I think it's just over a half hour without traffic. Traffic is not as bad on 495 as on 128, but you should add another 10-15 mins. Winter is not usually an issue absent major snow, in which case all bets are off.
Hopkinton itself seems to fit your description, as would Holliston and Southborough. Boxboro and Harvard are a bit closer to 495 and Boxboro and Acton share a high school. There are also nice towns along 495 such as Bolton, Stow, Northboro, Berlin. Shrewsbury is also nice and Franklin to the south is liked by those who live there.
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