Living Near Sheffield

15 of the 101 towns sit within fifty driving minutes of Sheffield, and roughly 567 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.

Sheffield, the point the drive times are measured to

Within 20 Minutes

Towns within 20 minutes of Sheffield: 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	Already Commute
Great Barrington Berkshire	13 min	$518,000	$7,024/yr	cable	yes	≈161
Egremont Berkshire	15 min	$601,400	$3,957/yr	no wired cable	yes	≈30

20 to 35 minutes

Towns 20 to 35 minutes of Sheffield: 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	Already Commute
New Marlborough Berkshire	22 min	$534,100	$3,851/yr	no wired cable	yes	≈68
Monterey Berkshire	23 min	$620,850	$4,483/yr	no wired cable	yes	≈12
Alford Berkshire	25 min	$1,066,450	$4,340/yr	town fibre	yes	≈9
Stockbridge Berkshire	27 min	$702,200	$4,891/yr	cable	yes	≈14
West Stockbridge Berkshire	32 min	$535,700	$5,629/yr	cable	yes	≈12
Lee Berkshire	35 min	$371,350	$4,208/yr	cable	yes	≈53
Mount Washington Berkshire	35 min	$436,000	$2,603/yr	no wired cable	tuitions out	below the count floor
Sandisfield Berkshire	35 min	$407,100	$3,212/yr	cable	tuitions out	≈12

35 to 50 minutes

Towns 35 to 50 minutes of Sheffield: 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	Already Commute
Tyringham Berkshire	36 min	$563,500	$3,736/yr	cable	tuitions out	below the count floor
Lenox Berkshire	37 min	$543,800	$5,488/yr	cable	yes	≈22
Otis Berkshire	37 min	$449,300	$2,678/yr	town fibre	tuitions out	≈40
Richmond Berkshire	37 min	$531,400	$5,447/yr	cable	tuitions out	below the count floor
Tolland Hampden	48 min	$326,850	$2,598/yr	cable	yes	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 from openrouteservice by HeiGIT, map data from OpenStreetMap; town assessment rolls and certified tax rates. Checked 2026-09-19.
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.