What stands out worked out from the figures below

Cheshire has the most people working from home (19.1%).

Windham has the most affordable homes ($210k 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	Cheshire	Windham
People
Population	29,040Highest	23,961Lowest
Median age	44.9±1.4Highest 9% above CT	33.7±1.9Lowest 18% below CT
Kids under 18	21.9%±2.3Highest CT: 20.2%	20.1%±2.4Lowest CT: 20.2%
	Cheshire and Windham are within the Census margin of error here, so we can’t say which is really higher.
Age 65+	21.3%±1.8Highest CT: 18.5%	14.3%±1.9Lowest CT: 18.5%
Bachelor’s degree+adults 25+	60.7%Highest CT: 42.5%	22.7%Lowest CT: 42.5%
Enrolled in collegeshare of residents	4.5%±1.1Lowest CT: 7.1%	15.2%±1.8Highest CT: 7.1%
Cost of living
Household incomemedian	$146,528±$12kHighest 53% above CT	$55,736±$5kLowest 42% below CT
Home valuemedian, owner-occupied	$440,000±$17kHighest 20% above CT	$209,800±$9kLowest 43% below CT
Rentmedian gross, monthly	$1,398±$116Highest 6% below CT	$1,107±$69Lowest 26% below CT
Property taxmedian, yearly	$7,755Highest 17% above CT	$4,633Lowest 30% below CT
Renters paying 30%+of income on rent	44.9%±6.3Lowest CT: 52.6%	57.1%±8.1Highest CT: 52.6%
	Windham and Cheshire are within the Census margin of error here, so we can’t say which is really higher.
Below poverty line	5%Lowest CT: 10%	20.7%Highest CT: 10%
Housing
Homeownersof occupied homes	86.6%Highest CT: 66.5%	47.4%Lowest CT: 66.5%
Typical home builtmedian year	1974Highest 7 yrs newer than CT	1956Lowest 11 yrs older than CT
Getting to work
Average commuteone way	29 minHighest 9% above CT	24 minLowest 8% below CT
Work from home	19.1%±2.7Highest CT: 16%	6.1%±1.7Lowest CT: 16%
Schools
Public school scoresrank in state, math + reading	#18 of 149 in CT	#143 of 149 in CT
School district	Cheshire School District	Connecticut Technical Education and Career System · Eastern Connecticut Regional Educational Service Center (EAS
High school in town	Cheshire High School	Windham High School
Students per teacherat that high school	11.6Highest	9.8Lowest
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.