Compare towns
Derby vs Windsor vs Winchester
Cost, people, housing, commute and schools, side by side, each benchmarked against Connecticut.
What stands out worked out from the figures below
Derby has the most renters (38.1% rent).
Windsor has the highest household income ($105k).
Winchester has the oldest population (median age 49.1).
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 | Derby | Windsor | Winchester |
|---|---|---|---|
| Your priorities | |||
| People | |||
| Population | 12,487 |
29,468Highest |
10,284Lowest |
| Growth since 20102010 → 2020 census | -4.5% CT: +0.9% |
— | — |
| Median age | 46.4±3.1 13% above CT |
43.7±1.9Lowest 6% above CT |
49.1±6.2Highest 19% above CT |
| Winchester and Derby are within the Census margin of error here, so we can’t say which is really higher. | |||
| Kids under 18 | 14.6%±2.9Lowest CT: 20.2% |
19.2%±2.1Highest CT: 20.2% |
15.4%±2.9 CT: 20.2% |
| Windsor and Winchester are within the Census margin of error here, so we can’t say which is really higher. | |||
| Age 65+ | 21.1%±3.9 CT: 18.5% |
20%±2Lowest CT: 18.5% |
27.4%±5.1Highest CT: 18.5% |
| Winchester and Derby are within the Census margin of error here, so we can’t say which is really higher. | |||
| Bachelor’s degree+adults 25+ | 35.6% CT: 42.5% |
43.2%Highest CT: 42.5% |
27.8%Lowest CT: 42.5% |
| Enrolled in collegeshare of residents | 5.9%±2Highest CT: 7.1% |
5.9%±1.3Highest CT: 7.1% |
4.2%±1.7Lowest CT: 7.1% |
| Cost of living | |||
| Household incomemedian | $79,500±$11k 17% below CT |
$104,725±$8kHighest 9% above CT |
$66,519±$12kLowest 31% below CT |
| Home valuemedian, owner-occupied | $256,700±$21k 30% below CT |
$305,200±$11kHighest 17% below CT |
$249,500±$17kLowest 32% below CT |
| Rentmedian gross, monthly | $1,452±$95 about the CT average |
$1,681±$62Highest 13% above CT |
$1,174±$116Lowest 21% below CT |
| Property taxmedian, yearly | $5,510Highest 17% below CT |
$5,351 19% below CT |
$4,780Lowest 28% below CT |
| Renters paying 30%+of income on rent | 53.9%±12.6Highest CT: 52.6% |
44.9%±10.9Lowest CT: 52.6% |
48.9%±15.8 CT: 52.6% |
| Derby and Winchester are within the Census margin of error here, so we can’t say which is really higher. | |||
| Below poverty line | 10.8% CT: 10% |
6.7%Lowest CT: 10% |
12.8%Highest CT: 10% |
| Housing | |||
| Homeownersof occupied homes | 61.9%Lowest CT: 66.5% |
82.4%Highest CT: 66.5% |
65.8% CT: 66.5% |
| Typical home builtmedian year | 1967 same as CT |
1970Highest 3 yrs newer than CT |
1955Lowest 12 yrs older than CT |
| Getting to work | |||
| Average commuteone way | 27 minHighest about the CT average |
21 minLowest 19% below CT |
26 min about the CT average |
| Work from home | 15.1%±4.8 CT: 16% |
16.1%±3.2Highest CT: 16% |
6.9%±2.7Lowest CT: 16% |
| Windsor and Derby 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 | #138 of 149 in CT | #117 of 149 in CT | #97 of 149 in CT |
| School district | Derby School District | Capitol Region Education Council · Windsor School District | Explorations District · Regional School District 07 |
| High school in town | Derby High School | Windsor High School | Northwestern Regional High School |
| Students per teacherat that high school | 9.7Lowest |
10.2Highest |
9.7Lowest |
| 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.