Winter Park Streets: New England Avenue The earliest settlers of Winter Park hailed from New England, hence "New England Avenue."  Then Now This photograph of New England Avenue was taken sometime between 1882 and 1887.  The view is from the Seminole Hotel, looking west towards Park Avenue and the South Florida Railroad.  The Winter Park Public Library now stands on the corner to the left of the trolley car, which transported guests back and forth between the railroad and the hotel.   New England Avenue 2001.