What stands out worked out from the figures below

Stockbridge has grown the fastest since 2010 (+3.6%).

Windsor has the most kids (15.8% 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	Windsor
People
Population	2,056Highest	1,065Lowest
Growth since 20102010 → 2020 census	+3.6%Highest MA: +7.4%	-7.6%Lowest MA: +7.4%
Median age	63.7±3.5Highest 59% above MA	44.8±6.4Lowest 12% above MA
Kids under 18	8.4%±4.3Lowest MA: 19.4%	15.8%±5.1Highest MA: 19.4%
	Windsor and Stockbridge are within the Census margin of error here, so we can’t say which is really higher.
Age 65+	47%±7.5Highest MA: 17.9%	18.6%±4.9Lowest MA: 17.9%
Bachelor’s degree+adults 25+	62.4%Highest MA: 47.3%	41.5%Lowest MA: 47.3%
Enrolled in collegeshare of residents	3.5%±2.7Highest MA: 7.9%	2.7%±1.7Lowest MA: 7.9%
	Stockbridge and Windsor 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 41% above MA	$115,563±$10kLowest 11% above MA
	Stockbridge and Windsor are within the Census margin of error here, so we can’t say which is really higher.
Home valuemedian, owner-occupied	$600,000±$99kHighest 7% above MA	$389,700±$32kLowest 31% below MA
Rentmedian gross, monthly	$858±$375 51% below MA	—
Property taxmedian, yearly	$4,652Highest 22% below MA	$3,867Lowest 35% below MA
Renters paying 30%+of income on rent	60.8%±27Highest MA: 51.8%	0%±100Lowest MA: 51.8%
	Stockbridge and Windsor are within the Census margin of error here, so we can’t say which is really higher.
Below poverty line	7.2%Highest MA: 10%	3.8%Lowest MA: 10%
Housing
Homeownersof occupied homes	83.3%Lowest MA: 62.5%	96.2%Highest MA: 62.5%
Typical home builtmedian year	1958Lowest 6 yrs older than MA	1970Highest 6 yrs newer than MA
Getting to work
Average commuteone way	20 minLowest 33% below MA	37 minHighest 27% above MA
Work from home	52.4%±19.9Highest MA: 18.6%	21.2%±5.8Lowest MA: 18.6%
On TownTapestry
Old photos in History	None yet	None yet

MA 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.