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 home—it is a space designed to GATHER, ENTERTAIN, AND CREATE LASTING MEMORIES.