Rentometer, Inc. | Data as of 10/23/2025
Winter Park’s rental market blends historic charm with modern convenience, making it a coveted destination for renters across the Orlando metropolitan area. The city’s tree‑lined streets, boutique shopping districts, and renowned cultural institutions such as the Charles Hosmer Morse Museum of American Art create a vibrant backdrop for a diverse housing inventory. Residents enjoy easy access to the scenic chain of lakes, scenic bike trails, and the popular Park Avenue corridor, which is dotted with cafés, galleries, and outdoor dining options that foster a lively community atmosphere.
Apartment options in Winter Park cater to a wide range of lifestyle preferences. Studios and one‑bedroom units typically fall within the $1,600‑$1,700 range, while two‑bedroom apartments are commonly priced around $2,100. Larger three‑bedroom apartments approach the $2,800‑$2,900 bracket, reflecting the premium associated with spacious layouts near downtown amenities. For those seeking the privacy of a house, one‑bedroom homes align closely with the apartment market, whereas two‑bedroom houses generally start in the $2,400 range. Expansive three‑bedroom residences often command near $3,300, and premium four‑plus bedroom homes can exceed $5,800, offering ample room for families or home‑based offices.
Winter Park’s neighborhoods, including the historic North Railway District and the upscale Berry Hill area, contribute distinct character to the rental landscape. Proximity to top‑rated schools, reputable medical centers, and excellent transit links to Orlando’s business districts enhances the city’s appeal for professionals, retirees, and young families alike. Whether you’re drawn by the cultural vibrancy, the scenic lakeside parks, or the upscale residential streets, Winter Park provides a dynamic and welcoming environment for renters seeking both convenience and quality of life.
| Property Type | Bedrooms | Average | Median | Min - Max | 25th - 75th |
|---|---|---|---|---|---|
| Apartment | Studio | $1,658 | $1,650 | $1,290 - $2,089 | $1,323 - $1,941 |
| Apartment | 1 Bedroom | $1,704 | $1,635 | $885 - $2,361 | $1,372 - $2,003 |
| Apartment | 2 Bedroom | $2,113 | $2,025 | $1,300 - $2,956 | $1,700 - $2,520 |
| Apartment | 3 Bedroom | $2,744 | $2,870 | $1,990 - $3,416 | $2,397 - $3,349 |
| House | 1 Bedroom | $1,658 | $1,625 | $1,050 - $2,300 | $1,350 - $2,000 |
| House | 2 Bedroom | $2,454 | $2,235 | $1,600 - $4,530 | $2,000 - $2,725 |
| House | 3 Bedroom | $3,329 | $3,000 | $1,825 - $8,500 | $2,595 - $3,650 |
| House | 4+ Bedroom | $5,861 | $5,050 | $2,200 - $12,000 | $3,800 - $7,995 |
In the current period, the average rent in Winter Park was $1,632 for Studio, $1,695 for 1 Bedroom, $2,294 for 2 Bedroom, $3,270 for 3 Bedroom, and $5,446 for 4+ Bedroom.
Data provided by Rentometer, Inc.