Popular retirement cities are experiencing rising home prices, making affordability a challenge for many retirees. Key markets like Naples, Sarasota, Scottsdale, Asheville, San Diego, Charleston, Nashville, Suttons Bay, Cape Coral, Sedona, and Boise have high average home values and additional costs such as insurance, taxes, maintenance, and healthcare. Retirees should carefully evaluate total expenses and consider more affordable locations or renting before buying.