What stands out worked out from the figures below

Douglas has the most expensive homes ($471k median).

Windsor has the shortest commute (21 min average).

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	Douglas	Windsor
People
Population	9,207Lowest	29,468Highest
Growth since 20102010 → 2020 census	+6% U.S.: +7.4%	—
Median age	44±2.6Highest 13% above U.S.	43.7±1.9Lowest 12% above U.S.
	Douglas and Windsor are within the Census margin of error here, so we can’t say which is really higher.
Kids under 18	21.2%±3.8Highest U.S.: 22%	19.2%±2.1Lowest U.S.: 22%
	Douglas and Windsor are within the Census margin of error here, so we can’t say which is really higher.
Age 65+	15.4%±3.1Lowest U.S.: 17.2%	20%±2Highest U.S.: 17.2%
	Windsor and Douglas are within the Census margin of error here, so we can’t say which is really higher.
Bachelor’s degree+adults 25+	41.7%Lowest U.S.: 35.7%	43.2%Highest U.S.: 35.7%
Enrolled in collegeshare of residents	5.4%±2.3Lowest U.S.: 6.4%	5.9%±1.3Highest U.S.: 6.4%
	Windsor and Douglas are within the Census margin of error here, so we can’t say which is really higher.
Cost of living
Household incomemedian	$152,267±$10kHighest 89% above U.S.	$104,725±$8kLowest 30% above U.S.
Home valuemedian, owner-occupied	$470,600±$29kHighest 41% above U.S.	$305,200±$11kLowest 8% below U.S.
Rentmedian gross, monthly	$1,503±$697Lowest 6% above U.S.	$1,681±$62Highest 19% above U.S.
	Windsor and Douglas are within the Census margin of error here, so we can’t say which is really higher.
Property taxmedian, yearly	$6,338Highest 103% above U.S.	$5,351Lowest 72% above U.S.
Renters paying 30%+of income on rent	33.9%±17.4Lowest U.S.: 51.1%	44.9%±10.9Highest U.S.: 51.1%
	Windsor and Douglas are within the Census margin of error here, so we can’t say which is really higher.
Below poverty line	4.8%Lowest U.S.: 12.5%	6.7%Highest U.S.: 12.5%
Housing
Homeownersof occupied homes	83.8%Highest U.S.: 65.2%	82.4%Lowest U.S.: 65.2%
Typical home builtmedian year	1986Highest 6 yrs newer than U.S.	1970Lowest 10 yrs older than U.S.
Getting to work
Average commuteone way	34 minHighest 28% above U.S.	21 minLowest 19% below U.S.
Work from home	20.9%±4.9Highest U.S.: 15.1%	16.1%±3.2Lowest U.S.: 15.1%
	Douglas 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	#177 of 282 in MA	#117 of 149 in CT
School district	Douglas	Capitol Region Education Council · Windsor School District
High school in town	Douglas High School	Windsor High School
Students per teacherat that high school	7.2Lowest	10.2Highest
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.