In some situations, there can be legal issues to owning property abroad. Gallo, of Escapeartist.com, encourages people to set up and own their property in the name of a Panamanian or British Virgin Islands corporation. When you go to sell it, you sell the corporation and the property just switches hands, easing transfer of title, Gallo says.

Taxes and legal issues

Many countries try to lure foreign retirees. Belize's nearly decade-old Retired Persons Incentive Act, for instance, allows retirees over age 45 to import their personal effects duty free and to earn retirement income tax free.

Countries from Italy to Panama to South Africa and Thailand offer a "pensioner visa" or "retirement visa" to Americans who can prove a certain level of monthly income. The visas can provide a variety of benefits, such as automatic discounts on certain purchases and the ability to obtain a local passport.

Still, the Internal Revenue Service taxes Americans on income no matter where it's earned in the world. Tax regimens vary widely overseas, and you may or may not be subject to local taxes. Many countries have tax treaties with the United States to alleviate double taxation. A list of countries with such tax treaties is available at IRS.gov; search "tax treaties A to Z."