What stands out worked out from the figures below

East Hampton has the highest household income ($125k).

Winchester has the most affordable homes ($250k 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	East Hampton	Winchester
People
Population	12,925Highest	10,284Lowest
Median age	43.6±3.7Lowest 6% above CT	49.1±6.2Highest 19% above CT
	Winchester and East Hampton are within the Census margin of error here, so we can’t say which is really higher.
Kids under 18	21.4%±3Highest CT: 20.2%	15.4%±2.9Lowest CT: 20.2%
Age 65+	20.8%±2.8Lowest CT: 18.5%	27.4%±5.1Highest CT: 18.5%
	Winchester and East Hampton are within the Census margin of error here, so we can’t say which is really higher.
Bachelor’s degree+adults 25+	39%Highest CT: 42.5%	27.8%Lowest CT: 42.5%
Enrolled in collegeshare of residents	5.2%±1.8Highest CT: 7.1%	4.2%±1.7Lowest CT: 7.1%
	East Hampton and Winchester are within the Census margin of error here, so we can’t say which is really higher.
Cost of living
Household incomemedian	$124,577±$11kHighest 30% above CT	$66,519±$12kLowest 31% below CT
Home valuemedian, owner-occupied	$349,000±$14kHighest 5% below CT	$249,500±$17kLowest 32% below CT
Rentmedian gross, monthly	$1,393±$150Highest 6% below CT	$1,174±$116Lowest 21% below CT
	East Hampton and Winchester are within the Census margin of error here, so we can’t say which is really higher.
Property taxmedian, yearly	$6,681Highest about the CT average	$4,780Lowest 28% below CT
Renters paying 30%+of income on rent	48.7%±16.4Lowest CT: 52.6%	48.9%±15.8Highest CT: 52.6%
	Winchester and East Hampton are within the Census margin of error here, so we can’t say which is really higher.
Below poverty line	4%Lowest CT: 10%	12.8%Highest CT: 10%
Housing
Homeownersof occupied homes	85.5%Highest CT: 66.5%	65.8%Lowest CT: 66.5%
Typical home builtmedian year	1977Highest 10 yrs newer than CT	1955Lowest 12 yrs older than CT
Getting to work
Average commuteone way	30 minHighest 11% above CT	26 minLowest about the CT average
Work from home	12.7%±2.4Highest CT: 16%	6.9%±2.7Lowest CT: 16%
Schools
Public school scoresrank in state, math + reading	#75 of 149 in CT	#97 of 149 in CT
School district	East Hampton School District	Explorations District · Regional School District 07
High school in town	East Hampton High School	Northwestern Regional High School
Students per teacherat that high school	11.3Highest	9.7Lowest
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.