One or more photo(s) has been virtually staged. In Sarasota's desired West of Trail enclave of Cherokee Park, 1655 South Drive, masterfully designed three story estate where thoughtful architecture meets effortless luxury. Positioned on a homesite that is not in a Special Flood Hazard Area and enhanced with full home hurricane impact glass and a whole home generator, this residence offers the rare combination of refinement and peace of mind. Spanning 6,355+ square feet, the home features five bedrooms, five full baths and four half baths, with a layout tailored for grand entertaining and everyday ease. A rear three car garage, accessed discreetly from South Lodge Drive, preserves the home's striking street presence. Inside, the main level unfolds into a wide open living experience with a great room with wet bar, formal dining, and a showpiece chef's kitchen outfitted with Wolf dual oven six burner range, dual side by side 36 Sub Zero Over and Under Refrigerator/Freezers, a Wolf microwave drawer, a Wolf warming drawer, and built in Miele espresso machine. The first floor primary suite is a private retreat, complete with an in home gym, a spa inspired bath and dual custom fitted closets. A beautifully appointed guest suite (fifth bedroom) with en suite bath also anchors the main level. Access to the upper floors is seamless via a dramatic staircase with custom wrought iron railings or the private elevator. Upstairs, three additional en suite bedrooms include custom walk in closets, one thoughtfully designed with built in bunk beds, plus a bonus club room with built in desks and additional laundry for added convenience. Outdoors, the property transforms into a walled and gated resort style oasis featuring a gas heated saltwater pool with sun shelf and spa, and an artificial turf lounge/play area. A screened entertainment lounge with a convenient half pool bath connects to a full outdoor kitchen with sink, TV and gas grill, all complemented by a pergola and a mosquito misting system, ideal for Sarasota's seasons. Above the garage, a spectacular casita style retreat, accessible by the homes second private interior elevator or exterior spiral staircase, elevates entertaining to an entirely new level with a 2,000 bottle refrigerated wine room, a fully equipped wet bar, mini fridge, clear ice maker, and dishwasher. Go onto the covered terrace with a gas fireplace, then unwind on the third floor in the private, pool like infinity edge spa, an experience that feels equal parts boutique resort and private club. Ideally in walking distance to A rated Southside Elementary School, Southside Village, Sarasota Memorial Hospital, downtown Sarasota and short drive to the world famous sands of Siesta Key Beach, this is a rare opportunity to own a bespoke residence in one of Sarasota's treasured neighborhoods.