Compare towns

Dover vs Windsor vs Chilmark

Cost, people, housing, commute and schools, side by side, each benchmarked against Massachusetts.

What stands out worked out from the figures below

Dover has the highest household income ($250k).
Windsor has the most affordable homes ($390k median).
Chilmark has grown the fastest since 2010 (+40%).

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
1,065Lowest
1,578
Growth since 20102010 → 2020 census
+8.3%
MA: +7.4%
-7.6%Lowest
MA: +7.4%
+40%Highest
MA: +7.4%
Median age
47.5±4
19% above MA
44.8±6.4Lowest
12% above MA
53.6±8.1Highest
34% above MA
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%±4.8Highest
MA: 19.4%
15.8%±5.1Lowest
MA: 19.4%
16.7%±4.3
MA: 19.4%
Dover and Chilmark are within the Census margin of error here, so we can’t say which is really higher.
Age 65+
15.5%±3.5Lowest
MA: 17.9%
18.6%±4.9
MA: 17.9%
36.2%±12.4Highest
MA: 17.9%
Bachelor’s degree+adults 25+
83.4%Highest
MA: 47.3%
41.5%Lowest
MA: 47.3%
68.1%
MA: 47.3%
Enrolled in collegeshare of residents
9.4%±4.8Highest
MA: 7.9%
2.7%±1.7Lowest
MA: 7.9%
2.7%±2.6Lowest
MA: 7.9%
Cost of living
Household incomemedian
$250,001Highest
140% above MA
$115,563±$10kLowest
11% above MA
$168,750±$28k
62% above MA
Home valuemedian, owner-occupied
$1,308,300±$149k
133% above MA
$389,700±$32kLowest
31% below MA
$1,895,300±$281kHighest
237% above MA
Rentmedian gross, monthly — —
$2,750±$2k
56% above MA
Property taxmedian, yearly
$10,000+Highest
at least 67% above MA
$3,867Lowest
35% below MA
$4,485
25% below MA
Renters paying 30%+of income on rent
100%±100Highest
MA: 51.8%
0%±100Lowest
MA: 51.8%
30.8%±59.9
MA: 51.8%
Dover and Chilmark are within the Census margin of error here, so we can’t say which is really higher.
Below poverty line
3.3%Lowest
MA: 10%
3.8%
MA: 10%
4.1%Highest
MA: 10%
Housing
Homeownersof occupied homes
97.9%Highest
MA: 62.5%
96.2%
MA: 62.5%
89.4%Lowest
MA: 62.5%
Typical home builtmedian year
1967Lowest
3 yrs newer than MA
1970
6 yrs newer than MA
1984Highest
20 yrs newer than MA
Getting to work
Average commuteone way
37 min
26% above MA
37 minHighest
27% above MA
32 minLowest
8% above MA
Work from home
37.4%±8.8Highest
MA: 18.6%
21.2%±5.8Lowest
MA: 18.6%
25.7%±11
MA: 18.6%
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

MA 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.