What stands out worked out from the figures below

Killingly has the most affordable homes ($289k median).

Winchester has the most expensive homes ($1215k 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	Killingly	Winchester
People
Population	17,867Lowest	23,406Highest
Growth since 20102010 → 2020 census	—	+7.5% U.S.: +7.4%
Median age	39.5±3Lowest about the U.S. average	42.5±1.9Highest 9% above U.S.
	Winchester and Killingly are within the Census margin of error here, so we can’t say which is really higher.
Kids under 18	19.8%±2.3Lowest U.S.: 22%	27.6%±2.3Highest U.S.: 22%
Age 65+	19.7%±2.4Highest U.S.: 17.2%	18%±2Lowest U.S.: 17.2%
	Killingly and Winchester are within the Census margin of error here, so we can’t say which is really higher.
Bachelor’s degree+adults 25+	22.9%Lowest U.S.: 35.7%	79.5%Highest U.S.: 35.7%
Enrolled in collegeshare of residents	5.4%±1.9Highest U.S.: 6.4%	4.9%±1.3Lowest U.S.: 6.4%
	Killingly and Winchester are within the Census margin of error here, so we can’t say which is really higher.
Cost of living
Household incomemedian	$84,350±$8kLowest 4% above U.S.	$230,198±$21kHighest 185% above U.S.
Home valuemedian, owner-occupied	$288,600±$15kLowest 13% below U.S.	$1,215,200±$39kHighest 265% above U.S.
Rentmedian gross, monthly	$1,044±$141Lowest 26% below U.S.	$2,279±$481Highest 61% above U.S.
Property taxmedian, yearly	$3,922Lowest 26% above U.S.	$10,000+Highest at least 221% above U.S.
Renters paying 30%+of income on rent	42.8%±10.9Highest U.S.: 51.1%	39.3%±13.3Lowest U.S.: 51.1%
	Killingly and Winchester are within the Census margin of error here, so we can’t say which is really higher.
Below poverty line	11.4%Highest U.S.: 12.5%	4.7%Lowest U.S.: 12.5%
Housing
Homeownersof occupied homes	71.6%Lowest U.S.: 65.2%	81.7%Highest U.S.: 65.2%
Typical home builtmedian year	1968Highest 12 yrs older than U.S.	1954Lowest 26 yrs older than U.S.
Getting to work
Average commuteone way	28 minLowest 6% above U.S.	31 minHighest 19% above U.S.
Work from home	11.1%±2.3Lowest U.S.: 15.1%	33.8%±3Highest U.S.: 15.1%
Schools
Public school scoresrank in state, math + reading	#136 of 149 in CT	#11 of 282 in MA
School district	Connecticut Technical Education and Career System · Eastern Connecticut Regional Educational Service Center (EAS	Winchester
High school in town	Killingly High School	Winchester High School
Students per teacherat that high school	11.1Lowest	14.8Highest
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.