Compare towns
Chesterfield 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
Chesterfield has the shortest commute (31 min average).
Oakham has the oldest population (median age 49).
Windsor has the most people working from home (21.2%).
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.
| Measure | Chesterfield | Oakham | Windsor |
|---|---|---|---|
| Your priorities | |||
| People | |||
| Population | 1,055Lowest |
1,639Highest |
1,065 |
| Growth since 20102010 → 2020 census | -2.9% MA: +7.4% |
-2.7%Highest MA: +7.4% |
-7.6%Lowest MA: +7.4% |
| Median age | 44.3±7.6Lowest 11% 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 | 19.1%±5.1Highest MA: 19.4% |
18.2%±3.1 MA: 19.4% |
15.8%±5.1Lowest MA: 19.4% |
| Chesterfield and Oakham 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% |
21.4%±2.3 MA: 17.9% |
18.6%±4.9Lowest MA: 17.9% |
| Chesterfield and Oakham 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% |
40.3% MA: 47.3% |
41.5%Highest MA: 47.3% |
| Enrolled in collegeshare of residents | 2.7%±1.9Lowest MA: 7.9% |
3.8%±2.1Highest MA: 7.9% |
2.7%±1.7Lowest MA: 7.9% |
| Oakham 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±$11k about the MA average |
$102,000±$20kLowest about the MA average |
$115,563±$10kHighest 11% above MA |
| Windsor and Chesterfield 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 |
$420,100±$20kHighest 25% below MA |
$389,700±$32kLowest 31% below MA |
| Oakham and Chesterfield are within the Census margin of error here, so we can’t say which is really higher. | |||
| Rentmedian gross, monthly | $1,078±$409Lowest 39% below MA |
$1,174±$81Highest 33% below MA |
— |
| Oakham and Chesterfield are within the Census margin of error here, so we can’t say which is really higher. | |||
| Property taxmedian, yearly | $5,969Highest about the MA average |
$4,103 32% below MA |
$3,867Lowest 35% below MA |
| Renters paying 30%+of income on rent | 10.3%±84.4 MA: 51.8% |
27.8%±69.1Highest MA: 51.8% |
0%±100Lowest MA: 51.8% |
| Oakham and Chesterfield 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% |
4.4% MA: 10% |
3.8%Lowest MA: 10% |
| Housing | |||
| Homeownersof occupied homes | 92.2% 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 | 31 minLowest 7% above MA |
39 minHighest 32% above MA |
37 min 27% above MA |
| Work from home | 13.4%±6.7 MA: 18.6% |
9.6%±3.8Lowest MA: 18.6% |
21.2%±5.8Highest 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 | Chesterfield-Goshen | 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.