Hello, future Winter Park residents! If you’re considering buying a home in Winter Park, selling your charming property, or investing in this upscale suburb, you’re in for a treat. Nestled among scenic lakes and oak-lined streets, Winter Park combines small-town charm with proximity to Orlando’s excitement. This friendly guide covers real estate essentials, market insights, events, history, and the best places to shop, dine, and enjoy life here.

Scenic Boat Tour – Winter Park | Winter Park, FL | 32789
The Winter Park Real Estate Landscape
In 2025, Winter Park’s median home price sits at about $763,000, up 1.3% from last year, with homes selling quickly in desirable ZIP codes like 32789. The market favors sellers, but buyers can find gems in areas like the Vias or lakefront properties. For investors, high-end rentals yield strong returns due to affluent demographics.
Neighborhoods like Park Avenue District and Windsong are top picks for their luxury homes and community vibe.
Buying a Home in Winter Park
Buying in Winter Park? Focus on pre-approvals and home inspections, especially for historic homes. Methods include conventional loans or VA for veterans. Expect a competitive market—act fast on listings matching “Winter Park homes for sale.”
Selling Your Property in Winter Park
To sell effectively, highlight unique features like lake views or proximity to Rollins College. Best time: Spring, when buyers flock to events. Use staging and online marketing for top dollar.
Investing Strategies in Winter Park
Investors love Winter Park for its stable appreciation and rental demand from professionals. Consider luxury flips or vacation rentals. Key phrases: “Winter Park real estate investment” point to high cap rates in commercial spots.
News and Updates
2025 updates show steady growth, with new library expansions and cultural investments. The area remains a haven from Orlando’s hustle, with low unemployment.
Events and Activities
Join the Winter Park Sidewalk Art Festival or Bach Festival. Scenic Boat Tours on the chain of lakes are a must-do, offering views of mansions and wildlife.
History Snapshot
Founded in 1881 as a resort town, Winter Park boomed with railroads and became home to Rollins College in 1885. Winter Park is now a must visit cultural gem in the Orlando area.
Shopping, Dining, and Exploration
Stroll Park Avenue for boutiques and galleries. Dine at AVA MediterrAegean or Prato. Visit Mead Botanical Garden or Kraft Azalea Park for serene outings.
Let’s get started on your Winter Park home search journey! Schedule an appointment at SCHEDULE APPOINTMENT, call or text 407-603-1664, or visit www.realtorstephens.com.

