Compare towns

Dedham vs Oakham vs Windsor

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

What stands out worked out from the figures below

Dedham has grown the fastest since 2010 (+2.6%).
Oakham has the oldest population (median age 49).
Windsor has the most affordable homes ($390k median).

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.

MeasureDedhamOakhamWindsor
People
Population
25,237Highest
1,639
1,065Lowest
Growth since 20102010 → 2020 census
+2.6%Highest
MA: +7.4%
-2.7%
MA: +7.4%
-7.6%Lowest
MA: +7.4%
Median age
44.6±1.6Lowest
12% above MA
49±2.3Highest
23% above MA
44.8±6.4
12% above MA
Oakham and Windsor are within the Census margin of error here, so we can’t say which is really higher.
Kids under 18
18.6%±1.9Highest
MA: 19.4%
18.2%±3.1
MA: 19.4%
15.8%±5.1Lowest
MA: 19.4%
Dedham and Oakham are within the Census margin of error here, so we can’t say which is really higher.
Age 65+
21.9%±2Highest
MA: 17.9%
21.4%±2.3
MA: 17.9%
18.6%±4.9Lowest
MA: 17.9%
Dedham and Oakham are within the Census margin of error here, so we can’t say which is really higher.
Bachelor’s degree+adults 25+
55%Highest
MA: 47.3%
40.3%Lowest
MA: 47.3%
41.5%
MA: 47.3%
Enrolled in collegeshare of residents
5.6%±1Highest
MA: 7.9%
3.8%±2.1
MA: 7.9%
2.7%±1.7Lowest
MA: 7.9%
Dedham and Oakham are within the Census margin of error here, so we can’t say which is really higher.
Cost of living
Household incomemedian
$128,955±$10kHighest
24% above MA
$102,000±$20kLowest
about the MA average
$115,563±$10k
11% above MA
Dedham and Windsor are within the Census margin of error here, so we can’t say which is really higher.
Home valuemedian, owner-occupied
$661,800±$16kHighest
18% above MA
$420,100±$20k
25% below MA
$389,700±$32kLowest
31% below MA
Rentmedian gross, monthly
$2,042±$182Highest
16% above MA
$1,174±$81Lowest
33% below MA
—
Property taxmedian, yearly
$7,918Highest
32% above MA
$4,103
32% below MA
$3,867Lowest
35% below MA
Renters paying 30%+of income on rent
56.4%±10Highest
MA: 51.8%
27.8%±69.1
MA: 51.8%
0%±100Lowest
MA: 51.8%
Dedham and Oakham are within the Census margin of error here, so we can’t say which is really higher.
Below poverty line
5.6%Highest
MA: 10%
4.4%
MA: 10%
3.8%Lowest
MA: 10%
Housing
Homeownersof occupied homes
73.4%Lowest
MA: 62.5%
91.6%
MA: 62.5%
96.2%Highest
MA: 62.5%
Typical home builtmedian year
1956Lowest
8 yrs older than MA
1979Highest
15 yrs newer than MA
1970
6 yrs newer than MA
Getting to work
Average commuteone way
29 minLowest
about the MA average
39 minHighest
32% above MA
37 min
27% above MA
Work from home
20%±2.7
MA: 18.6%
9.6%±3.8Lowest
MA: 18.6%
21.2%±5.8Highest
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 #119 of 282 in MA — —
School district Dedham Quabbin —
High school in town Dedham High None in town —
Students per teacherat that high school
10.4
— —
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.