What stands out worked out from the figures below

Douglas has the most people working from home (20.9%).

Windsor has the most affordable homes ($170k median).

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	9,207Highest	2,060Lowest
Growth since 20102010 → 2020 census	+6%Highest U.S.: +7.4%	+3.5%Lowest U.S.: +7.4%
Median age	44±2.6Lowest 13% above U.S.	44.6±12.3Highest 15% above U.S.
	Windsor and Douglas 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%	21.1%±8.8Lowest 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%	29.2%±8Highest U.S.: 17.2%
Bachelor’s degree+adults 25+	41.7%Highest U.S.: 35.7%	40%Lowest U.S.: 35.7%
Enrolled in collegeshare of residents	5.4%±2.3Highest U.S.: 6.4%	1.2%±1.4Lowest U.S.: 6.4%
Cost of living
Household incomemedian	$152,267±$10kHighest 89% above U.S.	$51,197±$4kLowest 37% below U.S.
Home valuemedian, owner-occupied	$470,600±$29kHighest 41% above U.S.	$170,300±$22kLowest 49% below U.S.
Rentmedian gross, monthly	$1,503±$697Highest 6% above U.S.	$1,002±$107Lowest 29% below U.S.
	Douglas and Windsor 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.	$4,878Lowest 56% above U.S.
Renters paying 30%+of income on rent	33.9%±17.4Highest U.S.: 51.1%	31.4%±20Lowest U.S.: 51.1%
	Douglas and Windsor 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%	7.8%Highest U.S.: 12.5%
Housing
Homeownersof occupied homes	83.8%Highest U.S.: 65.2%	51.6%Lowest U.S.: 65.2%
Typical home builtmedian year	1986Highest 6 yrs newer than U.S.	1938Lowest 42 yrs older than U.S.
Getting to work
Average commuteone way	34 minHighest 28% above U.S.	22 minLowest 16% below U.S.
Work from home	20.9%±4.9Highest U.S.: 15.1%	6.6%±4.7Lowest U.S.: 15.1%
Schools
Public school scoresrank in state, math + reading	#177 of 282 in MA	#61 of 70 in VT
School district	Douglas	—
High school in town	Douglas High School	—
Students per teacherat that high school	7.2	—
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.