What stands out worked out from the figures below

Windham has the most affordable homes ($389k median).

Winchester has the most expensive homes ($1215k 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	Windham	Winchester
People
Population	19,188Lowest	23,406Highest
Growth since 20102010 → 2020 census	+8.4%Highest U.S.: +7.4%	+7.5%Lowest U.S.: +7.4%
Median age	41.8±1.8Lowest 7% above U.S.	42.5±1.9Highest 9% above U.S.
	Winchester and Windham are within the Census margin of error here, so we can’t say which is really higher.
Kids under 18	19.2%±2.7Lowest U.S.: 22%	27.6%±2.3Highest U.S.: 22%
Age 65+	15.9%±2.1Lowest U.S.: 17.2%	18%±2Highest U.S.: 17.2%
	Winchester and Windham are within the Census margin of error here, so we can’t say which is really higher.
Bachelor’s degree+adults 25+	44.2%Lowest U.S.: 35.7%	79.5%Highest U.S.: 35.7%
Enrolled in collegeshare of residents	3.9%±1.1Lowest U.S.: 6.4%	4.9%±1.3Highest U.S.: 6.4%
	Winchester and Windham are within the Census margin of error here, so we can’t say which is really higher.
Cost of living
Household incomemedian	$107,934±$14kLowest 34% above U.S.	$230,198±$21kHighest 185% above U.S.
Home valuemedian, owner-occupied	$388,900±$22kLowest 17% above U.S.	$1,215,200±$39kHighest 265% above U.S.
Rentmedian gross, monthly	$1,232±$332Lowest 13% below U.S.	$2,279±$481Highest 61% above U.S.
Property taxmedian, yearly	$3,938Lowest 26% above U.S.	$10,000+Highest at least 221% above U.S.
Renters paying 30%+of income on rent	32.7%±14.7Lowest U.S.: 51.1%	39.3%±13.3Highest U.S.: 51.1%
	Winchester and Windham 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%	4.7%Highest U.S.: 12.5%
Housing
Homeownersof occupied homes	84.6%Highest U.S.: 65.2%	81.7%Lowest U.S.: 65.2%
Typical home builtmedian year	1985Highest 5 yrs newer than U.S.	1954Lowest 26 yrs older than U.S.
Getting to work
Average commuteone way	26 minLowest about the U.S. average	31 minHighest 19% above U.S.
Work from home	19%±4.1Lowest U.S.: 15.1%	33.8%±3Highest U.S.: 15.1%
Schools
Public school scoresrank in state, math + reading	#95 of 133 in ME	#11 of 282 in MA
School district	RSU 14	Winchester
High school in town	Windham High School	Winchester High School
Students per teacherat that high school	12.1Lowest	14.8Highest
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.