Compare towns

Cheshire vs Ware 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 the oldest population (median age 53.7).
Ware has grown the fastest since 2010 (+2%).
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.

MeasureCheshireWareWindsor
People
Population
3,216
10,048Highest
1,065Lowest
Growth since 20102010 → 2020 census
+0.7%
MA: +7.4%
+2%Highest
MA: +7.4%
-7.6%Lowest
MA: +7.4%
Median age
53.7±4.5Highest
34% above MA
43.1±4.7Lowest
8% above MA
44.8±6.4
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%
19.1%±3.5Highest
MA: 19.4%
15.8%±5.1
MA: 19.4%
Ware and Windsor 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%
20.6%±3.4
MA: 17.9%
18.6%±4.9Lowest
MA: 17.9%
Cheshire and Ware are within the Census margin of error here, so we can’t say which is really higher.
Bachelor’s degree+adults 25+
26.9%
MA: 47.3%
24%Lowest
MA: 47.3%
41.5%Highest
MA: 47.3%
Enrolled in collegeshare of residents
5%±2.5Highest
MA: 7.9%
4.4%±2.2
MA: 7.9%
2.7%±1.7Lowest
MA: 7.9%
Cheshire and Ware are within the Census margin of error here, so we can’t say which is really higher.
Cost of living
Household incomemedian
$69,803±$14k
33% below MA
$67,475±$15kLowest
35% below MA
$115,563±$10kHighest
11% above MA
Home valuemedian, owner-occupied
$268,200±$48kLowest
52% below MA
$289,700±$28k
48% below MA
$389,700±$32kHighest
31% below MA
Rentmedian gross, monthly —
$1,043±$109
41% below MA
—
Property taxmedian, yearly
$3,005Lowest
50% below MA
$4,237Highest
29% below MA
$3,867
35% below MA
Renters paying 30%+of income on rent
21.2%±24
MA: 51.8%
64.3%±16.2Highest
MA: 51.8%
0%±100Lowest
MA: 51.8%
Below poverty line
8.6%
MA: 10%
11.8%Highest
MA: 10%
3.8%Lowest
MA: 10%
Housing
Homeownersof occupied homes
89%
MA: 62.5%
72.3%Lowest
MA: 62.5%
96.2%Highest
MA: 62.5%
Typical home builtmedian year
1964
same as MA
1960Lowest
4 yrs older than MA
1970Highest
6 yrs newer than MA
Getting to work
Average commuteone way
29 min
about the MA average
28 minLowest
about the MA average
37 minHighest
27% above MA
Work from home
4.4%±2.7Lowest
MA: 18.6%
12.3%±3.8
MA: 18.6%
21.2%±5.8Highest
MA: 18.6%
Windsor and Ware 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 #267 of 282 in MA —
School district Hoosac Valley Regional Ware —
High school in town Hoosac Valley High School Ware Junior/Senior High School —
Students per teacherat that high school
10.5Lowest
11.1Highest
—
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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.