East Hampton, NY, United States

Living in East Hampton is a pricey proposition, with a median home price of $895,000 compared to the national median of $225,000. The population of 28,385 swells with wealthy summer residents, driving up the cost of living to 168% of the national average. Bureaucracy is a persistent headache, with the town's government split between an elected Town Board and the historic Trustees of the Freeholders, whose decisions on issues like draining Georgica Pond can flood nearby celebrity homes. Despite the town's susceptibility to hurricanes and nor'easters, East Hampton remains an enclave for the elite, attracting artists, politicians, and the entertainment elite seeking a posh summer retreat.