What stands out worked out from the figures below

Cheshire has the most homeowners (89%).

Windham has the most renters (52.6% 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	Cheshire	Windham
People
Population	3,216Lowest	23,961Highest
Growth since 20102010 → 2020 census	+0.7% U.S.: +7.4%	—
Median age	53.7±4.5Highest 38% above U.S.	33.7±1.9Lowest 13% below U.S.
Kids under 18	15.3%±4.2Lowest U.S.: 22%	20.1%±2.4Highest U.S.: 22%
	Windham and Cheshire are within the Census margin of error here, so we can’t say which is really higher.
Age 65+	30.5%±7.1Highest U.S.: 17.2%	14.3%±1.9Lowest U.S.: 17.2%
Bachelor’s degree+adults 25+	26.9%Highest U.S.: 35.7%	22.7%Lowest U.S.: 35.7%
Enrolled in collegeshare of residents	5%±2.5Lowest U.S.: 6.4%	15.2%±1.8Highest U.S.: 6.4%
Cost of living
Household incomemedian	$69,803±$14kHighest 14% below U.S.	$55,736±$5kLowest 31% below U.S.
	Cheshire and Windham are within the Census margin of error here, so we can’t say which is really higher.
Home valuemedian, owner-occupied	$268,200±$48kHighest 19% below U.S.	$209,800±$9kLowest 37% below U.S.
Rentmedian gross, monthly	—	$1,107±$69 22% below U.S.
Property taxmedian, yearly	$3,005Lowest 4% below U.S.	$4,633Highest 49% above U.S.
Renters paying 30%+of income on rent	21.2%±24Lowest U.S.: 51.1%	57.1%±8.1Highest U.S.: 51.1%
Below poverty line	8.6%Lowest U.S.: 12.5%	20.7%Highest U.S.: 12.5%
Housing
Homeownersof occupied homes	89%Highest U.S.: 65.2%	47.4%Lowest U.S.: 65.2%
Typical home builtmedian year	1964Highest 16 yrs older than U.S.	1956Lowest 24 yrs older than U.S.
Getting to work
Average commuteone way	29 minHighest 10% above U.S.	24 minLowest 8% below U.S.
Work from home	4.4%±2.7Lowest U.S.: 15.1%	6.1%±1.7Highest U.S.: 15.1%
	Windham and Cheshire 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	#274 of 282 in MA	#143 of 149 in CT
School district	Hoosac Valley Regional	Connecticut Technical Education and Career System · Eastern Connecticut Regional Educational Service Center (EAS
High school in town	Hoosac Valley High School	Windham High School
Students per teacherat that high school	10.5Highest	9.8Lowest
On TownTapestry
Old photos in History	None yet	None yet

U.S. 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.