Your price point limits you a lot. Some things to look for in a New England boat.
Shoal draft is very important to anyone wishing to cruise. Many nice places that need 5 feet or less, preferably less.
Pilot house or full enclosure would be nice, it rains a lot. At least look at a boat for how airy it is, you could be stuck down below in a rainy harbor for days at time.
Good powering abilities, light winds are normal.
I ended up with a power boat while there based by Old Saybrook which gave me the ability to visit lots of places with limited time. I always figured if I had to go back something like a Gemini 305 would be an ideal boat. I've never had a multi but seems like NE would be a good place for one, especially with the ability to keep it on a mooring. Out of your price range however.
So I think you should probably look at an older CB fiberglass boat. I doubt you could find a multihull in your price range, unless it's home built.