1858History
The immediate area of the city was first inhabited by people of European descent in 1858, when David Mizell Jr.
1870History
It got a post office and a new name—"Osceola"—in 1870.
1880Infrastructure
The area did not develop rapidly until 1880, when a South Florida Railroad track connecting Orlando and Sanford was laid a few miles west of Osceola.
1881History
Chapman, and they assembled a very large tract of land for $13,000 on July 4, 1881.
1885Government
In 1885, a group of businessmen started the Winter Park Company and incorporated it with the Florida Legislature; Chase and Chapman sold the town to the new company.
1886Architecture
In 1886, the Seminole Hotel on Lake Osceola opened.
1887Government
On October 21, 1887, the town was officially incorporated as the "Town of Winter Park", and, in 1925, it was reincorporated as the "City of Winter Park".
1888History
President Grover Cleveland visited the area and was given a huge reception at the Seminole Hotel on February 23, 1888.
1904History
=== Peacocks ===
In 1904, Charles Hosmer Morse became the biggest landowner in Winter Park.
1917History
The orange was introduced and cataloged by Buckeye Nursery in 1917, the year W.
1936Civil Rights
Roosevelt in March 1936.
1945History
In 1945, Morse's granddaughter Jeannette and her husband Hugh McKean moved to the land, and soon after they added peacocks.
1976Education
Reagan gave a campaign speech at Rollins College and stayed at the Langford in 1976.
1981Architecture
In May 1981, during a period of record-low water levels in Florida's limestone aquifer, a massive sinkhole opened near the corner of Denning Drive and Fairbanks Avenue.
1987History
Besides a 1987 incident in which the bottom of the lake suddenly dropped 20 feet (6.1 m), causing erosion on the southern rim, the stabilized sinkhole has been generally quiet.
1999Culture
The Langford was celebrated in a party in late 1999, closed, and was demolished.
2002Government
Margaret Mary Catholic Church
Winter Park Historical Museum
Winter Park Playhouse, founded in 2002.
2009Infrastructure
Diver reports from 2009 suggest that the lake has since been used to dispose of unwanted vehicles.
2010History
As of the 2010 United States census, there were 27,852 people, 11,995 households, and 6,419 families residing in the city.
2012Government
President Barack Obama visited Rollins College on August 2, 2012, to give a speech that was part of his re-election campaign.
2014Education
The remaining parcel was redeveloped and in 2014, a boutique hotel named the Alfond Inn, owned and operated by Rollins College opened at the site of the original Langford Hotel.
2016Government
Former Republican Congressman John Mica lost reelection in 2016 to newcomer and Democrat Stephanie Murphy.
2020History
== Demographics ==
As of the 2020 United States census, there were 29,795 people, 13,072 households, and 7,055 families residing in the city.
2021Education
It opened in late 2021 on a new world-class campus designed by world-renowned architect Sir David Adjaye.
2023Education
It is the second most expensive college in the state, as of the 2023-2024 academic year the tuition at Rollins is $58,300 per year.