Compare towns
Chester vs Windsor vs Essex
Cost, people, housing, commute and schools, side by side, each benchmarked against Connecticut.
What stands out worked out from the figures below
Chester has the most renters (26.8% rent).
Windsor has the most affordable homes ($305k median).
Essex has the most expensive homes ($552k 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 | Chester | Windsor | Essex |
|---|---|---|---|
| Your priorities | |||
| People | |||
| Population | 3,825Lowest |
29,468Highest |
6,794 |
| Median age | 54±3.4Highest 31% above CT |
43.7±1.9Lowest 6% above CT |
52.4±3.6 27% above CT |
| Chester and Essex are within the Census margin of error here, so we can’t say which is really higher. | |||
| Kids under 18 | 17.5%±4.9 CT: 20.2% |
19.2%±2.1Highest CT: 20.2% |
16.2%±3.3Lowest CT: 20.2% |
| Windsor and Chester are within the Census margin of error here, so we can’t say which is really higher. | |||
| Age 65+ | 26.8%±4Highest CT: 18.5% |
20%±2Lowest CT: 18.5% |
26.4%±3.8 CT: 18.5% |
| Chester and Essex are within the Census margin of error here, so we can’t say which is really higher. | |||
| Bachelor’s degree+adults 25+ | 47.9% CT: 42.5% |
43.2%Lowest CT: 42.5% |
54.9%Highest CT: 42.5% |
| Enrolled in collegeshare of residents | 4%±2.9Lowest CT: 7.1% |
5.9%±1.3 CT: 7.1% |
8.7%±3.7Highest CT: 7.1% |
| Essex and Windsor are within the Census margin of error here, so we can’t say which is really higher. | |||
| Cost of living | |||
| Household incomemedian | $109,191±$18kHighest 14% above CT |
$104,725±$8k 9% above CT |
$104,395±$7kLowest 9% above CT |
| Chester and Windsor are within the Census margin of error here, so we can’t say which is really higher. | |||
| Home valuemedian, owner-occupied | $442,200±$25k 21% above CT |
$305,200±$11kLowest 17% below CT |
$552,000±$53kHighest 50% above CT |
| Rentmedian gross, monthly | $1,549±$247Lowest 4% above CT |
$1,681±$62Highest 13% above CT |
$1,623±$326 9% above CT |
| Windsor and Essex are within the Census margin of error here, so we can’t say which is really higher. | |||
| Property taxmedian, yearly | $6,364Highest 4% below CT |
$5,351Lowest 19% below CT |
$5,678 15% below CT |
| Renters paying 30%+of income on rent | 57.4%±22.1Highest CT: 52.6% |
44.9%±10.9 CT: 52.6% |
38.5%±9.7Lowest CT: 52.6% |
| Chester and Windsor are within the Census margin of error here, so we can’t say which is really higher. | |||
| Below poverty line | 11.8%Highest CT: 10% |
6.7% CT: 10% |
3.2%Lowest CT: 10% |
| Housing | |||
| Homeownersof occupied homes | 73.2%Lowest CT: 66.5% |
82.4%Highest CT: 66.5% |
78.1% CT: 66.5% |
| Typical home builtmedian year | 1969Lowest 2 yrs newer than CT |
1970 3 yrs newer than CT |
1971Highest 4 yrs newer than CT |
| Getting to work | |||
| Average commuteone way | 28 minHighest 7% above CT |
21 minLowest 19% below CT |
27 min 3% above CT |
| Work from home | 18.3%±5.6 CT: 16% |
16.1%±3.2Lowest CT: 16% |
19.4%±4.6Highest CT: 16% |
| Essex and Chester 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 | #8 of 149 in CT | #117 of 149 in CT | #33 of 149 in CT |
| School district | Chester School District | Capitol Region Education Council · Windsor School District | Essex School District |
| High school in town | None in town | Windsor High School | None in town |
| Students per teacherat that high school | — | 10.2 |
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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.