What stands out worked out from the figures below

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

Winchester has the oldest population (median age 49.1).

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	Middletown	Winchester
People
Population	47,958Highest	10,284Lowest
Growth since 20102010 → 2020 census	+0.1% CT: +0.9%	—
Median age	38.1±1.5Lowest 7% below CT	49.1±6.2Highest 19% above CT
Kids under 18	14.3%±1.3Lowest CT: 20.2%	15.4%±2.9Highest CT: 20.2%
	Winchester and Middletown are within the Census margin of error here, so we can’t say which is really higher.
Age 65+	16.5%±1.3Lowest CT: 18.5%	27.4%±5.1Highest CT: 18.5%
Bachelor’s degree+adults 25+	40.2%Highest CT: 42.5%	27.8%Lowest CT: 42.5%
Enrolled in collegeshare of residents	15.5%±1.4Highest CT: 7.1%	4.2%±1.7Lowest CT: 7.1%
Cost of living
Household incomemedian	$79,438±$6kHighest 17% below CT	$66,519±$12kLowest 31% below CT
	Middletown and Winchester are within the Census margin of error here, so we can’t say which is really higher.
Home valuemedian, owner-occupied	$295,300±$11kHighest 20% below CT	$249,500±$17kLowest 32% below CT
Rentmedian gross, monthly	$1,446±$45Highest about the CT average	$1,174±$116Lowest 21% below CT
Property taxmedian, yearly	$6,412Highest 3% below CT	$4,780Lowest 28% below CT
Renters paying 30%+of income on rent	47.7%±5.3Lowest CT: 52.6%	48.9%±15.8Highest CT: 52.6%
	Winchester and Middletown are within the Census margin of error here, so we can’t say which is really higher.
Below poverty line	12%Lowest CT: 10%	12.8%Highest CT: 10%
Housing
Homeownersof occupied homes	52.9%Lowest CT: 66.5%	65.8%Highest CT: 66.5%
Typical home builtmedian year	1972Highest 5 yrs newer than CT	1955Lowest 12 yrs older than CT
Getting to work
Average commuteone way	23 minLowest 12% below CT	26 minHighest about the CT average
Work from home	14.1%±1.8Highest CT: 16%	6.9%±2.7Lowest CT: 16%
Schools
Public school scoresrank in state, math + reading	#121 of 149 in CT	#97 of 149 in CT
School district	Connecticut Technical Education and Career System · Department of Mental Health and Addiction Services	Explorations District · Regional School District 07
High school in town	Middletown High School	Northwestern Regional High School
Students per teacherat that high school	11.8Highest	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.