Compare towns

Derry vs Windsor vs Chester

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

What stands out worked out from the figures below

Derry has the most renters (40.9% rent).
Windsor has the most kids (25.2% under 18).
Chester has the most expensive homes ($552k 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.

MeasureDerryWindsorChester
People
Population
21,339Highest
254Lowest
5,300
Growth since 20102010 → 2020 census
+3.9%Lowest
NH: +4.6%
—
+9.7%Highest
NH: +4.6%
Median age
41±3
5% below NH
40.2±18.8Lowest
7% below NH
47.2±3.8Highest
9% above NH
Chester and Derry are within the Census margin of error here, so we can’t say which is really higher.
Kids under 18
19.9%±2.8
NH: 18.2%
25.2%±14.7Highest
NH: 18.2%
19.6%±3.7Lowest
NH: 18.2%
Windsor and Derry are within the Census margin of error here, so we can’t say which is really higher.
Age 65+
14.8%±2Lowest
NH: 20.1%
15.7%±8
NH: 20.1%
17.4%±4Highest
NH: 20.1%
Chester and Windsor are within the Census margin of error here, so we can’t say which is really higher.
Bachelor’s degree+adults 25+
36.7%
NH: 40.6%
12.6%Lowest
NH: 40.6%
41.1%Highest
NH: 40.6%
Enrolled in collegeshare of residents
7.2%±2.2Highest
NH: 6%
3.9%±4.2Lowest
NH: 6%
4.4%±2.1
NH: 6%
Derry and Chester are within the Census margin of error here, so we can’t say which is really higher.
Cost of living
Household incomemedian
$91,673±$11kLowest
7% below NH
$103,750±$40k
5% above NH
$142,212±$19kHighest
44% above NH
Chester and Windsor are within the Census margin of error here, so we can’t say which is really higher.
Home valuemedian, owner-occupied
$391,200±$23k
about the NH average
$337,500±$40kLowest
16% below NH
$552,300±$42kHighest
37% above NH
Rentmedian gross, monthly
$1,549±$137
4% above NH
— —
Property taxmedian, yearly
$7,278
9% above NH
$3,381Lowest
49% below NH
$8,464Highest
27% above NH
Renters paying 30%+of income on rent
54.7%±9.5
NH: 48.2%
66.7%±100Highest
NH: 48.2%
19%±72.7Lowest
NH: 48.2%
Windsor and Derry are within the Census margin of error here, so we can’t say which is really higher.
Below poverty line
4.4%
NH: 7.2%
10.8%Highest
NH: 7.2%
4%Lowest
NH: 7.2%
Housing
Homeownersof occupied homes
59.1%Lowest
NH: 72.8%
96.5%
NH: 72.8%
97.7%Highest
NH: 72.8%
Typical home builtmedian year
1982Lowest
3 yrs newer than NH
1983
4 yrs newer than NH
1991Highest
12 yrs newer than NH
Getting to work
Average commuteone way
29 minLowest
10% above NH
32 min
21% above NH
35 minHighest
31% above NH
Work from home
14.2%±3.5Lowest
NH: 16.8%
15%±16.5
NH: 16.8%
16.4%±5.1Highest
NH: 16.8%
Chester and Windsor 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 #60 of 120 in NH — #90 of 120 in NH
School district — — Chester School District
High school in town — — None in town
On TownTapestry
Old photos in History None yet None yet None yet

NH 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.