1,733

Chilmark Homes

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  • 88 & 90 Quenames Rd, Chilmark, MA 02535
    88 & 90 Quenames Rd, Chilmark, MA 02535
    88 & 90 Quenames Rd, Chilmark, MA 02535
    /25

    $3,600,000

    • 3 Beds
    • 3 Baths
    • 4,382 Sq Ft

    88 & 90 Quenames Rd, Chilmark, MA 02535

    Make your own Chilmark dream come true!12.6 +/- acres of prime land allows you to create your own familycompound or Island Farm. Enjoy the peacefulness of the Chilmarkwith room to expand. Two separate buildable lots provides you uniqueoptions. The Main house has three bedrooms, three bathrooms, twostudies, multiple living spaces and a large three-car garage

    Julianna Flanders Flanders Real Estate

    88 & 90 Quenames Rd, Chilmark, MA 02535
  • 391 Middle Rd, Chilmark, MA 02535
    391 Middle Rd, Chilmark, MA 02535
    391 Middle Rd, Chilmark, MA 02535
    /34

    $6,100,000 Sold Oct 16, 2024

    • 3,859 Sq Ft
    • $1,581/SF
    • 38 Days On Market
    • 6 Beds
    • 4.5 Baths
    • Built 1941

    391 Middle Rd, Chilmark, MA 02535

    This iconic property and location is truly a once-in-a-lifetime opportunity. Exceptional house and guest house that is ready to move into . The exterior resonates with what is beloved about Chilmark but the interior is contemporary and fresh. The main house has views overlooking the Keith farm and the Atlantic Ocean beyond, old stone walls and open meadows. A new owner will have the gratification

    Jill Napior Tea Lane Associates

    391 Middle 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
  • 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 House,

    Julianna Flanders Flanders Real Estate

    11 By the Woods, 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

    $430,000 Sold Oct 10, 2024

    • Land
    • 0.60 Acre
    • $716,667 per Acre
    • 0 Days On Market

    0 Beach Lot Quansoo Unit 42634, Chilmark, MA 02535

    Not listed in LINK.

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    0 Beach Lot Quansoo Unit 42634, Chilmark, MA 02535
    • 5 Oyster Ln, Chilmark, MA 02535
      5 Oyster Ln, Chilmark, MA 02535
      5 Oyster Ln, Chilmark, MA 02535
      /29

      Est $2,089,173 Not Listed For Sale

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

      5 Oyster Ln, Chilmark, MA 02535

      5 Oyster Ln, Chilmark, MA 02535
  • 18 Spruce Gate Rd, Chilmark, MA 02535
    18 Spruce Gate Rd, Chilmark, MA 02535
    18 Spruce Gate Rd, Chilmark, MA 02535
    /52

    $12,500,000

    • 5 Beds
    • 3.5 Baths
    • 3,700 Sq Ft

    18 Spruce Gate Rd, Chilmark, MA 02535

    Welcome to an extraordinary ocean view coastal sanctuary set within the exclusive gates of Squibnocket Farm—a 450+ acre private community with access to over 2 miles of oceanfront, 1.5 miles of pond frontage, and 300+ acres of conservation land. Set on a peaceful, pastoral landscape abutting 17 acres of preserved land, this stately home was designed and built by Soikkeli & Company, one of the

    Alyssa Halisky Wallace & Co. Sotheby's

    18 Spruce Gate Rd, Chilmark, MA 02535
  • 7 Flanders Ln, Chilmark, MA 02535
    7 Flanders Ln, Chilmark, MA 02535
    7 Flanders Ln, Chilmark, MA 02535
    /29

    $1,680,000 Sold Oct 09, 2024

    • 1,200 Sq Ft
    • $1,400/SF
    • 4 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1954

    7 Flanders Ln, Chilmark, MA 02535

    Sweet, renovated cottage in Menemsha. Classic Vineyard home that is move-in ready! You'll find a renovated kitchen, central A/C, new bathrooms and fresh interior which still maintains the cottage charm of the original house. Open living room through to kitchen with all three bedrooms on the main level. The house is at the beginning of Flanders Lane just 1/4 mile from the Village of Menemsha

    Meg Bodnar Tea Lane Associates

    7 Flanders Ln, Chilmark, MA 02535
    • 15 Marsh Rd, Chilmark, MA 02535
      15 Marsh Rd, Chilmark, MA 02535
      15 Marsh Rd, Chilmark, MA 02535
      /17

      Est $2,023,930 Not Listed For Sale

      • 2 Beds
      • 1.5 Baths
      • 800 Sq Ft

      15 Marsh Rd, Chilmark, MA 02535

      15 Marsh Rd, Chilmark, MA 02535
  • 34 Edys Island Way, Chilmark, MA 02535
    34 Edys Island Way, Chilmark, MA 02535
    34 Edys Island Way, Chilmark, MA 02535
    /43

    $7,450,000

    • 5 Beds
    • 2.5 Baths
    • 2,269 Sq Ft

    34 Edys Island Way, Chilmark, MA 02535

    Waterfront house and guest house with a private dock on Menemsha Pond. This location is in the heart of Menemsha, a waterfront enclave within walking distance of this classic Harbor. Built and cared for over four generations by anIsland legacy family, this property is unique among Island estates for its combination of privacy yet convenience and seclusion yet expansive views. To the

    Jill Napior Tea Lane Associates

    34 Edys Island 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
    • 0.00 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
    • 21 Tea Ln, Chilmark, MA 02535
      21 Tea Ln, Chilmark, MA 02535
      21 Tea Ln, Chilmark, MA 02535
      /11

      Est $2,337,637 Not Listed For Sale

      21 Tea Ln, Chilmark, MA 02535

      21 Tea Ln, Chilmark, MA 02535
  • 37 Bijah's Way, Chilmark, MA 02535
    37 Bijah's Way, Chilmark, MA 02535
    37 Bijah's Way, Chilmark, MA 02535
    /16

    $1,325,000

    • Land
    • 4.40 Acres
    • $301,136 per Acre

    37 Bijah's Way, Chilmark, MA 02535

    This quiet and lovely four-and-a-half-acre lot in Chilmark is set on a gentle rise, bounded on one side by an old stone wall. The land features graceful trees and a distant water view is possible from a second floor. The lot has been staked, including a proposed home site at the highest elevation. There are so many outstanding possibilities for a future Buyer to build their dream home on this

    Elissa Lash Tea Lane Associates

    37 Bijah's Way, 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 Tower Ln, Chilmark, MA 02535
      31 Tower Ln, Chilmark, MA 02535
      31 Tower Ln, Chilmark, MA 02535
      /6

      Est $2,583,500 Not Listed For Sale

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

      31 Tower Ln, Chilmark, MA 02535

      31 Tower Ln, 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
  • 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
    • 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
  • 3 Fulling Mill Rd, Chilmark, MA 02535
    3 Fulling Mill Rd, Chilmark, MA 02535
    3 Fulling Mill Rd, Chilmark, MA 02535
    /48

    $1,795,000

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

    3 Fulling Mill Rd, Chilmark, MA 02535

    Tucked away in a prime location just off Middle Road is this bright modern home offering the perfect blend of comfort and style. The main level features a large bedroom or first-floor office and a full bath, while the upper floor boasts two additional bedrooms and a beautifully appointed bathroom with a steam shower and double vanity. The open concept living and dining areas flow effortlessly

    Jill Napior Tea Lane Associates

    3 Fulling Mill Rd, Chilmark, MA 02535
  • 7 Yardarm Ln, Chilmark, MA 02535
    7 Yardarm Ln, Chilmark, MA 02535
    /2

    $2,099,400 Sold Oct 31, 2024

    • 1,836 Sq Ft
    • $1,143/SF
    • 0 Days On Market
    • 2 Beds
    • 2.5 Baths
    • Built 1967

    7 Yardarm Ln, Chilmark, MA 02535

    Not listed in LINK.

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    7 Yardarm Ln, Chilmark, 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
  • 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
    • 31 Cross Rip Ln, Chilmark, MA 02535
      31 Cross Rip Ln, Chilmark, MA 02535
      31 Cross Rip Ln, Chilmark, MA 02535
      /20

      Est $1,207,708 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
  • 25 Fulling Mill Rd, Chilmark, MA 02535
    25 Fulling Mill Rd, Chilmark, MA 02535
    25 Fulling Mill Rd, Chilmark, MA 02535
    /31

    $2,450,000

    • 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

    Thomas Wallace Wallace & Co. Sotheby's International Realty

    25 Fulling Mill Rd, Chilmark, MA 02535
    • 34 Old Farm Rd, Chilmark, MA 02535
      34 Old Farm Rd, Chilmark, MA 02535
      34 Old Farm Rd, Chilmark, MA 02535
      /27

      Est $4,426,213 Not Listed For Sale

      • 4 Beds
      • 4.5 Baths
      • 3,800 Sq Ft

      34 Old Farm Rd, Chilmark, MA 02535

      34 Old Farm Rd, Chilmark, MA 02535
  • 345 North Rd, Chilmark, MA 02535
    345 North Rd, Chilmark, MA 02535
    345 North Rd, Chilmark, MA 02535
    /23

    $1,625,000

    • 5 Beds
    • 5 Baths
    • 2,316 Sq Ft

    345 North Rd, Chilmark, MA 02535

    Abutting hundreds of acres of conservation land and walking trails leading to the second-highest point on Martha's Vineyard with views of the Elizabeth Islands, this classically-styled house with detached guest quarters offers 5 total bedrooms and 4 full baths plus an outdoor shower. The primary bedroom suite is a generous size and has its own small deck that overlooks the charming front yard.

    Mark Jenkins Wallace & Co. Sotheby's International Realty

    345 North 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
  • 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
    • 1.40 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
    • 18 Greenhouse Ln, Chilmark, MA 02535
      18 Greenhouse Ln, Chilmark, MA 02535
      18 Greenhouse Ln, Chilmark, MA 02535
      /12

      Est $1,270,362 Not Listed For Sale

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

      18 Greenhouse Ln, Chilmark, MA 02535

      18 Greenhouse 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

    $16,500,000

    • 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
    • 22 Tabor Hills, Chilmark, MA 02535
      22 Tabor Hills, Chilmark, MA 02535
      22 Tabor Hills, Chilmark, MA 02535
      /17

      Est $2,808,292 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
  • 11 Greenhouse Ln, Chilmark, MA 02535
    11 Greenhouse Ln, Chilmark, MA 02535
    11 Greenhouse Ln, Chilmark, MA 02535
    /27

    $3,350,000

    • 3 Beds
    • 2 Baths
    • 1,562 Sq Ft

    11 Greenhouse Ln, Chilmark, MA 02535

    11 Greenhouse Lane...an incredible opportunity to own in this sought after private enclave with deeded private south shore beach and pond access close by...this charming vintage cape enjoys views over wetlands out to the Atlantic beyond! Three bedrooms, two baths, living room with fireplace, dining area, updated kitchen, screened porch and outside shower. The owners have taken full advantage of

    Deb Hancock Hancock Real Estate

    11 Greenhouse Ln, 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 $5,142,628 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
  • 100 Gosnolds Way, Chilmark, MA 02535
    100 Gosnolds Way, Chilmark, MA 02535
    100 Gosnolds Way, Chilmark, MA 02535
    /46

    $3,500,000

    • 4 Beds
    • 2.5 Baths
    • 2,383 Sq Ft

    100 Gosnolds Way, Chilmark, MA 02535

    Well designed and maintained home, situated on 5 acres in a private, desirable neighborhood. Open floor plan with high ceilings that allows a lot of great light into house. The screened in porch is perfect for family dinners or relaxing. Nice water views of Vineyard Sound & the Elizabeth Islands. Short walk to the Brickyard Beach on the North Shore, rights are included with property, where

    Julianna Flanders Flanders Real Estate

    100 Gosnolds Way, Chilmark, MA 02535
    • 24 Blacksmith Valley Rd, Chilmark, MA 02535
      24 Blacksmith Valley Rd, Chilmark, MA 02535
      /2

      Est $5,743,762 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
  • 9 Beetlebung Grove Way, Chilmark, MA 02535
    9 Beetlebung Grove Way, Chilmark, MA 02535
    9 Beetlebung Grove Way, Chilmark, MA 02535
    /39

    $2,495,000 Pending

    • 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
    • 1 Crowberry Ln, Chilmark, MA 02535
      1 Crowberry Ln, Chilmark, MA 02535
      1 Crowberry Ln, Chilmark, MA 02535
      /9

      Est $1,059,028 Not Listed For Sale

      1 Crowberry Ln, Chilmark, MA 02535

      1 Crowberry Ln, Chilmark, MA 02535
  • 00 Eliot Ave Unit 17, Chilmark, MA 02535
    00 Eliot Ave Unit 17, Chilmark, MA 02535
    00 Eliot Ave Unit 17, Chilmark, MA 02535
    /3

    $110,000 Pending

    • Land
    • 0.70 Acre
    • $157,143 per Acre

    00 Eliot Ave Unit 17, Chilmark, MA 02535

    Enjoy access to beautiful Stonewall Beach located in Chilmark. It has great swimming and fishing!This is not a buildable lot.

    Julianna Flanders Flanders Real Estate

    00 Eliot Ave Unit 17, Chilmark, MA 02535
    • 15 Lake Rd, Chilmark, MA 02535
      15 Lake Rd, Chilmark, MA 02535
      15 Lake Rd, Chilmark, MA 02535
      /21

      Est $3,789,693 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
  • 32 Stonewall Rd Unit 2.1, Chilmark, MA 02535
    32 Stonewall Rd Unit 2.1, Chilmark, MA 02535
    32 Stonewall Rd Unit 2.1, Chilmark, MA 02535
    /17

    $1,900,000 Pending

    • Land
    • 3.30 Acres
    • $575,758 per Acre

    32 Stonewall Rd Unit 2.1, Chilmark, MA 02535

    South shore beachy living in Stonewall Association with private parking and access to a lovely swim and surf beach in a beloved area of Chilmark. There are second floor water views over Squibnocket Point and the Atlantic Ocean. This lot is fully engineered and ready to be built on! Single-family dwelling, plus a detached bedroom and accessory buildings, permitted according to the Chilmark

    Jill Napior Tea Lane Associates

    32 Stonewall Rd Unit 2.1, Chilmark, MA 02535

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