6. Cumberland, Maryland

Tucked into the Appalachian Mountains in Western Maryland, Cumberland is a historic transportation hub that offers a remarkably low cost of living while keeping you within a few hours’ drive of Washington, D.C., and Baltimore. The architectural heritage of the city is striking, and determined buyers can find beautiful historic brick homes requiring just a little TLC for under $100,000.

Cumberland appeals to retirees who want a quiet, scenic environment with a strong historical identity. The Great Allegheny Passage provides incredible opportunities for outdoor recreation right in your backyard. Maryland’s tax landscape is generally considered less friendly to retirees than states further south, but the sheer affordability of the real estate in Cumberland often offsets the broader state tax burden.