What stands out worked out from the figures below

Chester has the most people working from home (18.3%).

Webster has the youngest population (median age 39.9).

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	Chester	Webster
People
Population	3,825Lowest	17,748Highest
Growth since 20102010 → 2020 census	—	+6% U.S.: +7.4%
Median age	54±3.4Highest 39% above U.S.	39.9±2.9Lowest about the U.S. average
Kids under 18	17.5%±4.9Lowest U.S.: 22%	19.6%±2.9Highest U.S.: 22%
	Webster 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%	19.6%±2.5Lowest U.S.: 17.2%
Bachelor’s degree+adults 25+	47.9%Highest U.S.: 35.7%	25.3%Lowest U.S.: 35.7%
Enrolled in collegeshare of residents	4%±2.9Lowest U.S.: 6.4%	5.8%±1.6Highest U.S.: 6.4%
	Webster 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±$18kHighest 35% above U.S.	$72,895±$6kLowest 10% below U.S.
Home valuemedian, owner-occupied	$442,200±$25kHighest 33% above U.S.	$361,500±$12kLowest 9% above U.S.
Rentmedian gross, monthly	$1,549±$247Highest 10% above U.S.	$1,228±$81Lowest 13% below U.S.
	Chester and Webster 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.	$3,999Lowest 28% above U.S.
Renters paying 30%+of income on rent	57.4%±22.1Highest U.S.: 51.1%	45.7%±6.7Lowest U.S.: 51.1%
	Chester and Webster are within the Census margin of error here, so we can’t say which is really higher.
Below poverty line	11.8%Lowest U.S.: 12.5%	12.7%Highest U.S.: 12.5%
Housing
Homeownersof occupied homes	73.2%Highest U.S.: 65.2%	59.8%Lowest U.S.: 65.2%
Typical home builtmedian year	1969Highest 11 yrs older than U.S.	1962Lowest 18 yrs older than U.S.
Getting to work
Average commuteone way	28 minLowest 7% above U.S.	31 minHighest 16% above U.S.
Work from home	18.3%±5.6Highest U.S.: 15.1%	8%±2.5Lowest U.S.: 15.1%
Schools
Public school scoresrank in state, math + reading	#8 of 149 in CT	#271 of 282 in MA
School district	Chester School District	Webster
High school in town	None in town	Bartlett High School
Students per teacherat that high school	—	11.6
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.