What stands out worked out from the figures below

Windsor has the most people working from home (16.1%).

Winchester has the most renters (34.2% rent).

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	Windsor	Winchester
People
Population	29,468Highest	10,284Lowest
Median age	43.7±1.9Lowest 6% above CT	49.1±6.2Highest 19% above CT
	Winchester and Windsor are within the Census margin of error here, so we can’t say which is really higher.
Kids under 18	19.2%±2.1Highest CT: 20.2%	15.4%±2.9Lowest CT: 20.2%
	Windsor and Winchester are within the Census margin of error here, so we can’t say which is really higher.
Age 65+	20%±2Lowest CT: 18.5%	27.4%±5.1Highest CT: 18.5%
Bachelor’s degree+adults 25+	43.2%Highest CT: 42.5%	27.8%Lowest CT: 42.5%
Enrolled in collegeshare of residents	5.9%±1.3Highest CT: 7.1%	4.2%±1.7Lowest CT: 7.1%
	Windsor and Winchester are within the Census margin of error here, so we can’t say which is really higher.
Cost of living
Household incomemedian	$104,725±$8kHighest 9% above CT	$66,519±$12kLowest 31% below CT
Home valuemedian, owner-occupied	$305,200±$11kHighest 17% below CT	$249,500±$17kLowest 32% below CT
Rentmedian gross, monthly	$1,681±$62Highest 13% above CT	$1,174±$116Lowest 21% below CT
Property taxmedian, yearly	$5,351Highest 19% below CT	$4,780Lowest 28% below CT
Renters paying 30%+of income on rent	44.9%±10.9Lowest CT: 52.6%	48.9%±15.8Highest CT: 52.6%
	Winchester 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%	12.8%Highest CT: 10%
Housing
Homeownersof occupied homes	82.4%Highest CT: 66.5%	65.8%Lowest CT: 66.5%
Typical home builtmedian year	1970Highest 3 yrs newer than CT	1955Lowest 12 yrs older than CT
Getting to work
Average commuteone way	21 minLowest 19% below CT	26 minHighest about the CT average
Work from home	16.1%±3.2Highest CT: 16%	6.9%±2.7Lowest CT: 16%
Schools
Public school scoresrank in state, math + reading	#117 of 149 in CT	#97 of 149 in CT
School district	Capitol Region Education Council · Windsor School District	Explorations District · Regional School District 07
High school in town	Windsor High School	Northwestern Regional High School
Students per teacherat that high school	10.2Highest	9.7Lowest
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.