Compare towns

Windsor vs Lee vs Dedham vs Chesterfield

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

What stands out worked out from the figures below

Windsor has the most people working from home (21.2%).
Lee has the shortest commute (18 min average).
Dedham has grown the fastest since 2010 (+2.6%).
Chesterfield has the most kids (19.1% under 18).

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.

MeasureWindsorLeeDedhamChesterfield
People
Population
1,065
5,719
25,237Highest
1,055Lowest
Growth since 20102010 → 2020 census
-7.6%Lowest
MA: +7.4%
-2.6%
MA: +7.4%
+2.6%Highest
MA: +7.4%
-2.9%
MA: +7.4%
Median age
44.8±6.4
12% above MA
55.2±5.8Highest
38% above MA
44.6±1.6
12% above MA
44.3±7.6Lowest
11% above MA
Lee and Windsor are within the Census margin of error here, so we can’t say which is really higher.
Kids under 18
15.8%±5.1
MA: 19.4%
12.6%±5Lowest
MA: 19.4%
18.6%±1.9
MA: 19.4%
19.1%±5.1Highest
MA: 19.4%
Chesterfield and Dedham are within the Census margin of error here, so we can’t say which is really higher.
Age 65+
18.6%±4.9Lowest
MA: 17.9%
33.4%±6.1Highest
MA: 17.9%
21.9%±2
MA: 17.9%
24.3%±4.2
MA: 17.9%
Lee and Chesterfield are within the Census margin of error here, so we can’t say which is really higher.
Bachelor’s degree+adults 25+
41.5%
MA: 47.3%
44.1%
MA: 47.3%
55%Highest
MA: 47.3%
34.3%Lowest
MA: 47.3%
Enrolled in collegeshare of residents
2.7%±1.7Lowest
MA: 7.9%
5%±2.1
MA: 7.9%
5.6%±1Highest
MA: 7.9%
2.7%±1.9Lowest
MA: 7.9%
Dedham and Lee are within the Census margin of error here, so we can’t say which is really higher.
Cost of living
Household incomemedian
$115,563±$10k
11% above MA
$83,750±$13kLowest
19% below MA
$128,955±$10kHighest
24% above MA
$103,967±$11k
about the MA average
Dedham and Windsor are within the Census margin of error here, so we can’t say which is really higher.
Home valuemedian, owner-occupied
$389,700±$32k
31% below MA
$352,700±$19kLowest
37% below MA
$661,800±$16kHighest
18% above MA
$390,800±$48k
30% below MA
Rentmedian gross, monthly —
$1,375±$212
22% below MA
$2,042±$182Highest
16% above MA
$1,078±$409Lowest
39% below MA
Property taxmedian, yearly
$3,867Lowest
35% below MA
$3,980
34% below MA
$7,918Highest
32% above MA
$5,969
about the MA average
Renters paying 30%+of income on rent
0%±100Lowest
MA: 51.8%
57.3%±21.2Highest
MA: 51.8%
56.4%±10
MA: 51.8%
10.3%±84.4
MA: 51.8%
Lee and Dedham are within the Census margin of error here, so we can’t say which is really higher.
Below poverty line
3.8%Lowest
MA: 10%
7.2%Highest
MA: 10%
5.6%
MA: 10%
6.4%
MA: 10%
Housing
Homeownersof occupied homes
96.2%Highest
MA: 62.5%
71.1%Lowest
MA: 62.5%
73.4%
MA: 62.5%
92.2%
MA: 62.5%
Typical home builtmedian year
1970
6 yrs newer than MA
1959
5 yrs older than MA
1956Lowest
8 yrs older than MA
1976Highest
12 yrs newer than MA
Getting to work
Average commuteone way
37 minHighest
27% above MA
18 minLowest
38% below MA
29 min
about the MA average
31 min
7% above MA
Work from home
21.2%±5.8Highest
MA: 18.6%
16.4%±7.8
MA: 18.6%
20%±2.7
MA: 18.6%
13.4%±6.7Lowest
MA: 18.6%
Windsor and Dedham 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 — #209 of 282 in MA #119 of 282 in MA —
School district — Lee Dedham Chesterfield-Goshen
High school in town — Lee Middle/High School Dedham High None in town
Students per teacherat that high school —
9.2Lowest
10.4Highest
—
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MA 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.