Winter Park : Florida


What It Is Like to Retire in Winter Park

Winter Park is an historic resort and retirement town in the Orlando and Kissimmee area of Central Florida. It is a planned community built along a group of lakes including Lake Osceola. Its streets and parks (it claims it has the most parks per capita of any Florida city) along with its architecture make it a must-visit destination.  Several U.S. Presidents including Chester Arthur, Grover Cleveland, and Franklin D. Roosevelt visited the city.  The city is relatively prosperous and has a very high cultural base.  The prestigious Winter Park Sidewalk Arts Festival attracts 350,000 visitors from around the country. Rollins College, Full Sail University, and Valencia Community College make Winter Park a college town as well. The scenic Olde Winter Park area features small, winding brick streets, and a canopy of old Southern Live Oak and Camphor trees, draped with Spanish Moss. The early photo (public domain) shows the Hotel Alabama, since converted into condominiums.

Where to Retire in Winter Park and Home Prices

There are many pretty streets and neighborhoods in town, or you can live in a development outside of town (see Active Communities link at left). Zillow reports the median home value was $416,963 in early 2022, up over 24% during the past year.


What Is Special about Winter Park

Winter Park was the first centrally planned community in Florida. The main street includes retail and public civic buildings, art galleries, a private liberal arts college (Rollins), museums, a park, a train station, a golf course country club, a historic cemetery, and a beach and boat launch.  The Winter Park Sidewalk Arts Festival is one of the top juried art shows in the country.  Winter Park has more park space per capita than any other city in Florida.

What Is Not Special about Winter Park

There has been some discussion on various boards about Winter Park having some rundown areas, particularly in the Goldenrod and University areas. Others say that is probably associated with neighborhoods where students are renting.

Who Will Like Retirement in Winter Park

People who want to live in established community that has benefited from central planning will like Winter Park. Also, if you are looking for a college town in Central Florida this is a good bet.

Local Economy Is Driven by

Tourism, retirees, and its colleges are key parts of the Winter Park economy.

Climate and Physical Environment

Winter Park is north of Orllando in an area of large lakes.  The average July high is 92 and the average January low is 50. June is the wettest month with over 7" of rain.

Restaurants & Cultural Scene

The Charles Hosmer Morse Museum of American Art houses the largest collection of Tiffany glass on Earth.  The Winter Park Sidewalk Art Festival attracts 350,000 visitors a year, and it is just one of the cultural attractions of Winter Park, along with the Bach Festival and the Councours d'Elegance. Rollins College has cultural events as well.


The Crime Index in Winter Park is 349, which is below  the U.S. average of 394. Most crime appears to be of the non-violent type. Like any older town with a university area, there will be some run-down areas. Posters on various sites say Winter Park Village is a high crime area.

Medical Facilities

There are a number of hospitals less than 10 miles away in Orlando.


Winter Park enjoys an Amtrak station. Nearby Orlando Airport is one of the busiest in the nation.

Valuable Links

City of Winter Park

Wikipedia page for Winter Park.
Winter Park Chamber of Commerce


What people are saying about Winter Park

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