This timeless Neoclassical Italian estate has been thoughtfully refreshed and returns to market with renewed appeal. Situated on a prime .71 acre corner lot, the 7,916 SF property includes a main residence of over 7,100 SF, a detached guest house, and a poolside catering suite. The private covered boat dock is located just steps away across the street in historic Kraft Azalea Gardendelivering direct lake access and boating on Lake Maitland without the upkeep of a waterfront backyard. Inside, fresh neutral interiors and updated landscaping frame elegant arrival and living spaces. The thoughtful layout offers 5 bedrooms and 5 full plus 4 half baths, including a 550 SF guest house. Expansive entertaining areas flow seamlessly to a private courtyard with heated pool and spa, covered dining, outdoor grill, wood burning fireplace, and multiple terraces. Highlights include a grand primary suite with dual bathrooms and closets, a two story wardrobe with office, an impressive entertainment room, and a gourmet kitchen outfitted with Viking appliances, a newly replaced double oven, and trash compactor. For large scale entertaining, the detached pool house doubles as a catering suite with prep sink, refrigerator, and wall to wall storage. Built by renowned builder Charles Clayton, the home is a masterpiece of solid block construction and timeless detail featuring imported Parisian fireplaces, solid marble columns, both marble and travertine floors, and Venetian plaster walls. A new barrel tile roof (2023) adds lasting value and peace of mind. Ideally located across from Kraft Azalea Garden and near Rollins College, the estate offers a rare combination of waterfront tranquility and walkable access to Park Avenues world class dining, boutiques, and museums. The Winter Park Racquet Club is also just a short golf cart ride away. This is an opportunity to capture a legacy property at a fair value, with the heaviest aesthetic updates complete and future equity ready to grow.