In the second half of the 1920s Winnaretta devoted her energies to publicly oriented works of mécénat. This change of direction in her patronage activities— away from musical projects, and towards houses, buildings, and institutions—began, oddly enough, with her brother Paris's newest financial scheme: the opening of a luxury country club in South Florida.

The publicity and royal accolades that Paris Singer had garnered from the conversion of the Wigwam into a war hospital failed to attract the wealthy investors to his European business ventures as he had hoped. His affair with Isadora Duncan had ended unhappily, despite his offer to purchase Madison Square Garden for her use as the New York branch of her dancing school. At the same time his wife Lillie, fed up with his amorous dalliances, obtained a French divorce. Plagued with financial woes and chronic heart problems, the indefatigable entrepreneur relocated to Florida and, in 1919, acquired a large property in the middle of a swamp, with a single dirt road running through it. He devised a plan to convert “Joe's Alligator Farm” into a convalescent and rehabilitation facility for wounded French and English officers returning from the war. To build the facility, Paris called upon the talents of another eccentrically brilliant amateur architect, Addison Mizner, who, with the Singer fortune at his disposal, built a manor house in “Bastard-Spanish-Moorish-Romanesque-Gothic-Renaissance- Bull-Market-Damn the Expense Style.” Paris solicited investors from the same group of wealthy Europeans who had endowed beds at the Wigwam. Unfortunately, the facility failed to attract convalescing soldiers. Facing the grim prospect of another financial failure, Paris had the idea of converting the building into a private social club. He had Mizner build a ring of private residential “cottages” to surround the manor house; he financed the transformation of the property's dusty dirt road into Worth Avenue—Palm Beach's future equivalent of Hollywood's Rodeo Drive. The Duchesse de Richelieu—the recently widowed Princesse Alice of Monaco— was enlisted to take charge of the décor. The success of the newly-born “Everglades Club” was instantaneous: from the first launch of advance publicity in 1925, the elite of two continents made plans to travel to Florida in order to discover this new palace of elitism.