What stands out worked out from the figures below

Winchester has the most affordable homes ($250k median).

Webster has the most expensive homes ($362k 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	Winchester	Webster
People
Population	10,284Lowest	17,748Highest
Growth since 20102010 → 2020 census	—	+6% U.S.: +7.4%
Median age	49.1±6.2Highest 26% above U.S.	39.9±2.9Lowest about the U.S. average
Kids under 18	15.4%±2.9Lowest U.S.: 22%	19.6%±2.9Highest 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+	27.4%±5.1Highest U.S.: 17.2%	19.6%±2.5Lowest U.S.: 17.2%
Bachelor’s degree+adults 25+	27.8%Highest U.S.: 35.7%	25.3%Lowest U.S.: 35.7%
Enrolled in collegeshare of residents	4.2%±1.7Lowest U.S.: 6.4%	5.8%±1.6Highest 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	$66,519±$12kLowest 18% below U.S.	$72,895±$6kHighest 10% 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	$249,500±$17kLowest 25% below U.S.	$361,500±$12kHighest 9% above U.S.
Rentmedian gross, monthly	$1,174±$116Lowest 17% below U.S.	$1,228±$81Highest 13% 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	$4,780Highest 53% above U.S.	$3,999Lowest 28% above U.S.
Renters paying 30%+of income on rent	48.9%±15.8Highest U.S.: 51.1%	45.7%±6.7Lowest 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	12.8%Highest U.S.: 12.5%	12.7%Lowest U.S.: 12.5%
Housing
Homeownersof occupied homes	65.8%Highest U.S.: 65.2%	59.8%Lowest U.S.: 65.2%
Typical home builtmedian year	1955Lowest 25 yrs older than U.S.	1962Highest 18 yrs older than U.S.
Getting to work
Average commuteone way	26 minLowest about the U.S. average	31 minHighest 16% above U.S.
Work from home	6.9%±2.7Lowest U.S.: 15.1%	8%±2.5Highest 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	#97 of 149 in CT	#271 of 282 in MA
School district	Explorations District · Regional School District 07	Webster
High school in town	Northwestern Regional High School	Bartlett High School
Students per teacherat that high school	9.7Lowest	11.6Highest
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.