Compare towns
Windsor vs Ware vs Webster vs Chesterfield
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 most people working from home (21.2%).
Ware has the most affordable homes ($290k median).
Webster has grown the fastest since 2010 (+6%).
Chesterfield has the most expensive homes ($391k 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.
| Measure | Windsor | Ware | Webster | Chesterfield |
|---|---|---|---|---|
| Your priorities | ||||
| People | ||||
| Population | 1,065 |
10,048 |
17,748Highest |
1,055Lowest |
| Growth since 20102010 → 2020 census | -7.6%Lowest MA: +7.4% |
+2% MA: +7.4% |
+6%Highest MA: +7.4% |
-2.9% MA: +7.4% |
| Median age | 44.8±6.4Highest 12% above MA |
43.1±4.7 8% above MA |
39.9±2.9Lowest about the MA average |
44.3±7.6 11% above MA |
| Windsor and Chesterfield are within the Census margin of error here, so we can’t say which is really higher. | ||||
| Kids under 18 | 15.8%±5.1Lowest MA: 19.4% |
19.1%±3.5 MA: 19.4% |
19.6%±2.9Highest MA: 19.4% |
19.1%±5.1 MA: 19.4% |
| Webster and Ware 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% |
20.6%±3.4 MA: 17.9% |
19.6%±2.5 MA: 17.9% |
24.3%±4.2Highest MA: 17.9% |
| Chesterfield and Ware are within the Census margin of error here, so we can’t say which is really higher. | ||||
| Bachelor’s degree+adults 25+ | 41.5%Highest MA: 47.3% |
24%Lowest MA: 47.3% |
25.3% MA: 47.3% |
34.3% MA: 47.3% |
| Enrolled in collegeshare of residents | 2.7%±1.7Lowest MA: 7.9% |
4.4%±2.2 MA: 7.9% |
5.8%±1.6Highest MA: 7.9% |
2.7%±1.9Lowest MA: 7.9% |
| Webster and Ware are within the Census margin of error here, so we can’t say which is really higher. | ||||
| Cost of living | ||||
| Household incomemedian | $115,563±$10kHighest 11% above MA |
$67,475±$15kLowest 35% below MA |
$72,895±$6k 30% below MA |
$103,967±$11k about the MA average |
| Windsor and Chesterfield are within the Census margin of error here, so we can’t say which is really higher. | ||||
| Home valuemedian, owner-occupied | $389,700±$32k 31% below MA |
$289,700±$28kLowest 48% below MA |
$361,500±$12k 36% below MA |
$390,800±$48kHighest 30% below MA |
| Chesterfield and Windsor are within the Census margin of error here, so we can’t say which is really higher. | ||||
| Rentmedian gross, monthly | — | $1,043±$109Lowest 41% below MA |
$1,228±$81Highest 30% below MA |
$1,078±$409 39% below MA |
| Webster and Chesterfield 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 |
$4,237 29% below MA |
$3,999 33% below MA |
$5,969Highest about the MA average |
| Renters paying 30%+of income on rent | 0%±100Lowest MA: 51.8% |
64.3%±16.2Highest MA: 51.8% |
45.7%±6.7 MA: 51.8% |
10.3%±84.4 MA: 51.8% |
| Ware and Webster 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% |
11.8% MA: 10% |
12.7%Highest MA: 10% |
6.4% MA: 10% |
| Housing | ||||
| Homeownersof occupied homes | 96.2%Highest MA: 62.5% |
72.3% MA: 62.5% |
59.8%Lowest MA: 62.5% |
92.2% MA: 62.5% |
| Typical home builtmedian year | 1970 6 yrs newer than MA |
1960Lowest 4 yrs older than MA |
1962 2 yrs older than MA |
1976Highest 12 yrs newer than MA |
| Getting to work | ||||
| Average commuteone way | 37 minHighest 27% above MA |
28 minLowest about the MA average |
31 min 5% above MA |
31 min 7% above MA |
| Work from home | 21.2%±5.8Highest MA: 18.6% |
12.3%±3.8 MA: 18.6% |
8%±2.5Lowest MA: 18.6% |
13.4%±6.7 MA: 18.6% |
| Windsor and Chesterfield 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 | — | #267 of 282 in MA | #271 of 282 in MA | — |
| School district | — | Ware | Webster | Chesterfield-Goshen |
| High school in town | — | Ware Junior/Senior High School | Bartlett High School | None in town |
| Students per teacherat that high school | — | 11.1Lowest |
11.6Highest |
— |
| 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.