What stands out worked out from the figures below

Windsor has the highest household income ($104k).

Brookline has the most people working from home (20.6%).

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	Windsor	Brookline
People
Population	254Lowest	531Highest
Growth since 20102010 → 2020 census	—	+1.9% U.S.: +7.4%
Median age	40.2±18.8Lowest 3% above U.S.	45.1±2.7Highest 16% above U.S.
	Brookline and Windsor are within the Census margin of error here, so we can’t say which is really higher.
Kids under 18	25.2%±14.7Highest U.S.: 22%	20%±6Lowest U.S.: 22%
	Windsor and Brookline are within the Census margin of error here, so we can’t say which is really higher.
Age 65+	15.7%±8Lowest U.S.: 17.2%	19.6%±4.2Highest U.S.: 17.2%
	Brookline and Windsor are within the Census margin of error here, so we can’t say which is really higher.
Bachelor’s degree+adults 25+	12.6%Lowest U.S.: 35.7%	41.1%Highest U.S.: 35.7%
Enrolled in collegeshare of residents	3.9%±4.2Highest U.S.: 6.4%	3.2%±1.6Lowest U.S.: 6.4%
	Windsor and Brookline are within the Census margin of error here, so we can’t say which is really higher.
Cost of living
Household incomemedian	$103,750±$40kHighest 29% above U.S.	$80,833±$16kLowest about the U.S. average
	Windsor and Brookline are within the Census margin of error here, so we can’t say which is really higher.
Home valuemedian, owner-occupied	$337,500±$40kHighest about the U.S. average	$290,700±$37kLowest 13% below U.S.
	Windsor and Brookline are within the Census margin of error here, so we can’t say which is really higher.
Rentmedian gross, monthly	—	$1,732±$232 23% above U.S.
Property taxmedian, yearly	$3,381Lowest 8% above U.S.	$5,000Highest 60% above U.S.
Renters paying 30%+of income on rent	66.7%±100Highest U.S.: 51.1%	47.8%±94.7Lowest U.S.: 51.1%
	Windsor and Brookline are within the Census margin of error here, so we can’t say which is really higher.
Below poverty line	10.8%Highest U.S.: 12.5%	6.2%Lowest U.S.: 12.5%
Housing
Homeownersof occupied homes	96.5%Highest U.S.: 65.2%	84.9%Lowest U.S.: 65.2%
Typical home builtmedian year	1983Highest 3 yrs newer than U.S.	1975Lowest 5 yrs older than U.S.
Getting to work
Average commuteone way	32 minHighest 22% above U.S.	28 minLowest 8% above U.S.
Work from home	15%±16.5Lowest U.S.: 15.1%	20.6%±5.2Highest U.S.: 15.1%
	Brookline and Windsor are within the Census margin of error here, so we can’t say which is really higher.
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.