Since I see more and more people here wishing to retire in Italy or at least live in Italy for extended periods after retirement, I’m posting the info at the bottom on how to apply for the long term ELECTIVE RESIDENCY VISA. The visa is for 365 days but it is renewed yearly at the Questura (State Police Headquarter) while in Italy, if one wishes to stay longer. Income requirements are not that high. Full Health insurance (Medicare doesn’t cover you overseas) I don’t think costs more than $200/mo. You can actually buy into the Italian National Health System for even less (I think it’s a few hundreds a year).
NEW TAX PROVISION AFTER 2019: The new budget law passed last week provides for a tax break for foreigners wishing to retire in Southern Italy (Abruzzo, Molise, Campania, Puglia, Basilicata, Calabria, Sicily, Sardinia) in municipalities with a population under 20,000. The tax break consists in one income flat tax of 7% for the first 5 years to be applied to all non Italian income sources (pensions, annuities, investment dividends and capital gains).
If you buy a house in Italy, where you plan to reside, there is no property tax on your first home (this is true for Italians too). The average cost of a house in Sicily, for example, is €1100-€1600 per sq. mt. (About $110-$160 per sq.ft). Since the tax break applies to municipalities with population under 20,000, the prices tend to be lower than in bigger cities.