A Racing Legend’s Dashing Retreat on Florida’s Gulf Coast Just Listed for $5.2 Million

Retired racecar driver Hurley Haywood, who built his career on stamina, is waving the checkered flag on the Florida retreat he custom built for the long haul more than a decade ago, putting his stunning coastal residence in St. Augustine up for grabs at $5.2 million.

Few drivers can match Haywood’s resume. He is one of a rare group to win endurance racing’s Triple Crown, with triumphs at the 24 Hours of Le Mans, the Rolex 24 at Daytona, and the 12 Hours of Sebring. Retiring in 2012 after a 40-year career, he chose Florida’s historic Gulf Coast to slow down. 

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According to the listing agents Jane Chefan and Jessica Chefan Hansen of One Sotheby’s International Realty, the legendary endurance driver bought the property in 2012 for $725,000 and chose to build his dream home from scratch, rather than renovating the original structure.

Set within one of St. Augustine’s most desirable waterfront enclaves and an easy walk from downtown, the roughly 4,200-square-foot residence was designed by Cronk Duch Architects. Inside, soaring ceilings and a sweeping wooden staircase create a striking first impression, while rich heart-of-pine floors ground the bright interiors and black-framed French doors open to picturesque water views.

The central kitchen anchors the home—a chef-ready space with high-end appliances and an open layout that connects directly to the living and dining areas. Nearby, a tailored wet bar with custom cabinetry and a 140-bottle Sub-Zero wine cooler stands ready for post-dinner pours.

Premium perks, including a private theater, a sauna, a residential elevator, a whole-house Sonos system, and a built-in safe, are thoughtfully integrated, while two detached casitas provide flexibility for guests, extended family, or an executive office suite.

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Upstairs, the primary suite leans serene, with oversized windows and a marble-clad bath featuring a water-view soaking tub and glass-enclosed shower. Out back, the property settles fully into resort territory with a heated saltwater lap pool, a cabana bath, and a gas fire pit overlooking the water. A newer dock has been decked out with boat and jet ski lifts, and, in a detail that feels especially on-brand, the three-car garage comes equipped with a vehicle lift—a subtle nod to Haywood’s racing pedigree.

After building a vaunted career defined by tenacious staying power, it’s no surprise Haywood’s home reflects the same philosophy—thoughtfully designed, carefully constructed, and built to withstand the test of time.

Click here to see more photos of the St. Augustine estate.