Nestled on one of Sarasota's most sought-after streets, this classic brick residence on South Drive presents a rare opportunity to own a truly special property in the heart of Cherokee Park. Lovingly maintained by its original owner, the home rests on an exceptional, oversized lot - enhanced by deeded access from South Lodge Drive, adding a unique level of privacy and convenience. The timeless two-story design features generously scaled living spaces that exude warmth and charm. The main floor offers three well-appointed bedrooms, two and a half bathrooms, formal living and dining rooms, and a welcoming family room that flows seamlessly into the kitchen. A cozy den/library with custom built-ins provides a peaceful retreat for work or relaxation. The upper level is dedicated to the expansive primary suite, complete with two full bathrooms and abundant space to fret your ideal sanctuary. Outdoors, a canopy of mature trees and lush landscaping surround the pool and deck - perfect for entertaining. Located outside of the flood zone and just minutes from Siesta Key Beach, Southside Village, and Downtown Sarasota, this property offers endless potential to renovate, expand, or build new in one of the city's most desirable neighborhoods.