What stands out worked out from the figures below

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

Windsor has the most affordable homes ($170k 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	Windsor
People
Population	17,748Highest	2,060Lowest
Growth since 20102010 → 2020 census	+6%Highest U.S.: +7.4%	+3.5%Lowest U.S.: +7.4%
Median age	39.9±2.9Lowest about the U.S. average	44.6±12.3Highest 15% above U.S.
	Windsor and Webster are within the Census margin of error here, so we can’t say which is really higher.
Kids under 18	19.6%±2.9Lowest U.S.: 22%	21.1%±8.8Highest U.S.: 22%
	Windsor and Webster 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%	29.2%±8Highest U.S.: 17.2%
	Windsor and Webster are within the Census margin of error here, so we can’t say which is really higher.
Bachelor’s degree+adults 25+	25.3%Lowest U.S.: 35.7%	40%Highest U.S.: 35.7%
Enrolled in collegeshare of residents	5.8%±1.6Highest U.S.: 6.4%	1.2%±1.4Lowest U.S.: 6.4%
Cost of living
Household incomemedian	$72,895±$6kHighest 10% below U.S.	$51,197±$4kLowest 37% below U.S.
Home valuemedian, owner-occupied	$361,500±$12kHighest 9% above U.S.	$170,300±$22kLowest 49% below U.S.
Rentmedian gross, monthly	$1,228±$81Highest 13% below U.S.	$1,002±$107Lowest 29% below U.S.
Property taxmedian, yearly	$3,999Lowest 28% above U.S.	$4,878Highest 56% above U.S.
Renters paying 30%+of income on rent	45.7%±6.7Highest U.S.: 51.1%	31.4%±20Lowest U.S.: 51.1%
	Webster and Windsor are within the Census margin of error here, so we can’t say which is really higher.
Below poverty line	12.7%Highest U.S.: 12.5%	7.8%Lowest U.S.: 12.5%
Housing
Homeownersof occupied homes	59.8%Highest U.S.: 65.2%	51.6%Lowest U.S.: 65.2%
Typical home builtmedian year	1962Highest 18 yrs older than U.S.	1938Lowest 42 yrs older than U.S.
Getting to work
Average commuteone way	31 minHighest 16% above U.S.	22 minLowest 16% below U.S.
Work from home	8%±2.5Highest U.S.: 15.1%	6.6%±4.7Lowest U.S.: 15.1%
	Webster and Windsor 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	#61 of 70 in VT
School district	Webster	—
High school in town	Bartlett High School	—
Students per teacherat that high school	11.6	—
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.