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Chilmark Homes for Sale

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  • 34 Ebens Ln Unit 20 and 22, Chilmark, MA 02535
    34 Ebens Ln Unit 20 and 22, Chilmark, MA 02535
    34 Ebens Ln Unit 20 and 22, Chilmark, MA 02535
    /21

    $2,725,000

    • Land
    • 7.6 Acres
    • $358,553 per Acre

    34 Ebens Ln Unit 20 and 22, Chilmark, MA 02535

    This rare two-lot offering off Middle Road in Chilmark presents a private sanctuary abutting approximately 50 acres of conservation land. The gently rolling landscape is accented by ancient stone walls and striking glacial boulders, creating a setting of timeless Vineyard character. Ideal for a generational compound or two distinct residences, the property offers both serenity and convenience —

    Peyton Wallace Studio Realty

    34 Ebens Ln Unit 20 and 22, Chilmark, MA 02535
  • 46 Tercel Ln, Chilmark, MA 02535
    46 Tercel Ln, Chilmark, MA 02535
    46 Tercel Ln, Chilmark, MA 02535
    /17

    $1,650,000

    • 2 Beds
    • 1 Bath
    • 716 Sq Ft

    46 Tercel 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 comfort

    Stacy Ickes Donnelly + Co.

    46 Tercel Ln, Chilmark, MA 02535
  • 46 Tiercel Ln, Chilmark, MA 02535
    46 Tiercel Ln, Chilmark, MA 02535
    46 Tiercel Ln, 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
  • 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
  • 18 Spruce Gate Rd, Chilmark, MA 02535
    18 Spruce Gate Rd, Chilmark, MA 02535
    18 Spruce Gate 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
  • 99 Cygnet Way Unit 103, Chilmark, MA 02535
    99 Cygnet Way Unit 103, Chilmark, MA 02535
    99 Cygnet Way Unit 103, Chilmark, MA 02535
    /7

    $400,000

    • Land
    • 0.2 Acre
    • $2,000,000 per Acre

    99 Cygnet Way Unit 103, Chilmark, MA 02535

    Escape the crowds at Lucy Vincent and Squibnocket and take advantage of this very rare opportunity to own a private, 17 member, Atlantic Ocean beach lot at Thumb Cove (abuts Hancock Beach). Included in the sale of this property is a deeded .2 acres of sandy beach, a deeded parking spot at Chilmark Pond and the right to launch boats from a dock in the pond. Sail, kayak, row, swim(!) or motor

    Russell Maloney Russell Maloney Real Estate

    99 Cygnet Way Unit 103, Chilmark, MA 02535
  • 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
  • 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
  • 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
  • 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
  • 174 Middle Rd, Chilmark, MA 02535
    174 Middle Rd, Chilmark, MA 02535
    174 Middle Rd, Chilmark, MA 02535
    /40

    $1,895,000

    • 4 Beds
    • 3.5 Baths
    • 2,061 Sq Ft

    174 Middle Rd, Chilmark, MA 02535

    Nestled in the heart of Chilmark, this four-bedroom home offers a blend of comfort, convenience, and timeless Vineyard charm. Thoughtfully designed with distinct, well-proportioned rooms, the home centers around an expansive, sunlit, eat-in kitchen featuring dual ovens, elegant granite countertops, and extensive custom cherry wood built-ins that combine beauty and practicality. The welcoming

    Sheila Morse Island Real Estate

    174 Middle 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
  • 16 South Rd, Chilmark, MA 02535
    16 South Rd, Chilmark, MA 02535
    16 South Rd, Chilmark, MA 02535
    /36

    $2,500,000

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

    16 South Rd, Chilmark, MA 02535

    Where Vineyard history meets pastoral beauty.Classic, lovingly restored 1800’s Chilmark farmhouse with multiple outbuildings, which includes a large barn with second floor loft, a run-in barn with two horse stalls, both overlook an expansive, pastoral fenced pasture for horses to run or field games to be played. This historic farmhouse home offers four bedrooms, three baths and has been updated

    Michele Casavant Vineyard Village Realty

    16 South Rd, Chilmark, MA 02535
  • 122 Old Farm Rd, Chilmark, MA 02535
    122 Old Farm Rd, Chilmark, MA 02535
    122 Old Farm Rd, Chilmark, MA 02535
    /36

    $4,950,000

    • 5 Beds
    • 4 Baths
    • 3,413 Sq Ft

    122 Old Farm Rd, Chilmark, MA 02535

    An incomparable setting in Chilmark, a beautifully renovated 5-bedroom home, stunning landscape and hardscape, all on three separate building lots totaling almost 14 acres - this is Allerton farm. The historic house has been expanded with new additions to create a thoroughly modern residence that nevertheless retains a charm that could not be achieved without technical expertise, attention to

    Mark Jenkins Wallace & Co. Sotheby's

    122 Old Farm Rd, Chilmark, MA 02535
  • 124 Old Farm Rd Unit 122, 116, Chilmark, MA 02535
    124 Old Farm Rd Unit 122, 116, Chilmark, MA 02535
    124 Old Farm Rd Unit 122, 116, Chilmark, MA 02535
    /34

    $4,950,000

    • 5 Beds
    • 4.5 Baths
    • 3,413 Sq Ft

    124 Old Farm Rd Unit 122, 116, Chilmark, MA 02535

    An incomparable setting in Chilmark, a beautifully renovated 5-bedroom home, stunning landscape and hardscape, all on three separate building lots totaling almost 14 acres - this is Allerton farm. The historic house has been expanded with new additions to create a thoroughly modern residence that nevertheless retains a charm that could not be achieved without technical expertise, attention to

    Mark Jenkins Wallace & Co. Sotheby's International Realty

    124 Old Farm Rd Unit 122, 116, Chilmark, MA 02535
  • 44 Cencelle St, Chilmark, MA 02535
    44 Cencelle St, Chilmark, MA 02535
    44 Cencelle St, Chilmark, MA 02535
    /46

    $6,750,000

    • 3 Beds
    • 3 Baths
    • 3,432 Sq Ft

    44 Cencelle St, Chilmark, MA 02535

    This private 21-acre Chilmark estate with ocean views, tucked away in the rolling hills and farmlands of Chilmark, offers sweeping ocean views to the south and a rare sense of seclusion and serenity. At the heart of the property is a striking modern style home, thoughtfully designed to bring the outdoors in. Expansive walls of glass flood the interior with natural light and frame panoramic views

    Meg Bodnar Tea Lane Associates

    44 Cencelle St, Chilmark, MA 02535
  • 4 Cedar Ln Unit 2.2, Chilmark, MA 02535
    4 Cedar Ln Unit 2.2, Chilmark, MA 02535
    4 Cedar Ln Unit 2.2, Chilmark, MA 02535
    /33

    $1,985,000

    • Land
    • 3.58 Acres
    • $554,469 per Acre

    4 Cedar Ln Unit 2.2, Chilmark, MA 02535

    Premier Build-Ready Lot with Private Beach AccessGet to know Stonewall Association, one of Chilmark’s most sought-after enclaves on the South Shore. This sunny, build-ready parcel offers a rare opportunity to own land with deeded private access to Stonewall Beach—a beloved destination for swimming, surfing, excellent fishing and summer memories. Set on beautifully contoured land with

    Jill Napior Tea Lane Associates

    4 Cedar Ln Unit 2.2, 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

    Julianna Flanders Flanders Real Estate

    11 By the Woods, 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
  • 37 Bijah's Way Unit 96, 101, 102, Chilmark, MA 02535
    37 Bijah's Way Unit 96, 101, 102, Chilmark, MA 02535
    37 Bijah's Way Unit 96, 101, 102, 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
  • 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
  • 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
  • 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 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
  • 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
  • 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
Massachusetts Dukes County Marthas Vineyard Chilmark

Real Estate & Homes for Sale in Chilmark, Marthas Vineyard

Learn more about living in Chilmark

Frequently Asked Questions

Is Chilmark a good place to live?
Chilmark is a good place to live. Chilmark is considered very car-dependent and somewhat bikeable. Chilmark is a neighborhood with a crime score of 1, making it safer than the average neighborhood in the U.S. Chilmark has 1 park for recreational activities. It is sparse in population with 0.1 people per acre and a median age of 56. The average household income is $161,487 which is above the national average. College graduates make up 64.4% of residents. A majority of residents in Chilmark are home owners, with 20.4% of residents renting and 79.6% of residents owning their home. A local real estate agent serving Chilmark can help you decide if this neighborhood is the right one for you. Learn more on our Chilmark neighborhood guide.
Is Chilmark, MA a safe neighborhood?
Chilmark, MA is safer than the average neighborhood in the United States. It received a crime score of 1 out of 10.
How much do you need to make to afford a house in Chilmark?
The median home price in Chilmark is $3,800,000. If you put a 20% down payment of $760,000 and had a 30-year fixed mortgage with an interest rate of 6.26%, your estimated principal and interest payment would be $18,740 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $803K a year to afford the median home price in Chilmark. Learn how much home you can afford with our Home Affordability Calculator. The average household income in Chilmark is $161K.
What are the best public schools in Chilmark?
The best public schools that serve Chilmark are:
What are the most popular zip codes in Chilmark, Marthas Vineyard, MA?
The most popular zip codes in Chilmark, Marthas Vineyard, MA include 02535, 02568, 02575, 02539 and 02536.
What are the most popular neighborhoods near Chilmark, Marthas Vineyard, MA?
The most popular neighborhoods near Chilmark, Marthas Vineyard, MA are Aquinnah, West Tisbury, Edgartown, Vineyard Haven and Oak Bluffs.

Home Trends in Chilmark, MA

On average, homes in Chilmark, Marthas Vineyard sell after 113 days on the market compared to the national average of 53 days. The median sale price for homes in Chilmark, Marthas Vineyard over the last 12 months is $3,436,250, up 49% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$3,436,250
Median Single Family Sale Price
$3,500,000
Average Price Per Sq Ft
$1,855
Number of Homes for Sale
21
Last 12 months Home Sales
26
Months of Supply
9.70
Median List Price
$3,800,000
Median Change From 1st List Price
7%
Median Home Sale Price YoY Change
49%
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