What stands out worked out from the figures below

Stockbridge has the most people working from home (52.4%).

Windham has the most kids (17.5% under 18).

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	Stockbridge	Windham
People
Population	2,056Highest	594Lowest
Growth since 20102010 → 2020 census	+3.6% U.S.: +7.4%	—
Median age	63.7±3.5Highest 64% above U.S.	44.2±7.4Lowest 14% above U.S.
Kids under 18	8.4%±4.3Lowest U.S.: 22%	17.5%±7.9Highest U.S.: 22%
	Windham and Stockbridge are within the Census margin of error here, so we can’t say which is really higher.
Age 65+	47%±7.5Highest U.S.: 17.2%	23.2%±8.1Lowest U.S.: 17.2%
Bachelor’s degree+adults 25+	62.4%Highest U.S.: 35.7%	48.1%Lowest U.S.: 35.7%
Enrolled in collegeshare of residents	3.5%±2.7Highest U.S.: 6.4%	0.8%±1.1Lowest U.S.: 6.4%
	Stockbridge and Windham are within the Census margin of error here, so we can’t say which is really higher.
Cost of living
Household incomemedian	$146,250±$67kHighest 81% above U.S.	$94,500±$12kLowest 17% above U.S.
	Stockbridge and Windham are within the Census margin of error here, so we can’t say which is really higher.
Home valuemedian, owner-occupied	$600,000±$99kHighest 80% above U.S.	$353,900±$20kLowest 6% above U.S.
Rentmedian gross, monthly	$858±$375 39% below U.S.	—
Property taxmedian, yearly	$4,652Lowest 49% above U.S.	$5,951Highest 91% above U.S.
Renters paying 30%+of income on rent	60.8%±27Highest U.S.: 51.1%	41.2%±94Lowest U.S.: 51.1%
	Stockbridge and Windham are within the Census margin of error here, so we can’t say which is really higher.
Below poverty line	7.2%Lowest U.S.: 12.5%	9.9%Highest U.S.: 12.5%
Housing
Homeownersof occupied homes	83.3%Highest U.S.: 65.2%	82.9%Lowest U.S.: 65.2%
Typical home builtmedian year	1958Lowest 22 yrs older than U.S.	1982Highest 2 yrs newer than U.S.
Getting to work
Average commuteone way	20 minLowest 26% below U.S.	27 minHighest about the U.S. average
Work from home	52.4%±19.9Highest U.S.: 15.1%	20.5%±5.6Lowest U.S.: 15.1%
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.