Above is a snapshot look at the real estate market in Winter Park, FL. In Winter Park, FL, the median house price is $340,400, making the price 104% higher than that the average for Florida. Therefore, the affordability of Winter Park, FL area real estate is less affordable than the real estate in other areas of Florida. In addition, Winter Park, FL has a median rent price of $1,068; this price is 3% higher than that the average rental price for Florida. 65.6% of residents in Winter Park, FL are homeowners, and the average amount of people who reside in each home is 2.3. Winter Park, FL has a wide array of real estate options available, ranging from cost-friendly condos to high-end luxury homes. We filter listings by number of bathrooms and bedrooms, price and area to simplify the search process for Winter Park, FL real estate for sale.