What stands out worked out from the figures below

Derby has the most people working from home (15.1%).

Winchester has the most homeowners (65.8%).

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	Derby	Winchester
People
Population	12,487Highest	10,284Lowest
Growth since 20102010 → 2020 census	-4.5% CT: +0.9%	—
Median age	46.4±3.1Lowest 13% above CT	49.1±6.2Highest 19% above CT
	Winchester and Derby are within the Census margin of error here, so we can’t say which is really higher.
Kids under 18	14.6%±2.9Lowest CT: 20.2%	15.4%±2.9Highest CT: 20.2%
	Winchester and Derby are within the Census margin of error here, so we can’t say which is really higher.
Age 65+	21.1%±3.9Lowest CT: 18.5%	27.4%±5.1Highest CT: 18.5%
	Winchester and Derby are within the Census margin of error here, so we can’t say which is really higher.
Bachelor’s degree+adults 25+	35.6%Highest CT: 42.5%	27.8%Lowest CT: 42.5%
Enrolled in collegeshare of residents	5.9%±2Highest CT: 7.1%	4.2%±1.7Lowest CT: 7.1%
	Derby and Winchester are within the Census margin of error here, so we can’t say which is really higher.
Cost of living
Household incomemedian	$79,500±$11kHighest 17% below CT	$66,519±$12kLowest 31% below CT
	Derby and Winchester are within the Census margin of error here, so we can’t say which is really higher.
Home valuemedian, owner-occupied	$256,700±$21kHighest 30% below CT	$249,500±$17kLowest 32% below CT
	Derby and Winchester are within the Census margin of error here, so we can’t say which is really higher.
Rentmedian gross, monthly	$1,452±$95Highest about the CT average	$1,174±$116Lowest 21% below CT
Property taxmedian, yearly	$5,510Highest 17% below CT	$4,780Lowest 28% below CT
Renters paying 30%+of income on rent	53.9%±12.6Highest CT: 52.6%	48.9%±15.8Lowest CT: 52.6%
	Derby and Winchester are within the Census margin of error here, so we can’t say which is really higher.
Below poverty line	10.8%Lowest CT: 10%	12.8%Highest CT: 10%
Housing
Homeownersof occupied homes	61.9%Lowest CT: 66.5%	65.8%Highest CT: 66.5%
Typical home builtmedian year	1967Highest same as CT	1955Lowest 12 yrs older than CT
Getting to work
Average commuteone way	27 minHighest about the CT average	26 minLowest about the CT average
Work from home	15.1%±4.8Highest CT: 16%	6.9%±2.7Lowest CT: 16%
Schools
Public school scoresrank in state, math + reading	#138 of 149 in CT	#97 of 149 in CT
School district	Derby School District	Explorations District · Regional School District 07
High school in town	Derby High School	Northwestern Regional High School
Students per teacherat that high school	9.7	9.7
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.