What stands out worked out from the figures below

Middleton has the most expensive homes ($743k 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	Middleton	Windsor
People
Population	9,816Highest	254Lowest
Growth since 20102010 → 2020 census	+8.8% U.S.: +7.4%	—
Median age	43.1±2Highest 11% above U.S.	40.2±18.8Lowest 3% above U.S.
	Middleton and Windsor are within the Census margin of error here, so we can’t say which is really higher.
Kids under 18	17.2%±3Lowest U.S.: 22%	25.2%±14.7Highest U.S.: 22%
	Windsor and Middleton are within the Census margin of error here, so we can’t say which is really higher.
Age 65+	18.1%±2.9Highest U.S.: 17.2%	15.7%±8Lowest U.S.: 17.2%
	Middleton and Windsor are within the Census margin of error here, so we can’t say which is really higher.
Bachelor’s degree+adults 25+	41.7%Highest U.S.: 35.7%	12.6%Lowest U.S.: 35.7%
Enrolled in collegeshare of residents	3.9%±1.4 U.S.: 6.4%	3.9%±4.2 U.S.: 6.4%
Cost of living
Household incomemedian	$167,402±$29kHighest 107% above U.S.	$103,750±$40kLowest 29% above U.S.
	Middleton and Windsor are within the Census margin of error here, so we can’t say which is really higher.
Home valuemedian, owner-occupied	$742,700±$48kHighest 123% above U.S.	$337,500±$40kLowest about the U.S. average
Rentmedian gross, monthly	$1,407±$284 about the U.S. average	—
Property taxmedian, yearly	$8,785Highest 182% above U.S.	$3,381Lowest 8% above U.S.
Renters paying 30%+of income on rent	25.7%±25.3Lowest U.S.: 51.1%	66.7%±100Highest U.S.: 51.1%
	Windsor and Middleton are within the Census margin of error here, so we can’t say which is really higher.
Below poverty line	3.4%Lowest U.S.: 12.5%	10.8%Highest U.S.: 12.5%
Housing
Homeownersof occupied homes	92.7%Lowest U.S.: 65.2%	96.5%Highest U.S.: 65.2%
Typical home builtmedian year	1986Highest 6 yrs newer than U.S.	1983Lowest 3 yrs newer than U.S.
Getting to work
Average commuteone way	30 minLowest 14% above U.S.	32 minHighest 22% above U.S.
Work from home	12.5%±3.4Lowest U.S.: 15.1%	15%±16.5Highest U.S.: 15.1%
	Windsor and Middleton 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	#71 of 282 in MA	—
School district	Middleton	—
High school in town	None in town	—
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.