Compare towns

Windsor vs Brookline vs Cheshire

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

What stands out worked out from the figures below

Windsor has the highest household income ($116k).
Brookline has grown the fastest since 2010 (+1.9%).
Cheshire has the oldest population (median age 53.7).

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.

MeasureWindsorBrooklineCheshire
People
Population
1,065
531Lowest
3,216Highest
Growth since 20102010 → 2020 census
-7.6%Lowest
U.S.: +7.4%
+1.9%Highest
U.S.: +7.4%
+0.7%
U.S.: +7.4%
Median age
44.8±6.4Lowest
15% above U.S.
45.1±2.7
16% above U.S.
53.7±4.5Highest
38% above U.S.
Kids under 18
15.8%±5.1
U.S.: 22%
20%±6Highest
U.S.: 22%
15.3%±4.2Lowest
U.S.: 22%
Brookline and Windsor are within the Census margin of error here, so we can’t say which is really higher.
Age 65+
18.6%±4.9Lowest
U.S.: 17.2%
19.6%±4.2
U.S.: 17.2%
30.5%±7.1Highest
U.S.: 17.2%
Cheshire and Brookline 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
U.S.: 35.7%
41.1%
U.S.: 35.7%
26.9%Lowest
U.S.: 35.7%
Enrolled in collegeshare of residents
2.7%±1.7Lowest
U.S.: 6.4%
3.2%±1.6
U.S.: 6.4%
5%±2.5Highest
U.S.: 6.4%
Cheshire and Brookline 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
43% above U.S.
$80,833±$16k
about the U.S. average
$69,803±$14kLowest
14% below U.S.
Home valuemedian, owner-occupied
$389,700±$32kHighest
17% above U.S.
$290,700±$37k
13% below U.S.
$268,200±$48kLowest
19% below U.S.
Rentmedian gross, monthly —
$1,732±$232
23% above U.S.
—
Property taxmedian, yearly
$3,867
24% above U.S.
$5,000Highest
60% above U.S.
$3,005Lowest
4% below U.S.
Renters paying 30%+of income on rent
0%±100Lowest
U.S.: 51.1%
47.8%±94.7Highest
U.S.: 51.1%
21.2%±24
U.S.: 51.1%
Brookline and Cheshire are within the Census margin of error here, so we can’t say which is really higher.
Below poverty line
3.8%Lowest
U.S.: 12.5%
6.2%
U.S.: 12.5%
8.6%Highest
U.S.: 12.5%
Housing
Homeownersof occupied homes
96.2%Highest
U.S.: 65.2%
84.9%Lowest
U.S.: 65.2%
89%
U.S.: 65.2%
Typical home builtmedian year
1970
10 yrs older than U.S.
1975Highest
5 yrs older than U.S.
1964Lowest
16 yrs older than U.S.
Getting to work
Average commuteone way
37 minHighest
41% above U.S.
28 minLowest
8% above U.S.
29 min
10% above U.S.
Work from home
21.2%±5.8Highest
U.S.: 15.1%
20.6%±5.2
U.S.: 15.1%
4.4%±2.7Lowest
U.S.: 15.1%
Windsor and Brookline 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 — — #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
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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.