What stands out worked out from the figures below

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

Winchester has the oldest population (median age 49.1).

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