Winding Oaks - Tradition Series

Welcome to Winding Oaks, a new master-planned community set on the grounds of one of the world’s most historic horse farms. Winding Oaks celebrates and embraces the rich heritage of Ocala’s Equestrian background while embracing the future.


Located in Ocala, Florida, off SW 49th Avenue and next to the brand-new Winding Oaks Elementary School opening Fall of 2025, Winding Oaks offers a rare opportunity to own a home in a place where history, nature, and lifestyle come together. Ocala’s central location gives you the option to explore the best of central Florida. Your new home is located within minutes to SR-200 and under 15-minutes to I-75. Watch events at the World Equestrian Center, visit historic Downtown Ocala, or go ziplining at The Canyons Zip Line & Adventure Park nearby. Homeowners have great access to a variety of entertainment, dining, shopping, and healthcare options available throughout the area.


Winding Oaks holds a legacy that was once home to championship horses and now opens a new chapter, inviting families, professionals, and retirees to be a part of the new era of Winding Oaks. This community will feature a wide variety of floorplans to suit every stage of life, from stylish single-family homes to spacious MultiGEN homes, all built with today’s quality standards and energy-efficient features in mind. Soon, an amenity center in Winding Oaks will offer residents places to relax, gather & play, whether it’s a walk along scenic trails to the preserved historic horse cemetery, spending an afternoon at the pool and clubhouse, or soaking in the picturesque green spaces with mature Oak Trees.


Offering open-concept floorplans, perfect for spending quality time with family and friends, each home is equipped with quartz countertops, stainless-steel appliances, and a state-of-the art smart home system. Come home to Winding Oaks, where its heritage lives on while building for what’s next. Join our VIP list today and be the first to know when sales begin.