Someone in their late fifties or early sixties is looking at Sarasota, doing the napkin math, and wants to know if $5,500 a month actually works there. Sarasota sits in a strange middle zone: cheaper than Naples, pricier than Ocala, and saddled with a cost structure that has changed meaningfully in recent years. Here is... Can You Retire in Sarasota on $5,500 a Month? Only If These 3 Things Are True.