What stands out worked out from the figures below

Winchester has the oldest population (median age 49.1).

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	Winchester	Middletown
People
Population	10,284Lowest	47,958Highest
Growth since 20102010 → 2020 census	—	+0.1% CT: +0.9%
Median age	49.1±6.2Highest 19% above CT	38.1±1.5Lowest 7% below CT
Kids under 18	15.4%±2.9Highest CT: 20.2%	14.3%±1.3Lowest 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+	27.4%±5.1Highest CT: 18.5%	16.5%±1.3Lowest CT: 18.5%
Bachelor’s degree+adults 25+	27.8%Lowest CT: 42.5%	40.2%Highest CT: 42.5%
Enrolled in collegeshare of residents	4.2%±1.7Lowest CT: 7.1%	15.5%±1.4Highest CT: 7.1%
Cost of living
Household incomemedian	$66,519±$12kLowest 31% below CT	$79,438±$6kHighest 17% 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	$249,500±$17kLowest 32% below CT	$295,300±$11kHighest 20% below CT
Rentmedian gross, monthly	$1,174±$116Lowest 21% below CT	$1,446±$45Highest about the CT average
Property taxmedian, yearly	$4,780Lowest 28% below CT	$6,412Highest 3% below CT
Renters paying 30%+of income on rent	48.9%±15.8Highest CT: 52.6%	47.7%±5.3Lowest 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	12.8%Highest CT: 10%	12%Lowest CT: 10%
Housing
Homeownersof occupied homes	65.8%Highest CT: 66.5%	52.9%Lowest CT: 66.5%
Typical home builtmedian year	1955Lowest 12 yrs older than CT	1972Highest 5 yrs newer than CT
Getting to work
Average commuteone way	26 minHighest about the CT average	23 minLowest 12% below CT
Work from home	6.9%±2.7Lowest CT: 16%	14.1%±1.8Highest CT: 16%
Schools
Public school scoresrank in state, math + reading	#97 of 149 in CT	#121 of 149 in CT
School district	Explorations District · Regional School District 07	Connecticut Technical Education and Career System · Department of Mental Health and Addiction Services
High school in town	Northwestern Regional High School	Middletown High School
Students per teacherat that high school	9.7Lowest	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.