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Finding the cheapest place to retire means more than cutting expenses, you need to beware of the tax climate. Not every state will be an affordable place to retire. Forty of the 50 states give a variety of tax breaks to retirees. Seven have no state income taxes for all residents, and eight gave property tax relief to homeowners over 65. Fourteen give homestead exemptions to all homeowners. Most states will allow you to deduct some portion of your government, military or private pension when calculating your income tax.