What stands out worked out from the figures below

Redding has the most people working from home (32.5%).

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	Redding	Winchester
People
Population	8,780Lowest	10,284Highest
Median age	52±2Highest 27% above CT	49.1±6.2Lowest 19% above CT
	Redding and Winchester are within the Census margin of error here, so we can’t say which is really higher.
Kids under 18	19.1%±2.8Highest CT: 20.2%	15.4%±2.9Lowest CT: 20.2%
	Redding and Winchester are within the Census margin of error here, so we can’t say which is really higher.
Age 65+	26.4%±3.3Lowest CT: 18.5%	27.4%±5.1Highest CT: 18.5%
	Winchester and Redding are within the Census margin of error here, so we can’t say which is really higher.
Bachelor’s degree+adults 25+	72.1%Highest CT: 42.5%	27.8%Lowest CT: 42.5%
Enrolled in collegeshare of residents	3.8%±1.8Lowest CT: 7.1%	4.2%±1.7Highest CT: 7.1%
	Winchester and Redding are within the Census margin of error here, so we can’t say which is really higher.
Cost of living
Household incomemedian	$186,060±$15kHighest 94% above CT	$66,519±$12kLowest 31% below CT
Home valuemedian, owner-occupied	$706,300±$33kHighest 93% above CT	$249,500±$17kLowest 32% below CT
Rentmedian gross, monthly	$2,101±$304Highest 41% above CT	$1,174±$116Lowest 21% below CT
Property taxmedian, yearly	$10,000+Highest at least 51% above CT	$4,780Lowest 28% below CT
Renters paying 30%+of income on rent	64.9%±19.3Highest CT: 52.6%	48.9%±15.8Lowest CT: 52.6%
	Redding and Winchester 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	91.6%Highest CT: 66.5%	65.8%Lowest CT: 66.5%
Typical home builtmedian year	1972Highest 5 yrs newer than CT	1955Lowest 12 yrs older than CT
Getting to work
Average commuteone way	36 minHighest 36% above CT	26 minLowest about the CT average
Work from home	32.5%±4.9Highest CT: 16%	6.9%±2.7Lowest CT: 16%
Schools
Public school scoresrank in state, math + reading	#14 of 149 in CT	#97 of 149 in CT
School district	Redding School District · Regional School District 09	Explorations District · Regional School District 07
High school in town	Joel Barlow High School	Northwestern Regional High School
Students per teacherat that high school	11.1Highest	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.