What stands out worked out from the figures below

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

Windsor has the most affordable homes ($390k 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	1,065Lowest
Growth since 20102010 → 2020 census	+7.5%Highest MA: +7.4%	-7.6%Lowest MA: +7.4%
Median age	42.5±1.9Lowest 6% above MA	44.8±6.4Highest 12% above MA
	Windsor and Winchester are within the Census margin of error here, so we can’t say which is really higher.
Kids under 18	27.6%±2.3Highest MA: 19.4%	15.8%±5.1Lowest MA: 19.4%
Age 65+	18%±2Lowest MA: 17.9%	18.6%±4.9Highest MA: 17.9%
	Windsor and Winchester 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 MA: 47.3%	41.5%Lowest MA: 47.3%
Enrolled in collegeshare of residents	4.9%±1.3Highest MA: 7.9%	2.7%±1.7Lowest MA: 7.9%
	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 121% above MA	$115,563±$10kLowest 11% above MA
Home valuemedian, owner-occupied	$1,215,200±$39kHighest 116% above MA	$389,700±$32kLowest 31% below MA
Rentmedian gross, monthly	$2,279±$481 29% above MA	—
Property taxmedian, yearly	$10,000+Highest at least 67% above MA	$3,867Lowest 35% below MA
Renters paying 30%+of income on rent	39.3%±13.3Highest MA: 51.8%	0%±100Lowest MA: 51.8%
	Winchester and Windsor are within the Census margin of error here, so we can’t say which is really higher.
Below poverty line	4.7%Highest MA: 10%	3.8%Lowest MA: 10%
Housing
Homeownersof occupied homes	81.7%Lowest MA: 62.5%	96.2%Highest MA: 62.5%
Typical home builtmedian year	1954Lowest 10 yrs older than MA	1970Highest 6 yrs newer than MA
Getting to work
Average commuteone way	31 minLowest 8% above MA	37 minHighest 27% above MA
Work from home	33.8%±3Highest MA: 18.6%	21.2%±5.8Lowest MA: 18.6%
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

MA 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.