Compare towns

Chester vs Windsor vs Derry

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

What stands out worked out from the figures below

Chester has the highest household income ($142k).
Windsor has the most affordable homes ($338k median).
Derry has the most renters (29.8% 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.

MeasureChesterWindsorDerry
People
Population
5,300
254Lowest
34,116Highest
Growth since 20102010 → 2020 census
+9.7%Highest
NH: +4.6%
—
+3.6%Lowest
NH: +4.6%
Median age
47.2±3.8Highest
9% above NH
40.2±18.8Lowest
7% below NH
40.3±1.6
7% below NH
Kids under 18
19.6%±3.7Lowest
NH: 18.2%
25.2%±14.7Highest
NH: 18.2%
20.7%±2.1
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+
17.4%±4Highest
NH: 20.1%
15.7%±8
NH: 20.1%
15.2%±1.6Lowest
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+
41.1%Highest
NH: 40.6%
12.6%Lowest
NH: 40.6%
37.4%
NH: 40.6%
Enrolled in collegeshare of residents
4.4%±2.1
NH: 6%
3.9%±4.2Lowest
NH: 6%
6.1%±1.5Highest
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
$142,212±$19kHighest
44% above NH
$103,750±$40kLowest
5% above NH
$108,944±$7k
10% above NH
Home valuemedian, owner-occupied
$552,300±$42kHighest
37% above NH
$337,500±$40kLowest
16% below NH
$432,000±$17k
7% above NH
Rentmedian gross, monthly — —
$1,547±$138
4% above NH
Property taxmedian, yearly
$8,464Highest
27% above NH
$3,381Lowest
49% below NH
$8,103
22% above NH
Renters paying 30%+of income on rent
19%±72.7Lowest
NH: 48.2%
66.7%±100Highest
NH: 48.2%
51.6%±9
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%Lowest
NH: 7.2%
10.8%Highest
NH: 7.2%
4%Lowest
NH: 7.2%
Housing
Homeownersof occupied homes
97.7%Highest
NH: 72.8%
96.5%
NH: 72.8%
70.2%Lowest
NH: 72.8%
Typical home builtmedian year
1991Highest
12 yrs newer than NH
1983Lowest
4 yrs newer than NH
1983Lowest
4 yrs newer than NH
Getting to work
Average commuteone way
35 minHighest
31% above NH
32 min
21% above NH
31 minLowest
16% above NH
Work from home
16.4%±5.1Highest
NH: 16.8%
15%±16.5Lowest
NH: 16.8%
16%±2.8
NH: 16.8%
Chester and Derry 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 #90 of 120 in NH — #60 of 120 in NH
School district Chester School District — Derry Cooperative School District · Pinkerton Academy School District
High school in town None in town — Pinkerton Academy
Students per teacherat that high school — —
13.9
On TownTapestry
Old photos in Our Story 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.