Martha’s Vineyard’s most coveted up-island towns. At the heart of the home lies a professionally designed chef’s kitchen, featuring bespoke cabinetry, honed Carrara marble countertops, Wolf stove and wall oven, Sub-Zero refrigerator, Miele dishwasher, Kohler farmhouse sink, and Rohl satin nickel gooseneck faucet. A custom bar is appointed with

    Jennifer B. DaSilva Compass

    53 Stoney Hill Rd, Vineyard Haven, MA 02568
  • 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
  • 25 Osprey Ln, Chilmark, MA 02535
    25 Osprey Ln, Chilmark, MA 02535
    25 Osprey Ln, Chilmark, MA 02535
    /37

    $7,289,000 Sold Oct 15, 2025

    • 3,777 Sq Ft
    • $1,930/SF
    • 77 Days On Market
    • 4 Beds
    • 5 Baths
    • Built 1988

    25 Osprey Ln, Chilmark, MA 02535

    Spectacular views from one of the most sought after private enclaves on Chilmark's South Shore. This lovely home was built to take advantage of this magical location. Just steps to the shared dock on the shores of Upper Chilmark Pond and minutes to the extraordinary deeded Atlantic Beach front. The homeowners worked with world renowned architects, Crissman & Solomon, along with revolutionary

    Deb Hancock Hancock Real Estate

    25 Osprey Ln, Chilmark, MA 02535
    • 30 Pond Ln, Vineyard Haven, MA 02568
      30 Pond Ln, Vineyard Haven, MA 02568
      30 Pond Ln, Vineyard Haven, MA 02568
      /14

      Est $2,461,695 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 2,926 Sq Ft

      30 Pond Ln, Vineyard Haven, MA 02568

      30 Pond Ln, Vineyard Haven, MA 02568
  • 11 By the Woods, Chilmark, MA 02535
    11 By the Woods, Chilmark, MA 02535
    11 By the Woods, Chilmark, MA 02535
    /35

    $2,850,000

    • 4 Beds
    • 3 Baths
    • 2,967 Sq Ft

    11 By the Woods, Chilmark, MA 02535

    Dreamlike Chilmark retreat on 4.5+/- acres overlooking the Chilmark Pond & Atlantic Ocean beyond. Uniquely designed with European and medieval history in mind. The House has 3 bedrooms, 3 bathrooms, an atrium dining area, a two-story library, a kitchen, and a pantry/wet bar. Charming garden and plantings surround the home.A must-see to appreciate all the special touches throughout the Main

    Julianna Flanders Flanders Real Estate

    11 By the Woods, Chilmark, MA 02535
  • 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

    Karen Overtoom Karen M. Overtoom R.E.

    56 Chilmark Rd, Chilmark, MA 02535
  • 24 Alex Way, Vineyard Haven, MA 02568
    24 Alex Way, Vineyard Haven, MA 02568
    24 Alex Way, Vineyard Haven, MA 02568
    /34

    $2,175,000 Sold Oct 10, 2025

    • 2,879 Sq Ft
    • $755/SF
    • 89 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1985

    24 Alex Way, Vineyard Haven, MA 02568

    24 Alex Way is an opportunity to embrace the extraordinary Elias and Langmuir legacy which dramatically changed a 140 acre rural West Tisbury landscape in 1972 into the Nat's Farm community of 26 home sites. The home overlooks the 56 acres that Nat's Farm donated to Sheriff's Meadow Foundation and the incomparable Misty Meadows Equine Learning Center and homes along Elias Lane. Jane Langmuir,

    Elissa Lash Tea Lane Associates

    24 Alex Way, Vineyard Haven, MA 02568
    • 16 Rock Pond Rd, Vineyard Haven, MA 02568
      16 Rock Pond Rd, Vineyard Haven, MA 02568
      16 Rock Pond Rd, Vineyard Haven, MA 02568
      /36

      Est $1,179,160 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 1,780 Sq Ft

      16 Rock Pond Rd, Vineyard Haven, MA 02568

      16 Rock Pond Rd, Vineyard Haven, MA 02568

Showing Results 1 - 40, Page 1 of 18

Massachusetts Dukes County West Tisbury

Real Estate & Homes

How to Buy a Home How to Finance a Home How to Sell a Home

Find More Real Estate & Homes for Sale by State

Top Cities with Homes For Sale

Top Counties with Homes For Sale

More Real Estate For Sale Near Me

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage

Copyright © 2025 CoStar Group