Rare opportunity to own a beautifully updated estate-style home with attached guest house on an idyllic cul-de-sac lot in the highly sought-after gated North Naples community of Monterey. Designed for both everyday comfort and exceptional entertaining, this home features a stunning private outdoor space, including a resort-style pool and spa with sun shelf and expansive covered lanai spaces perfect for outdoor dining and lounging. The main residence showcases soaring ceilings, updated kitchen and baths, spacious formal and casual living areas, and pocketing sliders that seamlessly blend indoor and outdoor living. Beyond an inviting office space, the attached guest quarters, also accessible by private entrance, offer a full kitchen, two bedrooms, two bathrooms, dining/living area and a generous living/playroom - all opening directly to the spectacular outdoor oasis; ideal for long-term guests, multigenerational living, an au pair, or private retreat space. Monterey is one of North Naples' premier gated communities, featuring 24-hour guard-gated security and an unmatched central location close to A-rated schools, world-class shopping and dining, downtown Naples, and the area's renowned white-sand beaches. Residents enjoy exceptional amenities including three Har-Tru tennis courts, pickleball and sports court, a large shaded playground, community pool with cabanas, renovated clubhouse and fitness center, summer swim team, year-round social events, and popular onsite food trucks. A truly special property offering space, flexibility, privacy, and value in one of Naples' most desirable neighborhoods.