Living Near Windsor
37 of the 101 towns sit within fifty driving minutes of Windsor, and roughly 50 people across the region already commute to work there. Minutes are town centre to workplace on open roads, without traffic, your street and your rush hour will differ.
Within 20 Minutes
| Town | Drive | Median Home (Assessed) | Tax on Median | Wired Internet | Schools Through 12 | Already Commute |
|---|---|---|---|---|---|---|
| Dalton Berkshire | 14 min | $315,300 | $5,319/yr | cable | yes | ≈9 |
| Cummington Hampshire | 16 min | $330,000 | $4,122/yr | town fibre | yes | below the count floor |
| Savoy Berkshire | 17 min | $207,950 | $3,019/yr | cable | tuitions out | below the count floor |
| Plainfield Hampshire | 20 min | $244,850 | $4,300/yr | town fibre | yes | below the count floor |
| Worthington Hampshire | 20 min | $350,300 | $4,880/yr | cable | tuitions out | ≈2 |
20 to 35 minutes
| Town | Drive | Median Home (Assessed) | Tax on Median | Wired Internet | Schools Through 12 | Already Commute |
|---|---|---|---|---|---|---|
| Peru Berkshire | 21 min | $267,800 | $4,309/yr | cable | yes | ≈9 |
| Hinsdale Berkshire | 22 min | $355,700 | $3,781/yr | cable | yes | below the count floor |
| Adams Berkshire | 24 min | $246,850 | $3,858/yr | cable | yes | ≈2 |
| Pittsfield Berkshire | 25 min | $256,500 | $4,516/yr | cable | yes | ≈14 |
| Cheshire Berkshire | 26 min | $305,000 | $3,227/yr | cable | yes | ≈1 |
| Chesterfield Hampshire | 27 min | $360,500 | $5,501/yr | town fibre | yes | below the count floor |
| Goshen Hampshire | 27 min | $338,000 | $4,700/yr | town fibre | yes | below the count floor |
| Lanesborough Berkshire | 29 min | $309,850 | $5,357/yr | cable | yes | ≈2 |
| Washington Berkshire | 29 min | $336,450 | $4,650/yr | town fibre | yes | ≈1 |
| Hawley Franklin | 32 min | $250,300 | $4,055/yr | cable | yes | below the count floor |
| North Adams Berkshire | 32 min | $191,450 | $3,057/yr | cable | yes | ≈2 |
| Ashfield Franklin | 35 min | $359,500 | $5,116/yr | town fibre | yes | below the count floor |
35 to 50 minutes
| Town | Drive | Median Home (Assessed) | Tax on Median | Wired Internet | Schools Through 12 | Already Commute |
|---|---|---|---|---|---|---|
| Becket Berkshire | 36 min | $328,200 | $3,170/yr | town fibre | yes | ≈3 |
| Clarksburg Berkshire | 36 min | $211,100 | $2,594/yr | cable | tuitions out | below the count floor |
| Williamsburg Hampshire | 37 min | $393,700 | $6,303/yr | cable | yes | below the count floor |
| New Ashford Berkshire | 39 min | $442,500 | $2,505/yr | town fibre | tuitions out | below the count floor |
| Buckland Franklin | 40 min | $315,300 | $5,278/yr | cable | yes | below the count floor |
| Lenox Berkshire | 40 min | $543,800 | $5,488/yr | cable | yes | below the count floor |
| Charlemont Franklin | 41 min | $277,400 | $4,663/yr | town fibre | yes | below the count floor |
| Middlefield Hampshire | 41 min | $234,550 | $3,959/yr | cable | yes | below the count floor |
| Richmond Berkshire | 41 min | $531,400 | $5,447/yr | cable | tuitions out | below the count floor |
| Williamstown Berkshire | 41 min | $466,450 | $6,728/yr | cable | yes | below the count floor |
| Florida Berkshire | 43 min | $213,000 | $1,764/yr | cable | tuitions out | ≈2 |
| Huntington Hampshire | 43 min | $298,300 | $4,406/yr | cable | yes | below the count floor |
| Westhampton Hampshire | 43 min | $305,700 | $6,221/yr | cable | yes | below the count floor |
| Lee Berkshire | 45 min | $371,350 | $4,208/yr | cable | yes | ≈2 |
| West Stockbridge Berkshire | 45 min | $535,700 | $5,629/yr | cable | yes | below the count floor |
| Chester Hampden | 46 min | $214,100 | $3,867/yr | cable | yes | below the count floor |
| Montgomery Hampden | 48 min | $325,200 | $3,769/yr | cable | yes | below the count floor |
| Conway Franklin | 49 min | $404,800 | $5,911/yr | cable | yes | below the count floor |
| Hancock Berkshire | 49 min | $352,600 | $769/yr | cable | tuitions out | below the count floor |
| Monroe Franklin | 49 min | $146,400 | $1,483/yr | cable | tuitions out | below the count floor |
Reading This Honestly
- Drive times are computed town centre to workplace over the open road network, free of traffic. A hilltown's own roads, snow, and rush hour all add real minutes.
- Median home values are assessed values from the towns' own rolls, asking prices run different, usually higher.
- "Already commute" counts come from the federal commute census, which counts jobs by workplace, small flows fall below its floor and show as such, never as zero.
- "Tuitions out" means older students attend a neighbouring district by arrangement, every grade has a school.
Sources
- Drive times over the open road network (OpenStreetMap); town assessment rolls and certified tax rates. Checked 2026-08-05.
- Federal commute census (LODES). Figures through 2022.
"Figures through" is the period the publisher's data describes; "checked" is only when we last asked. The full sourcing: sources and method.