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 2 Wauwompauque Trl estimated to be worth?

Trulia's estimated value for 2 Wauwompauque Trl in Chilmark, MA is $2,156,800 .

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 2 Wauwompauque Trl?

The closest schools to 2 Wauwompauque Trl 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 2 Wauwompauque Trl?

The lot at 2 Wauwompauque Trl in Chilmark, MA is about 1.8 acres .

OFF MARKET

$2,156,800

Trulia Estimate

4 Beds
3 Baths
2,096 sqft (on 1.80 acres)

2 Wauwompauque Trl, Chilmark, MA 02535

Est. Refi. Payment $12,407/mo*

Refinance Your Home

Home Value

Trulia Estimate

$2.16M

Since last month

$28K (+1.3%)

Since last year

$36K (-1.7%)

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 +73% in the last 10 years

Month	Estimated value
2026
November 2026	$2.15M
October 2026	$2.14M
September 2026	$2.12M
August 2026	$2.16M
July 2026	$2.12M
June 2026	$2.2M
May 2026	$2.2M
April 2026	$2.17M
March 2026	$2.18M
February 2026	$2.13M
January 2026	$2.04M
2025
December 2025	$2.09M
November 2025	$2.13M
October 2025	$2.19M
September 2025	$2.07M
August 2025	$2.15M
July 2025	$2.18M
June 2025	$2.09M
May 2025	$2.1M
April 2025	$2.09M
March 2025	$2.06M
February 2025	$2.03M
January 2025	$2M
2024
December 2024	$1.95M
November 2024	$1.98M
October 2024	$2.26M
September 2024	$2.28M
August 2024	$2.31M
July 2024	$2.34M
June 2024	$2.35M
May 2024	$2.33M
April 2024	$2.27M
March 2024	$2.25M
February 2024	$2.25M
January 2024	$2.2M
2023
December 2023	$2.17M
November 2023	$2.33M
October 2023	$2.42M
September 2023	$2.43M
August 2023	$2.39M
July 2023	$2.49M
June 2023	$2.43M
May 2023	$2.4M
April 2023	$2.29M
March 2023	$2.3M
February 2023	$2.26M
January 2023	$2.23M
2022
December 2022	$2.27M
November 2022	$2.32M
October 2022	$2.35M
September 2022	$2.34M
August 2022	$2.36M
July 2022	$2.42M
June 2022	$2.44M
May 2022	$2.46M
April 2022	$2.4M
March 2022	$2.25M
February 2022	$2.04M
January 2022	$2.01M
2021
December 2021	$2.1M
November 2021	$2.13M
October 2021	$2.11M
September 2021	$2.07M
August 2021	$2.06M
July 2021	$2.06M
June 2021	$1.93M
May 2021	$1.71M
April 2021	$1.7M
March 2021	$1.64M
February 2021	$1.65M
January 2021	$1.61M
2020
December 2020	$1.61M
November 2020	$1.59M
October 2020	$1.57M
September 2020	$1.56M
August 2020	$1.59M
July 2020	$1.6M
June 2020	$1.6M
May 2020	$1.59M
April 2020	$1.58M
March 2020	$1.58M
February 2020	$1.33M
January 2020	$1.33M
2019
December 2019	$1.33M
November 2019	$1.33M
October 2019	$1.35M
September 2019	$1.35M
August 2019	$1.36M
July 2019	$1.33M
June 2019	$1.32M
May 2019	$1.32M
April 2019	$1.32M
March 2019	$1.34M
February 2019	$1.32M
January 2019	$1.33M
2018
December 2018	$1.32M
November 2018	$1.31M
October 2018	$1.28M
September 2018	$1.3M
August 2018	$1.32M
July 2018	$1.35M
June 2018	$1.26M
May 2018	$1.28M
April 2018	$1.24M
March 2018	$1.22M
February 2018	$1.2M
January 2018	$1.21M
2017
December 2017	$1.24M
November 2017	$1.22M
October 2017	$1.2M
September 2017	$1.28M
August 2017	$1.25M
July 2017	$1.25M
June 2017	$1.28M
May 2017	$1.26M
April 2017	$1.29M
March 2017	$1.26M
February 2017	$1.23M
January 2017	$1.24M
2016
December 2016	$1.22M
November 2016	$1.24M

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
6 Trails End, Chilmark, MA	0.53	Single-Family Home	$2,700,000	09/16/26	4	3	2,346
308 South Road, Chilmark, MA	0.16	Single-Family Home	$6,500,000	09/18/26	4	4.5	3,490
6 Tabor Hls, Chilmark, MA	1.03	Single-Family Home	$2,100,000	11/25/25	4	3	2,544
205 South Rd, Chilmark, MA	0.86	Single-Family Home	$4,550,000	10/06/26	4	4.5	6,162
60 Meeting House Rd, Chilmark, MA	0.76	Single-Family Home	$6,100,000	03/24/26	6	7	5,660
300 North Road 18 Belhaven Way, Chilmark, MA	1.84	Single-Family Home	$2,800,000	08/27/26	4	3.5	2,515
28 Black Point Road, Chilmark, MA	1.78	Single-Family Home	$2,850,000	11/06/26	3	3	1,469
300 North Rd, Chilmark, MA	1.84	Single-Family Home	$2,800,000	08/27/26	2	3	2,515
7 Black Point Rd, Chilmark, MA	1.86	Single-Family Home	$3,625,000	10/20/26	4	3.5	3,702
16 South Rd, Chilmark, MA	2.37	Single-Family Home	$2,325,000	10/14/26	4	3	2,350

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
8 Wauwompauque Trl, Chilmark, MA 02535	0.07	$5,300,000	5	3.5	2,210	For Sale
5 Wauwompauque Trl, Chilmark, MA 02535	0.08	$5,694,400	4	3	4,298	Off Market
8 N Abels Hill Rd, Chilmark, MA 02535	0.08	$2,476,300	4	3	1,300	Off Market
10 N Abels Hill Rd, Chilmark, MA 02535	0.09	$1,656,500	4	3	2,850	Off Market
5 N Abels Hill Rd, Chilmark, MA 02535	0.10	-	7	5	4,052	Off Market
18 Wauwompauque Trl, Chilmark, MA 02535	0.10	$1,593,600	3	2	1,745	Off Market
23 N Abels Hill Rd, Chilmark, MA 02535	0.12	$3,618,600	4	2	1,500	Off Market
20&21 Wauwompauque Trl, Chilmark, MA 02535	0.13	-	-	-	-	Off Market
20 & 21 Wauwompauque Trl, Chilmark, MA 02535	0.13	-	-	-	-	Off Market
20 Wauwompauque Trl, Chilmark, MA 02535	0.13	$3,216,800	4	3	3,034	Off Market
28 N Abels Hill Rd, Chilmark, MA 02535	0.15	$2,754,600	4	3	1,960	Off Market
308 South Road, Chilmark, MA 02535	0.16	$6,500,000	4	4.5	3,490	Recently Sold
285 South Rd, Chilmark, MA 02535	0.17	$4,586,700	5	3	2,824	Off Market
11 Seaward Way, Chilmark, MA 02535	0.18	$1,384,000	4	3	1,763	Off Market
33 N Abels Hill Rd, Chilmark, MA 02535	0.19	$4,429,000	5	4	3,100	Off Market
281 South Rd, Chilmark, MA 02535	0.19	$11,922,900	4	5	2,369	Off Market
5 Chappaquoit Rd, Chilmark, MA 02535	0.20	$3,945,200	4	4	2,932	Off Market
23 Redwing Ln, Chilmark, MA 02535	0.20	$2,721,600	4	3	2,208	Off Market
322 South Rd, Chilmark, MA 02535	0.21	$3,090,900	3	3	1,392	Off Market
19 Seaward Way, Chilmark, MA 02535	0.21	-	5	3	2,555	Off Market

Local Information

Map ViewExplore the area around 2 Wauwompauque Trl.
Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
Shop & Eat

-- mins to

Commute Destination

Home Highlights

Single-Family Home

Built in 1961

1.8 acre lot

2,096 sqft

$1,029/sqft

About this House

This single-family home is located at 2 Wauwompauque Trl, Chilmark, MA. 2 Wauwompauque Trl is in Chilmark, MA and in ZIP code 02535. This property has 4 bedrooms, 3 bathrooms and approximately 2,096 sqft of floor space. This property has a lot size of 1.80 acres and was built in 1961.

2 Wauwompauque Trl, Chilmark, MA 02535 is a 4 bedroom, 3 bathroom, 2,096 sqft single-family home built in 1961. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $2,156,800, with a rent estimate of $6,228/month.

Home Details for 2 Wauwompauque Trl

Interior Features
Heating & Cooling Heating: OilHeating Fuel: Oil
Levels, Entrance, & Accessibility Stories: 2
Interior Details Number of Rooms: 7

Exterior Features
Exterior Home Features Roof: AsphaltExterior: Wood

Property Information
Year Built Year Built: 1961Year Updated: 1978
Property Type / Style Property Type: Single Family HomeArchitecture: Cape Cod

Community
Units in Building: 1

Lot Information
Lot Area: 1.80 acres

Price and Tax history

Year	Property tax	Tax assessment
2025	$4,197	$1,865,200

Home facts updated by county records

Additional Cost

Market trends in Chilmark

Last updated October 2026

Avg. sale price

—

Sale-to-List Price

—

Price per sq ft

—

Available listings

Sourced by Trulia Market Trends

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

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 2 Wauwompauque Trl

What is 2 Wauwompauque Trl estimated to be worth?
Trulia's estimated value for 2 Wauwompauque Trl in Chilmark, MA is $2,156,800.
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 2 Wauwompauque Trl?
The closest schools to 2 Wauwompauque Trl 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 2 Wauwompauque Trl?
The lot at 2 Wauwompauque Trl in Chilmark, MA is about 1.8 acres.

Apartments for Rent

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Off Market Homes Near 2 Wauwompauque Trl

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SOLD
NOV 6, 2026
$2,850,000
3 bd
3 ba
1,469 sqft
28 Black Point Road,
Chilmark, MA 02535
Island Real Estate
SOLD
OCT 14, 2026
$2,325,000
4 bd
3 ba
2,350 sqft
16 South Rd,
Chilmark, MA 02535
Vineyard Village Realty
SOLD
SEP 30, 2026
$1,650,000
5 bd
3 ba
2,552 sqft
10 Danls Way,
West Tisbury, MA 02575
Studio Realty
SOLD
SEP 16, 2026
$2,700,000
4 bd
3 ba
2,346 sqft
6 Trails End,
Chilmark, MA 02535
Russell Maloney Real Estate
SOLD
AUG 27, 2026
$2,800,000
2 bd
3 ba
2,515 sqft
300 North Rd,
Chilmark, MA 02535
Tea Lane Associates
SOLD
AUG 27, 2026
$2,800,000
4 bd
3.5 ba
2,515 sqft
300 North Road 18 Belhaven Way,
Chilmark, MA 02535
Wallace & Co. Sotheby's
SOLD
AUG 5, 2026
$2,013,500
4 bd
3.5 ba
2,428 sqft
35 Nats Farm Ln,
West Tisbury, MA 02575
Wallace & Co. Sotheby's
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
OFF MARKET
Est. $2,136,400
4 bd
3 ba
2,544 sqft
6 Tabor Hls,
Chilmark, MA 02535
Sandpiper Realty
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Chilmark
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Homes for sale near 2 Wauwompauque Trl

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2.6 ACRES
$5,300,000
5 bd
3.5 ba
2,210 sqft
8 Wauwompauque Trl,
Chilmark, MA 02535
Tea Lane Associates
3.8 ACRES
$2,850,000
4 bd
2.5 ba
2,630 sqft
11 Lookout Pl,
Chilmark, MA 02535
Tea Lane Associates
4 ACRES
$9,875,000
6 bd
5.5 ba
3,758 sqft
6 Wakeman Rd,
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
9.61 ACRES
$15,400,000
6 bd
8 ba
6,967 sqft
8 Snail Road,
Chilmark, MA 02535
Corcoran Property Advisors
17.16 ACRES
$4,975,000
4 bd
3 ba
3,432 sqft
44 Cencelle St,
Chilmark, MA 02535
Tea Lane Associates
2.36 ACRES
$2,150,000
1 bd
1 ba
726 sqft
18 Allen Farm Rd,
Chilmark, MA 02535
Kendall & Kendall
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.
3.9 ACRES
$3,900,000
3 bd
4 ba
2,960 sqft
3 Bens Way,
Chilmark, MA 02535
Russell Maloney Real Estate
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Chilmark
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