Grande Oaks began its long and storied history in 1959 as Rolling Hills Country Club, one of South Florida’s first, and best, golf courses. Although it was not yet a private golf club, for many of South Florida's social elite, it was the place to be seen.
Through the years, Rolling Hills Country Club played host to a number of notable people, including Jackie Gleason, George C. Scott, Johnny Unitas, and Joe "Willie" Namath. Between 1979 and 1980, the film Caddyshack was filmed here, bringing its own cast of notables.