What stands out worked out from the figures below

Hebron has the most people working from home (27.2%).

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	Hebron	Winchester
People
Population	9,157Lowest	10,284Highest
Median age	45.1±2.7Lowest 10% above CT	49.1±6.2Highest 19% above CT
	Winchester and Hebron are within the Census margin of error here, so we can’t say which is really higher.
Kids under 18	20.8%±3.3Highest CT: 20.2%	15.4%±2.9Lowest CT: 20.2%
	Hebron and Winchester are within the Census margin of error here, so we can’t say which is really higher.
Age 65+	18.6%±2.4Lowest CT: 18.5%	27.4%±5.1Highest CT: 18.5%
Bachelor’s degree+adults 25+	52.7%Highest CT: 42.5%	27.8%Lowest CT: 42.5%
Enrolled in collegeshare of residents	5.9%±2.1Highest CT: 7.1%	4.2%±1.7Lowest CT: 7.1%
	Hebron and Winchester are within the Census margin of error here, so we can’t say which is really higher.
Cost of living
Household incomemedian	$142,500±$23kHighest 49% above CT	$66,519±$12kLowest 31% below CT
Home valuemedian, owner-occupied	$385,800±$15kHighest 5% above CT	$249,500±$17kLowest 32% below CT
Rentmedian gross, monthly	$1,635±$241Highest 10% above CT	$1,174±$116Lowest 21% below CT
Property taxmedian, yearly	$8,263Highest 24% above CT	$4,780Lowest 28% below CT
Renters paying 30%+of income on rent	61.5%±28.4Highest CT: 52.6%	48.9%±15.8Lowest CT: 52.6%
	Hebron and Winchester are within the Census margin of error here, so we can’t say which is really higher.
Below poverty line	4.1%Lowest CT: 10%	12.8%Highest CT: 10%
Housing
Homeownersof occupied homes	88.8%Highest CT: 66.5%	65.8%Lowest CT: 66.5%
Typical home builtmedian year	1986Highest 19 yrs newer than CT	1955Lowest 12 yrs older than CT
Getting to work
Average commuteone way	33 minHighest 23% above CT	26 minLowest about the CT average
Work from home	27.2%±4.6Highest CT: 16%	6.9%±2.7Lowest CT: 16%
Schools
Public school scoresrank in state, math + reading	#28 of 149 in CT	#97 of 149 in CT
School district	Hebron School District · Regional School District 08	Explorations District · Regional School District 07
High school in town	RHAM High School	Northwestern Regional High School
Students per teacherat that high school	9.3Lowest	9.7Highest
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.