A unique generational property set on 1.66 acres in Pine Ridge, featuring four distinct structures: a main residence, club room, flex space and guest house. Designed for seamless indoor-outdoor living, the open floor plan flows effortlessly to a resort-style pool and spa, outdoor kitchen featuring a gas grill, pizza oven and Evo grill, expansive dining and lounge areas, and a cozy fire pit. The gourmet kitchen is appointed with Wolf and Sub-Zero appliances, complemented by a butler's pantry with wine storage. The main residence offers five bedrooms, each with an en-suite bath, along with an upstairs bonus room. The master is a private sanctuary featuring a spa-inspired marble bath, soaking tub, dual showers, steam shower and outdoor shower. The versatile club room offers endless possibilities as a game room, studio, office or additional suite, while the separate flex space is ideal for a gym, art studio or garage. A two-bedroom, two-bath guest house with a full kitchen provides comfortable accommodations for family and guests. Recent driveway enhancements include an extended driveway with additional parking and a convenient turnaround area, adding both functionality and ease of access. Ideally located near Naples' beautiful beaches, Mercato and Waterside Shops, this extraordinary estate offers a rare combination of privacy, versatility and convenience. A truly exceptional opportunity and must-see property.