Compare towns

Windsor vs Florida 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%).
Florida has the most affordable homes ($247k median).
Chesterfield has grown the fastest since 2010 (-2.9%).

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.

MeasureWindsorFloridaChesterfield
People
Population
1,065Highest
668Lowest
1,055
Growth since 20102010 → 2020 census
-7.6%
MA: +7.4%
-7.7%Lowest
MA: +7.4%
-2.9%Highest
MA: +7.4%
Median age
44.8±6.4
12% above MA
56.1±4.4Highest
40% above MA
44.3±7.6Lowest
11% above MA
Kids under 18
15.8%±5.1
MA: 19.4%
11.5%±3.1Lowest
MA: 19.4%
19.1%±5.1Highest
MA: 19.4%
Chesterfield and Windsor 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%
30.1%±4.6Highest
MA: 17.9%
24.3%±4.2
MA: 17.9%
Florida 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%Highest
MA: 47.3%
24.3%Lowest
MA: 47.3%
34.3%
MA: 47.3%
Enrolled in collegeshare of residents
2.7%±1.7Lowest
MA: 7.9%
4.2%±2.6Highest
MA: 7.9%
2.7%±1.9Lowest
MA: 7.9%
Florida and Windsor are within the Census margin of error here, so we can’t say which is really higher.
Cost of living
Household incomemedian
$115,563±$10kHighest
11% above MA
$86,875±$17kLowest
16% below MA
$103,967±$11k
about the MA average
Windsor and Chesterfield 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
$246,800±$19kLowest
56% below MA
$390,800±$48kHighest
30% below MA
Chesterfield and Windsor are within the Census margin of error here, so we can’t say which is really higher.
Rentmedian gross, monthly —
$867±$256Lowest
51% below MA
$1,078±$409Highest
39% below MA
Chesterfield and Florida are within the Census margin of error here, so we can’t say which is really higher.
Property taxmedian, yearly
$3,867
35% below MA
$1,894Lowest
68% below MA
$5,969Highest
about the MA average
Renters paying 30%+of income on rent
0%±100Lowest
MA: 51.8%
16.7%±100Highest
MA: 51.8%
10.3%±84.4
MA: 51.8%
Florida and Chesterfield 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%
5.8%
MA: 10%
6.4%Highest
MA: 10%
Housing
Homeownersof occupied homes
96.2%Highest
MA: 62.5%
91.3%Lowest
MA: 62.5%
92.2%
MA: 62.5%
Typical home builtmedian year
1970Lowest
6 yrs newer than MA
1978Highest
14 yrs newer than MA
1976
12 yrs newer than MA
Getting to work
Average commuteone way
37 minHighest
27% above MA
26 minLowest
10% below MA
31 min
7% above MA
Work from home
21.2%±5.8Highest
MA: 18.6%
6.4%±2.6Lowest
MA: 18.6%
13.4%±6.7
MA: 18.6%
Windsor and Chesterfield are within the Census margin of error here, so we can’t say which is really higher.
Schools
School district — Florida Chesterfield-Goshen
High school in town — None in town None in town
On TownTapestry
Old photos in History None yet None yet None yet

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.