Compare towns

Chilmark vs Plainfield vs Windsor

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

What stands out worked out from the figures below

Chilmark has grown the fastest since 2010 (+40%).
Plainfield has the most affordable homes ($309k median).
Windsor has the youngest population (median age 44.8).

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.

MeasureChilmarkPlainfieldWindsor
People
Population
1,578Highest
616Lowest
1,065
Growth since 20102010 → 2020 census
+40%Highest
MA: +7.4%
-2.3%
MA: +7.4%
-7.6%Lowest
MA: +7.4%
Median age
53.6±8.1Highest
34% above MA
50.6±9.5
27% above MA
44.8±6.4Lowest
12% above MA
Chilmark and Plainfield are within the Census margin of error here, so we can’t say which is really higher.
Kids under 18
16.7%±4.3
MA: 19.4%
19%±9.3Highest
MA: 19.4%
15.8%±5.1Lowest
MA: 19.4%
Plainfield and Chilmark are within the Census margin of error here, so we can’t say which is really higher.
Age 65+
36.2%±12.4Highest
MA: 17.9%
29.5%±7.1
MA: 17.9%
18.6%±4.9Lowest
MA: 17.9%
Chilmark and Plainfield are within the Census margin of error here, so we can’t say which is really higher.
Bachelor’s degree+adults 25+
68.1%Highest
MA: 47.3%
52.6%
MA: 47.3%
41.5%Lowest
MA: 47.3%
Enrolled in collegeshare of residents
2.7%±2.6Lowest
MA: 7.9%
5.4%±2.5Highest
MA: 7.9%
2.7%±1.7Lowest
MA: 7.9%
Plainfield and Chilmark are within the Census margin of error here, so we can’t say which is really higher.
Cost of living
Household incomemedian
$168,750±$28kHighest
62% above MA
$63,500±$14kLowest
39% below MA
$115,563±$10k
11% above MA
Home valuemedian, owner-occupied
$1,895,300±$281kHighest
237% above MA
$309,000±$47kLowest
45% below MA
$389,700±$32k
31% below MA
Rentmedian gross, monthly
$2,750±$2kHighest
56% above MA
$1,292±$558Lowest
27% below MA
—
Chilmark and Plainfield are within the Census margin of error here, so we can’t say which is really higher.
Property taxmedian, yearly
$4,485Highest
25% below MA
$4,458
26% below MA
$3,867Lowest
35% below MA
Renters paying 30%+of income on rent
30.8%±59.9
MA: 51.8%
40%±100Highest
MA: 51.8%
0%±100Lowest
MA: 51.8%
Plainfield and Chilmark are within the Census margin of error here, so we can’t say which is really higher.
Below poverty line
4.1%
MA: 10%
16.9%Highest
MA: 10%
3.8%Lowest
MA: 10%
Housing
Homeownersof occupied homes
89.4%Lowest
MA: 62.5%
98%Highest
MA: 62.5%
96.2%
MA: 62.5%
Typical home builtmedian year
1984Highest
20 yrs newer than MA
1974
10 yrs newer than MA
1970Lowest
6 yrs newer than MA
Getting to work
Average commuteone way
32 minLowest
8% above MA
38 minHighest
30% above MA
37 min
27% above MA
Work from home
25.7%±11
MA: 18.6%
26.2%±8.8Highest
MA: 18.6%
21.2%±5.8Lowest
MA: 18.6%
Plainfield and Chilmark are within the Census margin of error here, so we can’t say which is really higher.
Schools
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.