Is there wildlife in Chilmark, MA?

As of early 2026, 100% of users say there's wildlife

Are there community events in Chilmark, MA?

As of early 2026, 100% of users say there are community events

Is a car needed in Chilmark, MA?

As of early 2026, 100% of users say car is needed

Are yards well-kept in Chilmark, MA?

As of early 2026, 100% of users say yards are well-kept

Are neighbors friendly in Chilmark, MA?

As of early 2026, 78% of users say neighbors are friendly

Is Chilmark, MA dog-friendly?

As of early 2026, 75% of users say it's dog friendly

Would people walk alone at night in Chilmark, MA?

As of early 2026, 75% of users say people would walk alone at night

Is parking easy in Chilmark, MA?

As of early 2026, 67% of users say parking is easy

Is Chilmark, MA quiet?

As of early 2026, 67% of users say it's quiet

Do residents of Chilmark, MA plan to stay at least 5 years?

As of early 2026, 60% of users say they plan to stay for at least 5 years

Does Chilmark, MA show holiday spirit?

As of early 2026, 43% of users say there's holiday spirit

Is Chilmark, MA walkable to restaurants?

As of early 2026, 33% of users say it's walkable to restaurants

What is 239 Middle Rd estimated to be worth?

Trulia's estimated value for 239 Middle Rd in Chilmark, MA is $1,337,400 .

What is the price history for 239 Middle Rd?

239 Middle Rd in Chilmark, MA last sold for $940,000 in October 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 239 Middle Rd?

The closest schools to 239 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 239 Middle Rd?

The lot at 239 Middle Rd in Chilmark, MA is about 2 acres .

OFF MARKET

$1,337,400

Trulia Estimate

2 Beds
1 Bath
1,228 sqft (on 2 acres)

239 Middle Rd, Chilmark, MA 02535

Est. Refi. Payment $7,960/mo*

Refinance Your Home

Currently Off Market - Sold Oct 15, 2021 for $940,000

Home Value

Trulia Estimate

$1.34M

Since last month

$27K (+2%)

Since last year

$109K (+8.9%)

Since last sale

$397K (+42.3%)

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 +66% in the last 10 years

Month	Estimated value
2026
October 2026	$1.34M
September 2026	$1.33M
August 2026	$1.31M
July 2026	$1.31M
June 2026	$1.35M
May 2026	$1.32M
April 2026	$1.3M
March 2026	$1.3M
February 2026	$1.28M
January 2026	$1.29M
2025
December 2025	$1.31M
November 2025	$1.29M
October 2025	$1.23M
September 2025	$1.23M
August 2025	$1.24M
July 2025	$1.24M
June 2025	$1.25M
May 2025	$1.26M
April 2025	$1.25M
March 2025	$1.25M
February 2025	$1.24M
January 2025	$1.22M
2024
December 2024	$1.2M
November 2024	$1.21M
October 2024	$1.29M
September 2024	$1.29M
August 2024	$1.31M
July 2024	$1.32M
June 2024	$1.32M
May 2024	$1.33M
April 2024	$1.3M
March 2024	$1.29M
February 2024	$1.27M
January 2024	$1.25M
2023
December 2023	$1.24M
November 2023	$1.3M
October 2023	$1.33M
September 2023	$1.33M
August 2023	$1.33M
July 2023	$1.32M
June 2023	$1.25M
May 2023	$1.17M
April 2023	$1.12M
March 2023	$1.12M
February 2023	$1.1M
January 2023	$1.08M
2022
December 2022	$1.1M
November 2022	$1.13M
October 2022	$1.13M
September 2022	$1.14M
August 2022	$1.15M
July 2022	$1.17M
June 2022	$1.19M
May 2022	$1.2M
April 2022	$1.19M
March 2022	$1.17M
February 2022	$1.12M
January 2022	$1.07M
2021
December 2021	$1.06M
November 2021	$1.05M
October 2021	$1.01M
September 2021	$966K
August 2021	$978K
July 2021	$983K
June 2021	$944K
May 2021	$890K
April 2021	$884K
March 2021	$862K
February 2021	$883K
January 2021	$855K
2020
December 2020	$845K
November 2020	$836K
October 2020	$824K
September 2020	$825K
August 2020	$854K
July 2020	$855K
June 2020	$861K
May 2020	$869K
April 2020	$872K
March 2020	$868K
February 2020	$869K
January 2020	$864K
2019
December 2019	$862K
November 2019	$865K
October 2019	$856K
September 2019	$844K
August 2019	$856K
July 2019	$848K
June 2019	$842K
May 2019	$834K
April 2019	$838K
March 2019	$812K
February 2019	$819K
January 2019	$833K
2018
December 2018	$842K
November 2018	$822K
October 2018	$818K
September 2018	$822K
August 2018	$833K
July 2018	$827K
June 2018	$834K
May 2018	$831K
April 2018	$815K
March 2018	$807K
February 2018	$806K
January 2018	$834K
2017
December 2017	$840K
November 2017	$850K
October 2017	$818K
September 2017	$821K
August 2017	$810K
July 2017	$826K
June 2017	$825K
May 2017	$834K
April 2017	$820K
March 2017	$810K
February 2017	$777K
January 2017	$793K
2016
December 2016	$814K
November 2016	$815K
October 2016	$807K

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	0.29	Single-Family Home	$1,775,000	11/07/25	3	2	1,728
6 Tabor Hls, Chilmark, MA	0.19	Single-Family Home	$2,100,000	11/25/25	4	3	2,544
6 Trails End, Chilmark, MA	0.55	Single-Family Home	$2,700,000	09/16/26	4	3	2,346
300 North Rd, Chilmark, MA	0.91	Single-Family Home	$2,800,000	08/27/26	2	3	2,515
300 North Road 18 Belhaven Way, Chilmark, MA	0.91	Single-Family Home	$2,800,000	08/27/26	4	3.5	2,515
9 Beetlebung Grove Way, Chilmark, MA	1.29	Single-Family Home	$2,225,000	10/24/25	4	3	2,968
308 South Road, Chilmark, MA	1.06	Single-Family Home	$6,500,000	09/18/26	4	4.5	3,490
25 Osprey Ln, Chilmark, MA	1.12	Single-Family Home	$7,289,000	10/15/25	4	5	3,777
18 Homeward Way, Chilmark, MA	1.05	Single-Family Home	$4,325,000	12/05/25	5	2.5	3,885
60 Meeting House Rd, Chilmark, MA	0.89	Single-Family Home	$6,100,000	03/24/26	6	7	5,660

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
3 Carey Rise, Chilmark, MA 02535	0.05	$2,261,100	6	3	2,630	Off Market
2 Tabor House Rd, Chilmark, MA 02535	0.06	$1,176,000	3	3	1,848	Off Market
Tabor House Rd, Chilmark, MA 02535	0.06	-	-	-	-	Off Market
235 Middle Rd, Chilmark, MA 02535	0.06	$1,927,700	3	2	1,992	Off Market
4 Tabor House Rd, Chilmark, MA 02535	0.08	$2,670,000	5	3.5	2,900	Off Market
240 Middle Rd, Chilmark, MA 02535	0.08	-	5	2	1,233	Off Market
12 Carey Rise, Chilmark, MA 02535	0.10	$1,145,100	4	2	1,520	Off Market
8 Tree Frog Ln, Chilmark, MA 02535	0.11	$1,618,500	2	1	878	Off Market
3 Tabor House Rd, Chilmark, MA 02535	0.13	$1,590,200	3	2	3,018	Off Market
43 Tabor House Rd #1, Chilmark, MA 02535	0.14	$1,500,800	Studio	1	1,280	Off Market
252 Middle Rd, Chilmark, MA 02535	0.14	$1,641,700	3	1.5	1,224	Off Market
12 Greystone, Chilmark, MA 02535	0.14	$4,818,000	4	4	2,802	Off Market
12 Graystone, Chilmark, MA 02535	0.14	-	-	-	-	Off Market
Cencelle St, Chilmark, MA 02535	0.14	-	-	-	-	Off Market
14 Cencelle, Chilmark, MA 02535	0.15	-	2	1	682	Off Market
11 Greystone, Chilmark, MA 02535	0.15	$3,255,500	4	2	1,765	Off Market
2 Tree Frog Ln, Chilmark, MA 02535	0.16	-	-	-	-	Off Market
9 Tree Frog Ln, Chilmark, MA 02535	0.19	-	3	2	2,701	Off Market
6 Tabor Hls, Chilmark, MA 02535	0.19	$2,115,700	4	3	2,544	Off Market
6 Whippoorwill Rd, Chilmark, MA 02535	0.19	$1,538,100	3	2	1,576	Off Market

Local Information

Map ViewExplore the area around 239 Middle Rd.
Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
Shop & Eat

-- mins to

Commute Destination

Home Highlights

Single-Family Home

Built in 1977

2 acre lot

1,228 sqft

$1,089/sqft

About this House

This single-family home is located at 239 Middle Rd, Chilmark, MA. 239 Middle Rd is in Chilmark, MA and in ZIP code 02535. This property has 2 bedrooms, 1 bathroom and approximately 1,228 sqft of floor space. This property has a lot size of 2.00 acres and was built in 1977.

239 Middle Rd, Chilmark, MA 02535 is a 2 bedroom, 1 bathroom, 1,228 sqft single-family home built in 1977. It last sold for $940,000 on Oct 15, 2021. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $1,337,400, with a rent estimate of $3,721/month.

Home Details for 239 Middle Rd

Interior Features
Heating & Cooling Heating: ElectricHeating Fuel: Electric
Levels, Entrance, & Accessibility Stories: 1
Interior Details Number of Rooms: 4

Exterior Features
Exterior Home Features Roof: AsphaltExterior: Wood

Property Information
Year Built Year Built: 1977Year Updated: 1978
Property Type / Style Property Type: Single Family HomeArchitecture: Cape Cod

Community
Units in Building: 1

Lot Information
Lot Area: 2.00 acres

Price and Tax history

Date	Event	Price
Oct 15, 2021 Source: LINK #38941	Sold	$940,000

Year	Property tax	Tax assessment
2025	$2,487	$1,105,500

Additional Cost

Market trends in Chilmark

Last updated September 2026

Avg. sale price

—

Sale-to-List Price

—

Price per sq ft

—

Available listings

8MoM

Around this home

West Tisbury Elementary School
PK-8
Public
334 Students
Up-Island Regional School District
7/10
GreatSchools Rating
Parent Rating Average
Kids rule the school. No accountability. Bullying is not taken seriously.
Parent Review
2y ago
5 Reviews

View nearby schools on GreatSchools

The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

What Locals Say about Chilmark

This October

Trick-or-Treat Score

Built from what locals say about this neighborhood.

100% say there are community events
78% say neighbors are friendly
43% say there's holiday spirit

Trulia Trick or TreatStart Ghost Hunt

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.
12y ago
"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 239 Middle Rd

What is 239 Middle Rd estimated to be worth?
Trulia's estimated value for 239 Middle Rd in Chilmark, MA is $1,337,400.
What is the price history for 239 Middle Rd?
239 Middle Rd in Chilmark, MA last sold for $940,000 in October 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 239 Middle Rd?
The closest schools to 239 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 239 Middle Rd?
The lot at 239 Middle Rd in Chilmark, MA is about 2 acres.

Apartments for Rent

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Off Market Homes Near 239 Middle Rd

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SOLD
SEP 30, 2026
$1,650,000
5 bd
3 ba
2,552 sqft
10 Danls Way,
West Tisbury, MA 02575
Studio Realty
SOLD
JUL 20, 2026
$1,375,000
5 bd
4 ba
1,856 sqft
651 State Rd,
Tisbury, MA 02568
SOLD
JUL 20, 2026
$1,375,000
5 bd
4 ba
2,516 sqft
651 State Rd,
West Tisbury, MA 02575
Feiner Real Estate
SOLD
JUL 17, 2026
$1,029,000
4 bd
2 ba
1,564 sqft
40 Scotchmans Ln,
West Tisbury, MA 02575
Donnelly + Co
SOLD
JUN 3, 2026
$1,000,000
2 bd
1 ba
576 sqft
31 North Rd,
Chilmark, MA 02535
Russell Maloney Real Estate
SOLD
MAR 24, 2026
$1,470,000
4 bd
2 ba
1,600 sqft
654 Lighthouse Rd,
Aquinnah, MA 02535
Tea Lane Associates
SOLD
DEC 18, 2025
$1,075,000
1 Crowberry Ln,
Chilmark, MA 02535
Russell Maloney Real Estate
OFF MARKET
Est. $1,815,500
3 bd
2 ba
1,728 sqft
3 Fulling Mill Rd,
Chilmark, MA 02535
Tea Lane Associates
OFF MARKET
25 Plum Bush Point Rd,
West Tisbury, MA 02575
Tea Lane Associates
OFF MARKET
49 Cobbs Hill Rd,
Chilmark, MA 02535
Wallace & Co. Sotheby's
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Homes for sale near 239 Middle Rd

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3.3 ACRES
$1,995,000
4 bd
3 ba
1,918 sqft
25 Fulling Mill Road,
Chilmark, MA 02535
Wallace & Co. Sotheby's International Realty
3.3 ACRES
$1,995,000
4 bd
3 ba
1,918 sqft
21 & 25 Fulling Mill Rd,
Chilmark, MA 02535
Jessica Holtham, Wallace & Co. Sotheby's International Realty
3.5 ACRES
$1,649,000
3 bd
2 ba
1,540 sqft
43 N Slope Lane,
Chilmark, MA 02535
North Star Real Estate, LLC
17.16 ACRES
$4,975,000
4 bd
3 ba
3,432 sqft
44 Cencelle St,
Chilmark, MA 02535
Tea Lane Associates
2.6 ACRES
$5,300,000
5 bd
3.5 ba
2,210 sqft
8 Wauwompauque Trl,
Chilmark, MA 02535
Tea Lane Associates
4.5 ACRES
$2,650,000
4 bd
3 ba
2,967 sqft
11 By The Woods,
Chilmark, MA 02535
Flanders Real Estate
3.9 ACRES
$3,900,000
3 bd
4 ba
2,960 sqft
3 Bens Way,
Chilmark, MA 02535
Russell Maloney Real Estate
3.1 ACRES
$3,295,000
3 bd
3 ba
2,500 sqft
27 Clambelly Rd,
Chilmark, MA 02535
Flanders Real Estate
4.3 ACRES
$3,795,000
4 bd
3.5 ba
3,426 sqft
96 Hammett Ln,
Chilmark, MA 02535
Karen M. Overtoom R.E.
0.5 ACRES
$1,375,000
5 bd
5 ba
2,266 sqft
345 North Rd,
Chilmark, MA 02535
Flanders Real Estate
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Chilmark
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