What stands out worked out from the figures below

Deep River has the most people working from home (15.2%).

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	Deep River	Winchester
People
Population	4,458Lowest	10,284Highest
Median age	46.2±5.6Lowest 12% above CT	49.1±6.2Highest 19% above CT
	Winchester and Deep River are within the Census margin of error here, so we can’t say which is really higher.
Kids under 18	16.6%±4.7Highest CT: 20.2%	15.4%±2.9Lowest CT: 20.2%
	Deep River and Winchester are within the Census margin of error here, so we can’t say which is really higher.
Age 65+	22.1%±4.1Lowest CT: 18.5%	27.4%±5.1Highest CT: 18.5%
	Winchester and Deep River are within the Census margin of error here, so we can’t say which is really higher.
Bachelor’s degree+adults 25+	44.6%Highest CT: 42.5%	27.8%Lowest CT: 42.5%
Enrolled in collegeshare of residents	3.8%±2.2Lowest CT: 7.1%	4.2%±1.7Highest CT: 7.1%
	Winchester and Deep River are within the Census margin of error here, so we can’t say which is really higher.
Cost of living
Household incomemedian	$90,253±$19kHighest 6% below CT	$66,519±$12kLowest 31% below CT
	Deep River and Winchester are within the Census margin of error here, so we can’t say which is really higher.
Home valuemedian, owner-occupied	$362,200±$26kHighest about the CT average	$249,500±$17kLowest 32% below CT
Rentmedian gross, monthly	$1,221±$185Highest 18% below CT	$1,174±$116Lowest 21% below CT
	Deep River and Winchester are within the Census margin of error here, so we can’t say which is really higher.
Property taxmedian, yearly	$6,092Highest 8% below CT	$4,780Lowest 28% below CT
Renters paying 30%+of income on rent	58.2%±22.9Highest CT: 52.6%	48.9%±15.8Lowest CT: 52.6%
	Deep River and Winchester are within the Census margin of error here, so we can’t say which is really higher.
Below poverty line	8.2%Lowest CT: 10%	12.8%Highest CT: 10%
Housing
Homeownersof occupied homes	69.2%Highest CT: 66.5%	65.8%Lowest CT: 66.5%
Typical home builtmedian year	1974Highest 7 yrs newer than CT	1955Lowest 12 yrs older than CT
Getting to work
Average commuteone way	24 minLowest 9% below CT	26 minHighest about the CT average
Work from home	15.2%±5.6Highest CT: 16%	6.9%±2.7Lowest CT: 16%
	Deep River 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	#70 of 149 in CT	#97 of 149 in CT
School district	Deep River School District · Regional School District 04	Explorations District · Regional School District 07
High school in town	Valley Regional 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.