What stands out worked out from the figures below

Chester has the most affordable homes ($442k median).

Roxbury has the most expensive homes ($715k 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	Chester	Roxbury
People
Population	3,825Highest	2,185Lowest
Median age	54±3.4Lowest 31% above CT	54.7±1.8Highest 33% above CT
	Roxbury and Chester are within the Census margin of error here, so we can’t say which is really higher.
Kids under 18	17.5%±4.9Highest CT: 20.2%	14.3%±4Lowest CT: 20.2%
	Chester and Roxbury are within the Census margin of error here, so we can’t say which is really higher.
Age 65+	26.8%±4Lowest CT: 18.5%	31%±5.5Highest CT: 18.5%
	Roxbury and Chester are within the Census margin of error here, so we can’t say which is really higher.
Bachelor’s degree+adults 25+	47.9%Lowest CT: 42.5%	65.2%Highest CT: 42.5%
Enrolled in collegeshare of residents	4%±2.9Lowest CT: 7.1%	5.8%±3.3Highest CT: 7.1%
	Roxbury 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 14% above CT	$123,864±$27kHighest 29% above CT
	Roxbury and Chester are within the Census margin of error here, so we can’t say which is really higher.
Home valuemedian, owner-occupied	$442,200±$25kLowest 21% above CT	$714,500±$77kHighest 95% above CT
Rentmedian gross, monthly	$1,549±$247Lowest 4% above CT	$1,713±$418Highest 15% above CT
	Roxbury and Chester are within the Census margin of error here, so we can’t say which is really higher.
Property taxmedian, yearly	$6,364Lowest 4% below CT	$6,591Highest about the CT average
Renters paying 30%+of income on rent	57.4%±22.1Lowest CT: 52.6%	61.5%±48.3Highest CT: 52.6%
	Roxbury and Chester are within the Census margin of error here, so we can’t say which is really higher.
Below poverty line	11.8%Highest CT: 10%	3.7%Lowest CT: 10%
Housing
Homeownersof occupied homes	73.2%Lowest CT: 66.5%	82.7%Highest CT: 66.5%
Typical home builtmedian year	1969Lowest 2 yrs newer than CT	1981Highest 14 yrs newer than CT
Getting to work
Average commuteone way	28 minLowest 7% above CT	37 minHighest 38% above CT
Work from home	18.3%±5.6Highest CT: 16%	17.4%±6.6Lowest CT: 16%
	Chester and Roxbury 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	—
School district	Chester School District	Regional School District 12
High school in town	None in town	None in town
On TownTapestry
Old photos in History	None yet	None yet

CT 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.