Price Improvement! Tucked behind towering hedges on a coveted brick-lined street, this estate sits on an approximately ½-acre corner lot, providing modern functionality, Old World charm, and a fabulous lifestyle. Notable updates include newer HVAC 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. (Ask for the $400K list of improvements!) The main residence spans over 3,600+ SF with 4 Bedrooms, 4 Bathrooms, and an attached 2-car garage. Across the brick driveway is a detached, fully equipped 700+ SF Studio Apartment (5th Bedroom) located above an additional 2-car garage, as well as an air-conditioned outdoor bar. With two dwellings, a 4-car garage, and an expansive outdoor entertaining spaces on ½ acre, this home is a true private compound. The 30 foot wide family room with 12-foot ceilings, a gas fireplace, multiple French doors, and open to the kitchen....this home is perfect for entertaining. With a rear southern exposure, natural light pours in with views of the brick-paver pool deck and lush, fenced-in backyard. The open kitchen includes a NEW Sub-Zero refrigerator, natural gas Wolf range, and 2 Miele dishwashers. Enjoy casual dining at the large copper-topped island's Breakfast bar or the spacious dinette area. Just beyond the kitchen, a dining room and adjacent den (currently used as a library & office) offers flexible living options. A side entrance opens to a covered porch overlooking a generous side yard framed by tall Podocarpus hedges... ideal for future dog run or a circular driveway. Downstairs, three additional bedrooms feature vaulted ceilings and access to three full baths. Privately positioned upstairs, the expansive primary suite offers a quiet retreat, highlighted by a recent luxury bathroom renovation with elegant custom finishes. Features include a large glass shower with three showerheads, dual vanities, a Toto washlet, and custom cabinetry with linen storage. French doors from both the bedroom and bath open to a covered balcony overlooking the backyard and pool, while three custom walk-in closets create a true dressing room experience. If you only need 2 closets...it's easy to convert one of the three closets into an office or hobby room upstairs. Designed for entertaining, the outdoor living is equally impressive. A sprawling lawn surrounds the large saltwater pool and expansive paver patio for lounging and dining. A covered, air-conditioned bar is designed with custom cabinetry, exquisite lighting, a copper sink, dishwasher, wine fridge, and beverage fridge...all secured by an electronic storm shutter. The extended bar seamlessly serves the adjacent tent-covered lounge area with a natural gas grill, complete with a pool bath and outdoor shower. The detached studio apartment, positioned above the second 2-car garage, features a private entry along with a full kitchen and bath, making it ideal for extended stays or flexible living arrangements. Located just minutes from vibrant Park Avenue, this distinctive Winter Park compound is a one of a kind destination! Ask for a floorplan and the list of $400K in updates!