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Lorraine Leedy Stewart is a longtime Winter Park resident whose family owned and operated " Leedy's ". " Leedy's ", a well known department store located on Park Avenue, was in operation for over 60 years.
The Lorraine Stewart Postcard Collection contains approximately 117 postcards ranging in time from the late 1880's to the 1990's. The postcards reflect many unique images particularly Rollins College, early Winter Park buildings, streets, scenes and homes. Below is a sampling from that collection.
The Colony Theater opened in 1939 and operated as a theater for 36 years before closing September 28, 1975. This Art Deco building, a landmark in Winter Park, is located at 329 Park Avenue South. © Absolute Photography – Used by permission Click on thumbnail to view larger image.
The Winter Park Sidewalk Art Festival, held on the third weekend each March, had its beginnings in historic Central Park in March of 1960. Over the years, this nationally acclaimed fine arts festival has grown in popularity and stature. It attracts more than 250,000 people throughout the U.S. and abroad.
The cover of the 1964-65 Winter Park Telephone Directory features the Sidewalk Art Festival. A copy of the telephone directory can be found in the Winter Park Public Library Archives collection. Click on thumbnail to view larger image.
The Venetian Canal is one of several narrow, winding canals connecting lakes Maitland, Osceola and Virginia. In the late 1800's, these canals were deep streams and navigable by poling, paddling, and in some cases by motor boat.
The main purpose of the canals, besides providing access to the chain of lakes, was to maintain lake levels and avoid flooding. © Absolute Photography – Used by permission Click on thumbnail to view larger image.
In 1937, Captain Walt Meloon of the Pinecastle Boat Company announced a new attraction for Winter Park, "The Venice of America Scenic Pleasure Boat Tours", also called The Scenic Boat Tour. The 25- passenger boat "Scenic" made its maiden voyage around Lakes Virginia, Osceola, and Maitland with city officials and businessmen getting the first trip. The tours began officially on January 1, 1938. The boats were radio equipped, and a travelogue was given by the pilot.
The Scenic Boat Tour is still in business and offers the same interesting tour of the three lakes. Click here to access the official Scenic Boat Tour page. Click on thumbnail to view larger image.
Greeneda Court, built in 1947 by Raymond W. Greene, is a group of three office and apartment buildings of Mediterranean architecture, located at 110 - 120 Park Avenue South, Winter Park, Florida. Click on thumbnail to view larger image.
The Virginia Inn originally opened in 1882 as the Rogers House. From 1912 to 1915, it was the Seminole Inn. From 1915 to 1966, it was the Virginia Inn. The hotel site extended from Interlachen Avenue along Morse Boulevard and commanded a picturesque view of Lake Osceola. During its 84-year existence, the hotel was perhaps best known for its fine dining facilities. Click on thumbnail to view larger image.
On early maps of the area, maps dated before 1880, Lake Osceola was named Lake Mayo.   It is thought that the name change may have occured in the late 1870's, probably to honor the Seminole Indian Chief, Osceola. Click on thumbnail to view larger image.
Aloma Country Club opened with a big New Year's Eve party, December 31, 1926, to welcome 1927. Dr. Roland F. Hotard, with a group of investors had formed the Winter Park Golf Estates, Inc., purchased 360 acres of land, where the Winter Park Memorial Hospital is located today, to build a golf course and golf-course community. The anticipated growth never really materialized beyond a few short years. The Florida "land boom" of the late 1920's collasped, and the Great Depression sadly relegated the distinctive clubhouse to slow decay. In the early 1950's the site became the choice location to build the Winter Park Memorial Hospital. Click on thumbnail to view larger image.
The Boulevard, now Morse Boulevard named for Charles Hosmer Morse, originally ended at a railroad depot that blocked its connection to New York Avenue. In 1962 Morse Boulevard was extended west to Highway 17-92, making it the major east-west connection leading into downtown Winter Park. Click on thumbnail to view larger image.
For many years the Winter Park Shuffleboard Club was located at 451 S. Park Avenue with courts between the old City Hall and the former Chamber of Commerce building. In 1955 the club had more than 450 members and played matches against clubs from Kissimmee, Mt. Dora, Deland, Sanford, and Orlando. In the mid 1960's the club moved to Harper Street. Click on thumbnail to view larger image.
New England Avenue dates back to the original survey completed by S.A. Robinson in 1882 for Messrs. Chapman and Chase , founders of Winter Park. New England Avenue is bounded on the west by Denning Avenue and on the east by Chase Avenue. Click on thumbnail to view larger image.
The railroad depot shown here is the depot built in 1913. It replaced the original depot built in 1882 and was the first building built in Winter Park. The 1913 depot was torn down in 1962 to make way for the Morse Boulevard extension going west to connect with Highway 17-92. Click on thumbnail to view larger image.
Copyright Notice:
The copyright interests for material included in the Winter Park Public Library Archives Collection may not be transferred to the Library and therefore remain with the current copyright holders. For more information, please see our Copyright Information Page.
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