17 High Mark, Chilmark, MA 02535
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Property image
OFF MARKET

17 High Mark
Chilmark, MA 02535

  • 7 Beds
  • 5 Baths
  • 3,883 sqft (on 10.43 acres)

$6,375,500

Trulia Estimate
as of Aug 13, 2026
Est. Refi. Payment $35,171/mo*
Refinance Your Home

$6,375,500

Trulia Estimate
as of Aug 13, 2026
Est. Refi. Payment $35,171/mo*
Refinance Your Home
7 Beds
5 Baths
3,883 sqft
(on 10.43 acres)

Home Value

Trulia Estimate
$6.38M
Since last month
Decreased$339K (-5.1%)
Since last year
Decreased$30K (-0.5%)
Since last sale
Increased$2M (+39%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +151% in the last 10 years
MonthEstimated value
2026
August 2026$6.26M
July 2026$6.35M
June 2026$6.6M
May 2026$6.47M
April 2026$6.47M
March 2026$6.47M
February 2026$6.39M
January 2026$6.35M
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
18 Homeward Way, Chilmark, MA
0.68
Single-Family Home
$4,325,000
12/05/25
5
2.5
3,885
49 Gosnolds Way, Chilmark, MA
1.24
Single-Family Home
$4,850,000
12/05/25
5
3.5
4,044
31 N Slope Ln, Chilmark, MA
0.77
Single-Family Home
$2,475,000
09/05/25
4
3.5
2,300
94 Menemsha Inn Rd, Chilmark, MA
1.39
Single-Family Home
$8,178,500
10/27/25
6
4.5
4,104
25 Osprey Ln, Chilmark, MA
1.23
Single-Family Home
$7,289,000
10/15/25
4
5
3,777
6 Tabor Hls, Chilmark, MA
1.22
Single-Family Home
$2,100,000
11/25/25
4
3
2,544
3 Fulling Mill Rd, Chilmark, MA
0.81
Single-Family Home
$1,775,000
11/07/25
3
2
1,728
60 Meeting House Rd, Chilmark, MA
1.89
Single-Family Home
$6,100,000
03/24/26
6
7
5,660
10 Mollys Way, Chilmark, MA
1.28
Single-Family Home
$2,550,000
10/02/25
3
2
1,524
12 Squibnocket Rd, Chilmark, MA
2.50
Single-Family Home
$5,900,000
10/31/25
6
4.5
3,143

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
High Mark, Chilmark, MA 02535
0.01
$1,900,000
-
-
-
For Sale
1 Pond Mark, Chilmark, MA 02535
0.17
$4,025,000
3
2.5
1,316
Off Market
391 Middle Rd, Chilmark, MA 02535
0.39
$6,293,400
6
4.5
3,859
Off Market
493 South Rd, Chilmark, MA 02535
0.50
-
-
-
-
Off Market
43 N Slope Ln, Chilmark, MA 02535
0.69
$1,699,999
3
2
1,540
For Sale
18 Homeward Way, Chilmark, MA 02535
0.68
$4,325,000
5
2.5
3,885
Recently Sold
18 Allen Farm Rd, Chilmark, MA 02535
0.72
$2,250,000
1
1
726
For Sale
31 N Slope Ln, Chilmark, MA 02535
0.77
$2,537,800
4
3.5
2,300
Off Market
3 Fulling Mill Rd, Chilmark, MA 02535
0.81
$1,775,000
3
2
1,728
Recently Sold
44 Cencelle St, Chilmark, MA 02535
0.82
$4,975,000
4
3
3,432
For Sale
25 Fulling Mill Rd, Chilmark, MA 02535
0.85
$2,250,000
4
3
1,918
For Sale
21 & 25 Fulling Mill Rd, Chilmark, MA 02535
0.85
$2,250,000
4
3
1,918
For Sale

Local Information

  • Map ViewExplore the area around 17 High Mark.
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1928
Lot Size
10.43 acres
Living Area
3,883 sqft
Price/Sqft
$1,642

About this House

17 High Mark, circa 1928, sits atop Highmark Hill near the center of Chilmark. This unique compound is now exclusively offered for the first time in 49 years. Spread across 10.4 acres, the property consists of two parcels: 6.7 acres with the living spaces, and a 3.7 acre parcel for buffer or development. The larger parcel holds the main house, guest house, detached bedroom, artist studio, pool with outdoor shower and dressing room, tennis court, two car garage and workshop, with long, wide yards front and rear. Views to the Atlantic, Menemsha Pond, and Nomans are seen from many of the rooms of the main house and guest house. The main house has four bedrooms, living room with fireplace, dining room, office and gallery, kitchen and laundry room. The lower level has a library/media room, full bath, utility room, cedar closet and storage rooms. The guest house has 3 bedrooms, full bath and kitchen. The detached bedroom/bunk house has views to the Atlantic. Many of the amenities on this property allow for immediate enjoyment without special zoning permits and years of residency. Ample acreage allows for building expansion or relocation.
17 High Mark, Chilmark, MA 02535 is a 7 bedroom, 5 bathroom, 3,883 sqft single-family home built in 1928. It last sold for $4,500,000 on Aug 2, 2021. It is currently off market. The Trulia Estimate is $6,375,500, with a rent estimate of $7,405/month.

Home Details for 17 High Mark

Interior Features

Levels, Entrance, & Accessibility
Stories: 1Floors: Carpet, Hardwood
Interior Details
Number of Rooms: 9
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: Other
Pool
Pool

Property Information

Year Built
Year Built: 1928
Property Type / Style
Property Type: Single Family HomeArchitecture: Contemporary

Community

Units in Building: 1

Lot Information

Lot Area: 10.43 acres

Price and Tax history

DateEventPrice
Aug 2, 2021
Source: LINK #37278
Sold
$4,500,000
Jun 25, 2021
Source: Martha's Vineyard MLS #32000489
Pending
$4,900,000
Sep 14, 2020
Source: Agent Provided
Listed For Sale
$4,900,000

Market trends in Chilmark

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
39
8MoM
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Around this home

What Locals Say about Chilmark

At least 2 Trulia users voted on each feature.

  • 100 % Say there's wildlife

  • 100 % Say there are community events

  • 100 % Say car is needed

  • 100 % Say yards are well-kept

  • 78 % Say neighbors are friendly

  • 75 % Say it's dog friendly

  • 75 % Say people would walk alone at night

  • 67 % Say parking is easy

  • 67 % Say it's quiet

  • 60 % Say they plan to stay for at least 5 years

  • 43 % Say there's holiday spirit

  • 33 % Say it's walkable to restaurants

Sourced by Trulia users. Learn more about our methodology.
  • Elaine V.
    "I work and live here, and have been in Real estate here for over 20 years, I would recommend it to anyone who needs to feel a sense of community and enjoys nature. A wonderful place to live!!"
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Apartments for Rent

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Homes for sale near 17 High Mark

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Off Market Homes Near 17 High Mark

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Frequently asked questions about 17 High Mark

  • What is 17 High Mark estimated to be worth?
    Trulia's estimated value for 17 High Mark in Chilmark, MA is $6,375,500.
  • What is the price history for 17 High Mark?
    17 High Mark in Chilmark, MA last sold for $4,500,000 in August 2021.
  • Is Chilmark a buyer's or seller's market?
    Chilmark is currently a buyer's market, based on recent for-sale activity.
  • What are the closest schools to 17 High Mark?
    The closest schools to 17 High Mark in Chilmark, MA are Chilmark Elementary School (rated 8/10), Martha's Vineyard Regional High School (rated 6/10), West Tisbury Elementary School (Pre-K/Middle, rated 7/10).
  • Does 17 High Mark have a pool?
    Yes, 17 High Mark in Chilmark, MA has a pool.
  • How big is the lot at 17 High Mark?
    The lot at 17 High Mark in Chilmark, MA is about 10.4 acres.