Compare towns

Derby vs Orange vs Webster vs Winchester

Cost, people, housing, commute and schools, side by side, each benchmarked against the U.S..

What stands out worked out from the figures below

Orange has the highest household income ($142k).
Webster has the youngest population (median age 39.9).
Winchester has the oldest population (median age 49.1).

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.

MeasureDerbyOrangeWebsterWinchester
People
Population
12,487
14,315
17,748Highest
10,284Lowest
Growth since 20102010 → 2020 census
-4.5%Lowest
U.S.: +7.4%
+2.3%
U.S.: +7.4%
+6%Highest
U.S.: +7.4%
—
Median age
46.4±3.1
19% above U.S.
45.6±2.4
17% above U.S.
39.9±2.9Lowest
about the U.S. average
49.1±6.2Highest
26% above U.S.
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
U.S.: 22%
22.9%±2.5Highest
U.S.: 22%
19.6%±2.9
U.S.: 22%
15.4%±2.9
U.S.: 22%
Orange and Webster are within the Census margin of error here, so we can’t say which is really higher.
Age 65+
21.1%±3.9
U.S.: 17.2%
23%±2.7
U.S.: 17.2%
19.6%±2.5Lowest
U.S.: 17.2%
27.4%±5.1Highest
U.S.: 17.2%
Winchester and Orange are within the Census margin of error here, so we can’t say which is really higher.
Bachelor’s degree+adults 25+
35.6%
U.S.: 35.7%
59.4%Highest
U.S.: 35.7%
25.3%Lowest
U.S.: 35.7%
27.8%
U.S.: 35.7%
Enrolled in collegeshare of residents
5.9%±2Highest
U.S.: 6.4%
5.5%±2
U.S.: 6.4%
5.8%±1.6
U.S.: 6.4%
4.2%±1.7Lowest
U.S.: 6.4%
Derby and Webster are within the Census margin of error here, so we can’t say which is really higher.
Cost of living
Household incomemedian
$79,500±$11k
about the U.S. average
$142,325±$10kHighest
76% above U.S.
$72,895±$6k
10% below U.S.
$66,519±$12kLowest
18% below U.S.
Home valuemedian, owner-occupied
$256,700±$21k
23% below U.S.
$491,500±$17kHighest
48% above U.S.
$361,500±$12k
9% above U.S.
$249,500±$17kLowest
25% below U.S.
Rentmedian gross, monthly
$1,452±$95
about the U.S. average
$2,172±$161Highest
54% above U.S.
$1,228±$81
13% below U.S.
$1,174±$116Lowest
17% below U.S.
Property taxmedian, yearly
$5,510
77% above U.S.
$8,988Highest
188% above U.S.
$3,999Lowest
28% above U.S.
$4,780
53% above U.S.
Renters paying 30%+of income on rent
53.9%±12.6
U.S.: 51.1%
64%±12.1Highest
U.S.: 51.1%
45.7%±6.7Lowest
U.S.: 51.1%
48.9%±15.8
U.S.: 51.1%
Orange and Derby are within the Census margin of error here, so we can’t say which is really higher.
Below poverty line
10.8%
U.S.: 12.5%
3.9%Lowest
U.S.: 12.5%
12.7%
U.S.: 12.5%
12.8%Highest
U.S.: 12.5%
Housing
Homeownersof occupied homes
61.9%
U.S.: 65.2%
89.2%Highest
U.S.: 65.2%
59.8%Lowest
U.S.: 65.2%
65.8%
U.S.: 65.2%
Typical home builtmedian year
1967Highest
13 yrs older than U.S.
1964
16 yrs older than U.S.
1962
18 yrs older than U.S.
1955Lowest
25 yrs older than U.S.
Getting to work
Average commuteone way
27 min
about the U.S. average
28 min
4% above U.S.
31 minHighest
16% above U.S.
26 minLowest
about the U.S. average
Work from home
15.1%±4.8
U.S.: 15.1%
15.6%±2.9Highest
U.S.: 15.1%
8%±2.5
U.S.: 15.1%
6.9%±2.7Lowest
U.S.: 15.1%
Orange 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 #38 of 149 in CT #271 of 282 in MA #97 of 149 in CT
School district Derby School District — Webster Explorations District · Regional School District 07
High school in town Derby High School — Bartlett High School Northwestern Regional High School
Students per teacherat that high school
9.7Lowest
—
11.6Highest
9.7Lowest
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U.S. 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.