What stands out worked out from the figures below

Cheshire has the most affordable homes ($440k median).

Guilford has the most expensive homes ($516k 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	Cheshire	Guilford
People
Population	29,040Highest	22,108Lowest
Median age	44.9±1.4Lowest 9% above CT	51.1±1.9Highest 24% above CT
Kids under 18	21.9%±2.3Highest CT: 20.2%	20.8%±2.4Lowest CT: 20.2%
	Cheshire and Guilford are within the Census margin of error here, so we can’t say which is really higher.
Age 65+	21.3%±1.8Lowest CT: 18.5%	26.6%±2.7Highest CT: 18.5%
Bachelor’s degree+adults 25+	60.7%Highest CT: 42.5%	60.6%Lowest CT: 42.5%
Enrolled in collegeshare of residents	4.5%±1.1Highest CT: 7.1%	3.7%±1Lowest CT: 7.1%
	Cheshire and Guilford are within the Census margin of error here, so we can’t say which is really higher.
Cost of living
Household incomemedian	$146,528±$12kHighest 53% above CT	$137,816±$11kLowest 44% above CT
	Cheshire and Guilford are within the Census margin of error here, so we can’t say which is really higher.
Home valuemedian, owner-occupied	$440,000±$17kLowest 20% above CT	$515,800±$40kHighest 41% above CT
Rentmedian gross, monthly	$1,398±$116Lowest 6% below CT	$1,717±$128Highest 15% above CT
Property taxmedian, yearly	$7,755Lowest 17% above CT	$8,744Highest 32% above CT
Renters paying 30%+of income on rent	44.9%±6.3Lowest CT: 52.6%	47.4%±9Highest CT: 52.6%
	Guilford and Cheshire are within the Census margin of error here, so we can’t say which is really higher.
Below poverty line	5%Highest CT: 10%	2.8%Lowest CT: 10%
Housing
Homeownersof occupied homes	86.6%Highest CT: 66.5%	83.7%Lowest CT: 66.5%
Typical home builtmedian year	1974 7 yrs newer than CT	1974 7 yrs newer than CT
Getting to work
Average commuteone way	29 minHighest 9% above CT	26 minLowest about the CT average
Work from home	19.1%±2.7Lowest CT: 16%	21.7%±3.3Highest CT: 16%
	Guilford and Cheshire 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	#18 of 149 in CT	#15 of 149 in CT
School district	Cheshire School District	Guilford School District
High school in town	Cheshire High School	Guilford High School
Students per teacherat that high school	11.6Lowest	11.8Highest
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.