What stands out worked out from the figures below

Windham has the most affordable homes ($210k median).

Milton has the most people working from home (29.7%).

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	Windham	Milton
People
Population	23,961Lowest	28,587Highest
Growth since 20102010 → 2020 census	—	+6% U.S.: +7.4%
Median age	33.7±1.9Lowest 13% below U.S.	41.1±1.8Highest 6% above U.S.
Kids under 18	20.1%±2.4Lowest U.S.: 22%	25.3%±2.2Highest U.S.: 22%
Age 65+	14.3%±1.9Lowest U.S.: 17.2%	16.1%±1.8Highest U.S.: 17.2%
	Milton and Windham are within the Census margin of error here, so we can’t say which is really higher.
Bachelor’s degree+adults 25+	22.7%Lowest U.S.: 35.7%	71.9%Highest U.S.: 35.7%
Enrolled in collegeshare of residents	15.2%±1.8Highest U.S.: 6.4%	9.7%±1.1Lowest U.S.: 6.4%
Cost of living
Household incomemedian	$55,736±$5kLowest 31% below U.S.	$188,529±$15kHighest 134% above U.S.
Home valuemedian, owner-occupied	$209,800±$9kLowest 37% below U.S.	$933,200±$31kHighest 180% above U.S.
Rentmedian gross, monthly	$1,107±$69Lowest 22% below U.S.	$1,474±$281Highest 4% above U.S.
Property taxmedian, yearly	$4,633Lowest 49% above U.S.	$9,677Highest 210% above U.S.
Renters paying 30%+of income on rent	57.1%±8.1Highest U.S.: 51.1%	45.7%±20.9Lowest U.S.: 51.1%
	Windham and Milton are within the Census margin of error here, so we can’t say which is really higher.
Below poverty line	20.7%Highest U.S.: 12.5%	4.7%Lowest U.S.: 12.5%
Housing
Homeownersof occupied homes	47.4%Lowest U.S.: 65.2%	85.2%Highest U.S.: 65.2%
Typical home builtmedian year	1956Highest 24 yrs older than U.S.	1945Lowest 35 yrs older than U.S.
Getting to work
Average commuteone way	24 minLowest 8% below U.S.	31 minHighest 19% above U.S.
Work from home	6.1%±1.7Lowest U.S.: 15.1%	29.7%±2.9Highest U.S.: 15.1%
Schools
Public school scoresrank in state, math + reading	#143 of 149 in CT	#55 of 282 in MA
School district	Connecticut Technical Education and Career System · Eastern Connecticut Regional Educational Service Center (EAS	Milton
High school in town	Windham High School	Milton High
Students per teacherat that high school	9.8Lowest	12.4Highest
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.