Pleasantville is a suburb of New York City, located just 30 miles to the north in Westchester County. With a highly affluent population, Pleasantville has been voted one of the best places to live in New York several times. Living in Pleasantville offers residents a sparse suburban feel with a vibrant downtown, an award winning, highly rated school system, and a station on the Metro-North Rail Line, offering easy access to New York City’s Grand Central Terminal.