One or more photo(s) has been virtually staged. Experience prime lakefront living on the world-famous Winter Haven Chain of Lakes at 157 Lake Roy Drive—one of the most exceptional and hard-to-find properties to come on the market. Perfectly positioned on a quiet, crystal-clear lake with direct access to more than 20 connected lakes, this rare compound brings together a spacious 3,289 sqft main residence (4 beds/4 baths), a 550 sqft detached apartment (1 bed/1 bath), unmatched parking and storage capacity (15+ vehicles), and premier lakefront amenities—all on a waterfront setting that is nearly impossible to duplicate in Central Florida.
Thoughtfully updated and meticulously cared for, the property features new roofs on both structures (2018), complete replumbing (2019), new flooring throughout (2020), remodeled bathrooms (2020), a brand-new 2-ton A/C system in the apartment (2025), new irrigation pump (2023), upgraded landscape lighting (2025), natural-gas pool/spa heater (2019), and much more.
Inside the main residence, generous living spaces blend warmth, comfort, and functionality, creating a home designed equally for everyday relaxation and large-scale entertaining. The spacious kitchen offers abundant cabinetry, a center cooking island, breakfast bar, and a lakeview dinette positioned to capture nightly sunsets. Formal living and dining rooms accommodate gatherings with ease, while the inviting family room—with its brick natural-gas fireplace—creates a cozy backdrop for daily living.
The primary suite includes dual walk-in closets, split vanities, a jetted tub, and a large walk-in shower. Secondary bedrooms are well-sized, and the home’s storage capacity is exceptional throughout.
Where this property truly separates itself is outdoor living and entertainment potential. A natural gas–heated pool and spa, expansive covered and open decking, a cabana bath, panoramic sunset views, and a private boathouse with lift all come together to create a setting purpose-built for unforgettable gatherings. The extensive parking allows for 15+ vehicles, making this one of the few lakefront homes able to comfortably host large groups for holidays, events, and waterfront entertaining. Thoughtful landscape lighting sets a warm evening ambiance, highlighting the home’s beauty long after sunset.
Car collectors, hobbyists, and those needing significant workspace will appreciate the attached 29x21 garage with a 29x6 storage room, plus the massive 25x27 detached garage/workshop engineered with a vaulted ceiling suitable for a lift. The RV pad with 30-amp service adds even more versatility.
Perfect for multi-generational living, long-term guests, or private accommodations during holidays and special events, the detached apartment includes its own living room, bedroom, and full bath and is serviced by a brand-new 2-ton A/C system (2025).
Located on Lake Roy—one of the quietest and clearest lakes on the Chain—the property offers direct access to boating, fishing, lakefront dining, live music, and even seasonal LEGOLAND fireworks. A public boat ramp just one house away provides unmatched convenience for launching and retrieving boats.
Ideally situated between Tampa and Orlando, Winter Haven blends a vibrant small-town lifestyle with boutique dining, cultural events, and year-round recreation.
157 Lake Roy Drive is more than a lakefront home—it’s a rare waterfront compound offering space, privacy, storage, updates, entertainment capacity, and true Chain of Lakes living in one extraordinary package.