What stands out worked out from the figures below

Chester has the oldest population (median age 54).

Douglas has the highest household income ($152k).

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	Chester	Douglas
People
Population	3,825Lowest	9,207Highest
Growth since 20102010 → 2020 census	—	+6% U.S.: +7.4%
Median age	54±3.4Highest 39% above U.S.	44±2.6Lowest 13% above U.S.
Kids under 18	17.5%±4.9Lowest U.S.: 22%	21.2%±3.8Highest U.S.: 22%
	Douglas and Chester are within the Census margin of error here, so we can’t say which is really higher.
Age 65+	26.8%±4Highest U.S.: 17.2%	15.4%±3.1Lowest U.S.: 17.2%
Bachelor’s degree+adults 25+	47.9%Highest U.S.: 35.7%	41.7%Lowest U.S.: 35.7%
Enrolled in collegeshare of residents	4%±2.9Lowest U.S.: 6.4%	5.4%±2.3Highest U.S.: 6.4%
	Douglas and Chester are within the Census margin of error here, so we can’t say which is really higher.
Cost of living
Household incomemedian	$109,191±$18kLowest 35% above U.S.	$152,267±$10kHighest 89% above U.S.
Home valuemedian, owner-occupied	$442,200±$25kLowest 33% above U.S.	$470,600±$29kHighest 41% above U.S.
	Douglas and Chester are within the Census margin of error here, so we can’t say which is really higher.
Rentmedian gross, monthly	$1,549±$247Highest 10% above U.S.	$1,503±$697Lowest 6% above U.S.
	Chester and Douglas are within the Census margin of error here, so we can’t say which is really higher.
Property taxmedian, yearly	$6,364Highest 104% above U.S.	$6,338Lowest 103% above U.S.
Renters paying 30%+of income on rent	57.4%±22.1Highest U.S.: 51.1%	33.9%±17.4Lowest U.S.: 51.1%
	Chester and Douglas are within the Census margin of error here, so we can’t say which is really higher.
Below poverty line	11.8%Highest U.S.: 12.5%	4.8%Lowest U.S.: 12.5%
Housing
Homeownersof occupied homes	73.2%Lowest U.S.: 65.2%	83.8%Highest U.S.: 65.2%
Typical home builtmedian year	1969Lowest 11 yrs older than U.S.	1986Highest 6 yrs newer than U.S.
Getting to work
Average commuteone way	28 minLowest 7% above U.S.	34 minHighest 28% above U.S.
Work from home	18.3%±5.6Lowest U.S.: 15.1%	20.9%±4.9Highest U.S.: 15.1%
	Douglas and Chester 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	#8 of 149 in CT	#177 of 282 in MA
School district	Chester School District	Douglas
High school in town	None 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.