Tucked behind a gated entry on two point five acres of lush, wooded privacy, this exceptional Naples estate offers a rare and versatile opportunity with a primary residence and a guest residence, each with its own pool, perfectly suited for guest accommodations, multi-generational living or income-producing potential. The main residence embodies Florida charm, featuring a welcoming front porch, rich wood flooring throughout the main living areas, and seamless indoor-outdoor living. Designed for both everyday comfort and effortless entertaining, the home offers an array of flexible living spaces, including a formal dining room, living room, family room, and an expansive bonus room ideal for a media lounge, fitness studio, or game room. Outdoors, a large screened lanai, custom-designed pool, and an outdoor equipped summer kitchen with built-in grills create a private retreat framed by mature tropical foliage. Upstairs, the second floor is dedicated to a luxurious primary suite-your own private sanctuary-complete with custom walk-in closet and a spa-inspired ensuite bathroom all finished in a timeless understated aesthetic. Equally impressive, the fully detached guest residence offers approximately one thousand four hundred eighty square feet under air and its own private driveway. This spacious home lives like a residence of its own featuring a primary bedroom with ensuite bathroom large living room full kitchen dining or flex space den and a generous screened lanai with its own private pool. Ideal for extended family long-term guests or as a potential income-producing rental it provides exceptional flexibility without compromising privacy. Southern exposure with expansive acreage and a peaceful Olde Naples style setting just minutes from Naples' Gulf beaches shopping and dining this one-of-a-kind property delivers the perfect balance of seclusion and convenience. Estate opportunities like this in Livingston Woods are rare-where design space and versatility come together in truly extraordinary offering.