4,246

Chilmark, MA Homes

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  • /44

    $8,450,000

    • 6 Beds
    • 5 Baths
    • 4,104 Sq Ft

    94 Menemsha Inn Rd, Chilmark, MA 02535

    Walk to a private beach and enjoy the beautifully manicured gardens and landscape of this well-loved and privately situated home! Custom designed with a charming Vineyard feel and tasteful interior design. Water view from a gourmet kitchen and formal dining area. Large open living room and spacious bedrooms. Large deck with exceptional views of the North shore and Elizabeth Island's A large

    Julianna Flanders Flanders Real Estate

    94 Menemsha Inn Rd, Chilmark, MA 02535
  • /33

    $22,000 per month

    • 3 Beds
    • 2.5 Baths
    • 2,800 Sq Ft
    • House for Rent

    2 Strikers Way Ch211, Chilmark, MA 02535

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $5,500. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Just a short distance from Chilmark Store, this newly remodeled home features 3 bedrooms and 2 1/2 baths. High end finishes with a beachy island feel. The master is located on the first floor with en-suit bath. Fully equipped kitchen with a Cuisinart 14-cup programmable

    Karen Overtoom Karen M. Overtoom R.E.

    2 Strikers Way Ch211, Chilmark, MA 02535
  • /29

    $2,250,000 Sold Dec 27, 2024

    • 1,705 Sq Ft
    • $1320/SF
    • 5 Days On Market
    • 4 Beds
    • 3 Baths
    • Built 1976

    47 Stonebridge Rd, West Tisbury, MA 02568

    Lamberts Cove Beach access, first and second floor water views, and a warm and inviting home in a private West Tisbury location - that is what is on offer here. The home was recently upgraded with a new kitchen and bathrooms. The primary bedroom suite has even better views than those from the first floor. The walkout lower level is a two bedroom suite with full bath, sitting area, kitchenette,

    Mark Jenkins Wallace & Co. Sotheby's International Realty

    47 Stonebridge Rd, West Tisbury, MA 02568
    • /30

      Est $3,990,890 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,748 Sq Ft

      26 Pinkletink Rd, Chilmark, MA 02535

      26 Pinkletink Rd, Chilmark, MA 02535
  • /44

    $1,749,000

    • 4 Beds
    • 2 Baths
    • 2,320 Sq Ft

    26 Manaquayak Rd, Vineyard Haven, MA 02568

    Large comfortable and charming expanded Cape in a lovely setting very close to Lambert's Cove Beach and James Pond Preserve with special walking access to Swimming on Ice House Pond in the Manaquayak Preserve as well as deeded walking access to swim and boat on Seth's Pond. The living room is open to the beautiful newly-renovated kitchen and has an often-used wood-burning fireplace. There is a

    Candy DaRosa Feiner Real Estate

    26 Manaquayak Rd, Vineyard Haven, MA 02568
  • /35

    $22,000 per month

    • 4 Beds
    • 2 Baths
    • 2,290 Sq Ft
    • House for Rent

    36 Henry Hough Lane Ch206, Chilmark, MA 02535

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $5,500. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Water views, 3 acres and stone walls. At the end of a lane, enjoy the privacy offered by 49 acres of conservation land complete with walking trails. This house is a short distance from Lucy Vincent beach, as well as from Menemsha and Squibnocket. This spacious four

    Karen Overtoom Karen M. Overtoom R.E.

    36 Henry Hough Lane Ch206, Chilmark, MA 02535
  • /5

    $450,000 Sold Dec 12, 2024

    • 708 Sq Ft
    • $636/SF
    • 21 Days On Market
    • 2 Beds
    • 1 Bath
    • Built 1920

    1 Carroll Ln, Chilmark, MA 02535

    Discover the perfect blend of comfort and character in this delightful bungalow nestled in the heart of historic Chilmark. Surrounded by scenic landscapes and the serene beauty of Martha's Vineyard. This home will require substantial renovations and improvements or explore possibilities of a complete renovation. This property could be your idyllic escape and is less than a mile from Menemsha

    Nicholas Korba Landmarks at TODAY Real Estate

    1 Carroll Ln, Chilmark, MA 02535
    • /13

      Est $1,750,387 Not Listed For Sale

      • 3 Beds
      • 3 Baths
      • 2,073 Sq Ft

      127 Old County Rd, Vineyard Haven, MA 02568

      127 Old County Rd, Vineyard Haven, MA 02568
  • /37

    $7,975,000

    • 4 Beds
    • 5 Baths
    • 3,777 Sq Ft

    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
  • /29

    $34,000 per month

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

    15 Loon Lane Ch203, Chilmark, MA 02535

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $8,500. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Modern 4 bedroom home completed in 2019, in Menemsha. Located on a quiet road with waterviews from the upstairs bedrooms also offers views of the famous Menemsha sunsets from the deck. Sustainably harvested flooring features silky smooth and buttery hard wood floors from

    Karen Overtoom Karen M. Overtoom R.E.

    15 Loon Lane Ch203, Chilmark, MA 02535
  • /26

    $1,830,000 Sold Dec 05, 2024

    • 1,862 Sq Ft
    • $983/SF
    • 10 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1960

    82 South Rd, Chilmark, MA 02535

    This charming Chilmark home sits on over 3 acres and features an updated, move-in ready home, expansive outdoor living space with deck, lawn and firepit area, and a six-bedroom septic system for future expansion. The welcoming foyer opens into the dining room, kitchen and a large airy living room with vaulted ceiling and stone fireplace. Beyond the kitchen there are two bedrooms and a shared

    Meg Bodnar Tea Lane Associates

    82 South Rd, Chilmark, MA 02535
    • /17

      Est $1,436,275 Not Listed For Sale

      • 3 Beds
      • 3 Baths
      • 1,800 Sq Ft

      2 Pond View Farm Rd, Vineyard Haven, MA 02568

      2 Pond View Farm Rd, Vineyard Haven, MA 02568
  • /25

    $1,800,000

    • 4 Beds
    • 1.5 Baths
    • 1,592 Sq Ft

    5 Scottys Ln, Vineyard Haven, MA 02568

    Opportunity Knocks on Scotty's Lane! Prime West Tisbury Location with Seth's Pond Frontage. Imagine crafting your dream home on this coveted stretch of Lambert's Cove Road. 5 Scotty's Lane presents a rare chance to own property in a highly desirable area, just a short stroll from the pristine, town-owned Lambert's Cove Beach. Plus, enjoy direct frontage on Seth's Pond, a beloved Island swimming

    Idalyn Macchia Gilstad Wallace & Co. Sotheby's International Realty

    5 Scottys Ln, Vineyard Haven, MA 02568
  • /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
  • /4

    $1,350,000 Sold Dec 03, 2024

    • 2,179 Sq Ft
    • $620/SF
    • 0 Days On Market
    • 4 Beds
    • 2 Baths
    • Built 1987

    47 Willow Tree Hollow Rd, West Tisbury, MA 02568

    SERENE & PRIVATE WEST TISBURY PROPERTY - Down a country lane off West Tisbury Road, this 1.55 acre property is a serene location for a vacation or year round home. Set on a knoll with established gardens, the outdoor spaces are cool and inviting with a large deck, level back yard, and an outdoor shower. Newly painted walls and trim throughout. There is room to spread out and relax after a day

    Leslie Floyd Portfolio Real Estate Inc.

    47 Willow Tree Hollow Rd, West Tisbury, MA 02568
    • /30

      Est $1,457,837 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,464 Sq Ft

      88 Hopps Farm Rd, Vineyard Haven, MA 02568

      88 Hopps Farm Rd, Vineyard Haven, MA 02568
  • /35

    $2,495,000

    • 4 Beds
    • 3 Baths
    • 2,968 Sq Ft

    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
  • /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
  • /48

    $7,650,000 Sold Nov 21, 2024

    • 3,834 Sq Ft
    • $1995/SF
    • 48 Days On Market
    • 6 Beds
    • 5 Baths
    • Built 1995

    49 Tilton Rd, Chilmark, MA 02535

    Unique opportunity to enjoy a remarkable, secure, elevated Chilmark north shore 4 acre waterfront property with dramatic 180 degree year round sunset water views over the one mile Spring Point sandy coastline to Great Rock Bight, Menemsha Hills, Aquinnah shore, Gay Head Lighthouse and the Elizabeth Islands stretching almost to Woods Hole. This wide expanse of the Vineyard Sound enjoys endless

    Robert Kenney Tea Lane Associates

    49 Tilton Rd, Chilmark, MA 02535
    • /41

      Est $4,028,254 Not Listed For Sale

      • 5 Beds
      • 6 Baths
      • 4,521 Sq Ft

      89 Pond Rd, Vineyard Haven, MA 02568

      89 Pond Rd, Vineyard Haven, MA 02568
  • /29

    $1,925,000

    • 3 Beds
    • 3 Baths
    • 1,728 Sq Ft

    212 Charles Neck Way, Vineyard Haven, MA 02568

    This beautifully renovated contemporary South Shore retreat, located in a tranquil setting, features three bedrooms, two and one-half bathrooms, central air, all new appliances, in ground pool and mature perennial gardens galore! Sitting on 1.5 acres, this location provides easy access to Long Point Beach and the Red Pony Farm equestrian center and, includes access to the coveted Lamberts Cove

    Perry Patterson MV Luxury Homes

    212 Charles Neck Way, Vineyard Haven, MA 02568
  • /22

    $3,000 per month

    • 4 Beds
    • 2.5 Baths
    • 2,703 Sq Ft
    • House for Rent

    41 Oak Lane Wt147, West Tisbury, MA 02575

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $3,200. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Inside the front entrance is a large open living room with a comfortable L-shaped couch facing the floor to ceiling windows which look out onto the spacious tree lined back yard and a wall mounted flat screen television. Off the open concept living/dining room is a large

    Karen Overtoom Karen M. Overtoom R.E.

    41 Oak Lane Wt147, West Tisbury, MA 02575
  • /31

    $1,180,000 Sold Nov 21, 2024

    • 2,356 Sq Ft
    • $501/SF
    • 21 Days On Market
    • 3 Beds
    • 3 Baths
    • Built 1974

    43 Pin Oak Cir, West Tisbury, MA 02575

    West Tisbury with bells and whistles! This well tended to property has seen a LONG LIST of recent IMPROVEMENTS to make ownership easy and up-island life a breeze! Nicely tucked in and off of Old County Road means easy access to up island and down. The raised ranch style provides terrific living space duality. BOTH LEVELS have living rooms with fireplaces as well as renovated bathrooms and

    Grace Bishop Compass

    43 Pin Oak Cir, West Tisbury, MA 02575
    • /20

      Est $1,285,419 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,730 Sq Ft

      225 Longview Rd, Vineyard Haven, MA 02568

      225 Longview Rd, Vineyard Haven, MA 02568
  • /41

    $2,950,000

    • 4 Beds
    • 3 Baths
    • 2,424 Sq Ft

    19 Old Woods Rd, Chilmark, MA 02535

    Tucked away in the heart of Chilmark, this nearly 3-acre property blends rustic Vineyard charm with unique creative potential. Chilmark was a very special place for the former owner, American artist Thomas Hart Benton, who summered on the Island for 50 years. Professor and Art Historian, Erika Doss, said “the years he spent in Chilmark honed the artistic style and subjects that led to his

    Cheri Mason Landvest MV

    19 Old Woods Rd, Chilmark, MA 02535
  • /19

    $17,600 per month

    • 4 Beds
    • 2 Baths
    • 1,584 Sq Ft
    • House for Rent

    50 Carls Way, West Tisbury, MA 02575

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $4,400. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Looking for that perfect setting with a water view? This is the one!!This cute cape is privately set with a water view and direct water access to Town Pond. You can dock your canoes and kyacks here and access Tisbury Great Pond and then right out to the beach. There are

    Karen Overtoom Karen M. Overtoom R.E.

    50 Carls Way, West Tisbury, MA 02575
  • /3

    $275,000 Sold Nov 19, 2024

    • Land
    • 1.80 Acres
    • $152,778 per Acre
    • 143 Days On Market

    0 Lamberts Cove Rd, Vineyard Haven, MA 02568

    Wooded parcel in Vineyard Haven located off scenic Lamberts Cove Road. Conveniently located to Tisbury Center and neighboring Vineyard Open Land Foundation's Cranberry Acres. A recent survey has been completed, identifying right of way and wetlands, all other engineering and permitting is the responsibility of the buyer. A License to Sell issued by the Dukes Probate and Family Court is a

    Katherine Donahue Sandpiper Realty Inc

    0 Lamberts Cove Rd, Vineyard Haven, MA 02568
    • /2

      Est $2,230,169 Not Listed For Sale

      • 4 Beds
      • 4 Baths
      • 3,269 Sq Ft

      59 Field View Ln, Vineyard Haven, MA 02568

      59 Field View Ln, Vineyard Haven, MA 02568
  • /37

    $3,400,000

    • 5 Beds
    • 2 Baths
    • 3,133 Sq Ft

    19 Old Woods Rd, Chilmark, MA 02535

    Nestled in the heart of Chilmark, this 12.5-acre property offers two charming dwellings, each with 3 bedrooms, set in a landscape of privacy and timeless Vineyard character. Built in 1950 and 1963 for American artist, Thomas Hart Benton, the homes were lovingly created as a compound for friends and family to return to year after year. Tucked down a quiet driveway, the two share a special legacy

    Cheri Mason Landvest MV

    19 Old Woods Rd, Chilmark, MA 02535
  • /10

    $17,600 per month

    • 4 Beds
    • 3.5 Baths
    • 2,676 Sq Ft
    • House for Rent

    40 Summer Cir, West Tisbury, MA 02575

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $4,400. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This beautiful tasteful modern home has many charming elements. The bright open airy floor plan offers a generous kitchen, welcoming dining room and living room surrounded by windows and decks with an outdoor table and extra seating. An "upside down" house with the living

    Karen Overtoom Karen M. Overtoom R.E.

    40 Summer Cir, West Tisbury, MA 02575
  • /35

    $1,995,000 Sold Nov 15, 2024

    • 1,995 Sq Ft
    • $1000/SF
    • 47 Days On Market
    • 4 Beds
    • 3 Baths
    • Built 2003

    159 Charles Neck Way, Vineyard Haven, MA 02568

    The Whale House: Coastal-Inspired Living Near Long Point - This beautifully appointed residence is an ideal sanctuary for family and friends to indulge in relaxation and seaside splendor. The first floor welcomes you with a sun-filled open layout. A Living Area adorned with a gas fireplace sets the stage for cozy gatherings. The well-appointed Kitchen boasts a prep counter/breakfast bar and

    Wendy Harman Compass

    159 Charles Neck Way, Vineyard Haven, MA 02568
    • /43

      Not Listed For Sale

      • 4 Beds
      • 3.5 Baths
      • 2,674 Sq Ft

      39 Sarita Walker Rd, Vineyard Haven, MA 02568

      39 Sarita Walker Rd, Vineyard Haven, MA 02568
  • /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 House,

    Julianna Flanders Flanders Real Estate

    11 By the Woods, Chilmark, MA 02535
  • /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
  • /23

    $2,300,000 Sold Nov 08, 2024

    • 2,229 Sq Ft
    • $1032/SF
    • 11 Days On Market
    • 6 Beds
    • 4 Baths
    • Built 1989

    51 Blueberry Ridge Ln, Chilmark, MA 02535

    Rare opportunity to purchase a compound on large 8 acre parcel in Chilmark. Main House is 4 bedrooms, 2 1/2 baths on two levels. Oak floors, fieldstone fireplace and large screened in three season porch. Lower level offers a one car garage, workshop, large laundry room and storage room.The "Dinghy" is a detached cottage with 2 bedroom & full bath. The third building is a charming "pool house"

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

    51 Blueberry Ridge Ln, Chilmark, MA 02535
    • /41

      Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,598 Sq Ft

      566 Scrubby Neck Rd, Vineyard Haven, MA 02568

      566 Scrubby Neck Rd, Vineyard Haven, MA 02568
  • /52

    $6,750,000

    • 5 Beds
    • 4 Baths
    • 4,050 Sq Ft

    78 Hammett Rd, Chilmark, MA 02535

    Wonderful elevated Chilmark north shore 3.8 acre secure waterfront property with dramatic year round sunset water views to the Gay Head Lighthouse and Elizabeth Islands. The Vineyard Sound expanse enjoys peaceful sailing, fishing and other boating activity to enhance the ocean splendor. The 5 bedroom 3 1/2 bath 4,050 sq ft home is literally in move-in condition. Architect designed and built by

    Robert Kenney Tea Lane Associates

    78 Hammett Rd, Chilmark, MA 02535
  • /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
  • /41

    $1,090,000 Sold Nov 08, 2024

    • 2,552 Sq Ft
    • $427/SF
    • 5 Beds
    • 3 Baths
    • Built 1850

    10 Danls Way, West Tisbury, MA 02575

    ***Sale Price Note: Non-arm’s length transaction Joshua Slocom House

    Emma Kiley Bryant Landmarks at TODAY Real Estate

    10 Danls Way, West Tisbury, MA 02575
    • /15

      Est $2,586,098 Not Listed For Sale

      • 1 Bed
      • 1 Bath
      • 512 Sq Ft

      119 Old Thumb Point Rd, Vineyard Haven, MA 02568

      119 Old Thumb Point Rd, Vineyard Haven, MA 02568

Showing Results 81 - 120, Page 3 of 18

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