Performance indicators for the Winter Park short-term rental market based on reliable data.
Listings
Reliable / Active
Cap Rate
Middle-Earners Gross Yield
Revenue
Middle-Earners Revenue
Occupancy
Middle-Earners Occupancy
Home Value
Median Home Sale Price
Top Earners
Top-Earners Revenue
The highest-performing listings in Winter Park.
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Unfriendly to Investors
Winter Park bans rentals under 30 days in all residential zones (City Code 58‑71(aa)), with active enforcement and daily fines, eliminating viable STR operations and creating high legal risk for investors.
Local STR Agent
STR specialist · Winter Park, FL
Winter Park is a city in Orange County, Florida, United States. The population was 29,795 according to the 2020 census. It is part of the Orlando–Kissimmee–Sanford, Florida Metropolitan Statistical Area. Winter Park was founded as a resort community by northern business magnates in the late 19th and early 20th centuries^ . Its main street, called Park Avenue, is located in the middle of town. It includes civic buildings, retail, art galleries, a private liberal arts college (Rollins College), museums, a park, a train station, a golf course country club, a historic cemetery, and a beach and boat launch.