Compare towns

Windsor vs Whitman vs Cheshire

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

What stands out worked out from the figures below

Windsor has the most people working from home (21.2%).
Whitman has grown the fastest since 2010 (+4.4%).
Cheshire has the most affordable homes ($268k 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.

MeasureWindsorWhitmanCheshire
People
Population
1,065Lowest
15,295Highest
3,216
Growth since 20102010 → 2020 census
-7.6%Lowest
MA: +7.4%
+4.4%Highest
MA: +7.4%
+0.7%
MA: +7.4%
Median age
44.8±6.4
12% above MA
40.4±1.8Lowest
about the MA average
53.7±4.5Highest
34% above MA
Cheshire and Windsor are within the Census margin of error here, so we can’t say which is really higher.
Kids under 18
15.8%±5.1
MA: 19.4%
21.1%±3.5Highest
MA: 19.4%
15.3%±4.2Lowest
MA: 19.4%
Whitman and Windsor are within the Census margin of error here, so we can’t say which is really higher.
Age 65+
18.6%±4.9
MA: 17.9%
15.5%±2.1Lowest
MA: 17.9%
30.5%±7.1Highest
MA: 17.9%
Cheshire and Windsor are within the Census margin of error here, so we can’t say which is really higher.
Bachelor’s degree+adults 25+
41.5%Highest
MA: 47.3%
31.3%
MA: 47.3%
26.9%Lowest
MA: 47.3%
Enrolled in collegeshare of residents
2.7%±1.7Lowest
MA: 7.9%
5.1%±1.2Highest
MA: 7.9%
5%±2.5
MA: 7.9%
Whitman and Cheshire are within the Census margin of error here, so we can’t say which is really higher.
Cost of living
Household incomemedian
$115,563±$10kHighest
11% above MA
$108,933±$14k
5% above MA
$69,803±$14kLowest
33% below MA
Windsor and Whitman are within the Census margin of error here, so we can’t say which is really higher.
Home valuemedian, owner-occupied
$389,700±$32k
31% below MA
$472,700±$12kHighest
16% below MA
$268,200±$48kLowest
52% below MA
Rentmedian gross, monthly —
$1,771±$151
about the MA average
—
Property taxmedian, yearly
$3,867
35% below MA
$5,824Highest
about the MA average
$3,005Lowest
50% below MA
Renters paying 30%+of income on rent
0%±100Lowest
MA: 51.8%
61.9%±13.4Highest
MA: 51.8%
21.2%±24
MA: 51.8%
Below poverty line
3.8%Lowest
MA: 10%
7.9%
MA: 10%
8.6%Highest
MA: 10%
Housing
Homeownersof occupied homes
96.2%Highest
MA: 62.5%
71.4%Lowest
MA: 62.5%
89%
MA: 62.5%
Typical home builtmedian year
1970Highest
6 yrs newer than MA
1957Lowest
7 yrs older than MA
1964
same as MA
Getting to work
Average commuteone way
37 minHighest
27% above MA
36 min
24% above MA
29 minLowest
about the MA average
Work from home
21.2%±5.8Highest
MA: 18.6%
10.8%±2.4
MA: 18.6%
4.4%±2.7Lowest
MA: 18.6%
Schools
Public school scoresrank in state, math + reading — #191 of 282 in MA #274 of 282 in MA
School district — Whitman-Hanson Hoosac Valley Regional
High school in town — None in town Hoosac Valley High School
Students per teacherat that high school — —
10.5
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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.