1,739

Chilmark Homes

Section Image
    • 0 Beach Lot Quansoo #136, Chilmark, MA 02535
      0 Beach Lot Quansoo #136, Chilmark, MA 02535
      0 Beach Lot Quansoo #136, Chilmark, MA 02535
      /6

      Not Listed For Sale

      0 Beach Lot Quansoo #136, Chilmark, MA 02535

      0 Beach Lot Quansoo #136, Chilmark, MA 02535
  • 8 Snail Rd, Chilmark, MA 02535
    8 Snail Rd, Chilmark, MA 02535
    8 Snail Rd, Chilmark, MA 02535
    /60

    $14,000,000

    • 6 Beds
    • 7 Baths
    • 6,967 Sq Ft

    8 Snail Rd, Chilmark, MA 02535

    This exceptional Martha's Vineyard estate promises unmatched privacy and breathtaking views of the Atlantic Ocean and Chilmark Pond. Masterfully designed by acclaimed architect Rick Sundberg and built by renowned island builder Andrew Flake, this three-parcel property seamlessly blends modern sophistication with the timeless charm of the Vineyard. Upon entering, you are greeted by soaring

    Alyssa Halisky Wallace & Co. Sotheby's

    8 Snail Rd, Chilmark, MA 02535
  • 10 Rumpus Ridge Rd, Chilmark, MA 02535
    10 Rumpus Ridge Rd, Chilmark, MA 02535
    10 Rumpus Ridge Rd, Chilmark, MA 02535
    /32

    $1,050,000 Sold May 29, 2025

    • 1,701 Sq Ft
    • $617/SF
    • 28 Days On Market
    • 4 Beds
    • 2 Baths
    • Built 1960

    10 Rumpus Ridge Rd, Chilmark, MA 02535

    Discover this inviting two-unit property in the heart of Chilmark! Ideally situated near Chilmark General Store, Squibnocket, Menemsha, and the pristine shores of Lucy Vincent Beach, this home offers both convenience and charm. Thoughtfully updated for year-round comfort, the property features a new metal roof, new siding, solar panels, mini-split AC, and more. The main-level residence offers

    Peyton Wallace Studio Realty

    10 Rumpus Ridge Rd, Chilmark, MA 02535
    • 0 Gosnold's Way, Chilmark, MA 02535
      0 Gosnold's Way, Chilmark, MA 02535
      0 Gosnold's Way, Chilmark, MA 02535
      /13

      Not Listed For Sale

      0 Gosnold's Way, Chilmark, MA 02535

      0 Gosnold's Way, Chilmark, MA 02535
  • 16 Shotnaigher Ln, Chilmark, MA 02535
    16 Shotnaigher Ln, Chilmark, MA 02535
    16 Shotnaigher Ln, Chilmark, MA 02535
    /29

    $12,750,000

    • 4 Beds
    • 3.5 Baths
    • 2,050 Sq Ft

    16 Shotnaigher Ln, Chilmark, MA 02535

    New to market this completely renovated water view home is located in a private enclave of upscale homes fronting on Squibnocket Pond in Chilmark. There are 360 degree views from this 3.6 acre hilltop site offering views of the pond, Atlantic Ocean and north to Menemsha Pond and the Vineyard Sound. Sunrise and Sunset! This home, completely renovated in 2022 features a state of the art gourmet

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

    16 Shotnaigher Ln, Chilmark, MA 02535
  • 2 Squibnocket Rd, Chilmark, MA 02535
    2 Squibnocket Rd, Chilmark, MA 02535
    2 Squibnocket Rd, Chilmark, MA 02535
    /42

    $9,725,000 Sold Apr 24, 2025

    • 5,808 Sq Ft
    • $1,674/SF
    • 295 Days On Market
    • 6 Beds
    • 5.5 Baths
    • Built 2008

    2 Squibnocket Rd, Chilmark, MA 02535

    CHILMARK SOUTH SHORE WATER VIEW. This Squibnocket gem is a Hutker Arhictect-designed family compound, main house,& guest house on 4.5 acres. Live the ultimate up-Island life with captivating water views in every direction. The home is pristine and private, with many unique features. The chef's kitchen and dining area are serene, bright, and functional. Step up to what might be the best panorama

    Tina Miller Donnelly + Co.

    2 Squibnocket Rd, Chilmark, MA 02535
    • 0 Beach Lot Quansoo Unit 42634, Chilmark, MA 02535
      0 Beach Lot Quansoo Unit 42634, Chilmark, MA 02535
      0 Beach Lot Quansoo Unit 42634, Chilmark, MA 02535
      /6

      Not Listed For Sale

      0 Beach Lot Quansoo Unit 42634, Chilmark, MA 02535

      0 Beach Lot Quansoo Unit 42634, Chilmark, MA 02535
  • 25 Fulling Mill Rd, Chilmark, MA 02535
    25 Fulling Mill Rd, Chilmark, MA 02535
    25 Fulling Mill Rd, Chilmark, MA 02535
    /30

    $2,395,000

    • 4 Beds
    • 3 Baths
    • 1,918 Sq Ft

    25 Fulling Mill Rd, Chilmark, MA 02535

    Perched atop Fulling Mill Hill this distinctive contemporary main house plus guest house offers mid-century charm and a serene retreat set on 3.3 acres of mature oak and beech forest and bordered by an ancient stone wall. Designed by renowned Yale School of Architecture Dean Paul Mitarachi, the main house features a striking circular entryway framed by mature Asiatic gardens. Step inside to

    Tom Wallace Wallace & Co. Sotheby's International Realty

    25 Fulling Mill Rd, Chilmark, MA 02535
  • 2 Squibnocket Rd, Chilmark, MA 02535
    2 Squibnocket Rd, Chilmark, MA 02535
    2 Squibnocket Rd, Chilmark, MA 02535
    /52

    $9,525,000 Sold Apr 24, 2025

    • 5,808 Sq Ft
    • $1,640/SF
    • 297 Days On Market
    • 6 Beds
    • 5.5 Baths
    • Built 2008

    2 Squibnocket Rd, Chilmark, MA 02535

    CHILMARK SOUTH SHORE WATER VIEWS. This Squibnocket gem is a Hutker Architect-designed family compound on 4.5 acres. With captivating water views in every direction, this home is the perfect launch pad for the ultimate up-Island lifestyle. Grab your surf or paddle board and head down the path to Squibnocket Beach for a morning surf or swim. Pack the cooler with lunch from the Chilmark Store for a

    Tina Miller Donnelly + Co

    2 Squibnocket Rd, Chilmark, MA 02535
    • 0 Black Point Road Beach Lot 7, Chilmark, MA 02535
      0 Black Point Road Beach Lot 7, Chilmark, MA 02535
      0 Black Point Road Beach Lot 7, Chilmark, MA 02535
      /3

      Not Listed For Sale

      0 Black Point Road Beach Lot 7, Chilmark, MA 02535

      0 Black Point Road Beach Lot 7, Chilmark, MA 02535
  • 2 Other House Rd Unit 173, Chilmark, MA 02535
    2 Other House Rd Unit 173, Chilmark, MA 02535
    2 Other House Rd Unit 173, Chilmark, MA 02535
    /7

    $2,500,000

    • Land
    • 1.4 Acres
    • $1,785,714 per Acre

    2 Other House Rd Unit 173, Chilmark, MA 02535

    Rare opportunity to build on Chilmark's south shore. This 1.4 acre parcel should allow for new construction of 3,100 square feet and 24 feet in height, by right, with building department approval. Views to the Atlantic Ocean and Chilmark Pond can be seen from the second floor. This parcel comes with a dock on the pond which provides access to a beautiful barrier beach on the Atlantic. Well in

    Russell Maloney Russell Maloney Real Estate

    2 Other House Rd Unit 173, Chilmark, MA 02535
  • 493 South Rd, Chilmark, MA 02535
    493 South Rd, Chilmark, MA 02535
    /2

    $1,600,000 Sold Feb 04, 2025

    • Land
    • 3.6 Acres
    • $444,444 per Acre
    • 0 Days On Market

    493 South Rd, Chilmark, MA 02535

    Lovely pastoral lot within walking distance of beach and center of town.Perc test completed, septic being designed and well to be drilled shortly.Includes conservation restricted lot which consists of 10.6 acres.Build the home of your dreams in this amazing location.

    Julianna Flanders Flanders Real Estate

    493 South Rd, Chilmark, MA 02535
    • 5 Oyster Ln, Chilmark, MA 02535
      5 Oyster Ln, Chilmark, MA 02535
      5 Oyster Ln, Chilmark, MA 02535
      /29

      Est $1,915,777 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 1,108 Sq Ft

      5 Oyster Ln, Chilmark, MA 02535

      5 Oyster Ln, Chilmark, MA 02535
  • 64 Squibnocket Farm Rd, Chilmark, MA 02535
    64 Squibnocket Farm Rd, Chilmark, MA 02535
    64 Squibnocket Farm Rd, Chilmark, MA 02535
    /43

    $14,500,000

    • 4 Beds
    • 4.5 Baths
    • 3,705 Sq Ft

    64 Squibnocket Farm Rd, Chilmark, MA 02535

    Welcome to an extraordinary waterfront retreat, where luxury meets nature perfectly. This exclusive property offers unparalleled access to breathtaking views, serene landscapes, and the soothing sounds of water lapping against the shore. Squibnocket Farm Road is renowned for its unspoiled beauty and tranquility. This sophisticated gated community offers a sense of seclusion while remaining within

    Thomas Wallace Wallace & Co. Sotheby's

    64 Squibnocket Farm Rd, Chilmark, MA 02535
  • 4 Bartlett Woods, Chilmark, MA 02535
    4 Bartlett Woods, Chilmark, MA 02535
    4 Bartlett Woods, Chilmark, MA 02535
    /32

    $3,000,000 Sold Jan 09, 2025

    • 3,500 Sq Ft
    • $857/SF
    • 194 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 2023

    4 Bartlett Woods, Chilmark, MA 02535

    NEW BRIGHT & AIRY CONTEMPORARY OFF SOUTH ROAD! The house newly completed in 2023 & the one car garage in 2024 are nicely situated on a 4.56 acre lot. The 4 bedroom residence offers 3500 sf of finished living on two levels. On the first level are 2 primary bedrooms, each with en suite bathrooms, and a spacious open floor plan for living, dining and kitchen. An office off the kitchen allows you to

    Kathryn Tate Kathryn Tate Gothard

    4 Bartlett Woods, Chilmark, MA 02535
    • 15 Marsh Rd, Chilmark, MA 02535
      15 Marsh Rd, Chilmark, MA 02535
      15 Marsh Rd, Chilmark, MA 02535
      /17

      Est $1,847,704 Not Listed For Sale

      • 2 Beds
      • 1.5 Baths
      • 800 Sq Ft

      15 Marsh Rd, Chilmark, MA 02535

      15 Marsh Rd, Chilmark, MA 02535
  • 1 Crowberry Ln Unit 19, Chilmark, MA 02535
    1 Crowberry Ln Unit 19, Chilmark, MA 02535
    1 Crowberry Ln Unit 19, Chilmark, MA 02535
    /12

    $1,250,000 Pending

    • Land
    • 4.32 Acres
    • $289,352 per Acre

    1 Crowberry Ln Unit 19, Chilmark, MA 02535

    Ready to build, private, 4.3 acres in Chilmark located just off of North Road and minutes from the iconic fishing village of Menemsha. This parcel comes equipped with a well, 4 bedroom septic system, electricity and cable all in place for seamless development. There is an existing garden house that can be repurposed as a construction site shed and perhaps later an ADU. The lot has recently been

    Russell Maloney Russell Maloney Real Estate

    1 Crowberry Ln Unit 19, Chilmark, MA 02535
  • 1 Carroll Ln, Chilmark, MA 02535
    1 Carroll Ln, Chilmark, MA 02535
    1 Carroll Ln, 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
    • 5 Meetinghouse Rd, Chilmark, MA 02535
      5 Meetinghouse Rd, Chilmark, MA 02535
      5 Meetinghouse Rd, Chilmark, MA 02535
      /22

      Est $1,614,855 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 1,008 Sq Ft

      5 Meetinghouse Rd, Chilmark, MA 02535

      5 Meetinghouse Rd, Chilmark, MA 02535
  • 49 Gosnold's Way, Chilmark, MA 02535
    49 Gosnold's Way, Chilmark, MA 02535
    49 Gosnold's Way, Chilmark, MA 02535
    /51

    $4,950,000 Pending

    • 5 Beds
    • 3.5 Baths
    • 4,044 Sq Ft

    49 Gosnold's Way, Chilmark, MA 02535

    Perched high on the north shore with sweeping views of the Vineyard Sound, this expansive and private property is surrounded by Menemsha Hills conservation land and trails and offers broad water views, even from ground floor of house. The house is large and well maintained with an upside down floor plan allowing for high ceilings and bright spaces in the open plan kitchen/dining/living room, as

    Meg Bodnar Tea Lane Associates

    49 Gosnold's Way, Chilmark, MA 02535
  • 82 South Rd, Chilmark, MA 02535
    82 South Rd, Chilmark, MA 02535
    82 South Rd, 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
    • 21 Tea Ln, Chilmark, MA 02535
      21 Tea Ln, Chilmark, MA 02535
      21 Tea Ln, Chilmark, MA 02535
      /11

      Est $2,117,640 Not Listed For Sale

      21 Tea Ln, Chilmark, MA 02535

      21 Tea Ln, Chilmark, MA 02535
  • 34 Ebens Ln, Chilmark, MA 02535
    34 Ebens Ln, Chilmark, MA 02535
    34 Ebens Ln, Chilmark, MA 02535
    /4

    $1,449,000 Pending

    • Land
    • 3.9 Acres
    • $371,538 per Acre

    34 Ebens Ln, Chilmark, MA 02535

    Settled high on a peaceful ridge this 3.9-acre property is being offered with a long-term lease for 2.5 acres of prime restricted agricultural farmland abutting the property and the Tiasquam River. With the river running along the edge of the property this area is ideal for growing flowers, vegetables, and/or arbors. The land may also be used for grazing and housing livestock along with any

    Thomas Wallace Wallace & Co. Sotheby's

    34 Ebens Ln, Chilmark, MA 02535
  • 0 Quansoo Beach Lot Unit 49 43779, Chilmark, MA 02535
    0 Quansoo Beach Lot Unit 49 43779, Chilmark, MA 02535
    /2

    $440,000 Sold Sep 22, 2025

    • Land
    • 0 Acre
    • 0 Days On Market

    0 Quansoo Beach Lot Unit 49 43779, Chilmark, MA 02535

    Beach lot at Quansoo. Not Listed in LINK> Not a buildable lot.

    LINK Email Cache LINK

    0 Quansoo Beach Lot Unit 49 43779, Chilmark, MA 02535
    • 31 Tower Ln, Chilmark, MA 02535
      31 Tower Ln, Chilmark, MA 02535
      31 Tower Ln, Chilmark, MA 02535
      /6

      Est $2,497,000 Not Listed For Sale

      • 6 Beds
      • 4 Baths
      • 1,135 Sq Ft

      31 Tower Ln, Chilmark, MA 02535

      31 Tower Ln, Chilmark, MA 02535
  • 45 Quenames Rd Unit 30-02, Chilmark, MA 02535
    45 Quenames Rd Unit 30-02, Chilmark, MA 02535
    /2

    $900,000 Sold Sep 17, 2025

    • Land
    • 3.05 Acres
    • $295,082 per Acre
    • 83 Days On Market

    45 Quenames Rd Unit 30-02, Chilmark, MA 02535

    Handsome, large level parcel of land in Chilmark! Bounds are in, lot lines are flagged and brush cut, as well as a bit of the lot interior so that you can appreciate the size and orientation of the parcel. 6-Bedroom septic design has been approved and well will be installed soon. Quenames Road is off South Road, a short hop to West Tisbury village center with Alley's General Store, the Town's

    Candy DaRosa Feiner Real Estate

    45 Quenames Rd Unit 30-02, Chilmark, MA 02535
    • 99 Cygnet Way, Chilmark, MA 02535
      99 Cygnet Way, Chilmark, MA 02535
      99 Cygnet Way, Chilmark, MA 02535
      /8

      Not Listed For Sale

      99 Cygnet Way, Chilmark, MA 02535

      99 Cygnet Way, Chilmark, MA 02535
  • 0 North Rd Unit 40 43533, Aquinnah, MA 02535
    0 North Rd Unit 40 43533, Aquinnah, MA 02535
    /2

    $60,000 Sold Jul 01, 2025

    • Land
    • 0 Acre

    0 North Rd Unit 40 43533, Aquinnah, MA 02535

    Delightful piece of land in Chilmark

    Mark Jenkins Wallace & Co. Sotheby's

    0 North Rd Unit 40 43533, Aquinnah, MA 02535
    • 1 Old Rd N, Chilmark, MA 02535
      1 Old Rd N, Chilmark, MA 02535
      1 Old Rd N, Chilmark, MA 02535
      /35

      Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 516 Sq Ft

      1 Old Rd N, Chilmark, MA 02535

      1 Old Rd N, Chilmark, MA 02535
  • 3 Tennis Ln, Chilmark, MA 02535
    3 Tennis Ln, Chilmark, MA 02535
    /2

    $3,772,500 Sold May 29, 2025

    • 3,234 Sq Ft
    • $1,167/SF
    • 0 Days On Market
    • 4 Beds
    • 4.5 Baths
    • Built 1999

    3 Tennis Ln, Chilmark, MA 02535

    Elegantly appointed, this beautifully built home will absolutely delight you. The handsome, open living and dining rooms are anchored by an amazing Chef’s kitchen - large enough to happily accommodate multiple simultaneous cooks; while the dining room's fireplace wall invites family and friends to linger at the dinner table. There is a 1st floor study, a nicely-tucked away powder room and

    Candy DaRosa Feiner Real Estate

    3 Tennis Ln, Chilmark, MA 02535
    • 31 Cross Rip Ln, Chilmark, MA 02535
      31 Cross Rip Ln, Chilmark, MA 02535
      31 Cross Rip Ln, Chilmark, MA 02535
      /20

      Est $1,267,307 Not Listed For Sale

      • 1 Bed
      • 1 Bath
      • 512 Sq Ft

      31 Cross Rip Ln, Chilmark, MA 02535

      31 Cross Rip Ln, Chilmark, MA 02535
  • 26 Oyster Ln, Chilmark, MA 02535
    26 Oyster Ln, Chilmark, MA 02535
    /2

    $850,000 Sold Dec 13, 2024

    • Land
    • 3.04 Acres
    • $279,605 per Acre
    • 0 Days On Market

    26 Oyster Ln, Chilmark, MA 02535

    Not listed in LINK.

    LINK Email Cache LINK

    26 Oyster Ln, Chilmark, MA 02535
    • 68 Meeting House Rd, Chilmark, MA 02535
      68 Meeting House Rd, Chilmark, MA 02535
      68 Meeting House Rd, Chilmark, MA 02535
      /31

      Est $3,573,667 Not Listed For Sale

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

      68 Meeting House Rd, Chilmark, MA 02535

      68 Meeting House Rd, Chilmark, MA 02535
    • 277 North Rd, Chilmark, MA 02535
      277 North Rd, Chilmark, MA 02535
      277 North Rd, Chilmark, MA 02535
      /14

      Not Listed For Sale

      • 6 Beds
      • 3.5 Baths
      • 2,914 Sq Ft

      277 North Rd, Chilmark, MA 02535

      277 North Rd, Chilmark, MA 02535
    • 18 Greenhouse Ln, Chilmark, MA 02535
      18 Greenhouse Ln, Chilmark, MA 02535
      18 Greenhouse Ln, Chilmark, MA 02535
      /12

      Est $1,416,250 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 2,100 Sq Ft

      18 Greenhouse Ln, Chilmark, MA 02535

      18 Greenhouse Ln, Chilmark, MA 02535
    • 22 Tabor Hills, Chilmark, MA 02535
      22 Tabor Hills, Chilmark, MA 02535
      22 Tabor Hills, Chilmark, MA 02535
      /17

      Est $2,860,488 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 2,375 Sq Ft

      22 Tabor Hills, Chilmark, MA 02535

      22 Tabor Hills, Chilmark, MA 02535
    • 6 Post Oak Rd, Chilmark, MA 02535
      6 Post Oak Rd, Chilmark, MA 02535
      6 Post Oak Rd, Chilmark, MA 02535
      /39

      Est $4,453,231 Not Listed For Sale

      • 5 Beds
      • 6 Baths
      • 4,332 Sq Ft

      6 Post Oak Rd, Chilmark, MA 02535

      6 Post Oak Rd, Chilmark, MA 02535
    • 24 Blacksmith Valley Rd, Chilmark, MA 02535
      24 Blacksmith Valley Rd, Chilmark, MA 02535
      /2

      Est $4,870,705 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 1,952 Sq Ft

      24 Blacksmith Valley Rd, Chilmark, MA 02535

      24 Blacksmith Valley Rd, Chilmark, MA 02535
    • 15 Lake Rd, Chilmark, MA 02535
      15 Lake Rd, Chilmark, MA 02535
      15 Lake Rd, Chilmark, MA 02535
      /21

      Est $3,975,665 Not Listed For Sale

      • 5 Beds
      • 2.5 Baths
      • 1,980 Sq Ft

      15 Lake Rd, Chilmark, MA 02535

      15 Lake Rd, Chilmark, MA 02535
    • 5 Guerin Ln, Chilmark, MA 02535
      5 Guerin Ln, Chilmark, MA 02535
      5 Guerin Ln, Chilmark, MA 02535
      /25

      Est $3,317,780 Not Listed For Sale

      • 4 Beds
      • 4 Baths
      • 2,929 Sq Ft

      5 Guerin Ln, Chilmark, MA 02535

      5 Guerin Ln, Chilmark, MA 02535

Showing Results 81 - 120, Page 3 of 18

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