Sitting inside Three60 Market in East Naples, Rebecca Maddox places her iPhone flat on the table and picks up a butter knife, using it to point at a Google Earth image displayed on her screen. The image shows four plots of land along Bayshore Drive outlined in red. Maddox did not purchase just one of the properties—she purchased all four. Like a game of Monopoly, she had claimed a 3.5-acre stretch of the neighborhood’s most promising real estate.
Maddox already owned the opposite side of the street. Nearly a decade earlier, she began building her presence in the Bayshore Arts District by purchasing the Tipsy Seagull, a neglected waterfront restaurant. She stripped the building down to its foundation, preserving only the floor, and transformed the space into something entirely new.
“I was ‘the crazy blonde’ when I bought it,” says the 66-year-old Maddox, whose short gray hair is styled in a pixie cut. “I bet 100 different people—most of them men—have come to me since then and said, ‘Oh, I looked at this building, I was gonna do it.’ Well, ‘gonna, gonna, gonna’ doesn’t get you there.”
After moving from Philadelphia to Naples in 2001, Maddox began flipping residential properties with her brother as a hobby and a transition into retirement. Yet owning restaurants or developing destinations was never part of her original career path. Throughout her professional life, she worked in finance, accounting, and marketing; became an author and motivational speaker focused on female entrepreneurship; and founded a consulting firm that helped male-dominated industries better understand how to market and sell to women.
Although Maddox officially retired from finance in 2006, she continued creating new ventures as a developer. She launched Celebration Park, a bar and food truck destination across the water from Three60 Market, and later announced plans for a high-end wine venue featuring a modern glass structure surrounded by gardens.
The Bayshore Arts District, once known as an overlooked area of Naples, has undergone a dramatic transformation. What was once a neighborhood many avoided has become a growing destination for dining, entertainment, and creative businesses. Maddox is widely recognized as one of the pioneers who helped spark that change.
Recent developments, including Sicilia Pizza & Pub taking over the former Ship’s Inn and Ankrolab Brewing Co. transforming an old small-engine warehouse into a microbrewery, have continued the district’s evolution.
“I can’t say I had a grand vision of Bayshore being a cool, hip spot when I bought that first property,” Maddox says when asked what originally attracted her to the area. “The street found me, and I found out that I love developing destinations—I feel that I’m making a contribution to the community.”