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Winter Park Florida

Courteous of the Boston Public Library

Courteous of the Boston Public Library

Winter Park features open park space, residential neighborhoods, golf courses, and a street-side shopping district along Park Avenue. Wealthy businessmen established the city as a resort community in the late nineteenth century. The community developed slowly, but progressively became a popular destination with the addition of the railroad, connecting the city with surrounding cities. Eventually the town became a beautiful winter resort for northern visitors.

Winter Park is never lacking in fun activities and historic scenery, many of the town’s old buildings still remain and brick paved streets still in tact. Visitors and locals enjoy walking the old brick paved streets and gazing upon the carefully constructed architectural buildings of the past. The Hannibal Square is also an interesting place to tour; the square was once home to African Americans who worked the groves. Memoirs from the past can also be viewed at local museums; the most popular are the Enzian Theatre and the Albin Polasek Museum and Sculpture Gardens. Take a walk down the Cady Way Trail, distancing a total of six and a half miles long; the trail features the most beautiful homes of Winter Park.

Walking through the city, one can appreciate the ideas of great minds that became realities with the purchase of the small town. Once a developing resort community now exists as a suburb just minutes from Orlando, Kissimmee, etc.

Fast Facts

State: Florida
Founded: 1882
Incorporated: 1887
Population: 29203


Important Links


  1. 3 beds, 2 baths
    Home size: 1,673 sq ft
    Lot size: 6,534 sqft
    Year built: 1987
    Days on market: 1
  2. 5 beds, 8 baths
    Home size: 8,342 sq ft
    Lot size: 15,681 sqft
    Year built: 2004
    Days on market: 3
  3. 3 beds, 2 baths
    Home size: 1,412 sq ft
    Lot size: 8,276 sqft
    Year built: 1968
    Days on market: 3
  4. 4 beds, 4 baths
    Home size: 2,544 sq ft
    Lot size: 19.00 ac
    Year built: 1955
    Days on market: 3
  5. 4 beds, 6 baths
    Home size: 3,667 sq ft
    Lot size: 12,632 sqft
    Year built: 2002
    Days on market: 3
  6. 4 beds, 5 baths
    Home size: 4,462 sq ft
    Lot size: 11,761 sqft
    Year built: 2014
    Days on market: 4
  7. 4 beds, 3 baths
    Home size: 2,506 sq ft
    Lot size: 6,969 sqft
    Year built: 2018
    Days on market: 4
  8. 3 beds, 3 baths
    Home size: 2,336 sq ft
    Lot size: 10,018 sqft
    Year built: 1959
    Days on market: 4
  9. 3 beds, 2 baths
    Home size: 1,222 sq ft
    Lot size: 10,454 sqft
    Year built: 1958
    Days on market: 4
  10. 2 beds, 1 bath
    Home size: 1,356 sq ft
    Lot size: 6,534 sqft
    Year built: 1953
    Days on market: 5

See all City of Winter Park - Property Search.
(all data current as of 10/21/2018)

Listing information deemed reliable but not guaranteed. Read full disclaimer.