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 home’s 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.