What stands out worked out from the figures below

Milton has the most expensive homes ($933k 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	Milton	Windsor
People
Population	28,587Lowest	29,468Highest
Growth since 20102010 → 2020 census	+6% U.S.: +7.4%	—
Median age	41.1±1.8Lowest 6% above U.S.	43.7±1.9Highest 12% above U.S.
	Windsor and Milton are within the Census margin of error here, so we can’t say which is really higher.
Kids under 18	25.3%±2.2Highest U.S.: 22%	19.2%±2.1Lowest U.S.: 22%
Age 65+	16.1%±1.8Lowest U.S.: 17.2%	20%±2Highest U.S.: 17.2%
Bachelor’s degree+adults 25+	71.9%Highest U.S.: 35.7%	43.2%Lowest U.S.: 35.7%
Enrolled in collegeshare of residents	9.7%±1.1Highest U.S.: 6.4%	5.9%±1.3Lowest U.S.: 6.4%
Cost of living
Household incomemedian	$188,529±$15kHighest 134% above U.S.	$104,725±$8kLowest 30% above U.S.
Home valuemedian, owner-occupied	$933,200±$31kHighest 180% above U.S.	$305,200±$11kLowest 8% below U.S.
Rentmedian gross, monthly	$1,474±$281Lowest 4% above U.S.	$1,681±$62Highest 19% above U.S.
	Windsor and Milton are within the Census margin of error here, so we can’t say which is really higher.
Property taxmedian, yearly	$9,677Highest 210% above U.S.	$5,351Lowest 72% above U.S.
Renters paying 30%+of income on rent	45.7%±20.9Highest U.S.: 51.1%	44.9%±10.9Lowest U.S.: 51.1%
	Milton and Windsor 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%	6.7%Highest U.S.: 12.5%
Housing
Homeownersof occupied homes	85.2%Highest U.S.: 65.2%	82.4%Lowest U.S.: 65.2%
Typical home builtmedian year	1945Lowest 35 yrs older than U.S.	1970Highest 10 yrs older than U.S.
Getting to work
Average commuteone way	31 minHighest 19% above U.S.	21 minLowest 19% below U.S.
Work from home	29.7%±2.9Highest U.S.: 15.1%	16.1%±3.2Lowest U.S.: 15.1%
Schools
Public school scoresrank in state, math + reading	#55 of 282 in MA	#117 of 149 in CT
School district	Milton	Capitol Region Education Council · Windsor School District
High school in town	Milton High	Windsor High School
Students per teacherat that high school	12.4Highest	10.2Lowest
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.