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 suiteyour own private sanctuarycomplete 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 rarewhere design, space, and versatility come together in a truly extraordinary offering.