What stands out worked out from the figures below

Winchester has the oldest population (median age 49.1).

Ashford has the most people working from home (19.3%).

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	Winchester	Ashford
People
Population	10,284Highest	4,226Lowest
Median age	49.1±6.2Highest 19% above CT	37.9±10.3Lowest 8% below CT
	Winchester and Ashford are within the Census margin of error here, so we can’t say which is really higher.
Kids under 18	15.4%±2.9Lowest CT: 20.2%	18.5%±5.5Highest CT: 20.2%
	Ashford and Winchester are within the Census margin of error here, so we can’t say which is really higher.
Age 65+	27.4%±5.1Highest CT: 18.5%	18.9%±3.7Lowest CT: 18.5%
	Winchester and Ashford are within the Census margin of error here, so we can’t say which is really higher.
Bachelor’s degree+adults 25+	27.8%Lowest CT: 42.5%	35.3%Highest CT: 42.5%
Enrolled in collegeshare of residents	4.2%±1.7Lowest CT: 7.1%	4.4%±1.7Highest CT: 7.1%
	Ashford and Winchester are within the Census margin of error here, so we can’t say which is really higher.
Cost of living
Household incomemedian	$66,519±$12kLowest 31% below CT	$121,926±$23kHighest 27% above CT
Home valuemedian, owner-occupied	$249,500±$17kLowest 32% below CT	$334,800±$18kHighest 9% below CT
Rentmedian gross, monthly	$1,174±$116Lowest 21% below CT	$1,246±$208Highest 16% below CT
	Ashford and Winchester are within the Census margin of error here, so we can’t say which is really higher.
Property taxmedian, yearly	$4,780Lowest 28% below CT	$6,982Highest 5% above CT
Renters paying 30%+of income on rent	48.9%±15.8Highest CT: 52.6%	47%±26Lowest CT: 52.6%
	Winchester and Ashford are within the Census margin of error here, so we can’t say which is really higher.
Below poverty line	12.8%Highest CT: 10%	5.4%Lowest CT: 10%
Housing
Homeownersof occupied homes	65.8%Lowest CT: 66.5%	76.8%Highest CT: 66.5%
Typical home builtmedian year	1955Lowest 12 yrs older than CT	1982Highest 15 yrs newer than CT
Getting to work
Average commuteone way	26 minLowest about the CT average	34 minHighest 30% above CT
Work from home	6.9%±2.7Lowest CT: 16%	19.3%±5.5Highest CT: 16%
Schools
Public school scoresrank in state, math + reading	#97 of 149 in CT	#90 of 149 in CT
School district	Explorations District · Regional School District 07	Ashford School District
High school in town	Northwestern Regional High School	None in town
Students per teacherat that high school	9.7	—
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.