Winter Park Homes for Sale

Listed below are homes for sale in Winter Park, a city located in Orange County. These Winter Park real estate listings are updated every 15 minutes from the MLS. 

For additional information on any of these Winter Park homes for sale, just click the "Request More Information button located on the detail page of each listing. And to view any of the Winter Park listings you are interested in, click the "Schedule a Showing" button displayed on every property detail page to contact us and setup a time. In addition, we can provide you with disclosures, past sales history, dates and prices of properties recently sold nearby, and more.

And, if you haven't already, be sure to register for a free account to automatically receive email alerts whenever new Winter Park listings come on the market that match your specific criteria and save your favorite properties for quick and easy access.

Read more about Winter Park!

Winter Park July 14, 2024
Avg. DOM
Avg. $ / Sq.Ft.
Med. List Price
279 Properties
Page 1 of 24


search today's new listings by beds/baths, property size, listing status, days on market & more!

Winter Park 

What was once considered a winter resort, Winter Park is now known as a city bursting at the seams with art and culture. Just 15 minutes north of Downtown Orlando, Winter Park is a charming city where traditional charm meets healthy and sustainable innovation. With a weekly farmer’s market, multiple museums, and countless restaurants offering endless options for cuisines, a home in Winter Park is perfect for those looking to broaden their horizons. 


From its community center to its numerous public events, Winter Park’s residents are truly proud of their town. On Saturday mornings, head to the old train depot, a restored historical landmark, for the Winter Park Farmer’s Market where you can pick up local produce, as well as flowers, crafts, and more. Winter Park also hosts numerous events throughout the year, including the Winter Park Sidewalk Art Festival, one of the nation’s oldest and largest outdoor art festivals. Each December, experience Winter on the Avenue, where Park Avenue is completely transformed into a winter wonderland in order to kick off the holiday season.

Arts and Culture

Winter Park prides itself on being a city of arts and culture, and this proves true due to its clear dedication to uplifting art and history. Head over to the Morse Museum, located on Park Avenue, houses the world’s most comprehensive collection of works by Louis Comfort Tiffany, as well as housing American art pottery, paintings, and more. The Cornell Fine Arts Museum, found on Rollin College’s campus, is a teaching museum dedicated to stimulating transformative encounters with works of art. In addition to museums, Winter Park has a growing theater industry. Catch a play at the Winter Park Playhouse or Blue Bamboo Center for the Arts. For a relaxing experience, experience nature at either the Mead Botanical Garden or the Albin Polasek Museum & Sculpture Gardens. Whether you’re looking to take in the newest exhibit, expand your horizons in an immersive experience, or relax in nature, Winter Park is sure to have an offering that fits your interests. 


Winter Park boasts A-rated schools, classes, and seminars. Located in Orange County, schools have relatively small class sizes, ranging from 11 to 17 students per teacher. Winter Park is also home to Rollins College, the very first college in Florida. To learn more about Winter Park’s educational institutions, visit Winter Park’s education website. 

Foodie Culture

From traditional Turkish cuisine to multiple gastropubs, Winter Park has a variety of restaurants for you to pick from. Stroll down Park Avenue and stop at Bosphorous, known for their fresh ingredients and family-like hospitality. If you’re looking for a local brew and a good meal? The Ravenous Pig’s expansive menu is sure to satisfy everyone in your party. If you’re looking to satisfy your sweet tooth, The Glass Knife sells gorgeous baked goods that taste even better than they look. 

Perfect for those looking to surround themselves with arts and culture, Winter Park provides residents with a true community.

If you’re considering a home in Winter Park, contact Hector Leon of Orlando Florida Realty. 

Contact Us

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.