Discover an exceptional blend of architectural character, enduring craftsmanship, and private estate living in the heart of Naples' sought-after Oakes Estates. This distinctive property situated on 2.27 acres features a beautifully designed main residence, a separate guest house, and expansive indoor-outdoor living spaces, creating a rare opportunity for multigenerational living, entertaining, or a private family compound. The main residence offers 3 bedrooms plus a den, complemented by soaring 10-foot ceilings, 8-foot doors and distinctive Prairie-style 6-foot windows that fill the interiors with natural light. Custom, locally crafted solid rock maple cabinetry and unstained white oak flooring bring warmth and timeless sophistication to the living spaces. Reflecting a commitment to quality construction, the home features masonry construction, copper plumbing, and an uncommon design advantage: no interior load-bearing walls, offering exceptional flexibility for future customization, reconfiguration, or expansion. Additional features include a whole-house reverse osmosis water system, central vacuum with a new motor, a newer water heater, a 5-ton air-conditioning system, extra-deep garages providing generous storage, and a separate air-conditioned shed. Fresh interior and exterior paint further enhance the home's appeal. The separate guest house, built in 2006, offers approximately 1,100 square feet under air, with 2 bedrooms and 1.5 baths. Designed with the same appreciation for quality and comfort, it features polished concrete floors, impact-resistant PGT windows, granite countertops, luxury German cabinetry, and stainless steel appliances. Ideal for extended family, visiting guests, or a private living space, this residence adds remarkable versatility to the property. Outdoor living captures the essence of classic Florida Vernacular design. An expansive 1,541-square-foot covered and screened wraparound porch provides a welcoming setting for relaxing, dining, and entertaining throughout the seasons. The large gunite sport pool, featuring a unique deep end in the center, offers an inviting recreational retreat for all ages. With approximately 8,150 square feet under roof, the property combines generous scale with privacy, flexibility, and enduring construction. Situated in FEMA Flood Zone X and approximately 50 inches above the crown of the road, the estate offers additional peace of mind. Enjoy the tranquility and space that define Oakes Estates while remaining just minutes from Naples' renowned beaches, upscale dining, shopping, and everyday conveniences. A rare opportunity to own a character-rich Florida estate with exceptional craftsmanship, a separate guest residence, and the freedom to make the property uniquely your own.