[1][2] 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.

He enlisted a wealthy New Englander, Oliver E. Chapman, and they assembled a very large tract of land for $13,000 on July 4, 1881.

During this founding time, the Winter Park Post Office opened, and the railroad constructed a depot, connected to Osceola by a dirt road.

This was a resort complete with the luxuries of the day: gas lights, steam heating, a string orchestra, a formal dining room, a bowling alley, and long covered porches.

[citation needed] This street is now a cul de sac called Kiwi Circle that is part of one of the nicest neighborhoods in the town.

[1][2] The first president to visit was Chester A. Arthur, who reported that Winter Park was "the prettiest place I have seen in Florida",.

President Grover Cleveland visited the area and was given a huge reception at the Seminole Hotel on February 23, 1888.

He enjoyed the Bounding Horse Cart ride and stated that it was the most pleasant diversion of his Florida trip.

The New York Times reported on his visit that "The Philadelphian and Bostonian founders had done a good job with the town."

President Barack Obama visited Rollins College on August 2, 2012, to give a speech that was part of his re-election campaign.

Former Republican Congressman John Mica lost reelection in 2016 to newcomer and Democrat Stephanie Murphy.

Both have had a lot of support from both sides of the aisle and Murphy is credited with being one of the most centrist representatives in Congress today.

Its origins date back to 1885, when nine women organized to create a lending library for their small community, which was still in its infancy at the time.

It opened in late 2021 on a new world-class campus designed by world-renowned architect Sir David Adjaye.

In 1945, Morse's granddaughter Jeannette and her husband Hugh McKean moved to the land, and soon after they added peacocks.

[10][11] In 1972, Henry Swanson, an agricultural agent and "resident layman expert on Central Florida water," wrote a letter to the editor warning Orange County mayors of the sinkhole danger that could be posed by overdevelopment and excessive groundwater use.

[12] 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.

The sinkhole first appeared on the evening of May 8, 1981, near the house of Winter Park resident Mae Rose Williams.

[15] In a story in the Orlando Sentinel, she said that as the sun rose, she heard a noise "like giant beavers chewing" as the hole began to devour more of her land.

[15] By noon, as she realized that her home was slipping into the expanding hole, she and the family evacuated and removed their belongings.

The following fell into the sinkhole: five Porsches at a repair shop, a pickup truck with camper top, the Winter Park municipal pool, and large portions of Denning Drive.

A carnival-like atmosphere arose around the area, with vendors selling food, balloons, and T-shirts to visitors.

Workers were able to recover four of the six vehicles that fell into the sinkhole, including the travel trailer, whose owner drove it away, and three of the five Porsches.

[15] 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.

Famous guests included Dean Martin, Frank Sinatra, Ray Charles, Larry King, Hugh Hefner, John Denver, Langford winter resident Lady Bird Johnson, and President Ronald Reagan and his wife Nancy Reagan, who celebrated their 24th wedding anniversary there.

Much of this right of way has been converted to a rail-trail pedestrian/biking path in the form of the Cady Way Trail, which leads from Cady Way Park toward the Baldwin Park neighborhood and downtown Orlando, and in the opposite direction to Oviedo and beyond (via the Florida Trail), due to a new pedestrian bridge spanning Semoran Boulevard (SR 436) in Orange County.

This area includes the Isle of Sicily, a private drive that juts out into Lake Maitland with extremely expensive houses and residents such as Doc Rivers and Carrot Top.

There is a quaint, local feel to the town even though there are a lot of tourists, especially during the winter months and holidays.