1. WenhamWith its winding roads, rambling stone walls, tranquil lakes, and acres of woodlands, sleepy Wenham can still be considered rural, but it's got a sophisticated edge. The town boasts a strong sense of history, a high level of education among residents, a median household income almost double that of the state as a whole, and a penchant for sports like polo and golf.
It has a generally small inventory of single-family homes - only 20 sold last year - that appeal to parents with kids, and two new condo developments that sold briskly to empty nesters. Though the commute to downtown Boston is about 45 minutes, residents feel it's worth it for the small-town feel. People are very connected and caring, says Sarah Johnson, the town finance director. They watch out for each other.