Compare towns

Conway 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

Conway has the most people working from home (29.1%).
Oakham has grown the fastest since 2010 (-2.7%).
Windsor has the highest household income ($116k).

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.

MeasureConwayOakhamWindsor
People
Population
1,755Highest
1,639
1,065Lowest
Growth since 20102010 → 2020 census
-7.2%
MA: +7.4%
-2.7%Highest
MA: +7.4%
-7.6%Lowest
MA: +7.4%
Median age
55.6±3Highest
39% above MA
49±2.3
23% above MA
44.8±6.4Lowest
12% above MA
Kids under 18
16.5%±3.3
MA: 19.4%
18.2%±3.1Highest
MA: 19.4%
15.8%±5.1Lowest
MA: 19.4%
Oakham and Conway are within the Census margin of error here, so we can’t say which is really higher.
Age 65+
31.9%±4.1Highest
MA: 17.9%
21.4%±2.3
MA: 17.9%
18.6%±4.9Lowest
MA: 17.9%
Bachelor’s degree+adults 25+
60.5%Highest
MA: 47.3%
40.3%Lowest
MA: 47.3%
41.5%
MA: 47.3%
Enrolled in collegeshare of residents
2.6%±1.2Lowest
MA: 7.9%
3.8%±2.1Highest
MA: 7.9%
2.7%±1.7
MA: 7.9%
Oakham and Windsor are within the Census margin of error here, so we can’t say which is really higher.
Cost of living
Household incomemedian
$97,250±$11kLowest
6% below MA
$102,000±$20k
about the MA average
$115,563±$10kHighest
11% above MA
Windsor and Oakham are within the Census margin of error here, so we can’t say which is really higher.
Home valuemedian, owner-occupied
$395,900±$25k
30% below MA
$420,100±$20kHighest
25% below MA
$389,700±$32kLowest
31% below MA
Oakham and Conway are within the Census margin of error here, so we can’t say which is really higher.
Rentmedian gross, monthly
$1,800±$990Highest
about the MA average
$1,174±$81Lowest
33% below MA
—
Conway and Oakham are within the Census margin of error here, so we can’t say which is really higher.
Property taxmedian, yearly
$5,797Highest
3% below MA
$4,103
32% below MA
$3,867Lowest
35% below MA
Renters paying 30%+of income on rent
23.9%±33.6
MA: 51.8%
27.8%±69.1Highest
MA: 51.8%
0%±100Lowest
MA: 51.8%
Oakham and Conway are within the Census margin of error here, so we can’t say which is really higher.
Below poverty line
4.4%Highest
MA: 10%
4.4%Highest
MA: 10%
3.8%Lowest
MA: 10%
Housing
Homeownersof occupied homes
93.4%
MA: 62.5%
91.6%Lowest
MA: 62.5%
96.2%Highest
MA: 62.5%
Typical home builtmedian year
1976
12 yrs newer than MA
1979Highest
15 yrs newer than MA
1970Lowest
6 yrs newer than MA
Getting to work
Average commuteone way
24 minLowest
18% below MA
39 minHighest
32% above MA
37 min
27% above MA
Work from home
29.1%±8.5Highest
MA: 18.6%
9.6%±3.8Lowest
MA: 18.6%
21.2%±5.8
MA: 18.6%
Conway and Windsor are within the Census margin of error here, so we can’t say which is really higher.
Schools
School district Conway Quabbin —
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.