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 situated on a half-acre homesite in the gated Reserve at Tuscawilla. This 3,440 sq.ft. home is thoughtfully designed for both everyday living and EXCEPTIONAL ENTERTAINING, anchored by a truly standout outdoor space. From the moment you step inside, HIGH CEILINGS, a classic columned entryway, and abundant natural light draw you into the family room featuring a GAS FIREPLACE WITH MARBLE SURROUND and a direct view to the backyard—where this home truly shines. The SCREENED LANAI with UPDATED PAVERS (2023) opens to an outdoor oasis featuring an OVERSIZED 9-FOOT DEEP POOL, PROPANE-HEATED JETTED SPA, and a CUSTOM TENNESSEE RIVER ROCK SURROUND, with matching stone extending beyond the lanai to a separate FIRE PIT LOUNGE AREA for additional gathering space. Designed for hosting at every level, the COVERED L-SHAPED OUTDOOR BAR WITH KEGERATOR AND BEVERAGE REFRIGERATOR creates a central hub for entertaining, complemented by a FULL SUMMER KITCHEN WITH BUILT-IN VIKING GRILL AND TEXAS SMOKER. Inside, the home continues to support connection and functionality with a GOURMET KITCHEN featuring 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 that flows seamlessly into the main living areas. Formal living and dining spaces provide additional versatility, including a dining room anchored by a STUNNING TIFFANY-STYLE CHANDELIER. The private first-floor PRIMARY SUITE offers a REMODELED SPA-STYLE BATHROOM (2025) and a LARGE WALK-IN CLOSET WITH CUSTOM BUILT-IN ORGANIZATION. The split floor plan includes three additional bedrooms on the main level with a JACK AND JILL BATH, while the OVERSIZED UPSTAIRS PRIVATE SUITE with NEW WOOD-LOOK TILE provides flexible space for MULTI-GENERATIONAL LIVING, EXTENDED GUESTS, OR A PRIVATE RETREAT. Additional highlights 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 estate homes, tree-lined streets, and neighborhood events, with access to TOP-RATED SCHOOLS, TUSCAWILLA COUNTRY CLUB, THE CROSS SEMINOLE TRAIL, SR-434, AND 417, and convenient connectivity to surrounding areas including Winter Park, Oviedo, and Lake Mary. This is more than a home—it is a space designed to GATHER, ENTERTAIN, AND CREATE LASTING MEMORIES.