Compare towns
Rupert vs Winchester vs Dorset
Cost, people, housing, commute and schools, side by side, each benchmarked against the U.S..
What stands out worked out from the figures below
Rupert has the most affordable homes ($363k median).
Winchester has the most expensive homes ($1215k median).
Dorset has the shortest commute (22 min average).
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 | Rupert | Winchester | Dorset |
|---|---|---|---|
| Your priorities | |||
| People | |||
| Population | 676Lowest |
23,406Highest |
2,092 |
| Growth since 20102010 → 2020 census | -2.2%Lowest U.S.: +7.4% |
+7.5%Highest U.S.: +7.4% |
+5% U.S.: +7.4% |
| Median age | 57.8±9.7Highest 49% above U.S. |
42.5±1.9Lowest 9% above U.S. |
45.9±7.5 18% above U.S. |
| Rupert and Dorset are within the Census margin of error here, so we can’t say which is really higher. | |||
| Kids under 18 | 13.9%±3.7Lowest U.S.: 22% |
27.6%±2.3Highest U.S.: 22% |
24%±5.5 U.S.: 22% |
| Winchester and Dorset are within the Census margin of error here, so we can’t say which is really higher. | |||
| Age 65+ | 42.3%±8.1Highest U.S.: 17.2% |
18%±2Lowest U.S.: 17.2% |
21.9%±4.5 U.S.: 17.2% |
| Bachelor’s degree+adults 25+ | 30.6%Lowest U.S.: 35.7% |
79.5%Highest U.S.: 35.7% |
72.1% U.S.: 35.7% |
| Enrolled in collegeshare of residents | 2.1%±2.5Lowest U.S.: 6.4% |
4.9%±1.3Highest U.S.: 6.4% |
2.8%±2.1 U.S.: 6.4% |
| Winchester and Dorset are within the Census margin of error here, so we can’t say which is really higher. | |||
| Cost of living | |||
| Household incomemedian | $88,229±$36kLowest 9% above U.S. |
$230,198±$21kHighest 185% above U.S. |
$111,250±$40k 38% above U.S. |
| Home valuemedian, owner-occupied | $362,500±$63kLowest 9% above U.S. |
$1,215,200±$39kHighest 265% above U.S. |
$569,200±$57k 71% above U.S. |
| Rentmedian gross, monthly | — | $2,279±$481Highest 61% above U.S. |
$1,420±$296Lowest about the U.S. average |
| Property taxmedian, yearly | $4,594Lowest 47% above U.S. |
$10,000+Highest at least 221% above U.S. |
$7,489 140% above U.S. |
| Renters paying 30%+of income on rent | 20%±100Lowest U.S.: 51.1% |
39.3%±13.3 U.S.: 51.1% |
74.4%±22.5Highest U.S.: 51.1% |
| Dorset and Winchester are within the Census margin of error here, so we can’t say which is really higher. | |||
| Below poverty line | 6% U.S.: 12.5% |
4.7%Lowest U.S.: 12.5% |
11.2%Highest U.S.: 12.5% |
| Housing | |||
| Homeownersof occupied homes | 93.7%Highest U.S.: 65.2% |
81.7%Lowest U.S.: 65.2% |
90.7% U.S.: 65.2% |
| Typical home builtmedian year | 1955 25 yrs older than U.S. |
1954Lowest 26 yrs older than U.S. |
1972Highest 8 yrs older than U.S. |
| Getting to work | |||
| Average commuteone way | 27 min about the U.S. average |
31 minHighest 19% above U.S. |
22 minLowest 18% below U.S. |
| Work from home | 18.6%±9.2Lowest U.S.: 15.1% |
33.8%±3Highest U.S.: 15.1% |
29.3%±7.5 U.S.: 15.1% |
| Winchester and Dorset 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 | — | #11 of 282 in MA | — |
| School district | — | Winchester | Taconic and Green Regional School District #63 |
| High school in town | — | Winchester High School | None in town |
| Students per teacherat that high school | — | 14.8 |
— |
| On TownTapestry | |||
| Old photos in History | None yet | None yet | None yet |
U.S. 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.