Tucked behind towering hedges on a coveted brick-lined street, this estate sits on an approximately half-acre corner lot and has been enhanced with thoughtful improvements, delivering a rare combination of modern functionality, Old World charm, and a fabulous lifestyle. Notable updates include newer heating, ventilation and air conditioning systems (2020 and 2025), a tankless gas water heater, a fully renovated laundry room with new LG stackable washer and dryer, newer kitchen appliances, new copper gutters and downspouts, fresh exterior paint (2025), a newly designed primary bathroom, and much more. The main residence spans over three thousand six hundred square feet with an attached two-car garage and is complemented by a detached, fully equipped seven hundred square foot studio apartment located above an additional two-car garage, as well as an air-conditioned outdoor bar. With two dwellings, a four-car garage, expansive outdoor entertaining space on half acre, and surrounded by tall podocarpus hedges, this home is a true private compound. This is not just a home—it’s a destination! Enter the main residence into a dramatic living space featuring twelve-foot ceilings, a thirty-foot span, a gas fireplace, and walls of windows and doors. With a rear southern exposure, natural light pours in through five sets of French doors, offering views of the brick-paver pool deck and lush fenced grounds beyond. The family room flows seamlessly into the open kitchen elevated by newer luxury appliances including a Sub-Zero refrigerator, Wolf gas range, and dual Miele dishwashers. At the center, a copper-topped island anchors the space complemented by a wood-stained beadboard ceiling and a spacious dinette for casual dining. Just beyond the kitchen are large dining room and adjacent den (currently used as library and office) that offer flexible living options. A side entrance opens to covered porch overlooking generous side yard framed by tall privacy hedges—ideal for dog run or discreet boat storage. Downstairs three additional bedrooms feature vaulted ceilings and access to three well-appointed full bathrooms creating functional layout for family and guests. Privately positioned upstairs the expansive primary suite offers quiet retreat highlighted by recent full-scale luxury bathroom renovation with elegant custom finishes. Features include large glass shower with three showerheads dual vanities Toto washlet designer mood lighting custom cabinetry with linen storage. French doors from both bedroom and bath open to covered balcony overlooking backyard and pool while three custom walk-in closets create true dressing room experience with additional flexible space for office or hobby room. Designed for entertaining the outdoor living is equally impressive. A sprawling lawn surrounds large saltwater pool expansive paver patio for lounging dining covered air-conditioned bar outfitted with custom cabinetry exquisite lighting copper sink dishwasher wine fridge beverage fridge—all secured by electronic storm shutter. The extended bar seamlessly serves adjacent tent-covered lounge area complete with pool bath outdoor shower. The detached studio apartment positioned above second two-car garage features private entry along with full kitchen bath making it ideal for extended stays or flexible living arrangements. Located just minutes from vibrant Park Avenue this distinctive Winter Park compound blends curated finishes meaningful upgrades exceptional privacy.