What stands out worked out from the figures below

Webster has the most kids (21.8% under 18).

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	Webster	Winchester
People
Population	12,228Highest	10,284Lowest
Growth since 20102010 → 2020 census	+6.9% U.S.: +7.4%	—
Median age	37.2±2.1Lowest 4% below U.S.	49.1±6.2Highest 26% above U.S.
Kids under 18	21.8%±3.6Highest U.S.: 22%	15.4%±2.9Lowest U.S.: 22%
	Webster and Winchester are within the Census margin of error here, so we can’t say which is really higher.
Age 65+	15.7%±2.5Lowest U.S.: 17.2%	27.4%±5.1Highest U.S.: 17.2%
Bachelor’s degree+adults 25+	18.8%Lowest U.S.: 35.7%	27.8%Highest U.S.: 35.7%
Enrolled in collegeshare of residents	6%±1.8Highest U.S.: 6.4%	4.2%±1.7Lowest U.S.: 6.4%
	Webster and Winchester are within the Census margin of error here, so we can’t say which is really higher.
Cost of living
Household incomemedian	$63,837±$8kLowest 21% below U.S.	$66,519±$12kHighest 18% below U.S.
	Winchester and Webster are within the Census margin of error here, so we can’t say which is really higher.
Home valuemedian, owner-occupied	$333,100±$14kHighest about the U.S. average	$249,500±$17kLowest 25% below U.S.
Rentmedian gross, monthly	$1,198±$85Highest 15% below U.S.	$1,174±$116Lowest 17% below U.S.
	Webster and Winchester are within the Census margin of error here, so we can’t say which is really higher.
Property taxmedian, yearly	$3,234Lowest 4% above U.S.	$4,780Highest 53% above U.S.
Renters paying 30%+of income on rent	46.1%±7.4Lowest U.S.: 51.1%	48.9%±15.8Highest U.S.: 51.1%
	Winchester and Webster are within the Census margin of error here, so we can’t say which is really higher.
Below poverty line	16%Highest U.S.: 12.5%	12.8%Lowest U.S.: 12.5%
Housing
Homeownersof occupied homes	45.5%Lowest U.S.: 65.2%	65.8%Highest U.S.: 65.2%
Typical home builtmedian year	1954Lowest 26 yrs older than U.S.	1955Highest 25 yrs older than U.S.
Getting to work
Average commuteone way	28 minHighest 4% above U.S.	26 minLowest about the U.S. average
Work from home	7.1%±2.9Highest U.S.: 15.1%	6.9%±2.7Lowest U.S.: 15.1%
	Webster and Winchester are within the Census margin of error here, so we can’t say which is really higher.
Schools
Public school scoresrank in state, math + reading	#271 of 282 in MA	#97 of 149 in CT
School district	—	Explorations District · Regional School District 07
High school in town	—	Northwestern Regional High School
Students per teacherat that high school	—	9.7
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.