Compare towns

Dover vs Windsor vs Chilmark

Cost, people, housing, commute and schools, side by side, each benchmarked against the U.S..

What stands out worked out from the figures below

Dover has the highest household income ($250k).
Windsor has the most affordable homes ($338k median).
Chilmark has the most expensive homes ($1895k median).

What matters to you?

Pick a few. We’ll pull those rows to the top and mark which town comes out ahead on each. There’s no overall score: what matters is up to you.

MeasureDoverWindsorChilmark
People
Population
2,308Highest
254Lowest
1,578
Growth since 20102010 → 2020 census
+8.3%Lowest
U.S.: +7.4%
—
+40%Highest
U.S.: +7.4%
Median age
47.5±4
22% above U.S.
40.2±18.8Lowest
3% above U.S.
53.6±8.1Highest
38% above U.S.
Chilmark and Dover are within the Census margin of error here, so we can’t say which is really higher.
Kids under 18
20.9%±4.8
U.S.: 22%
25.2%±14.7Highest
U.S.: 22%
16.7%±4.3Lowest
U.S.: 22%
Windsor and Dover are within the Census margin of error here, so we can’t say which is really higher.
Age 65+
15.5%±3.5Lowest
U.S.: 17.2%
15.7%±8
U.S.: 17.2%
36.2%±12.4Highest
U.S.: 17.2%
Bachelor’s degree+adults 25+
83.4%Highest
U.S.: 35.7%
12.6%Lowest
U.S.: 35.7%
68.1%
U.S.: 35.7%
Enrolled in collegeshare of residents
9.4%±4.8Highest
U.S.: 6.4%
3.9%±4.2
U.S.: 6.4%
2.7%±2.6Lowest
U.S.: 6.4%
Dover and Windsor are within the Census margin of error here, so we can’t say which is really higher.
Cost of living
Household incomemedian
$250,001Highest
210% above U.S.
$103,750±$40kLowest
29% above U.S.
$168,750±$28k
109% above U.S.
Home valuemedian, owner-occupied
$1,308,300±$149k
293% above U.S.
$337,500±$40kLowest
about the U.S. average
$1,895,300±$281kHighest
470% above U.S.
Rentmedian gross, monthly — —
$2,750±$2k
95% above U.S.
Property taxmedian, yearly
$10,000+Highest
at least 221% above U.S.
$3,381Lowest
8% above U.S.
$4,485
44% above U.S.
Renters paying 30%+of income on rent
100%±100Highest
U.S.: 51.1%
66.7%±100
U.S.: 51.1%
30.8%±59.9Lowest
U.S.: 51.1%
Dover and Windsor are within the Census margin of error here, so we can’t say which is really higher.
Below poverty line
3.3%Lowest
U.S.: 12.5%
10.8%Highest
U.S.: 12.5%
4.1%
U.S.: 12.5%
Housing
Homeownersof occupied homes
97.9%Highest
U.S.: 65.2%
96.5%
U.S.: 65.2%
89.4%Lowest
U.S.: 65.2%
Typical home builtmedian year
1967Lowest
13 yrs older than U.S.
1983
3 yrs newer than U.S.
1984Highest
4 yrs newer than U.S.
Getting to work
Average commuteone way
37 minHighest
39% above U.S.
32 min
22% above U.S.
32 minLowest
19% above U.S.
Work from home
37.4%±8.8Highest
U.S.: 15.1%
15%±16.5Lowest
U.S.: 15.1%
25.7%±11
U.S.: 15.1%
Dover and Chilmark are within the Census margin of error here, so we can’t say which is really higher.
Schools
Public school scoresrank in state, math + reading #1 of 282 in MA — —
School district — — Up-Island Regional
High school in town — — None in town
On TownTapestry
Old photos in History None yet None yet None yet

U.S. average · Sources: U.S. Census Bureau, American Community Survey 5-year estimates 2020–2024; 2010 & 2020 decennial census; NCES Common Core of Data. “±” is the Census margin of error. Property tax is top-coded by the Census at $10,000+. School rank compares math and reading proficiency against the state average.