What stands out worked out from the figures below

Windsor has the most affordable homes ($305k median).

Weston has the most expensive homes ($1694k 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	Windsor	Weston
People
Population	29,468Highest	11,579Lowest
Growth since 20102010 → 2020 census	—	+5.2% U.S.: +7.4%
Median age	43.7±1.9Lowest 12% above U.S.	44.9±2.1Highest 15% above U.S.
	Weston and Windsor are within the Census margin of error here, so we can’t say which is really higher.
Kids under 18	19.2%±2.1Lowest U.S.: 22%	26%±3.8Highest U.S.: 22%
Age 65+	20%±2 U.S.: 17.2%	20%±2.8 U.S.: 17.2%
Bachelor’s degree+adults 25+	43.2%Lowest U.S.: 35.7%	84.3%Highest U.S.: 35.7%
Enrolled in collegeshare of residents	5.9%±1.3Lowest U.S.: 6.4%	9.8%±1.6Highest U.S.: 6.4%
Cost of living
Household incomemedian	$104,725±$8kLowest 30% above U.S.	$250,001Highest 210% above U.S.
Home valuemedian, owner-occupied	$305,200±$11kLowest 8% below U.S.	$1,694,400±$263kHighest 409% above U.S.
Rentmedian gross, monthly	$1,681±$62Lowest 19% above U.S.	$2,085±$809Highest 48% above U.S.
	Weston and Windsor are within the Census margin of error here, so we can’t say which is really higher.
Property taxmedian, yearly	$5,351Lowest 72% above U.S.	$10,000+Highest at least 221% above U.S.
Renters paying 30%+of income on rent	44.9%±10.9Lowest U.S.: 51.1%	69%±23Highest U.S.: 51.1%
	Weston and Windsor are within the Census margin of error here, so we can’t say which is really higher.
Below poverty line	6.7%Highest U.S.: 12.5%	2.9%Lowest U.S.: 12.5%
Housing
Homeownersof occupied homes	82.4%Lowest U.S.: 65.2%	87.5%Highest U.S.: 65.2%
Typical home builtmedian year	1970Highest 10 yrs older than U.S.	1964Lowest 16 yrs older than U.S.
Getting to work
Average commuteone way	21 minLowest 19% below U.S.	27 minHighest about the U.S. average
Work from home	16.1%±3.2Lowest U.S.: 15.1%	29.1%±5.2Highest U.S.: 15.1%
Schools
Public school scoresrank in state, math + reading	#117 of 149 in CT	#9 of 282 in MA
School district	Capitol Region Education Council · Windsor School District	Weston
High school in town	Windsor High School	Weston High
Students per teacherat that high school	10.2Lowest	10.9Highest
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.