Luxury estate in gated reserve at tuscawilla with resort style outdoor oasis designed for entertaining. Welcome to 109 cherry creek circle in winter springs, a 5 bedroom, 4 bath estate on a half acre homesite in the gated reserve at tuscawilla. This 3,440 sq. Ft. Home blends timeless design with a layout built for both everyday living and exceptional entertaining, centered around a truly standout outdoor space. Inside, high ceilings and a classic columned entry lead to a light filled family room with a gas fireplace and marble surround, positioned to capture views of the backyard oasis. The screened lanai with updated pavers (2023) opens to a true outdoor oasis featuring an oversized 9 foot deep pool and propane heated spa, surrounded by custom tennessee river rock, with matching stone extending to a separate fire pit lounge area that adds additional entertaining space. Designed for hosting, the covered l shaped bar with kegerator and beverage refrigerator creates a natural gathering point, complemented by a full summer kitchen with a built in viking grill and texas smoker. The gourmet kitchen continues the flow with a gas cooktop, built in double ovens, beverage station with cooler and ice maker, and a breakfast nook featuring a signature von jacobs ceiling detail, all connecting seamlessly to the main living areas. Formal living and dining spaces offer additional flexibility, including a dining room anchored by a tiffany style chandelier. The private first floor primary suite features a remodeled spa style bathroom (2025) and a large walk in closet with custom built in organization. Three additional bedrooms are located on the main level, including a jack and jill bath, while the oversized upstairs suite with new wood look tile provides flexible space for guests, extended stays, or a private retreat. Additional features include a 100 bottle temperature controlled wine cellar, tile and hardwood flooring, security wiring, and a 3 car side load garage with professionally finished floor. Major updates include roof (2017), hvac (2017), whole house replumb (2024), water heater (2026), and updated driveway and lanai pavers (2023). Located within the gated reserve at tuscawilla, known for its estate homes, tree lined streets, and community events, with access to top rated schools, tuscawilla country club, the cross seminole trail, sr 434, and 417, and convenient connectivity to winter park, oviedo, and lake mary. This is a home designed for gathering, hosting, and creating lasting memories. This is more than a homeit is a space designed to gather, entertain, and create lasting memories.