Under contract-accepting backup offers. Grand Southern charm and architectural elegance define this stately residence in one of Winter Park’s most desirable neighborhoods, set along a quiet brick-lined street just steps from Lake Chelton. Positioned on nearly half an acre, the home spans over five thousand two hundred square feet, offering five bedrooms, four and a half bathrooms, a designated office, a large, versatile media/game room, a three-car garage, and an expansive lanai with summer kitchen and resort style pool—all brought together in a smart well-planned layout ideal for effortless everyday living and exceptional entertaining. Step inside to a beautifully curated interior where rich architectural detail and livable design come together. Extensive custom millwork—seen in detailed moldings, trim work, and built-ins—adds depth and character throughout. The entry opens to gracious living and dining spaces, complemented by an impressive five hundred fifty-plus bottle temperature-controlled wine room. At the heart of the home is a beautifully appointed kitchen featuring white wood cabinetry, a six-burner gas range, an oversized quartz island, and a delightful breakfast nook that seamlessly connects to the family room featuring custom built-ins and fireplace—creating a natural gathering space. Tucked away, the first-floor primary suite offers a spacious sitting area, a beautifully customized closet with dressing area, and a luxurious bath with marble flooring, a large double-head walk-in shower, dual vanities, a free-standing tub, and built-in linen cabinetry—designed as a calming and private sanctuary. The first level also features a private guest bedroom with en-suite bathroom creating an ideal setup for friends and family. A generously sized laundry room offers abundant cabinetry and exceptional storage making everyday tasks feel effortless. Upstairs three spacious bedrooms and two full bathrooms provide comfortable accommodations with two bedrooms opening through French doors to the front double balcony—perfect for enjoying peaceful treetop views. The back of the home unfolds around a beautiful pool and spa with French doors from multiple rooms opening to the lanai creating a natural indoor-outdoor connection. Retractable screens allow for year-round enjoyment of the well-appointed summer kitchen making it ideal for both relaxed evenings and easy entertaining. Other notable highlights include: A whole house natural gas generator; extensive brick paver driveway & motor court; automated driveway gate; integrated sound system; security cameras; new roof 2024. Lastly this profound property offers top rated Winter Park schools and easy access to Park Avenue Downtown Orlando Audubon Park Garden District; Baldwin Park.