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

OFF MARKET

$3,710,700

Tax assessed value

7 Beds
7 Baths
4,509 sqft (on 9 acres)

55 Middle Rd, Chilmark, MA 02535

Home Value

Learn more about this home's value by checking out the value of nearby homes and how much similar homes have sold for.

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
50 Daggett Ave, Tisbury, MA	7.66	Apartment	$464,000	07/14/26	6	3	2,158

Home facts updated by county records

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
Lot 42 Middle Rd, Chilmark, MA 02535	0.10	-	-	-	-	Off Market
67 Middle Rd, Chilmark, MA 02535	0.10	-	4	2	2,536	Off Market
5 Sarah Brown Ln, Chilmark, MA 02535	0.10	$1,006,800	3	1	975	Off Market
36 Middle Rd, Chilmark, MA 02535	0.13	$1,392,700	5	2	1,917	Off Market
36 Middle Road Ch #229, Chilmark, MA 02535	0.13	$1,885,500	6	2	3,000	Off Market
37 Middle Rd, Chilmark, MA 02535	0.14	$2,781,400	6	1	2,557	Off Market
21 Sarah Brown Ln, Chilmark, MA 02535	0.19	$1,222,800	3	1	1,612	Off Market
75 Middle Rd, Chilmark, MA 02535	0.21	$1,280,300	3	2	1,575	Off Market
77 Middle Rd, Chilmark, MA 02535	0.23	$1,372,900	2	1	1,144	Off Market
9 Beechtree Rd, Chilmark, MA 02535	0.27	$2,085,300	4	3	1,884	Off Market
89 Middle Rd, Chilmark, MA 02535	0.30	-	7	4	3,865	Off Market
10 Beechtree Rd, Chilmark, MA 02535	0.30	$1,287,500	2	1	1,024	Off Market
8 Daisy Ln, Chilmark, MA 02535	0.36	$2,504,100	4	4	3,089	Off Market
9 Middle Rd, Chilmark, MA 02535	0.37	$1,526,700	4	1	832	Off Market
Hewing Fld, Chilmark, MA 02535	0.37	-	-	-	-	Off Market
Hewing Fld, Chilmark, MA 02535	0.37	-	-	-	-	Off Market
12 Middle Rd, Chilmark, MA 02535	0.40	$2,631,900	6	6	3,778	Off Market
13 Deer Path Ln, Chilmark, MA 02535	0.43	$3,338,800	4	4.5	3,194	Off Market
2 Daisy Ln, Chilmark, MA 02535	0.43	$1,553,500	3	2	1,623	Off Market
Daisy Ln, Chilmark, MA 02535	0.43	-	-	-	-	Off Market

Homes for rent near 55 Middle Rd

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Local Information

Map ViewExplore the area around 55 Middle Rd.
Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
Shop & Eat

-- mins to

Commute Destination

Home Highlights

Apartment

Built in 1880

9 acre lot

4,509 sqft

About this House

This apartment is located at 55 Middle Rd, Chilmark, MA. 55 Middle Rd is in Chilmark, MA and in ZIP code 02535. This property has 7 bedrooms, 7 bathrooms and approximately 4,509 sqft of floor space. This property has a lot size of 9.00 acres and was built in 1880.

55 Middle Rd, Chilmark, MA 02535 is a 7 bedroom, 7 bathroom, 4,509 sqft apartment built in 1880. This property is not currently displayed as for sale or rent on Trulia.

Home Details for 55 Middle Rd

Interior Features
Levels, Entrance, & Accessibility Stories: 2
Interior Details Number of Rooms: 12

Property Information
Year Built Year Built: 1880
Property Type / Style Property Type: ApartmentArchitecture: Cape Cod

Exterior Features
Exterior Home Features Exterior: Other

Community
Units in Building: 1

Lot Information
Lot Area: 9.00 acres

Price and Tax history

Year	Property tax	Tax assessment
2025	$8,349	$3,710,700

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

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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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Apartments for Rent

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Off Market Homes Near 55 Middle Rd

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SOLD
NOV 10, 2026
$3,650,000
6 bd
3.5 ba
3,070 sqft
30-40 Elias Ln,
West Tisbury, MA 02575
Tea Lane Associates
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 30, 2026
$1,230,000
4 bd
2 ba
1,436 sqft
145 Vineyard Meadow Fms Rd,
West Tisbury, MA 02575
Ocean Park Realty Inc
SOLD
OCT 21, 2026
$4,850,000
3 bd
2.5 ba
2,095 sqft
63 Putnam Rd,
Chilmark, MA 02535
Wendy Harman, Compass
SOLD
OCT 20, 2026
$3,625,000
4 bd
3.5 ba
3,702 sqft
7 Black Point Rd,
Chilmark, MA 02535
Tea Lane Associates
SOLD
OCT 19, 2026
$1,100,000
4 bd
2 ba
1,159 sqft
130 Vineyard Meadow Farms Rd,
West Tisbury, MA 02575
LINK
SOLD
OCT 14, 2026
$2,325,000
4 bd
3 ba
2,350 sqft
16 South Rd,
Chilmark, MA 02535
Vineyard Village Realty
SOLD
OCT 8, 2026
$1,075,000
3 bd
2 ba
1,800 sqft
52 Oak Knoll Rd,
West Tisbury, MA 02575
Donnelly + Co
SOLD
OCT 6, 2026
$4,550,000
4 bd
4.5 ba
6,162 sqft
205 South Rd,
Chilmark, MA 02535
Donnelly + Co
SOLD
OCT 6, 2026
$742,000
2 bd
2 ba
1,188 sqft
25 Vineyard Meadow Farms Rd,
West Tisbury, MA 02575
Feiner Real Estate
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