Compare towns

Windsor vs Stockbridge vs Oakham

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 youngest population (median age 44.8).
Stockbridge has grown the fastest since 2010 (+3.6%).
Oakham has the most kids (18.2% 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.

MeasureWindsorStockbridgeOakham
People
Population
1,065Lowest
2,056Highest
1,639
Growth since 20102010 → 2020 census
-7.6%Lowest
MA: +7.4%
+3.6%Highest
MA: +7.4%
-2.7%
MA: +7.4%
Median age
44.8±6.4Lowest
12% above MA
63.7±3.5Highest
59% above MA
49±2.3
23% above MA
Kids under 18
15.8%±5.1
MA: 19.4%
8.4%±4.3Lowest
MA: 19.4%
18.2%±3.1Highest
MA: 19.4%
Oakham 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%
47%±7.5Highest
MA: 17.9%
21.4%±2.3
MA: 17.9%
Bachelor’s degree+adults 25+
41.5%
MA: 47.3%
62.4%Highest
MA: 47.3%
40.3%Lowest
MA: 47.3%
Enrolled in collegeshare of residents
2.7%±1.7Lowest
MA: 7.9%
3.5%±2.7
MA: 7.9%
3.8%±2.1Highest
MA: 7.9%
Oakham and Stockbridge 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
$146,250±$67kHighest
41% above MA
$102,000±$20kLowest
about the MA average
Stockbridge 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±$32kLowest
31% below MA
$600,000±$99kHighest
7% above MA
$420,100±$20k
25% below MA
Rentmedian gross, monthly —
$858±$375Lowest
51% below MA
$1,174±$81Highest
33% below MA
Oakham and Stockbridge are within the Census margin of error here, so we can’t say which is really higher.
Property taxmedian, yearly
$3,867Lowest
35% below MA
$4,652Highest
22% below MA
$4,103
32% below MA
Renters paying 30%+of income on rent
0%±100Lowest
MA: 51.8%
60.8%±27Highest
MA: 51.8%
27.8%±69.1
MA: 51.8%
Stockbridge and Oakham 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%
4.4%
MA: 10%
Housing
Homeownersof occupied homes
96.2%Highest
MA: 62.5%
83.3%Lowest
MA: 62.5%
91.6%
MA: 62.5%
Typical home builtmedian year
1970
6 yrs newer than MA
1958Lowest
6 yrs older than MA
1979Highest
15 yrs newer than MA
Getting to work
Average commuteone way
37 min
27% above MA
20 minLowest
33% below MA
39 minHighest
32% above MA
Work from home
21.2%±5.8
MA: 18.6%
52.4%±19.9Highest
MA: 18.6%
9.6%±3.8Lowest
MA: 18.6%
Schools
School district — — Quabbin
High school 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.