Retirement in Massachusetts may seem tempting. It's a beautiful state with historic significance and an elegant cultural scene. Before you choose, remember those brutal, bone-chilling winters. Massachusetts is the third most expensive state in America. Only Hawaii and California are more expensive—and they've got much milder climates. Massachusetts also has fairly high taxes at 12.79%. Housing is expensive; the median price for a single-family home is $508,000. On the plus side, the Bay State has a higher life expectancy, especially for those who are wealthy, and its health care is rated highly.

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