Greenwich, CT, United States

With a population of 61,171, Greenwich is an affluent Connecticut town on the New York border, home to many hedge funds and financial firms. However, the tax burden is heavy, and bureaucracy can be a persistent headache. The town's proximity to Manhattan and upscale amenities make it appealing for the wealthy looking to live outside the city, but the cost of living is astronomical - the median home price hovers around $2.3 million.