Compare towns

Windsor vs Ware 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%).
Ware has grown the fastest since 2010 (+2%).
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.

MeasureWindsorWareCheshire
People
Population
1,065Lowest
10,048Highest
3,216
Growth since 20102010 → 2020 census
-7.6%Lowest
MA: +7.4%
+2%Highest
MA: +7.4%
+0.7%
MA: +7.4%
Median age
44.8±6.4
12% above MA
43.1±4.7Lowest
8% above MA
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%
19.1%±3.5Highest
MA: 19.4%
15.3%±4.2Lowest
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+
18.6%±4.9Lowest
MA: 17.9%
20.6%±3.4
MA: 17.9%
30.5%±7.1Highest
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+
41.5%Highest
MA: 47.3%
24%Lowest
MA: 47.3%
26.9%
MA: 47.3%
Enrolled in collegeshare of residents
2.7%±1.7Lowest
MA: 7.9%
4.4%±2.2
MA: 7.9%
5%±2.5Highest
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
$115,563±$10kHighest
11% above MA
$67,475±$15kLowest
35% below MA
$69,803±$14k
33% below MA
Home valuemedian, owner-occupied
$389,700±$32kHighest
31% below MA
$289,700±$28k
48% below MA
$268,200±$48kLowest
52% below MA
Rentmedian gross, monthly —
$1,043±$109
41% below MA
—
Property taxmedian, yearly
$3,867
35% below MA
$4,237Highest
29% below MA
$3,005Lowest
50% below MA
Renters paying 30%+of income on rent
0%±100Lowest
MA: 51.8%
64.3%±16.2Highest
MA: 51.8%
21.2%±24
MA: 51.8%
Below poverty line
3.8%Lowest
MA: 10%
11.8%Highest
MA: 10%
8.6%
MA: 10%
Housing
Homeownersof occupied homes
96.2%Highest
MA: 62.5%
72.3%Lowest
MA: 62.5%
89%
MA: 62.5%
Typical home builtmedian year
1970Highest
6 yrs newer than MA
1960Lowest
4 yrs older than MA
1964
same as MA
Getting to work
Average commuteone way
37 minHighest
27% above MA
28 minLowest
about the MA average
29 min
about the MA average
Work from home
21.2%±5.8Highest
MA: 18.6%
12.3%±3.8
MA: 18.6%
4.4%±2.7Lowest
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 — #267 of 282 in MA #274 of 282 in MA
School district — Ware Hoosac Valley Regional
High school in town — Ware Junior/Senior High School Hoosac Valley High School
Students per teacherat that high school —
11.1Highest
10.5Lowest
On TownTapestry
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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.