Compare towns

Winchester vs Killingly vs Chaplin vs Derby

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

What stands out worked out from the figures below

Winchester has the oldest population (median age 49.1).
Killingly has the most kids (19.8% under 18).
Chaplin has the most people working from home (18.1%).
Derby has the most renters (38.1% rent).

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.

MeasureWinchesterKillinglyChaplinDerby
People
Population
10,284
17,867Highest
2,070Lowest
12,487
Growth since 20102010 → 2020 census — — —
-4.5%
CT: +0.9%
Median age
49.1±6.2Highest
19% above CT
39.5±3Lowest
4% below CT
43.7±4.8
6% above CT
46.4±3.1
13% 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
15.4%±2.9
CT: 20.2%
19.8%±2.3Highest
CT: 20.2%
15.7%±4.2
CT: 20.2%
14.6%±2.9Lowest
CT: 20.2%
Killingly and Chaplin are within the Census margin of error here, so we can’t say which is really higher.
Age 65+
27.4%±5.1Highest
CT: 18.5%
19.7%±2.4Lowest
CT: 18.5%
20.9%±4.4
CT: 18.5%
21.1%±3.9
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+
27.8%
CT: 42.5%
22.9%Lowest
CT: 42.5%
25.4%
CT: 42.5%
35.6%Highest
CT: 42.5%
Enrolled in collegeshare of residents
4.2%±1.7Lowest
CT: 7.1%
5.4%±1.9
CT: 7.1%
10.1%±6.2Highest
CT: 7.1%
5.9%±2
CT: 7.1%
Chaplin and Derby are within the Census margin of error here, so we can’t say which is really higher.
Cost of living
Household incomemedian
$66,519±$12kLowest
31% below CT
$84,350±$8k
12% below CT
$97,846±$14kHighest
about the CT average
$79,500±$11k
17% below CT
Chaplin and Killingly are within the Census margin of error here, so we can’t say which is really higher.
Home valuemedian, owner-occupied
$249,500±$17kLowest
32% below CT
$288,600±$15kHighest
21% below CT
$255,200±$24k
30% below CT
$256,700±$21k
30% below CT
Killingly and Derby are within the Census margin of error here, so we can’t say which is really higher.
Rentmedian gross, monthly
$1,174±$116
21% below CT
$1,044±$141Lowest
30% below CT
$1,473±$275Highest
about the CT average
$1,452±$95
about the CT average
Chaplin and Derby are within the Census margin of error here, so we can’t say which is really higher.
Property taxmedian, yearly
$4,780
28% below CT
$3,922Lowest
41% below CT
$4,524
32% below CT
$5,510Highest
17% below CT
Renters paying 30%+of income on rent
48.9%±15.8
CT: 52.6%
42.8%±10.9
CT: 52.6%
33.6%±27.7Lowest
CT: 52.6%
53.9%±12.6Highest
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
12.8%Highest
CT: 10%
11.4%
CT: 10%
5.4%Lowest
CT: 10%
10.8%
CT: 10%
Housing
Homeownersof occupied homes
65.8%
CT: 66.5%
71.6%
CT: 66.5%
82.9%Highest
CT: 66.5%
61.9%Lowest
CT: 66.5%
Typical home builtmedian year
1955Lowest
12 yrs older than CT
1968
1 yr newer than CT
1979Highest
12 yrs newer than CT
1967
same as CT
Getting to work
Average commuteone way
26 minLowest
about the CT average
28 min
5% above CT
32 minHighest
22% above CT
27 min
about the CT average
Work from home
6.9%±2.7Lowest
CT: 16%
11.1%±2.3
CT: 16%
18.1%±10Highest
CT: 16%
15.1%±4.8
CT: 16%
Chaplin 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 #97 of 149 in CT #136 of 149 in CT — #138 of 149 in CT
School district Explorations District · Regional School District 07 Connecticut Technical Education and Career System · Eastern Connecticut Regional Educational Service Center (EAS Chaplin School District · Regional School District 11 Derby School District
High school in town Northwestern Regional High School Killingly High School Parish Hill High School Derby High School
Students per teacherat that high school
9.7
11.1Highest
7.5Lowest
9.7
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.