What stands out worked out from the figures below

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

Winchester has the most affordable homes ($250k 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	Winchester
People
Population	9,207Lowest	10,284Highest
Growth since 20102010 → 2020 census	+6% U.S.: +7.4%	—
Median age	44±2.6Lowest 13% above U.S.	49.1±6.2Highest 26% 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	21.2%±3.8Highest U.S.: 22%	15.4%±2.9Lowest 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+	15.4%±3.1Lowest U.S.: 17.2%	27.4%±5.1Highest U.S.: 17.2%
Bachelor’s degree+adults 25+	41.7%Highest U.S.: 35.7%	27.8%Lowest U.S.: 35.7%
Enrolled in collegeshare of residents	5.4%±2.3Highest U.S.: 6.4%	4.2%±1.7Lowest 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	$152,267±$10kHighest 89% above U.S.	$66,519±$12kLowest 18% below U.S.
Home valuemedian, owner-occupied	$470,600±$29kHighest 41% above U.S.	$249,500±$17kLowest 25% below U.S.
Rentmedian gross, monthly	$1,503±$697Highest 6% above U.S.	$1,174±$116Lowest 17% below 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	$6,338Highest 103% above U.S.	$4,780Lowest 53% above U.S.
Renters paying 30%+of income on rent	33.9%±17.4Lowest U.S.: 51.1%	48.9%±15.8Highest 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	4.8%Lowest U.S.: 12.5%	12.8%Highest U.S.: 12.5%
Housing
Homeownersof occupied homes	83.8%Highest U.S.: 65.2%	65.8%Lowest U.S.: 65.2%
Typical home builtmedian year	1986Highest 6 yrs newer than U.S.	1955Lowest 25 yrs older than U.S.
Getting to work
Average commuteone way	34 minHighest 28% above U.S.	26 minLowest about the U.S. average
Work from home	20.9%±4.9Highest U.S.: 15.1%	6.9%±2.7Lowest U.S.: 15.1%
Schools
Public school scoresrank in state, math + reading	#177 of 282 in MA	#97 of 149 in CT
School district	Douglas	Explorations District · Regional School District 07
High school in town	Douglas High School	Northwestern Regional High School
Students per teacherat that high school	7.2Lowest	9.7Highest
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.