Custom Waterfront Estate located in the heart of Winter Park with a covered Boat Dock on Lake Maitland, the largest of the Winter Park Chain of Lakes, and walking distance to historic Park Avenue. A timeless Neoclassical Italian home that exudes luxury and sophistication, spanning a total of 7,916 square feet. Built by Charles Clayton. Designed by Marc Michaels. The main house boasts over 7,100 sf with 4 bedrooms, 4 full bathrooms, and 3 half bathrooms. The detached Guest House/In-Law is approx. 500 sf, with 1 bedroom, 1 bathroom, two closets, and a wet bar. The detached Catering Room with half (pool) bath is approx. 350 sf with an additional refrigerator and wall-to-wall storage, conveniently attached to one of the two-car garages. Recently upgraded with a NEW barrel tile ROOF installed in 2023. Create lasting memories as you welcome friends and family into expansive spaces that seamlessly blend sophisticated indoor elegance with captivating outdoor beauty, perfect for everything from casual gatherings to spectacular soirées. Outfitted with the finest custom finishes, a gourmet chef's kitchen, equipped with top-of-the-line appliances, an oversized island, and a large dinette space. Awe-inspiring private courtyard with heated pool and spa, covered porch, outdoor grill, and several separate terraces. The impressive primary suite features an office and sitting area, with separate his and hers en-suite bathrooms and closets. Stunning two-story closet with office on the second floor and laundry room on the first floor. Impressive entertainment/media room with state-of-the-art projector, media equipment, and electronic blackout shades. The second story features a spacious loft, 3 bedrooms, 2 full bathrooms, the second laundry room, and two balconies. Storage is abundant throughout this property. You will find two oversized 2-car garages behind the electronic, gated, side-facing driveway, one of which features two kennels and a Tesla charging station. Ideally positioned within Winter Park's coveted central corridor, offering unparalleled access to cultural landmarks including the Charles Hosmer Morse Museum, Winter Park Museum of American Art, and the scenic Winter Park Chain of Lakes. Rollins College is just minutes away, with convenient proximity to UCF as well. Experience quintessential Winter Park living in this one-of-a-kind estate that combines waterfront tranquility with the convenience of being at the cultural and social epicenter of one of Central Florida's most sought-after communities.