What stands out worked out from the figures below

Windham has the most kids (20.1% under 18).

Middletown has the most people working from home (14.1%).

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	Windham	Middletown
People
Population	23,961Lowest	47,958Highest
Growth since 20102010 → 2020 census	—	+0.1% CT: +0.9%
Median age	33.7±1.9Lowest 18% below CT	38.1±1.5Highest 7% below CT
Kids under 18	20.1%±2.4Highest CT: 20.2%	14.3%±1.3Lowest CT: 20.2%
Age 65+	14.3%±1.9Lowest CT: 18.5%	16.5%±1.3Highest CT: 18.5%
	Middletown and Windham are within the Census margin of error here, so we can’t say which is really higher.
Bachelor’s degree+adults 25+	22.7%Lowest CT: 42.5%	40.2%Highest CT: 42.5%
Enrolled in collegeshare of residents	15.2%±1.8Lowest CT: 7.1%	15.5%±1.4Highest CT: 7.1%
	Middletown and Windham are within the Census margin of error here, so we can’t say which is really higher.
Cost of living
Household incomemedian	$55,736±$5kLowest 42% below CT	$79,438±$6kHighest 17% below CT
Home valuemedian, owner-occupied	$209,800±$9kLowest 43% below CT	$295,300±$11kHighest 20% below CT
Rentmedian gross, monthly	$1,107±$69Lowest 26% below CT	$1,446±$45Highest about the CT average
Property taxmedian, yearly	$4,633Lowest 30% below CT	$6,412Highest 3% below CT
Renters paying 30%+of income on rent	57.1%±8.1Highest CT: 52.6%	47.7%±5.3Lowest CT: 52.6%
	Windham and Middletown are within the Census margin of error here, so we can’t say which is really higher.
Below poverty line	20.7%Highest CT: 10%	12%Lowest CT: 10%
Housing
Homeownersof occupied homes	47.4%Lowest CT: 66.5%	52.9%Highest CT: 66.5%
Typical home builtmedian year	1956Lowest 11 yrs older than CT	1972Highest 5 yrs newer than CT
Getting to work
Average commuteone way	24 minHighest 8% below CT	23 minLowest 12% below CT
Work from home	6.1%±1.7Lowest CT: 16%	14.1%±1.8Highest CT: 16%
Schools
Public school scoresrank in state, math + reading	#143 of 149 in CT	#121 of 149 in CT
School district	Connecticut Technical Education and Career System · Eastern Connecticut Regional Educational Service Center (EAS	Connecticut Technical Education and Career System · Department of Mental Health and Addiction Services
High school in town	Windham High School	Middletown High School
Students per teacherat that high school	9.8Lowest	11.8Highest
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.