Living Near Windsor

37 of the 101 towns sit within fifty driving minutes of Windsor, and roughly 50 recorded job links connect residents across the region to workplaces there (2022, jobs rather than unique people). Minutes are town centre to workplace on open roads, without traffic, your street and your rush hour will differ.

Windsor, the point the drive times are measured to

Within 20 Minutes

Towns within 20 minutes of Windsor: the drive, the median assessed home, the tax on it, wired internet and whether the town's own schools run through grade 12. Towns listed alphabetically.
Town	Drive	Median Home (Assessed)	Tax on Median	Wired Internet	Schools Through 12	Recorded Job Links
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

Towns 20 to 35 minutes of Windsor: the drive, the median assessed home, the tax on it, wired internet and whether the town's own schools run through grade 12. Towns listed alphabetically.
Town	Drive	Median Home (Assessed)	Tax on Median	Wired Internet	Schools Through 12	Recorded Job Links
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	$3,969/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

Towns 35 to 50 minutes of Windsor: the drive, the median assessed home, the tax on it, wired internet and whether the town's own schools run through grade 12. Towns listed alphabetically.
Town	Drive	Median Home (Assessed)	Tax on Median	Wired Internet	Schools Through 12	Recorded Job Links
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	$2,513/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	$7,182/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	$4,411/yr	cable	yes	≈2
West Stockbridge Berkshire	45 min	$535,700	$5,629/yr	cable	yes	below the count floor
Chester Hampden	46 min	$224,200	$4,049/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	$5,754/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.
Recorded job links come from the 2022 Massachusetts main LODES file. Both home and workplace are in Massachusetts; interstate commutes are excluded. These are jobs, not unique people or daily trips. Only the top 25 origins or destinations are retained.
"Tuitions out" means older students attend a neighbouring district by arrangement, every grade has a school.

Sources

Drive times from openrouteservice by HeiGIT, map data from OpenStreetMap; town assessment rolls and certified tax rates. Checked 2026-11-02.
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.