Compare towns

Winsted vs Windham vs Derby vs Winchester

Cost, people, housing, commute and schools, side by side, each benchmarked against Connecticut.

What stands out worked out from the figures below

Winsted has the oldest housing (typical home built 1942).
Windham has the most kids (20.1% under 18).
Derby has the most people working from home (15.1%).
Winchester has the most homeowners (65.8%).

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.

MeasureWinstedWindhamDerbyWinchester
People
Population
6,977Lowest
23,961Highest
12,487
10,284
Growth since 20102010 → 2020 census
-6.7%Lowest
CT: +0.9%
—
-4.5%Highest
CT: +0.9%
—
Median age
47.6±7.3
16% above CT
33.7±1.9Lowest
18% below CT
46.4±3.1
13% above CT
49.1±6.2Highest
19% above CT
Winchester and Winsted are within the Census margin of error here, so we can’t say which is really higher.
Kids under 18
14.4%±3.3Lowest
CT: 20.2%
20.1%±2.4Highest
CT: 20.2%
14.6%±2.9
CT: 20.2%
15.4%±2.9
CT: 20.2%
Windham and Winchester are within the Census margin of error here, so we can’t say which is really higher.
Age 65+
25%±4.2
CT: 18.5%
14.3%±1.9Lowest
CT: 18.5%
21.1%±3.9
CT: 18.5%
27.4%±5.1Highest
CT: 18.5%
Winchester and Winsted are within the Census margin of error here, so we can’t say which is really higher.
Bachelor’s degree+adults 25+
26.8%
CT: 42.5%
22.7%Lowest
CT: 42.5%
35.6%Highest
CT: 42.5%
27.8%
CT: 42.5%
Enrolled in collegeshare of residents
4.9%±2.4
CT: 7.1%
15.2%±1.8Highest
CT: 7.1%
5.9%±2
CT: 7.1%
4.2%±1.7Lowest
CT: 7.1%
Cost of living
Household incomemedian
$64,871±$12k
32% below CT
$55,736±$5kLowest
42% below CT
$79,500±$11kHighest
17% below CT
$66,519±$12k
31% below CT
Derby and Winchester are within the Census margin of error here, so we can’t say which is really higher.
Home valuemedian, owner-occupied
$218,900±$14k
40% below CT
$209,800±$9kLowest
43% below CT
$256,700±$21kHighest
30% below CT
$249,500±$17k
32% below CT
Derby and Winchester are within the Census margin of error here, so we can’t say which is really higher.
Rentmedian gross, monthly
$1,183±$130
20% below CT
$1,107±$69Lowest
26% below CT
$1,452±$95Highest
about the CT average
$1,174±$116
21% below CT
Property taxmedian, yearly
$3,754Lowest
43% below CT
$4,633
30% below CT
$5,510Highest
17% below CT
$4,780
28% below CT
Renters paying 30%+of income on rent
45.5%±16.7Lowest
CT: 52.6%
57.1%±8.1Highest
CT: 52.6%
53.9%±12.6
CT: 52.6%
48.9%±15.8
CT: 52.6%
Windham and Derby are within the Census margin of error here, so we can’t say which is really higher.
Below poverty line
15.9%
CT: 10%
20.7%Highest
CT: 10%
10.8%Lowest
CT: 10%
12.8%
CT: 10%
Housing
Homeownersof occupied homes
54.7%
CT: 66.5%
47.4%Lowest
CT: 66.5%
61.9%
CT: 66.5%
65.8%Highest
CT: 66.5%
Typical home builtmedian year
1942Lowest
25 yrs older than CT
1956
11 yrs older than CT
1967Highest
same as CT
1955
12 yrs older than CT
Getting to work
Average commuteone way
25 min
5% below CT
24 minLowest
8% below CT
27 minHighest
about the CT average
26 min
about the CT average
Work from home
7.7%±3.5
CT: 16%
6.1%±1.7Lowest
CT: 16%
15.1%±4.8Highest
CT: 16%
6.9%±2.7
CT: 16%
Derby and Winsted 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 — #143 of 149 in CT #138 of 149 in CT #97 of 149 in CT
School district — Connecticut Technical Education and Career System · Eastern Connecticut Regional Educational Service Center (EAS Derby School District Explorations District · Regional School District 07
High school in town — Windham High School Derby High School Northwestern Regional High School
Students per teacherat that high school —
9.8Highest
9.7Lowest
9.7Lowest
On TownTapestry
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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.