Lakefront pool home on the Winter Haven Chain of Lakes with a detached apartment, 4 car garage, abundant open parking, RV parking pad, pool, dock and more! Perfectly positioned on Lake Roy, one of the Chains quietest and clearest lakes, this property delivers sunset views, calm waters, and direct boat access to 20 canal connected lakes for endless fishing, skiing, cruising, lakefront dining, live music, and seasonal LEGOLAND fireworks. The main residence features over 3,800 sqft of living space with 4 bedrooms, 2 full baths, and 2 half baths, plus a detached 550 sqft apartment with its own living room, bedroom, and bathideal for guests and extended family. Inside the main home, formal living and dining spaces lead to a well equipped kitchen with center island, breakfast bar, abundant cabinetry, and a lakeview dinette designed to capture nightly sunsets. The inviting family roomwith its brick natural gas fireplaceadds warmth and comfort for everyday living. The primary suite offers dual walk in closets, split vanities, a jetted tub, and walk in shower, while secondary bedrooms provide generous space and excellent storage. Outdoor living is where this property excels. Enjoy a natural gasheated pool and spa, expansive covered and open decking, cabana bath, panoramic lake views, and a private boathouse with liftcreating the ultimate lakefront playground. A public boat ramp just one home away adds exceptional convenience. Major updates ensure peace of mind, including: new roofs on both structures (2018), complete replumbing (2019), new flooring throughout (2020), remodeled bathrooms (2020), new irrigation pump (2023), upgraded landscape lighting (2025), natural gas pool/spa heater (2019), and a brand new 2 ton A/C in the apartment (2025). Located between Tampa and Orlando, this property offers the perfect blend of small town charm, recreation, and waterfront living. 157 Lake Roy Drive is more than a homeits a fully updated lakefront compound offering space, versatility, and true Winter Haven Chain of Lakes lifestyle.