A true American antique, this Massachusetts home predates 1750. After life as a birthing house, a nursing home, and a series of local-landmark eateries, the current owners, Kevin O'Shea and David Bowd, converted it back into a private home. They fell in love with the quirkiness and historical details. The original entry is intact and faces the harbor at the end of Cape Cod.
See more: If These Walls Could Talk: An Early-American Cape