Call us: 407-509-9279

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. 4 beds, 6 baths
    Home size: 5,194 sq ft
    Lot size: 24,393 sqft
    Year built: 2009
    Days on market: 1
  2. 3 beds, 2 baths
    Home size: 1,848 sq ft
    Lot size: 11,325 sqft
    Year built: 1956
    Days on market: 1
  3. 3 beds, 2 baths
    Home size: 1,850 sq ft
    Lot size: 6,969 sqft
    Year built: 1932
    Days on market: 1
  4. 4 beds, 3 baths
    Home size: 3,346 sq ft
    Lot size: 13,068 sqft
    Year built: 1952
    Days on market: 2
  5. 4 beds, 5 baths
    Home size: 2,982 sq ft
    Lot size: 10,454 sqft
    Year built: 2017
    Days on market: 2
  6. 4 beds, 2 baths
    Home size: 1,774 sq ft
    Lot size: 10,890 sqft
    Year built: 1968
    Days on market: 2
  7. 5 beds, 5 baths
    Home size: 4,224 sq ft
    Lot size: 16,988 sqft
    Year built: 1990
    Days on market: 2
  8. 3 beds, 4 baths
    Home size: 2,662 sq ft
    Lot size: 8,712 sqft
    Year built: 2005
    Days on market: 2
  9. 3 beds, 2 baths
    Home size: 1,366 sq ft
    Lot size: 10,454 sqft
    Year built: 1984
    Days on market: 2
  10. 3 beds, 3 baths
    Home size: 1,790 sq ft
    Lot size: 871 sqft
    Year built: 2007
    Days on market: 5

See all City of Winter Park - Property Search.
(all data current as of 10/18/2017)

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