37 Middle Rd, Chilmark, MA 02535
OFF MARKET

37 Middle Rd
Chilmark, MA 02535

  • 6 Beds
  • 1 Bath
  • 2,557 sqft (on 8.90 acres)

$2,790,100

Trulia Estimate
as of Aug 21, 2026
Est. Refi. Payment $15,361/mo*
Refinance Your Home

$2,790,100

Trulia Estimate
as of Aug 21, 2026
Est. Refi. Payment $15,361/mo*
Refinance Your Home
6 Beds
1 Bath
2,557 sqft
(on 8.90 acres)

Home Value

Trulia Estimate
$2.79M
Since last month
Increased$62K (+2.3%)
Since last year
Increased$5K (+0.2%)
Since last sale
Increased$2M (+115.5%)
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 +45% in the last 10 years
MonthEstimated value
2026
August 2026$2.8M
July 2026$2.74M
June 2026$2.9M
May 2026$2.86M
April 2026$2.84M
March 2026$2.82M
February 2026$2.8M
January 2026$2.73M
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
15 Old Farm Rd, Chilmark, MA
0.54
Single-Family Home
$3,710,000
03/12/26
3
5
3,171
124-116 122 Old Farm Rd, Chilmark, MA
0.90
Single-Family Home
$3,700,000
05/28/26
5
4
3,413
40 Scotchmans Ln, West Tisbury, MA
1.46
Single-Family Home
$1,029,000
07/17/26
4
2
1,564
9 Beetlebung Grove Way, Chilmark, MA
1.48
Single-Family Home
$2,225,000
10/24/25
4
3
2,968
60 Meeting House Rd, Chilmark, MA
1.34
Single-Family Home
$6,100,000
03/24/26
6
7
5,660
6 Tabor Hls, Chilmark, MA
1.71
Single-Family Home
$2,100,000
11/25/25
4
3
2,544
31 North Rd, Chilmark, MA
1.33
Single-Family Home
$1,000,000
06/03/26
2
1
576
19 S Vine Ln, West Tisbury, MA
1.98
Single-Family Home
$1,325,000
08/29/25
3
2
1,982
651 State Rd, West Tisbury, MA
2.19
Single-Family Home
$1,375,000
07/20/26
5
4
2,516
35 Nats Farm Ln, West Tisbury, MA
2.17
Single-Family Home
$2,013,500
08/05/26
4
3.5
2,428

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
25 Old Farm Rd, Chilmark, MA 02535
0.52
$3,780,500
5
6
2,497
Off Market
15 Old Farm Rd, Chilmark, MA 02535
0.54
$3,710,000
3
5
3,171
Recently Sold
78 Campbell Rd W, Vineyard Haven, MA 02568
0.58
$1,892,300
2
2
1,353
Off Market
37 Bijahs Way, Chilmark, MA 02535
0.61
$1,295,000
-
-
-
For Sale
26 Bijahs Way, Chilmark, MA 02535
0.73
$2,395,000
3
2
2,510
For Sale
50 Campbell Rd, West Tisbury, MA 02575
0.70
$2,094,300
2
2
1,370
Off Market
3 Tennis Ln, Chilmark, MA 02535
0.78
$3,835,400
4
4.5
3,234
Off Market
29 Old Nursery Ln, Chilmark, MA 02535
0.84
$2,150,000
4
2.5
2,522
For Sale
91 Music St, West Tisbury, MA 02575
0.80
$2,660,000
5
4.5
3,993
Off Market
Quenames Rd, Chilmark, MA 02535
0.83
-
-
-
-
Off Market
27 Clambelly Rd, Chilmark, MA 02535
0.87
$3,295,000
3
3
2,500
For Sale
82 South Rd, Chilmark, MA 02535
0.87
$1,927,300
3
2
1,862
Off Market

Local Information

  • Map ViewExplore the area around 37 Middle Rd.
  • Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1905
Lot Size
8.9 acres
Living Area
2,557 sqft
Price/Sqft
$1,091

About this House

This single-family home is located at 37 Middle Rd, Chilmark, MA. 37 Middle Rd is in Chilmark, MA and in ZIP code 02535. This property has 6 bedrooms, 1 bathroom and approximately 2,557 sqft of floor space. This property has a lot size of 8.90 acres and was built in 1905.
37 Middle Rd, Chilmark, MA 02535 is a 6 bedroom, 1 bathroom, 2,557 sqft single-family home built in 1905. It last sold for $1,300,000 on Apr 14, 2000. It is currently off market. The Trulia Estimate is $2,790,100, with a rent estimate of $5,065/month.

Home Details for 37 Middle Rd

Interior Features

Heating & Cooling
Heating: Forced Air, GasAir ConditioningHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 2
Interior Details
Number of Rooms: 8

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: Wood

Property Information

Year Built
Year Built: 1905Year Updated: 1966
Property Type / Style
Property Type: Single Family HomeArchitecture: Old Style

Community

Units in Building: 1

Lot Information

Lot Area: 8.90 acres

Price and Tax history

DateEventPrice
Apr 14, 2000
Source: N/A
Sold
$1,300,000

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!!"
    0
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LGBTQ Local Legal Protections

Frequently asked questions about 37 Middle Rd

  • What is 37 Middle Rd estimated to be worth?
    Trulia's estimated value for 37 Middle Rd in Chilmark, MA is $2,790,100.
  • What is the price history for 37 Middle Rd?
    37 Middle Rd in Chilmark, MA last sold for $1,300,000 in April 2000.
  • 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 37 Middle Rd?
    The closest schools to 37 Middle Rd 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 37 Middle Rd?
    The lot at 37 Middle Rd in Chilmark, MA is about 8.9 acres.

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