What stands out worked out from the figures below

Winchester has the most expensive homes ($1215k median).

Windsor has the most affordable homes ($338k 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	Windsor
People
Population	23,406Highest	254Lowest
Growth since 20102010 → 2020 census	+7.5% U.S.: +7.4%	—
Median age	42.5±1.9Highest 9% above U.S.	40.2±18.8Lowest 3% above U.S.
	Winchester and Windsor are within the Census margin of error here, so we can’t say which is really higher.
Kids under 18	27.6%±2.3Highest U.S.: 22%	25.2%±14.7Lowest U.S.: 22%
	Winchester and Windsor are within the Census margin of error here, so we can’t say which is really higher.
Age 65+	18%±2Highest U.S.: 17.2%	15.7%±8Lowest U.S.: 17.2%
	Winchester and Windsor are within the Census margin of error here, so we can’t say which is really higher.
Bachelor’s degree+adults 25+	79.5%Highest U.S.: 35.7%	12.6%Lowest U.S.: 35.7%
Enrolled in collegeshare of residents	4.9%±1.3Highest U.S.: 6.4%	3.9%±4.2Lowest U.S.: 6.4%
	Winchester and Windsor are within the Census margin of error here, so we can’t say which is really higher.
Cost of living
Household incomemedian	$230,198±$21kHighest 185% above U.S.	$103,750±$40kLowest 29% above U.S.
Home valuemedian, owner-occupied	$1,215,200±$39kHighest 265% above U.S.	$337,500±$40kLowest about the U.S. average
Rentmedian gross, monthly	$2,279±$481 61% above U.S.	—
Property taxmedian, yearly	$10,000+Highest at least 221% above U.S.	$3,381Lowest 8% above U.S.
Renters paying 30%+of income on rent	39.3%±13.3Lowest U.S.: 51.1%	66.7%±100Highest U.S.: 51.1%
	Windsor and Winchester are within the Census margin of error here, so we can’t say which is really higher.
Below poverty line	4.7%Lowest U.S.: 12.5%	10.8%Highest U.S.: 12.5%
Housing
Homeownersof occupied homes	81.7%Lowest U.S.: 65.2%	96.5%Highest U.S.: 65.2%
Typical home builtmedian year	1954Lowest 26 yrs older than U.S.	1983Highest 3 yrs newer than U.S.
Getting to work
Average commuteone way	31 minLowest 19% above U.S.	32 minHighest 22% above U.S.
Work from home	33.8%±3Highest U.S.: 15.1%	15%±16.5Lowest U.S.: 15.1%
	Winchester 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	#11 of 282 in MA	—
School district	Winchester	—
High school in town	Winchester High School	—
Students per teacherat that high school	14.8	—
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.