Compare towns

Brattleboro vs Windsor vs Chesterfield

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

What stands out worked out from the figures below

Brattleboro has grown the fastest since 2010 (+1.1%).
Windsor has the most affordable homes ($208k median).
Chesterfield has the highest household income ($102k).

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.

MeasureBrattleboroWindsorChesterfield
People
Population
12,122Highest
3,554Lowest
3,622
Growth since 20102010 → 2020 census
+1.1%Highest
U.S.: +7.4%
+0.2%
U.S.: +7.4%
-1.4%Lowest
U.S.: +7.4%
Median age
45.6±4.5
17% above U.S.
44.8±6.5Lowest
15% above U.S.
46.8±8.7Highest
20% above U.S.
Chesterfield and Brattleboro are within the Census margin of error here, so we can’t say which is really higher.
Kids under 18
19%±2.8Lowest
U.S.: 22%
19.5%±5.2
U.S.: 22%
21.5%±5.4Highest
U.S.: 22%
Chesterfield and Windsor are within the Census margin of error here, so we can’t say which is really higher.
Age 65+
25.5%±3.2Lowest
U.S.: 17.2%
29.7%±6.9Highest
U.S.: 17.2%
28.8%±7.3
U.S.: 17.2%
Windsor and Chesterfield are within the Census margin of error here, so we can’t say which is really higher.
Bachelor’s degree+adults 25+
46.5%Highest
U.S.: 35.7%
39.7%Lowest
U.S.: 35.7%
45.2%
U.S.: 35.7%
Enrolled in collegeshare of residents
4.1%±1.6Highest
U.S.: 6.4%
0.7%±0.8Lowest
U.S.: 6.4%
1.5%±1.4
U.S.: 6.4%
Brattleboro and Chesterfield are within the Census margin of error here, so we can’t say which is really higher.
Cost of living
Household incomemedian
$58,241±$8k
28% below U.S.
$52,484±$11kLowest
35% below U.S.
$102,370±$40kHighest
27% above U.S.
Chesterfield and Brattleboro are within the Census margin of error here, so we can’t say which is really higher.
Home valuemedian, owner-occupied
$257,300±$18k
23% below U.S.
$207,500±$31kLowest
38% below U.S.
$373,500±$33kHighest
12% above U.S.
Rentmedian gross, monthly
$1,074±$58
24% below U.S.
$1,026±$89Lowest
27% below U.S.
$1,324±$1kHighest
6% below U.S.
Chesterfield and Brattleboro are within the Census margin of error here, so we can’t say which is really higher.
Property taxmedian, yearly
$5,700
83% above U.S.
$5,209Lowest
67% above U.S.
$6,344Highest
103% above U.S.
Renters paying 30%+of income on rent
46.9%±9.6
U.S.: 51.1%
31.5%±17Lowest
U.S.: 51.1%
83.7%±100Highest
U.S.: 51.1%
Chesterfield and Brattleboro are within the Census margin of error here, so we can’t say which is really higher.
Below poverty line
17.8%Highest
U.S.: 12.5%
7.8%Lowest
U.S.: 12.5%
8.6%
U.S.: 12.5%
Housing
Homeownersof occupied homes
58.5%
U.S.: 65.2%
57.8%Lowest
U.S.: 65.2%
83.6%Highest
U.S.: 65.2%
Typical home builtmedian year
1955
25 yrs older than U.S.
1945Lowest
35 yrs older than U.S.
1981Highest
1 yr newer than U.S.
Getting to work
Average commuteone way
19 minLowest
28% below U.S.
23 min
14% below U.S.
25 minHighest
6% below U.S.
Work from home
17.9%±4
U.S.: 15.1%
10.3%±5Lowest
U.S.: 15.1%
18.9%±6.9Highest
U.S.: 15.1%
Chesterfield and Brattleboro 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 #33 of 70 in VT #61 of 70 in VT #52 of 120 in NH
School district Windham Southeast Unified Union School District #96 — Chesterfield School District
High school in town Brattleboro Union High School — None in town
Students per teacherat that high school
9.0
— —
On TownTapestry
Old photos in History 6 photos → 12 photos → 6 photos →

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.