What stands out worked out from the figures below

Chester has the most expensive homes ($442k median).

Windsor has the most affordable homes ($305k median).

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.

Raising kidsAffordabilityOwning a homeShort commuteWorking from homeYounger crowdSettled, older crowdGrowing town

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