What stands out worked out from the figures below

Webster has the most expensive homes ($362k median).

Winchester has the most affordable homes ($250k 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	Webster	Winchester
People
Population	17,748Highest	10,284Lowest
Growth since 20102010 → 2020 census	+6% U.S.: +7.4%	—
Median age	39.9±2.9Lowest about the U.S. average	49.1±6.2Highest 26% above U.S.
Kids under 18	19.6%±2.9Highest 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+	19.6%±2.5Lowest U.S.: 17.2%	27.4%±5.1Highest U.S.: 17.2%
Bachelor’s degree+adults 25+	25.3%Lowest U.S.: 35.7%	27.8%Highest U.S.: 35.7%
Enrolled in collegeshare of residents	5.8%±1.6Highest 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	$72,895±$6kHighest 10% below U.S.	$66,519±$12kLowest 18% below U.S.
	Webster and Winchester are within the Census margin of error here, so we can’t say which is really higher.
Home valuemedian, owner-occupied	$361,500±$12kHighest 9% above U.S.	$249,500±$17kLowest 25% below U.S.
Rentmedian gross, monthly	$1,228±$81Highest 13% 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	$3,999Lowest 28% above U.S.	$4,780Highest 53% above U.S.
Renters paying 30%+of income on rent	45.7%±6.7Lowest 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	12.7%Lowest U.S.: 12.5%	12.8%Highest U.S.: 12.5%
Housing
Homeownersof occupied homes	59.8%Lowest U.S.: 65.2%	65.8%Highest U.S.: 65.2%
Typical home builtmedian year	1962Highest 18 yrs older than U.S.	1955Lowest 25 yrs older than U.S.
Getting to work
Average commuteone way	31 minHighest 16% above U.S.	26 minLowest about the U.S. average
Work from home	8%±2.5Highest 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	Webster	Explorations District · Regional School District 07
High school in town	Bartlett High School	Northwestern Regional High School
Students per teacherat that high school	11.6Highest	9.7Lowest
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.