4. WinchesterWith a cost of living almost 72 percent higher than the national average, Winchester is at the high end of the financial spectrum, but many might be surprised to learn that, as of this writing, a three-bedroom condo could be had for $269,000, and 11 single-families under $600,000 were on the market. The town's popularity stems in part from its location less than 10 miles from downtown Boston, its two commuter-rail stops, and its great MCAS scores, but also from its friendly atmosphere.
People just really love that sense of community, says Susan Russo, sales manager at Century 21 Commonwealth in Winchester. It's an 'Ozzie and Harriet,' 'Leave It to Beaver' kind of life. In addition to several parks and the Middlesex Fells Reservation, there are town-sponsored events throughout the year, book clubs, fund-raising soirees, and educational activities for children. Homes are often older, the lots are typically large, and inventory can be low. People tend to stay even after their kids grow up and move on, Russo says.