16 Trails End, Chilmark, MA 02535
Property image
Property image
OFF MARKET

16 Trails End
Chilmark, MA 02535

  • 4 Beds
  • 2 Baths
  • 1,500 sqft (on 2 acres)

$2,077,400

Trulia Estimate
as of Aug 25, 2026

$2,077,400

Trulia Estimate
as of Aug 25, 2026
4 Beds
2 Baths
1,500 sqft
(on 2 acres)

Home Value

Trulia Estimate
$2.08M
Since last month
Decreased$13K (-0.6%)
Since last year
Increased$53K (+2.6%)
Since last sale
Increased$792K (+61.7%)
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 +84% in the last 10 years
MonthEstimated value
2026
August 2026$2.08M
July 2026$2.09M
June 2026$2.15M
May 2026$2.1M
April 2026$2.06M
March 2026$2.08M
February 2026$2.06M
January 2026$2.03M
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
3 Fulling Mill Rd, Chilmark, MA
0.42
Single-Family Home
$1,775,000
11/07/25
3
2
1,728
6 Tabor Hls, Chilmark, MA
0.60
Single-Family Home
$2,100,000
11/25/25
4
3
2,544
25 Osprey Ln, Chilmark, MA
0.71
Single-Family Home
$7,289,000
10/15/25
4
5
3,777
31 N Slope Ln, Chilmark, MA
1.27
Single-Family Home
$2,475,000
09/05/25
4
3.5
2,300
9 Beetlebung Grove Way, Chilmark, MA
1.72
Single-Family Home
$2,225,000
10/24/25
4
3
2,968
60 Meeting House Rd, Chilmark, MA
0.79
Single-Family Home
$6,100,000
03/24/26
6
7
5,660
18 Homeward Way, Chilmark, MA
1.36
Single-Family Home
$4,325,000
12/05/25
5
2.5
3,885
15 Old Farm Rd, Chilmark, MA
1.86
Single-Family Home
$3,710,000
03/12/26
3
5
3,171
49 Gosnolds Way, Chilmark, MA
1.82
Single-Family Home
$4,850,000
12/05/25
5
3.5
4,044
10 Mollys Way, Chilmark, MA
2.42
Single-Family Home
$2,550,000
10/02/25
3
2
1,524

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
31 Cross Rip Ln, Chilmark, MA 02535
0.21
$1,090,400
1
1
512
Off Market
27 Ocean View Farm Rd, Chilmark, MA 02535
0.27
$2,987,700
4
3
2,450
Off Market
21 & 25 Fulling Mill Rd, Chilmark, MA 02535
0.29
$2,250,000
4
3
1,918
For Sale
25 Fulling Mill Rd, Chilmark, MA 02535
0.29
$2,250,000
4
3
1,918
For Sale
22 Ocean View Farm Rd #B, Chilmark, MA 02535
0.35
$1,176,700
2
1.5
1,520
Off Market
3 Fulling Mill Rd, Chilmark, MA 02535
0.42
$1,775,000
3
2
1,728
Recently Sold
5 Ocean View Farm Rd, Chilmark, MA 02535
0.44
$2,475,200
3
1.5
1,342
Off Market
8 Wauwompauque Trl, Chilmark, MA 02535
0.44
$5,300,000
5
3.5
2,210
For Sale
10 N Abels Hill Rd, Chilmark, MA 02535
0.55
$1,653,300
4
3
2,850
Off Market
Cencelle, Chilmark, MA 02535
0.57
$1,275,000
-
-
-
For Sale
18 Allen Farm Rd, Chilmark, MA 02535
0.57
$2,250,000
1
1
726
For Sale
6 Tabor Hls, Chilmark, MA 02535
0.60
$2,100,000
4
3
2,544
Recently Sold

Local Information

  • Map ViewExplore the area around 16 Trails End.
  • Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1968
Lot Size
2 acres
Living Area
1,500 sqft
Price/Sqft
$1,385

About this House

One of the unique aspects of this hilltop home is it's location at the top of a rise where it captures the stunning water views looking westerly over the Atlantic to Squibnocket point and the amazing sunsets. Connect with nature within the abutting Land Bank preserve. Several favorite vantage points are the new master suite/office again with those amazing views, the cathedral ceiling living room with gas wood stove and the expansive deck. Free wheeling with a beach Jeep and most furnishings included and a short drive to exclusive Lucy Vincent Beach.. Shed for storage, Out door shower, air conditioning and excellent rental history.
16 Trails End, Chilmark, MA 02535 is a 4 bedroom, 2 bathroom, 1,500 sqft single-family home built in 1968. It last sold for $1,285,000 on Jun 26, 2020. It is currently off market. The Trulia Estimate is $2,077,400, with a rent estimate of $5,429/month.

Home Details for 16 Trails End

Interior Features

Levels, Entrance, & Accessibility
Stories: 2
Interior Details
Number of Rooms: 5

Exterior Features

Exterior Home Features
Roof: AsphaltDeckExterior: WoodPorch

Property Information

Year Built
Year Built: 1968Year Updated: 1997
Property Type / Style
Property Type: Single Family HomeArchitecture: Contemporary

Community

Units in Building: 1

Lot Information

Lot Area: 2.00 acres

Price and Tax history

DateEventPrice
Jun 26, 2020
Source: LINK #34723
Sold
$1,285,000
Feb 28, 2020
Source: Agent Provided
PriceChange
$1,295,000
Price decreased by 7%
Jan 25, 2020
Source: Agent Provided
PriceChange
$1,395,000
Price decreased by 7%
Oct 30, 2019
Source: Agent Provided
PriceChange
$1,495,000
Price decreased by 4%
Mar 20, 2019
Source: Agent Provided
Listed For Sale
$1,550,000

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

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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Frequently asked questions about 16 Trails End

  • What is 16 Trails End estimated to be worth?
    Trulia's estimated value for 16 Trails End in Chilmark, MA is $2,077,400.
  • What is the price history for 16 Trails End?
    16 Trails End in Chilmark, MA last sold for $1,285,000 in June 2020.
  • 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 16 Trails End?
    The closest schools to 16 Trails End 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).
  • How big is the lot at 16 Trails End?
    The lot at 16 Trails End in Chilmark, MA is about 2 acres.

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