Nestled on one of Winter Park's most picturesque brick-lined streets, this stunning Mediterranean residence offers a refined blend of timeless elegance and modern luxury. With six bedrooms, six full baths, and two half baths, this expansive 6,939-square-foot estate is designed for both grand entertaining and intimate everyday living—and is ideally suited as a multigenerational home. Originally built by esteemed custom homebuilder Ira Kitograd and recently renovated by George Driscoll, the property features a complete gut and renovation of the kitchen, family room, and luxurious master bath, elevating the home's design, flow, and functionality with exceptional craftsmanship and designer finishes. Beyond the arched glass French doors, the formal living room opens to a charming courtyard-style pool area, while a dedicated office with a fireplace and built-in bookshelves provides a quiet retreat. A guest suite with an ensuite bath offers private courtyard access. The formal dining room leads to a sprawling chef's kitchen featuring two oversized islands, high-end appliances—including a Lacanche range and Sub-Zero side-by-side refrigerator with a glass door, refrigeration drawers, warming drawers—a walk-in pantry, and a butler's pantry. Overlooking the kitchen, the family room showcases a vaulted arched ceiling, a fireplace, and a concealed TV with a remote-controlled screen. A study with a built-in desk and custom cabinetry is tucked off the family room, while a wall of glass sliders seamlessly connects the indoors to the covered lanai and courtyard. The private primary suite features a sitting area, an elegant renovated marble bath with a walk-in shower and marble flooring, and a custom walk-in closet. The second floor includes a media room with a large screen and equipment, a den or bonus room, and three additional bedrooms, each with an ensuite bath. Internet is hard-wired on both floors, making this home ideal for gaming, streaming, and working from home. Two laundry rooms, one on each level, add to the home's convenience. The outdoor living spaces are designed for both relaxation and entertaining, with a covered lanai, an expansive terra-cotta pool deck, and a sparkling pool framed by towering palms and lush Birds of Paradise. A long driveway leads to the rear-entry three-car garage, complete with a tremendous amount of custom storage cabinetry. Both the front and rear garages are air conditioned, and the main house's attached one-car garage includes a universal car charging station. Above the detached garage sits a spacious guest house, perfect for a nanny, estate manager, or visiting guests, featuring a living room, built-in kitchenette with wine refrigeration, beverage coolers, a microwave, and French doors leading to a private bedroom. The guest house's balcony overlooks the pool and courtyard, offering serene views and added privacy. A circular driveway with a centerpiece fountain enhances the estate's meticulously maintained curb appeal. Situated in the heart of Winter Park, this exquisite property offers the perfect blend of sophistication, comfort, privacy, and location.