Compare towns

Windsor vs Chester vs Plainfield

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

What stands out worked out from the figures below

Windsor has the shortest commute (21 min average).
Chester has the most expensive homes ($442k median).
Plainfield has the youngest population (median age 37).

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.

MeasureWindsorChesterPlainfield
People
Population
29,468Highest
3,825Lowest
15,141
Median age
43.7±1.9
6% above CT
54±3.4Highest
31% above CT
37±4.5Lowest
10% below CT
Kids under 18
19.2%±2.1
CT: 20.2%
17.5%±4.9Lowest
CT: 20.2%
19.4%±2.6Highest
CT: 20.2%
Plainfield and Windsor are within the Census margin of error here, so we can’t say which is really higher.
Age 65+
20%±2
CT: 18.5%
26.8%±4Highest
CT: 18.5%
16.6%±2.4Lowest
CT: 18.5%
Bachelor’s degree+adults 25+
43.2%
CT: 42.5%
47.9%Highest
CT: 42.5%
15%Lowest
CT: 42.5%
Enrolled in collegeshare of residents
5.9%±1.3Highest
CT: 7.1%
4%±2.9Lowest
CT: 7.1%
5.6%±1.8
CT: 7.1%
Windsor and Plainfield are within the Census margin of error here, so we can’t say which is really higher.
Cost of living
Household incomemedian
$104,725±$8k
9% above CT
$109,191±$18kHighest
14% above CT
$76,993±$8kLowest
20% below CT
Chester and Windsor are within the Census margin of error here, so we can’t say which is really higher.
Home valuemedian, owner-occupied
$305,200±$11k
17% below CT
$442,200±$25kHighest
21% above CT
$272,100±$16kLowest
26% below CT
Rentmedian gross, monthly
$1,681±$62Highest
13% above CT
$1,549±$247
4% above CT
$1,204±$70Lowest
19% below CT
Windsor and Chester are within the Census margin of error here, so we can’t say which is really higher.
Property taxmedian, yearly
$5,351
19% below CT
$6,364Highest
4% below CT
$4,209Lowest
37% below CT
Renters paying 30%+of income on rent
44.9%±10.9
CT: 52.6%
57.4%±22.1Highest
CT: 52.6%
39.8%±9.5Lowest
CT: 52.6%
Chester and Windsor are within the Census margin of error here, so we can’t say which is really higher.
Below poverty line
6.7%Lowest
CT: 10%
11.8%Highest
CT: 10%
8.7%
CT: 10%
Housing
Homeownersof occupied homes
82.4%Highest
CT: 66.5%
73.2%Lowest
CT: 66.5%
73.6%
CT: 66.5%
Typical home builtmedian year
1970
3 yrs newer than CT
1969Lowest
2 yrs newer than CT
1971Highest
4 yrs newer than CT
Getting to work
Average commuteone way
21 minLowest
19% below CT
28 minHighest
7% above CT
27 min
about the CT average
Work from home
16.1%±3.2
CT: 16%
18.3%±5.6Highest
CT: 16%
10%±4Lowest
CT: 16%
Chester and Windsor 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 #117 of 149 in CT #8 of 149 in CT #131 of 149 in CT
School district Capitol Region Education Council · Windsor School District Chester School District Plainfield School District
High school in town Windsor High School None in town Plainfield High School
Students per teacherat that high school
10.2Lowest
—
10.3Highest
On TownTapestry
Old photos in History None yet None yet None yet

CT 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.