Compare towns
Redding vs Winchester vs Weston
Cost, people, housing, commute and schools, side by side, each benchmarked against Connecticut.
What stands out worked out from the figures below
Redding has the oldest population (median age 52).
Winchester has the most affordable homes ($250k median).
Weston has the most expensive homes ($997k 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 | Redding | Winchester | Weston |
|---|---|---|---|
| Your priorities | |||
| People | |||
| Population | 8,780Lowest |
10,284 |
10,396Highest |
| Median age | 52±2Highest 27% above CT |
49.1±6.2 19% above CT |
45.7±2.7Lowest 11% above CT |
| Redding and Winchester are within the Census margin of error here, so we can’t say which is really higher. | |||
| Kids under 18 | 19.1%±2.8 CT: 20.2% |
15.4%±2.9Lowest CT: 20.2% |
26.4%±3.2Highest CT: 20.2% |
| Age 65+ | 26.4%±3.3 CT: 18.5% |
27.4%±5.1Highest CT: 18.5% |
17.3%±2.4Lowest CT: 18.5% |
| Winchester and Redding are within the Census margin of error here, so we can’t say which is really higher. | |||
| Bachelor’s degree+adults 25+ | 72.1% CT: 42.5% |
27.8%Lowest CT: 42.5% |
83.7%Highest CT: 42.5% |
| Enrolled in collegeshare of residents | 3.8%±1.8Lowest CT: 7.1% |
4.2%±1.7 CT: 7.1% |
5.3%±2.2Highest CT: 7.1% |
| Weston and Winchester are within the Census margin of error here, so we can’t say which is really higher. | |||
| Cost of living | |||
| Household incomemedian | $186,060±$15k 94% above CT |
$66,519±$12kLowest 31% below CT |
$250,001Highest 161% above CT |
| Home valuemedian, owner-occupied | $706,300±$33k 93% above CT |
$249,500±$17kLowest 32% below CT |
$996,700±$52kHighest 172% above CT |
| Rentmedian gross, monthly | $2,101±$304 41% above CT |
$1,174±$116Lowest 21% below CT |
$3,501Highest 135% above CT |
| Property taxmedian, yearly | $10,000+Highest at least 51% above CT |
$4,780Lowest 28% below CT |
$10,000+Highest at least 51% above CT |
| Renters paying 30%+of income on rent | 64.9%±19.3 CT: 52.6% |
48.9%±15.8Lowest CT: 52.6% |
77.9%±36.6Highest CT: 52.6% |
| Weston and Redding are within the Census margin of error here, so we can’t say which is really higher. | |||
| Below poverty line | 4% CT: 10% |
12.8%Highest CT: 10% |
1.8%Lowest CT: 10% |
| Housing | |||
| Homeownersof occupied homes | 91.6% CT: 66.5% |
65.8%Lowest CT: 66.5% |
96.9%Highest CT: 66.5% |
| Typical home builtmedian year | 1972Highest 5 yrs newer than CT |
1955Lowest 12 yrs older than CT |
1967 same as CT |
| Getting to work | |||
| Average commuteone way | 36 min 36% above CT |
26 minLowest about the CT average |
47 minHighest 76% above CT |
| Work from home | 32.5%±4.9 CT: 16% |
6.9%±2.7Lowest CT: 16% |
44.9%±7.5Highest CT: 16% |
| Weston and Redding 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 | #14 of 149 in CT | #97 of 149 in CT | #5 of 149 in CT |
| School district | Redding School District · Regional School District 09 | Explorations District · Regional School District 07 | Weston School District |
| High school in town | Joel Barlow High School | Northwestern Regional High School | Weston High School |
| Students per teacherat that high school | 11.1Highest |
9.7Lowest |
10.8 |
| 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.

