What stands out worked out from the figures below

Upton has the oldest population (median age 70.4).

Windsor has the most kids (25.2% 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	Upton	Windsor
People
Population	91Lowest	254Highest
Median age	70.4±0.4Highest 81% above U.S.	40.2±18.8Lowest 3% above U.S.
Kids under 18	0%±34.2Lowest U.S.: 22%	25.2%±14.7Highest U.S.: 22%
	Windsor and Upton are within the Census margin of error here, so we can’t say which is really higher.
Age 65+	80.2%±49.6Highest U.S.: 17.2%	15.7%±8Lowest U.S.: 17.2%
Bachelor’s degree+adults 25+	14.4%Highest U.S.: 35.7%	12.6%Lowest U.S.: 35.7%
Enrolled in collegeshare of residents	1.1%±12.5Lowest U.S.: 6.4%	3.9%±4.2Highest U.S.: 6.4%
	Windsor and Upton are within the Census margin of error here, so we can’t say which is really higher.
Cost of living
Household incomemedian	—	$103,750±$40k 29% above U.S.
Home valuemedian, owner-occupied	—	$337,500±$40k about the U.S. average
Property taxmedian, yearly	$731Lowest 77% below U.S.	$3,381Highest 8% above U.S.
Renters paying 30%+of income on rent	0%±100Lowest U.S.: 51.1%	66.7%±100Highest U.S.: 51.1%
	Windsor and Upton are within the Census margin of error here, so we can’t say which is really higher.
Below poverty line	0%Lowest U.S.: 12.5%	10.8%Highest U.S.: 12.5%
Housing
Homeownersof occupied homes	95.7%Lowest U.S.: 65.2%	96.5%Highest U.S.: 65.2%
Typical home builtmedian year	1979Lowest 1 yr older than U.S.	1983Highest 3 yrs newer than U.S.
Getting to work
Average commuteone way	24 minLowest 9% below U.S.	32 minHighest 22% above U.S.
Work from home	13%±12Lowest U.S.: 15.1%	15%±16.5Highest U.S.: 15.1%
	Windsor and Upton 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.