8. Syracuse, New York

New York is generally viewed as an expensive state, but Upstate New York tells a completely different economic story. Syracuse is a major university town that offers top-tier hospitals, diverse cultural amenities, college sports, and a bustling downtown. The housing market is remarkably accessible, with many solid, older homes trading hands for well under the $100,000 mark.

The presence of a major university injects vitality into the local economy and provides retirees with opportunities for lifelong learning and community engagement. However, similar to Illinois, you must brace for higher property taxes. Additionally, Syracuse is one of the snowiest cities in America. If you are willing to manage the winter weather and the tax rate, the cultural and medical benefits are hard to beat at this price point.