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Winding Oaks

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Community information

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352-660-1134

About our community

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.

Community amenities

  • Pool
  • Clubhouse
  • Fitness center
  • Pickleball courts
  • Dog park
  • Playground
  • Concrete block construction
  • Quartz countertops
  • Stainless-steel appliances
  • Smart home technology
  • Nearby SR-200
  • 15 minutes to I-75
  • World Equestrian Center close by
  • Nearby hospital and medical centers


Community information

Sun - Mon Call For Information

352-660-1134

Area Information

Find Your New Home in Ocala, FL

Ocala, FL, in Marion County, is a city steeped in history, culture, and natural beauty. Known as the “Horse Capital of the World,” it has hundreds of horse farms and equestrian attractions. The city also boasts affordable housing opportunities, including new construction homes by D.R. Horton, perfect for families, professionals, and retirees seeking quality construction in a community-focused and friendly environment. With its many cultural attractions, outdoor recreation, and economic opportunities, Ocala invites residents to enjoy a balanced and fulfilling lifestyle. Located in the community, Ocala International Airport provides regional travel convenience.

Community Life in Ocala, FL

Ocala’s many events and attractions unite residents throughout the year, including Light Up Ocala, transforming the downtown area into a festive wonderland each November. Patriotic Skies, a Fourth of July drone experience, showcases modern celebrations of Independence Day. Seasonal events such as the Ocala Food & Wine Festival and WEC Winter Wonderland entertain all ages. For art lovers, the Appleton Museum of Art and Ocala Civic Theatre provide enriching cultural experiences year-round. Educational opportunities abound with the College of Central Florida and other institutions nearby. Craft breweries like Infinite Ale Works, Big Hammock Brewing, and Hiatus Brewing and local vineyards like Katya Vineyards enhance the social scene, while historical attractions like Fort King National Historic Landmark add to the city’s connection to its provincial heritage.

Outdoor Fun in Ocala, FL

Outdoor adventuring will find Ocala brimming with activities and destinations. The crystal-clear waters of Silver Springs State Park invite visitors for kayaking, canoeing, and famous glass-bottom boat tours. The nearby Ocala National Forest offers hiking trails, camping sites, and unique geological features. Golfers enjoy courses like the Stone Creek Golf Club, Ocala Golf Club, Ocala Pals Golf and Country Club, The Club at Ocala Preserve, and the private Golden Ocala Golf & Equestrian Club and Country Club of Ocala. Parks like Rainbow Springs State Park and Scott Springs Park provide serene spaces for picnics, swimming, and exploring nature. With activities ranging from horseback riding to paddleboarding, Ocala makes it easy to enjoy Florida’s great outdoors.

Economic Importance in Ocala, FL

Ocala’s economy thrives thanks to a blend of industries that drive growth and create opportunities. Leading employers include Winco Manufacturing, Cardinal Glass, and HCA Florida Hospitals, ensuring job stability for professionals. The city also benefits from businesses such as Mondelēz International and REV Group, contributing to its diverse economic base. Ocala’s healthcare sector, supported by facilities like AdventHealth Ocala, remains a community pillar. Ocala is recognized as a dynamic environment for both established industries and emerging enterprises and appreciates the self-made entrepreneurial spirit. Ocala provides an appealing lifestyle for families, professionals, and retirees. With affordable, new move-in-ready homes by D.R. Horton, new residents can enjoy thoughtfully designed neighborhoods that prioritize convenience and community spirit. The city’s rich history, vibrant cultural scene, and abundant recreational opportunities create an environment where everyone can thrive. Whether you’re drawn to its equestrian heritage, its educational and economic opportunities, or its access to nature, Ocala has something special to offer every new homeowner. Move to Ocala and discover a place where life can flourish.
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