Tucked behind a gated entry on 2.5 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 bath, all finished in a timeless, understated aesthetic. Equally impressive, the fully detached guest residence offers approximately 1,480 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 bath, 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 a truly extraordinary offering.