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Leaving that early in the morning I would think would make the commute pretty easy. I'm guessing 40 minutes, depending on where in Boston you're going.
I live in Sherborn and love it. I like the small town feel, and love the fact that it's quiet and that the town has preserved so much open space. I adore Farm Pond and all the great trails. What I like about Wellesley is the easy access to shops and restaurants. I have friends who live there and can walk to everything whereas I have to drive (partly because of our distance from downtown but partly because there's no good sidewalk or bike path access along the main road into town). Also in Sherborn you'd likely get a much larger home lot. We picked Sherborn because it's peaceful and quiet and not overdeveloped but I also really like the easy access to Wellesley. The only downside I find is lack of easy train access. If I want to go to Boston I either park in Wellesley and take the train from there or have my husband drop me in Natick, because you can't park at that station unless you live in town.
We live in Sherborn and I spend most of my time here but I go to Wellesley for shopping, exercise (there's a great spin studio called Spynergy there), and lunch with my friends (my fave place is Cafe Mangal, which has delicious salads and sandwiches). We also enjoy Elm Bank, which is a beautiful place to stroll around and you can also kayak/canoe from there.
Anyhow, that's my two cents! Please feel free to PM me if you have other questions. We've been very happy with our choice to move here.
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