Welcome to a truly rare opportunity in the highly sought-after Oakes Estates, an area experiencing strong high-end growth and redevelopment. Situated on an expansive two and a half-acre parcel, this unique estate offers two single-family pool homes with no Homeowners Association fees and access to top-rated school districts-a combination that is increasingly hard to find. The main residence offers a flexible layout and serves as a true blank canvas, providing an exceptional opportunity to personalize and transform the space into your ultimate dream home. Architectural highlights include soaring ceilings exceeding twenty feet in select areas, a working fireplace, custom wood cabinetry, wood-cased windows, and quality Decora and KitchenAid appliances. Southern exposure fills the home with natural light, while the oversized garage, expansive lanai, pool, and dedicated pool bath make entertaining effortless. The second residence, offering over one thousand three hundred square feet, is perfectly positioned at the rear of the property, providing excellent privacy and separation from the main home. Built in 2000 with solid CBS construction, this charming three-bedroom, two-bathroom home features an open kitchen, two-car garage, and a private plunge pool. Currently tenant-occupied, it presents an ideal opportunity for rental income, guest accommodations, or the flexibility to live in the second home while completing your dream estate. This exceptional property allows for multiple lifestyle and investment options-live in one home and rent the other, accommodate multi-generational living or hold both as a strategic long-term asset. Enjoy the freedom of estate-style living while remaining just minutes from shopping, dining, and all that Naples has to offer. A rare opportunity to own two homes on one estate in Oakes Estates-properties like this seldom come available.