What stands out worked out from the figures below

Sterling has the most expensive homes ($499k median).

Windsor has the most affordable homes ($305k 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	Sterling	Windsor
People
Population	8,183Lowest	29,468Highest
Growth since 20102010 → 2020 census	+2.3% U.S.: +7.4%	—
Median age	51.5±1.8Highest 32% above U.S.	43.7±1.9Lowest 12% above U.S.
Kids under 18	18.6%±4.1Lowest U.S.: 22%	19.2%±2.1Highest U.S.: 22%
	Windsor and Sterling are within the Census margin of error here, so we can’t say which is really higher.
Age 65+	22.9%±4Highest U.S.: 17.2%	20%±2Lowest U.S.: 17.2%
	Sterling and Windsor are within the Census margin of error here, so we can’t say which is really higher.
Bachelor’s degree+adults 25+	48.3%Highest U.S.: 35.7%	43.2%Lowest U.S.: 35.7%
Enrolled in collegeshare of residents	4.8%±1.8Lowest U.S.: 6.4%	5.9%±1.3Highest U.S.: 6.4%
	Windsor and Sterling are within the Census margin of error here, so we can’t say which is really higher.
Cost of living
Household incomemedian	$129,063±$27kHighest 60% above U.S.	$104,725±$8kLowest 30% above U.S.
	Sterling and Windsor are within the Census margin of error here, so we can’t say which is really higher.
Home valuemedian, owner-occupied	$498,800±$48kHighest 50% above U.S.	$305,200±$11kLowest 8% below U.S.
Rentmedian gross, monthly	$1,699±$161Highest 20% above U.S.	$1,681±$62Lowest 19% above U.S.
	Sterling and Windsor are within the Census margin of error here, so we can’t say which is really higher.
Property taxmedian, yearly	$6,757Highest 117% above U.S.	$5,351Lowest 72% above U.S.
Renters paying 30%+of income on rent	46%±23.1Highest U.S.: 51.1%	44.9%±10.9Lowest U.S.: 51.1%
	Sterling and Windsor are within the Census margin of error here, so we can’t say which is really higher.
Below poverty line	6%Lowest U.S.: 12.5%	6.7%Highest U.S.: 12.5%
Housing
Homeownersof occupied homes	86.3%Highest U.S.: 65.2%	82.4%Lowest U.S.: 65.2%
Typical home builtmedian year	1980Highest same as U.S.	1970Lowest 10 yrs older than U.S.
Getting to work
Average commuteone way	34 minHighest 30% above U.S.	21 minLowest 19% below U.S.
Work from home	18.3%±6.2Highest U.S.: 15.1%	16.1%±3.2Lowest U.S.: 15.1%
	Sterling 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	#135 of 282 in MA	#117 of 149 in CT
School district	Wachusett	Capitol Region Education Council · Windsor School District
High school in town	None in town	Windsor High School
Students per teacherat that high school	—	10.2
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.