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.

MeasureReddingWinchesterWeston
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.