Compare towns

Cheshire vs Windsor

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

What stands out worked out from the figures below

Cheshire has grown the fastest since 2010 (+0.7%).
Windsor has the most people working from home (21.2%).

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.

MeasureCheshireWindsor
People
Population
3,216Highest
1,065Lowest
Growth since 20102010 → 2020 census
+0.7%Highest
MA: +7.4%
-7.6%Lowest
MA: +7.4%
Median age
53.7±4.5Highest
34% above MA
44.8±6.4Lowest
12% 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
15.3%±4.2Lowest
MA: 19.4%
15.8%±5.1Highest
MA: 19.4%
Windsor and Cheshire are within the Census margin of error here, so we can’t say which is really higher.
Age 65+
30.5%±7.1Highest
MA: 17.9%
18.6%±4.9Lowest
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+
26.9%Lowest
MA: 47.3%
41.5%Highest
MA: 47.3%
Enrolled in collegeshare of residents
5%±2.5Highest
MA: 7.9%
2.7%±1.7Lowest
MA: 7.9%
Cheshire and Windsor are within the Census margin of error here, so we can’t say which is really higher.
Cost of living
Household incomemedian
$69,803±$14kLowest
33% below MA
$115,563±$10kHighest
11% above MA
Home valuemedian, owner-occupied
$268,200±$48kLowest
52% below MA
$389,700±$32kHighest
31% below MA
Property taxmedian, yearly
$3,005Lowest
50% below MA
$3,867Highest
35% below MA
Renters paying 30%+of income on rent
21.2%±24Highest
MA: 51.8%
0%±100Lowest
MA: 51.8%
Cheshire and Windsor are within the Census margin of error here, so we can’t say which is really higher.
Below poverty line
8.6%Highest
MA: 10%
3.8%Lowest
MA: 10%
Housing
Homeownersof occupied homes
89%Lowest
MA: 62.5%
96.2%Highest
MA: 62.5%
Typical home builtmedian year
1964Lowest
same as MA
1970Highest
6 yrs newer than MA
Getting to work
Average commuteone way
29 minLowest
about the MA average
37 minHighest
27% above MA
Work from home
4.4%±2.7Lowest
MA: 18.6%
21.2%±5.8Highest
MA: 18.6%
Schools
Public school scoresrank in state, math + reading #274 of 282 in MA —
School district Hoosac Valley Regional —
High school in town Hoosac Valley High School —
Students per teacherat that high school
10.5
—
On TownTapestry
Old photos in Our Story 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.