What stands out worked out from the figures below

Deerfield has the most expensive homes ($415k median).

Windsor has the most kids (19.2% 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	Deerfield	Windsor
People
Population	5,158Lowest	29,468Highest
Growth since 20102010 → 2020 census	-0.7% U.S.: +7.4%	—
Median age	51.8±3.6Highest 33% above U.S.	43.7±1.9Lowest 12% above U.S.
Kids under 18	13.2%±3.7Lowest U.S.: 22%	19.2%±2.1Highest U.S.: 22%
Age 65+	22.9%±4.2Highest U.S.: 17.2%	20%±2Lowest U.S.: 17.2%
	Deerfield and Windsor are within the Census margin of error here, so we can’t say which is really higher.
Bachelor’s degree+adults 25+	44.4%Highest U.S.: 35.7%	43.2%Lowest U.S.: 35.7%
Enrolled in collegeshare of residents	7.9%±3.4Highest U.S.: 6.4%	5.9%±1.3Lowest U.S.: 6.4%
	Deerfield and Windsor are within the Census margin of error here, so we can’t say which is really higher.
Cost of living
Household incomemedian	$106,136±$14kHighest 31% above U.S.	$104,725±$8kLowest 30% above U.S.
	Deerfield and Windsor are within the Census margin of error here, so we can’t say which is really higher.
Home valuemedian, owner-occupied	$414,900±$37kHighest 25% above U.S.	$305,200±$11kLowest 8% below U.S.
Rentmedian gross, monthly	$1,334±$318Lowest 6% below U.S.	$1,681±$62Highest 19% above U.S.
	Windsor and Deerfield are within the Census margin of error here, so we can’t say which is really higher.
Property taxmedian, yearly	$5,824Highest 87% above U.S.	$5,351Lowest 72% above U.S.
Renters paying 30%+of income on rent	26.1%±15.1Lowest U.S.: 51.1%	44.9%±10.9Highest U.S.: 51.1%
	Windsor and Deerfield are within the Census margin of error here, so we can’t say which is really higher.
Below poverty line	7.8%Highest U.S.: 12.5%	6.7%Lowest U.S.: 12.5%
Housing
Homeownersof occupied homes	78.4%Lowest U.S.: 65.2%	82.4%Highest U.S.: 65.2%
Typical home builtmedian year	1972Highest 8 yrs older than U.S.	1970Lowest 10 yrs older than U.S.
Getting to work
Average commuteone way	18 minLowest 33% below U.S.	21 minHighest 19% below U.S.
Work from home	17.5%±6.2Highest U.S.: 15.1%	16.1%±3.2Lowest U.S.: 15.1%
	Deerfield and Windsor are within the Census margin of error here, so we can’t say which is really higher.
Schools
Public school scoresrank in state, math + reading	#156 of 282 in MA	#117 of 149 in CT
School district	Deerfield · Frontier	Capitol Region Education Council · Windsor School District
High school in town	Frontier Regional	Windsor High School
Students per teacherat that high school	11.1Highest	10.2Lowest
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.