Compare towns
Derby vs Winchester vs Windsor
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).
Winchester has the oldest population (median age 49.1).
Windsor has the highest household income ($105k).
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 | Winchester | Windsor |
|---|---|---|---|
| Your priorities | |||
| People | |||
| Population | 12,487 |
10,284Lowest |
29,468Highest |
| Growth since 20102010 → 2020 census | -4.5% CT: +0.9% |
— | — |
| Median age | 46.4±3.1 13% above CT |
49.1±6.2Highest 19% above CT |
43.7±1.9Lowest 6% 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% |
15.4%±2.9 CT: 20.2% |
19.2%±2.1Highest 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% |
27.4%±5.1Highest CT: 18.5% |
20%±2Lowest 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% |
27.8%Lowest CT: 42.5% |
43.2%Highest CT: 42.5% |
| Enrolled in collegeshare of residents | 5.9%±2Highest CT: 7.1% |
4.2%±1.7Lowest CT: 7.1% |
5.9%±1.3Highest CT: 7.1% |
| Cost of living | |||
| Household incomemedian | $79,500±$11k 17% below CT |
$66,519±$12kLowest 31% below CT |
$104,725±$8kHighest 9% above CT |
| Home valuemedian, owner-occupied | $256,700±$21k 30% below CT |
$249,500±$17kLowest 32% below CT |
$305,200±$11kHighest 17% below CT |
| Rentmedian gross, monthly | $1,452±$95 about the CT average |
$1,174±$116Lowest 21% below CT |
$1,681±$62Highest 13% above CT |
| Property taxmedian, yearly | $5,510Highest 17% below CT |
$4,780Lowest 28% below CT |
$5,351 19% below CT |
| Renters paying 30%+of income on rent | 53.9%±12.6Highest CT: 52.6% |
48.9%±15.8 CT: 52.6% |
44.9%±10.9Lowest 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% |
12.8%Highest CT: 10% |
6.7%Lowest CT: 10% |
| Housing | |||
| Homeownersof occupied homes | 61.9%Lowest CT: 66.5% |
65.8% CT: 66.5% |
82.4%Highest CT: 66.5% |
| Typical home builtmedian year | 1967 same as CT |
1955Lowest 12 yrs older than CT |
1970Highest 3 yrs newer than CT |
| Getting to work | |||
| Average commuteone way | 27 minHighest about the CT average |
26 min about the CT average |
21 minLowest 19% below CT |
| Work from home | 15.1%±4.8 CT: 16% |
6.9%±2.7Lowest CT: 16% |
16.1%±3.2Highest 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 | #97 of 149 in CT | #117 of 149 in CT |
| School district | Derby School District | Explorations District · Regional School District 07 | Capitol Region Education Council · Windsor School District |
| High school in town | Derby High School | Northwestern Regional High School | Windsor High School |
| Students per teacherat that high school | 9.7Lowest |
9.7Lowest |
10.2Highest |
| 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.