1,742

Chilmark Homes

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  • /42

    $3,990,000 Pending

    • 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
  • /32

    $42,000 total monthly price

    • 5 Beds
    • 2.5 Baths
    • 3,000 Sq Ft
    • House for Rent

    19 Lake Rd, Chilmark, MA 02535

    THIS IS A WEEKLY SUMMER RENTAL ONLY. SEE WEB SITE FOR WEEKLY PRICING. Sweeping views of Squibnocket Pond, Dunes, the South Shore, Nomans Land, to sunsets over Aquinnah. A great family getaway with access to Chilmark's famed Lucy Vincent and Squibnocket Beaches as well as a private association beach in Aquinnah. Roomy and inviting, this house offers 5 five bedrooms all with views, two livingrooms,

    Karen Overtoom Karen M. Overtoom R.E.

    19 Lake Rd, Chilmark, MA 02535
  • /22

    $1,607,000 Sold Jul 10, 2025

    10 N Abels Hill Rd, Chilmark, MA 02535

    • 4 Beds
    • 3 Baths
    • 2,850 Sq Ft
    • Built 1978

    Last Sold Summary

    • 39% Below List Price
    • $564/SF
    • 354 Days On Market

    Current Estimated Value $1,980,288

    Last Listing Agent Elissa Lash Tea Lane Associates

    10 N Abels Hill Rd, Chilmark, MA 02535
    • /12

      Est $2,449,380 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 1,342 Sq Ft

      5 Ocean View Farm Rd, Chilmark, MA 02535

      5 Ocean View Farm Rd, Chilmark, MA 02535
  • /20

    $1,650,000

    • 2 Beds
    • 1 Bath
    • 716 Sq Ft

    46 Tiercel Ln, Chilmark, MA 02535

    Nestled on a serene 3.32-acre parcel between North Road and Tabor House in Chilmark, this property blends privacy, charm, and great potential. A sweet 2 bedroom guest house—beautifully maintained and offering excellent rental income—sits amid rolling stone walls and mature trees, creating a peaceful woodland setting.Recent updates include a new roof, siding, and HVAC system, ensuring

    Stacy Ickes Donnelly + Co

    46 Tiercel Ln, Chilmark, MA 02535
  • /35

    $22,000 total monthly price

    • 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
  • /44

    $8,178,500 Sold Oct 27, 2025

    94 Menemsha Inn Rd, Chilmark, MA 02535

    • 6 Beds
    • 4.5 Baths
    • 4,104 Sq Ft
    • Built 2001

    Last Sold Summary

    • 3% Below List Price
    • $1,993/SF
    • 38 Days On Market

    Last Listing Agent Julianna Flanders Flanders Real Estate

    94 Menemsha Inn Rd, Chilmark, MA 02535
    • /19

      Est $2,754,266 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 2,450 Sq Ft

      27 Ocean View Farm Rd, Chilmark, MA 02535

      27 Ocean View Farm Rd, Chilmark, MA 02535
  • /16

    $1,295,000

    • Land
    • 4.4 Acres
    • $294,318 per Acre

    37 Bijah's Way Unit 96, 101, 102, 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 Unit 96, 101, 102, Chilmark, MA 02535
  • /39

    $110,000 total monthly price

    • 5 Beds
    • 5 Baths
    • 4,000 Sq Ft
    • House for Rent

    17 Round Pond Rd Ch240, Chilmark, MA 02535

    THIS IS A WEEKLY SUMMER RENTAL ONLY. See web site for pricing!! Newly constructed home has open concept living area with 270 degree water views, abundant natural sunlight, central AC, high end appliances, hardwood floors, rooftop deck with seating to view gorgeous island sunsets, access to several private beaches and high speed internet wifi.

    Karen Overtoom Karen M. Overtoom R.E.

    17 Round Pond Rd Ch240, Chilmark, MA 02535
  • /34

    $2,475,000 Sold Sep 05, 2025

    31 N Slope Ln, Chilmark, MA 02535

    • 4 Beds
    • 3.5 Baths
    • 2,300 Sq Ft
    • Built 1983

    Last Sold Summary

    • 15% Below List Price
    • $1,076/SF
    • 117 Days On Market

    Current Estimated Value $2,576,026

    Last Listing Agent Bill Rossi Studio Realty

    31 N Slope Ln, Chilmark, MA 02535
    • /69

      Est $2,406,935 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 2,034 Sq Ft

      276 South Rd, Chilmark, MA 02535

      276 South Rd, Chilmark, MA 02535
  • /43

    $7,350,000

    • 4 Beds
    • 4.5 Baths
    • 3,490 Sq Ft

    308 South Rd, Chilmark, MA 02535

    Waterfront South Shore Retreat with Private Dock and Water Views. Set on the edge of Chilmark Pond, this exceptional waterfront residence offers rare privacy, refined design, generous water views and easy pond access. Thoughtfully renovated in 2018, the home blends contemporary sophistication with the beauty of its natural environment. A private dock on the property provides direct pond access.

    Rose Ryley Wallace & Co. Sotheby's

    308 South Rd, Chilmark, MA 02535
  • /19

    $24,000 total monthly price

    • 4 Beds
    • 4 Baths
    • 2,000 Sq Ft
    • House for Rent

    44 Flanders Ln, Chilmark, MA 02535

    THIS IS A WEEKLY SUMMER RENTAL ONLY.!! SEE WEB SITE FOR WEEKLY PRICING. This house sits up the hill and looks toward Menemsha. It is private and protected by the trees. Visit town to watch sunsets in Menemsha, dine in one of the places to eat there or take in a day at the beach.Access to and parking for beautiful private association beach.

    Karen Overtoom Karen M. Overtoom R.E.

    44 Flanders Ln, Chilmark, MA 02535
  • /51

    $4,850,000 Sold Dec 05, 2025

    49 Gosnold's Way, Chilmark, MA 02535

    • 5 Beds
    • 3.5 Baths
    • 4,044 Sq Ft
    • Built 2003

    Last Sold Summary

    • 8% Below List Price
    • $1,199/SF
    • 115 Days On Market

    Last Listing Agent Meg Bodnar Tea Lane Associates

    49 Gosnold's Way, Chilmark, MA 02535
    • /37

      Est $2,068,421 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 1,900 Sq Ft

      2 Rockrose Path, Chilmark, MA 02535

      2 Rockrose Path, 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
  • /32

    $36,000 total monthly price

    • 3 Beds
    • 3.5 Baths
    • 2,600 Sq Ft
    • House for Rent

    29 Cemetery Rd Ch216, Chilmark, MA 02535

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $9,000. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Fabulous Chilmark home offers two levels of living space. On the first floor there is a fully equipped kitchen open to the dining room, a living room with fireplace, built-ins and sliders to a deck overlooking a meadow and the most incredible water views. There is a half

    Karen Overtoom Karen M. Overtoom R.E.

    29 Cemetery Rd Ch216, Chilmark, MA 02535
  • /21

    $435,000 Sold Aug 26, 2025

    0 Beach Lot Quansoo Unit 22503743, Chilmark, MA 02535

    • Land
    • 0.1 Acre
    • $4,350,000 per Acre

    Last Sold Summary

    • 3% Below List Price
    • 20 Days On Market

    Last Listing Agent Emma Bryant Landmarks at TODAY Real Estate

    0 Beach Lot Quansoo Unit 22503743, Chilmark, MA 02535
    • /20

      Est $2,780,935 Not Listed For Sale

      • 2 Beds
      • 2 Baths
      • 1,164 Sq Ft

      23 Black Point Rd, Chilmark, MA 02535

      23 Black Point Rd, Chilmark, MA 02535
  • /38

    $3,995,000

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

    96 Hammett Ln, Chilmark, MA 02535

    This 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
  • /29

    $34,000 total monthly price

    • 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
  • /44

    $37,000,000 Sold Jul 10, 2025

    41 Cobbs Hill Rd, Chilmark, MA 02535

    • 8 Beds
    • 5.5 Baths
    • 7,846 Sq Ft
    • Built 1993

    Last Sold Summary

    • 5% Below List Price
    • $4,716/SF
    • 39 Days On Market

    Last Listing Agent Brian Dougherty Corcoran Property Advisors

    41 Cobbs Hill Rd, Chilmark, MA 02535
    • /21

      Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 2,686 Sq Ft

      3 Pepperbush Ln, Chilmark, MA 02535

      3 Pepperbush Ln, 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
  • /9

    $10,800 total monthly price

    • 4 Beds
    • 2 Baths
    • 702 Sq Ft
    • House for Rent

    141 N Rd Ch202, Chilmark, MA 02535

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $2,700. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Chilmark Cottage Perfection!!! You will love this quaint Vineyard Style Cottage that has been meticulously designed to include all the amenities one could imagine. This vintage charmer really boasts a lot of Style. Inside you will find really beautiful hardwood floors, a

    Karen Overtoom Karen M. Overtoom R.E.

    141 N Rd Ch202, Chilmark, MA 02535
  • /43

    $2,100,000 Sold Nov 25, 2025

    6 Tabor Hills, Chilmark, MA 02535

    • 4 Beds
    • 3 Baths
    • 1,968 Sq Ft
    • Built 1993

    Last Sold Summary

    • 11% Below List Price
    • $1,067/SF
    • 50 Days On Market

    Last Listing Agent Dawn Bellante Sandpiper Realty Inc

    6 Tabor Hills, Chilmark, MA 02535
    • /29

      Est $2,389,190 Not Listed For Sale

      • 5 Beds
      • 3 Baths
      • 2,427 Sq Ft

      50 South Rd, Chilmark, MA 02535

      50 South 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
  • /8

    $7,900 total monthly price

    • 3 Beds
    • 2.5 Baths
    • 2,107 Sq Ft
    • House for Rent

    2 Paddock Cir, Chilmark, MA 02535

    Karen Overtoom Karen M. Overtoom R.E.

    2 Paddock Cir, Chilmark, MA 02535
  • /48

    $1,775,000 Sold Nov 07, 2025

    3 Fulling Mill Rd, Chilmark, MA 02535

    • 3 Beds
    • 2 Baths
    • 1,728 Sq Ft
    • Built 1976

    Last Sold Summary

    • 5% Below List Price
    • $1,027/SF
    • 170 Days On Market

    Last Listing Agent Jill Napior Tea Lane Associates

    3 Fulling Mill Rd, Chilmark, MA 02535
    • /50

      Est $2,307,508 Not Listed For Sale

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

      16 South Rd, Chilmark, MA 02535

      16 South Rd, Chilmark, MA 02535
  • /11

    $1,575,000

    • 2 Beds
    • 1 Bath
    • 896 Sq Ft

    45 Quenames Rd, Chilmark, MA 02535

    Set on a serene 3.02-acre parcel in Chilmark, 45 Quenames Road offers privacy, charm, and excellent potential. In a sunny clearing among mature trees, the maintained 2-bedroom house features first-floor living, an open kitchen and living area, two spacious bedrooms, a full bath with shower, an enormous three-season screened porch, a large outdoor shower, kitchen gardens, and a potting area with

    Dawn Bellante-Holand Sandpiper Realty

    45 Quenames Rd, Chilmark, MA 02535
  • /24

    $4,325,000 Sold Dec 05, 2025

    18 Homeward Way, Chilmark, MA 02535

    • 5 Beds
    • 2.5 Baths
    • 3,885 Sq Ft
    • Built 1986

    Last Sold Summary

    • 8% Below List Price
    • $1,113/SF
    • 8 Days On Market

    Last Listing Agent Bill Rossi Studio Realty

    18 Homeward Way, Chilmark, MA 02535
    • /24

      Est $2,420,206 Not Listed For Sale

      • 4 Beds
      • 5.5 Baths
      • 2,405 Sq Ft

      99 Hammett Rd, Chilmark, MA 02535

      99 Hammett Rd, Chilmark, MA 02535
  • /36

    $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 International Realty

    18 Spruce Gate Rd, Chilmark, MA 02535
  • /37

    $4,350,000 Sold Jan 07, 2026

    146 Quansoo Rd, Chilmark, MA 02535

    • 5 Beds
    • 3 Baths
    • 3,440 Sq Ft
    • Built 1988

    Last Sold Summary

    • 21% Below List Price
    • $1,265/SF
    • 155 Days On Market

    Last Listing Agent Meg Bodnar Tea Lane Associates

    146 Quansoo Rd, Chilmark, MA 02535
    • /48

      Not Listed For Sale

      • 6 Beds
      • 5 Baths
      • 3,834 Sq Ft

      49 Tilton Rd, Chilmark, MA 02535

      49 Tilton 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
  • /17

    $1,790,000 Sold Sep 23, 2025

    32 Stonewall Rd Unit 2.1, Chilmark, MA 02535

    • Land
    • 3.3 Acres
    • $542,424 per Acre

    Last Sold Summary

    • 15% Below List Price
    • 77 Days On Market

    Last Listing Agent Jill Napior Tea Lane Associates

    32 Stonewall Rd Unit 2.1, Chilmark, MA 02535

Showing Results 41 - 80, Page 2 of 18

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