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The history of Winter Park dates back to 1858 when an eight-acre plot of land was purchased by David Mizell, Jr. He called the area Lake View. For the next 29 years the area began to grow with the introduction of a railway line through the town. The City of Winter Park (the city was renamed in 1881) was then officially chartered in 1887, the City was originally developed as a winter resort for wealthy Northerners seeking refuge from the harsh winters and a tranquil place to rest and relax.

In 1887, it was recorded that professional burglars broke into the Ergood store (located at Morse Blvd and Park Ave) and blew the safe. The burglars took $300 and since there was no local police, Sheriff Mizell was contacted and he conducted the investigation. No one was ever caught so it was decided by the town's people to start their own local law enforcement office. This was the start of the Winter Park Police Department. The first officer was Alex Earl, the Town Marshall. In 1889 the first town jail was built. The jail was a small two door, square facility that housed only prisoners. The town police officer operated out of his own home. This system would last through 1915.

On March 17, 1898 the first murder occurred in Winter Park. It was reported that two men, in the Hannibal Square section of town, were fighting. The fight ended with one of the men being killed with a blow from an axe. The case was solved due to citizen intervention.

In 1915, the first actual police station was built. The police station was located at Park Ave and Lyman Ave. The police station was attached to City Hall. The building was constructed of stone and concrete, which lasted through 1962.

During the late 1920's, the first patrolman and motorcycle officer were hired starting the Patrol and Traffic divisions. These divisions have grown into the present Traffic and Patrol Divisions with a combined total of forty-eight officers.

In 1930, the Winter Park Police Department saw its first officer killed in the line of duty. Chief John O'Steen was responding to a bank robbery alarm when he was sideswiped by another car resulting in a fatal car crash. Since this incident, there has been no other line of duty deaths.

During 1949, radio equipment was added to the police vehicles allowing a dispatcher to notify officers of calls. Until 1957, Orange County Sheriffs Department dispatched for all police agencies in the county. Since 1957, The Winter Park Police Department has had their own dispatchers.

In the 1960's the Winter Park Police Department saw several changes. The first change was the addition of the K-9 Division. In 1962, the former police headquarters was constructed. This building did not change until 1978, when the second floor was added.

In 1975 The SWAT Team was formed. This unit is still active and has been expanded since it's conception.

The Neighborhood and Business Watch Programs began in 1980. These programs are designed to assist the citizens and local businesses in crime prevention.

Also in 1980, the Winter Park Police Department saw the start of the School Resource Officer program; one officer was assigned to the Winter Park High School. The School Resource Officer program has grown and now involves four schools.

The Winter Park Police Department has continued to grow and change since it's beginnings in 1887. In 2003, a new Public Safety Building had its grand opening. This facility provides a state of the art home for the police and fire departments.