As an always eager entrepreneur, Frederick DeBary turned his winter retreat into a profitable venture. He amassed over and planted orange groves. He built a packing house beside the lake pier and was one of the first citrus growers to sort oranges by size by rolling them down an inclined trough with variously sized holes. deBary also joined the profitable steamboat trade developing the DeBary Merchants Line. The steamboats ran from Jacksonville to Enterprise along the St. John's River. Until 1889, most of the steamers along the St. John's would be deBary boats.