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Be aware that anywhere within reasonable commuting distance to NYC (lower Fairfield County-Stamford, Darien, Norwalk, Westport, Fairfield) will cost you. Highways are unusable due to insane traffic so train is really your only option. Upper Ffld (Danbury, Newtown) is far more reasonable.
If you'll be going to Boston regularly, consider east of the Connecticut River, much further NE and way more affordable.
I can't imagine a requirement to be in both places regularly - the travel would be awful and commuting impossible.
The best way to get to Boston is Amtrak. But it's at least 2 hrs or more, each way, depending on where you are. Check their schedule to see what I mean. The Acela.