Compare towns
Deep River vs Winchester vs Chester
Cost, people, housing, commute and schools, side by side, each benchmarked against Connecticut.
What stands out worked out from the figures below
Deep River has the shortest commute (24 min average).
Winchester has the most affordable homes ($250k median).
Chester has the most expensive homes ($442k 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.
| Measure | Deep River | Winchester | Chester |
|---|---|---|---|
| Your priorities | |||
| People | |||
| Population | 4,458 |
10,284Highest |
3,825Lowest |
| Median age | 46.2±5.6Lowest 12% above CT |
49.1±6.2 19% above CT |
54±3.4Highest 31% above CT |
| Chester and Winchester are within the Census margin of error here, so we can’t say which is really higher. | |||
| Kids under 18 | 16.6%±4.7 CT: 20.2% |
15.4%±2.9Lowest CT: 20.2% |
17.5%±4.9Highest CT: 20.2% |
| Chester and Deep River 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% |
26.8%±4 CT: 18.5% |
| Winchester and Chester are within the Census margin of error here, so we can’t say which is really higher. | |||
| Bachelor’s degree+adults 25+ | 44.6% CT: 42.5% |
27.8%Lowest CT: 42.5% |
47.9%Highest CT: 42.5% |
| Enrolled in collegeshare of residents | 3.8%±2.2Lowest CT: 7.1% |
4.2%±1.7Highest CT: 7.1% |
4%±2.9 CT: 7.1% |
| Winchester and Chester are within the Census margin of error here, so we can’t say which is really higher. | |||
| Cost of living | |||
| Household incomemedian | $90,253±$19k 6% below CT |
$66,519±$12kLowest 31% below CT |
$109,191±$18kHighest 14% above CT |
| Chester and Deep River are within the Census margin of error here, so we can’t say which is really higher. | |||
| Home valuemedian, owner-occupied | $362,200±$26k about the CT average |
$249,500±$17kLowest 32% below CT |
$442,200±$25kHighest 21% above CT |
| Rentmedian gross, monthly | $1,221±$185 18% below CT |
$1,174±$116Lowest 21% below CT |
$1,549±$247Highest 4% above CT |
| Chester and Deep River are within the Census margin of error here, so we can’t say which is really higher. | |||
| Property taxmedian, yearly | $6,092 8% below CT |
$4,780Lowest 28% below CT |
$6,364Highest 4% below CT |
| Renters paying 30%+of income on rent | 58.2%±22.9Highest CT: 52.6% |
48.9%±15.8Lowest CT: 52.6% |
57.4%±22.1 CT: 52.6% |
| Deep River and Chester 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% |
11.8% CT: 10% |
| Housing | |||
| Homeownersof occupied homes | 69.2% CT: 66.5% |
65.8%Lowest CT: 66.5% |
73.2%Highest CT: 66.5% |
| Typical home builtmedian year | 1974Highest 7 yrs newer than CT |
1955Lowest 12 yrs older than CT |
1969 2 yrs newer than CT |
| Getting to work | |||
| Average commuteone way | 24 minLowest 9% below CT |
26 min about the CT average |
28 minHighest 7% above CT |
| Work from home | 15.2%±5.6 CT: 16% |
6.9%±2.7Lowest CT: 16% |
18.3%±5.6Highest CT: 16% |
| Chester and Deep River 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 | #8 of 149 in CT |
| School district | Deep River School District · Regional School District 04 | Explorations District · Regional School District 07 | Chester School District |
| High school in town | Valley Regional High School | Northwestern Regional High School | None in town |
| Students per teacherat that high school | 9.3Lowest |
9.7Highest |
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| On TownTapestry | |||
| Old photos in History | None yet | 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.