Oyster Bay, NY, United States

At over 300,000 residents, Oyster Bay is hardly the quaint Long Island hamlet one might expect. The population boom since the 1950s has turned this former farming community into a sprawling suburban behemoth, complete with all the bureaucratic headaches that come with governing such a large town. With 18 villages and 18 hamlets, the labyrinth of postal codes and local jurisdictions is a persistent source of frustration for residents. And while the town boasts a storied history dating back to the 1600s, its modern identity is more defined by the affluent commuter class that populates its neighborhoods. Oyster Bay may hold appeal for those seeking a convenient location within the New York metropolitan area, but its sheer size and complexity are a trade-off to consider.