Winter Park

Winter Park is well known for its numerous lakes and unique blend of natural beauty and vibrant, urban lifestyle. Park Avenue is the epicenter of the city showcasing incredible boutique and local shopping opportunities paired with great dining options. Discover some of the finest real estate central Florida has to offer. With real estate ranging from luxury properties, waterfront properties, residential neighborhoods, to condos in the downtown core, there is something for everyone in Winter Park.

Waterfront real estate in Winter Park, Florida Sunset over a lake in Winter Park, Florida

Winter Park Homes For Sale

About Winter Park, FL

In 1881 two New England businessmen Oliver Chapman and Loring A Chase purchased 600 acres bordering four large lakes - Maitland, Osceola, Virginia, and Killarney. This property was commonly referred to as a "necklace" of lakes surrounding the lush landscape that surrounded these lakes. Chapman and Chase planned to create a "planned community" for wealthy Northerners to live in during the winter months. This was the first "planned" community in Florida, and was aptly named "Winter Park". They designed the town around a central park and its main street - Parke Avenue. Soon, homes, churches, schools, markets, and more parks are constructed to make the Northerners feel more comfortable as they fled south from the harsh winter. Soon, pamphlets are sent North with the following verbiage 

“Winter Park is a beautiful winter resort for well-to-do people who wish to escape from the cold and blustering weather (which is) so helpful to colds, coughs, diphtheria, consumption, etc; a collection of beautiful villas in the midst of orange-groves upon acre-lots running to the shores of crystal lakes; a dozen or more large first-class hotels scattered along the 2 miles of lake-frontage — a resort that shall be for the winter what Saratoga, Long Branch, etc., are for the summer. SOCIETY is first-class. A social gathering in Winter Park Town Hall will bring together as refined and cultivated a company as can be found anywhere, representing nearly every State. “

Today, Winter Park offers some of the best dining, shopping, living, and entertainment experiences in all of Florida.  Park Avenue is still the "Main Street" and can be explored by foot, bike, car, or even by train. Dozens of shops, restaurants, and museums line the street making it one of the most enchanting walks in all of Central Florida

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Winter Park Attractions

Winter Park is well known for its many lakes and unique blend of natural beauty and vibrant, urban lifestyle. With so many different places to eat, drink, explore, or even boat - you will never feel like you don't have anything to do! If you would like to explore by foot, by car, by train, or even on one of their famous Canoe tours, you have the ability to explore the beautiful city and all of its history.

Winter Park also loves its art, but the epicenter of this city is definitely Park Avenue, a busy cobblestone street that truly has something for everyone. Some incredible boutique and local shopping can be found here, including some of the best dining experiences you’ll find in Florida. 

Award-winning chefs and restaurants create and cook delicious dishes at restaurants like The Ravenous Pig, a James Beard-nominated establishment.

There are nearly 70 parks in Winter Park and even more in neighboring Maitland, great recreational opportunities are plentiful supply. Winter Park and Maitland also host a variety of annual food, culture, and music festivals.

Winter Park Real Estate

Winter Park real estate offers some of the very best that Florida has to offer. Discover are luxury properties, waterfront properties, residential neighborhoods, or choose to be at the center of it all in the downtown core.

Winter Park homes for sale tend to be more expensive, luxury estates with massive yards listed at over a million dollars. The real estate market in Winter Park showcases several architectural styles, including classic Georgian, Florida, Mediterranean, modern, and more. There’s also vacant land available here with plenty of acres to build on and direct beach access.

Incredible features are found in all of the custom-built homes here in Winter Park, Florida. Every property is unique, but many of these features can include coffered ceilings, gas fireplaces, magnificent double staircases made of iron and wood, and sliding glass doors that extend to a private backyard with beach access and a pool area.

Interior features in these impressive estates with open concept layouts can include crown molding, high ceilings, impressive foyers, stone counters, wood cabinetry, and more. Three and four-bedroom options are the most common floor plans in these single-family homes but can reach as many as eight.

Families are delighted to have access to numerous top-rated schools in Winter Park as well as neighboring Maitland.

Winter Park Real Estate Stats

Average Home Price $500K
Lowest Listing Price $0
Highest Listing Price $218M
Total Property Listings 417,814
Avg. Days On Market 177
Avg. Price/SQFT $295

Property Types (active listings)

Kari Fleck, Owner & Broker

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