Definitely possible. Many people live aboard their sailboats through the winter in the greater Portland area and I'm sure along the rest of the coast, too. Most people protect their boat with some kind of cover and don't seem to do any winter sailing, although their are some hearty souls I see out there occasionally.
There are Maine winter liveaboards that participate on this forum, I'll sure they'll chime in eventually. What school are you going to?
who is staring at the sea is already sailing a little