What stands out worked out from the figures below

Winchester has the most affordable homes ($250k median).

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

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	Winchester	Douglas
People
Population	10,284Highest	9,207Lowest
Growth since 20102010 → 2020 census	—	+6% U.S.: +7.4%
Median age	49.1±6.2Highest 26% above U.S.	44±2.6Lowest 13% above U.S.
	Winchester and Douglas are within the Census margin of error here, so we can’t say which is really higher.
Kids under 18	15.4%±2.9Lowest U.S.: 22%	21.2%±3.8Highest U.S.: 22%
	Douglas and Winchester are within the Census margin of error here, so we can’t say which is really higher.
Age 65+	27.4%±5.1Highest U.S.: 17.2%	15.4%±3.1Lowest U.S.: 17.2%
Bachelor’s degree+adults 25+	27.8%Lowest U.S.: 35.7%	41.7%Highest U.S.: 35.7%
Enrolled in collegeshare of residents	4.2%±1.7Lowest U.S.: 6.4%	5.4%±2.3Highest U.S.: 6.4%
	Douglas and Winchester are within the Census margin of error here, so we can’t say which is really higher.
Cost of living
Household incomemedian	$66,519±$12kLowest 18% below U.S.	$152,267±$10kHighest 89% above U.S.
Home valuemedian, owner-occupied	$249,500±$17kLowest 25% below U.S.	$470,600±$29kHighest 41% above U.S.
Rentmedian gross, monthly	$1,174±$116Lowest 17% below U.S.	$1,503±$697Highest 6% above U.S.
	Douglas and Winchester are within the Census margin of error here, so we can’t say which is really higher.
Property taxmedian, yearly	$4,780Lowest 53% above U.S.	$6,338Highest 103% above U.S.
Renters paying 30%+of income on rent	48.9%±15.8Highest U.S.: 51.1%	33.9%±17.4Lowest U.S.: 51.1%
	Winchester and Douglas are within the Census margin of error here, so we can’t say which is really higher.
Below poverty line	12.8%Highest U.S.: 12.5%	4.8%Lowest U.S.: 12.5%
Housing
Homeownersof occupied homes	65.8%Lowest U.S.: 65.2%	83.8%Highest U.S.: 65.2%
Typical home builtmedian year	1955Lowest 25 yrs older than U.S.	1986Highest 6 yrs newer than U.S.
Getting to work
Average commuteone way	26 minLowest about the U.S. average	34 minHighest 28% above U.S.
Work from home	6.9%±2.7Lowest U.S.: 15.1%	20.9%±4.9Highest U.S.: 15.1%
Schools
Public school scoresrank in state, math + reading	#97 of 149 in CT	#177 of 282 in MA
School district	Explorations District · Regional School District 07	Douglas
High school in town	Northwestern Regional High School	Douglas High School
Students per teacherat that high school	9.7Highest	7.2Lowest
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.