Zillow Home Value Index: $307,900
Year-over-year change: -5.3%
Walk score (out of 100): 79
While the oldest subway system in America would love to take credit for the convenience of Boston and its surrounding areas, there's no way T riders would allow it. The Massachusetts Bay Transportation Authority moved more than 373 million riders through its light rail, commuter rail, ferries and busses last year, with 149 million of those riders taking a subway that has had portions running since 1897. The main reason Bostonians can walk to just about any point in the city and can live in neighborhoods such as Back Bay, Beacon Hill, the South End and Fenway without ever sitting behind the wheel of a car has less to do with the T than with a surrounding city that was planned long before cars were a reality. Those meandering streets Mayor Thomas Menino likes to refer to as "cow paths" were often just that; much of the city's Colonial-era survival was based on its density and residents' proximity to goods and services. "Cities that were largely built in World War II and post-World War II were built with the car at the center of them," Herst says. "When you think about cities like Boston and New York City, at least at the center of them, they were built into meaningful metropolises before the car."