What stands out worked out from the figures below

Roxbury has the most expensive homes ($715k median).

Chester has the most affordable homes ($442k 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	Roxbury	Chester
People
Population	2,185Lowest	3,825Highest
Median age	54.7±1.8Highest 33% above CT	54±3.4Lowest 31% 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	14.3%±4Lowest CT: 20.2%	17.5%±4.9Highest 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+	31%±5.5Highest CT: 18.5%	26.8%±4Lowest 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+	65.2%Highest CT: 42.5%	47.9%Lowest CT: 42.5%
Enrolled in collegeshare of residents	5.8%±3.3Highest CT: 7.1%	4%±2.9Lowest 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	$123,864±$27kHighest 29% above CT	$109,191±$18kLowest 14% 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	$714,500±$77kHighest 95% above CT	$442,200±$25kLowest 21% above CT
Rentmedian gross, monthly	$1,713±$418Highest 15% above CT	$1,549±$247Lowest 4% 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	$6,591Highest about the CT average	$6,364Lowest 4% below CT
Renters paying 30%+of income on rent	61.5%±48.3Highest CT: 52.6%	57.4%±22.1Lowest 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	3.7%Lowest CT: 10%	11.8%Highest CT: 10%
Housing
Homeownersof occupied homes	82.7%Highest CT: 66.5%	73.2%Lowest CT: 66.5%
Typical home builtmedian year	1981Highest 14 yrs newer than CT	1969Lowest 2 yrs newer than CT
Getting to work
Average commuteone way	37 minHighest 38% above CT	28 minLowest 7% above CT
Work from home	17.4%±6.6Lowest CT: 16%	18.3%±5.6Highest 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	Regional School District 12	Chester School District
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.