What stands out worked out from the figures below

Winchester has the most affordable homes ($250k median).

Warren has the most people working from home (15.9%).

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	Winchester	Warren
People
Population	10,284Highest	1,415Lowest
Median age	49.1±6.2Lowest 19% above CT	52±5Highest 27% above CT
	Warren and Winchester are within the Census margin of error here, so we can’t say which is really higher.
Kids under 18	15.4%±2.9Highest CT: 20.2%	11.2%±3Lowest CT: 20.2%
	Winchester and Warren are within the Census margin of error here, so we can’t say which is really higher.
Age 65+	27.4%±5.1Highest CT: 18.5%	25.8%±6.3Lowest CT: 18.5%
	Winchester and Warren are within the Census margin of error here, so we can’t say which is really higher.
Bachelor’s degree+adults 25+	27.8%Lowest CT: 42.5%	55.1%Highest CT: 42.5%
Enrolled in collegeshare of residents	4.2%±1.7Lowest CT: 7.1%	10.6%±9Highest CT: 7.1%
	Warren and Winchester are within the Census margin of error here, so we can’t say which is really higher.
Cost of living
Household incomemedian	$66,519±$12kLowest 31% below CT	$134,583±$33kHighest 41% above CT
Home valuemedian, owner-occupied	$249,500±$17kLowest 32% below CT	$450,000±$38kHighest 23% above CT
Rentmedian gross, monthly	$1,174±$116 21% below CT	—
Property taxmedian, yearly	$4,780Highest 28% below CT	$3,769Lowest 43% below CT
Renters paying 30%+of income on rent	48.9%±15.8Lowest CT: 52.6%	55.2%±63.8Highest CT: 52.6%
	Warren and Winchester are within the Census margin of error here, so we can’t say which is really higher.
Below poverty line	12.8%Highest CT: 10%	6.7%Lowest CT: 10%
Housing
Homeownersof occupied homes	65.8%Lowest CT: 66.5%	93.3%Highest CT: 66.5%
Typical home builtmedian year	1955Lowest 12 yrs older than CT	1984Highest 17 yrs newer than CT
Getting to work
Average commuteone way	26 minLowest about the CT average	31 minHighest 18% above CT
Work from home	6.9%±2.7Lowest CT: 16%	15.9%±2.7Highest CT: 16%
Schools
Public school scoresrank in state, math + reading	#97 of 149 in CT	—
School district	Explorations District · Regional School District 07	Regional School District 20
High school in town	Northwestern Regional High School	None in town
Students per teacherat that high school	9.7	—
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.