What stands out worked out from the figures below

Winchester has the most affordable homes ($250k median).

Preston has the highest household income ($117k).

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	Preston
People
Population	10,284Highest	4,821Lowest
Median age	49.1±6.2Highest 19% above CT	46.2±7Lowest 12% above CT
	Winchester and Preston 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%	18.7%±4.4Highest CT: 20.2%
	Preston 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%	23%±4.7Lowest CT: 18.5%
	Winchester and Preston 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%	28.5%Highest CT: 42.5%
Enrolled in collegeshare of residents	4.2%±1.7Lowest CT: 7.1%	4.9%±2.4Highest CT: 7.1%
	Preston 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	$116,648±$27kHighest 22% above CT
Home valuemedian, owner-occupied	$249,500±$17kLowest 32% below CT	$361,900±$13kHighest about the CT average
Rentmedian gross, monthly	$1,174±$116Lowest 21% below CT	$1,433±$1kHighest 4% below CT
	Preston and Winchester are within the Census margin of error here, so we can’t say which is really higher.
Property taxmedian, yearly	$4,780Highest 28% below CT	$4,749Lowest 29% below CT
Renters paying 30%+of income on rent	48.9%±15.8Lowest CT: 52.6%	52.6%±12.5Highest CT: 52.6%
	Preston and Winchester 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%	2.4%Lowest CT: 10%
Housing
Homeownersof occupied homes	65.8%Lowest CT: 66.5%	91.7%Highest CT: 66.5%
Typical home builtmedian year	1955Lowest 12 yrs older than CT	1970Highest 3 yrs newer than CT
Getting to work
Average commuteone way	26 minHighest about the CT average	22 minLowest 17% below CT
Work from home	6.9%±2.7Lowest CT: 16%	10.3%±6Highest CT: 16%
	Preston and Winchester 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	#97 of 149 in CT	#93 of 149 in CT
School district	Explorations District · Regional School District 07	Preston 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.