Officials: Crews searching for lost swimmer in Lake Osceola By FOX 35 News Staff Published Crews searching for lost swimmer in Lake Osceola A massive search operation was underway in Winter Park late Monday evening for a swimmer who was reported lost in Lake Osceola. WINTER PARK, Fla. - A massive search operation was underway in Winter Park late Monday evening for a swimmer who was reported lost in Lake Osceola. Officials say the swimmer is a 21-year-old man. He was reportedly on a boat with others but got off to swim and was not seen again. The search started at around 7:30 p.m. according to officials, and it now is considered a recovery mission.