Compare towns

Chesterfield vs Upton vs Windsor vs Williamsburg

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

What stands out worked out from the figures below

Chesterfield has the youngest population (median age 44.3).
Upton has grown the fastest since 2010 (+6.1%).
Windsor has the most homeowners (96.2%).
Williamsburg has the shortest commute (25 min average).

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.

MeasureChesterfieldUptonWindsorWilliamsburg
People
Population
1,055Lowest
8,189Highest
1,065
2,694
Growth since 20102010 → 2020 census
-2.9%
MA: +7.4%
+6.1%Highest
MA: +7.4%
-7.6%Lowest
MA: +7.4%
+0.9%
MA: +7.4%
Median age
44.3±7.6Lowest
11% above MA
46.4±4.8
16% above MA
44.8±6.4
12% above MA
50±2.4Highest
25% above MA
Williamsburg and Upton are within the Census margin of error here, so we can’t say which is really higher.
Kids under 18
19.1%±5.1
MA: 19.4%
23.2%±4.5Highest
MA: 19.4%
15.8%±5.1Lowest
MA: 19.4%
18.6%±4
MA: 19.4%
Upton and Chesterfield are within the Census margin of error here, so we can’t say which is really higher.
Age 65+
24.3%±4.2Highest
MA: 17.9%
20.7%±4.9
MA: 17.9%
18.6%±4.9Lowest
MA: 17.9%
22.7%±3.5
MA: 17.9%
Chesterfield and Williamsburg are within the Census margin of error here, so we can’t say which is really higher.
Bachelor’s degree+adults 25+
34.3%Lowest
MA: 47.3%
53.5%
MA: 47.3%
41.5%
MA: 47.3%
60.6%Highest
MA: 47.3%
Enrolled in collegeshare of residents
2.7%±1.9
MA: 7.9%
2.4%±1.3Lowest
MA: 7.9%
2.7%±1.7
MA: 7.9%
6.2%±2.7Highest
MA: 7.9%
Williamsburg and Chesterfield are within the Census margin of error here, so we can’t say which is really higher.
Cost of living
Household incomemedian
$103,967±$11kLowest
about the MA average
$155,508±$33kHighest
50% above MA
$115,563±$10k
11% above MA
$104,792±$21k
about the MA average
Upton and Windsor are within the Census margin of error here, so we can’t say which is really higher.
Home valuemedian, owner-occupied
$390,800±$48k
30% below MA
$576,700±$41kHighest
about the MA average
$389,700±$32kLowest
31% below MA
$403,100±$37k
28% below MA
Rentmedian gross, monthly
$1,078±$409
39% below MA
$948±$599Lowest
46% below MA
—
$1,420±$228Highest
19% below MA
Williamsburg and Chesterfield are within the Census margin of error here, so we can’t say which is really higher.
Property taxmedian, yearly
$5,969
about the MA average
$8,376Highest
40% above MA
$3,867Lowest
35% below MA
$5,761
4% below MA
Renters paying 30%+of income on rent
10.3%±84.4
MA: 51.8%
52.8%±31
MA: 51.8%
0%±100Lowest
MA: 51.8%
61%±28Highest
MA: 51.8%
Williamsburg and Upton are within the Census margin of error here, so we can’t say which is really higher.
Below poverty line
6.4%Highest
MA: 10%
3.2%
MA: 10%
3.8%
MA: 10%
2.3%Lowest
MA: 10%
Housing
Homeownersof occupied homes
92.2%
MA: 62.5%
86.7%
MA: 62.5%
96.2%Highest
MA: 62.5%
82.2%Lowest
MA: 62.5%
Typical home builtmedian year
1976
12 yrs newer than MA
1981Highest
17 yrs newer than MA
1970
6 yrs newer than MA
1955Lowest
9 yrs older than MA
Getting to work
Average commuteone way
31 min
7% above MA
35 min
22% above MA
37 minHighest
27% above MA
25 minLowest
13% below MA
Work from home
13.4%±6.7Lowest
MA: 18.6%
22.8%±5.3
MA: 18.6%
21.2%±5.8
MA: 18.6%
26.5%±6.7Highest
MA: 18.6%
Williamsburg and Upton 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 — #46 of 282 in MA — —
School district Chesterfield-Goshen Blackstone Valley Regional Vocational Technical · Mendon-Upton — Williamsburg
High school in town None in town Blackstone Valley — None in town
Students per teacherat that high school —
11.2
— —
On TownTapestry
Old photos in History None yet 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.