Community Spotlight: Winter Park

Home to some of the most expensive real estate in Central Florida, Winter Park is known for its idyllic Park Avenue, close proximity to downtown and the most luxurious homes in all of central Florida.

Pricing & History

With an average home price of around $500,000, Winter Park exudes Florida charm and luxury. Established in the late 1800’s as a railroad town and sort of escape for wealthy New Englanders, Winter Park served as a welcoming haven from the harsh, snowy winters. Today it is loved for its original brick lined streets, surrounding lakes and classic architecture that is a far cry from the conventional, new construction aesthetic we see today. If you’re looking to learn a little more, try taking a boat tour that leads you through the chain of lakes while highlighting the best parts of the city and its history.

Food Options

While there is no shortage of jaw dropping homes, Winter Park is also a destination for anyone seeking exquisite food and unique shopping opportunities. The Briarpatch is a brunch favorite while just down the street the Wine Room offers an incredible tasting experience for even the most seasoned wine connoisseur. We could go on and on about the countless food and drink offerings, but a few of our favorites are New General and Austin’s for coffee, Hillstone and Prato for a nice meal and Peterbrooke Chocolatier and the Glass Knife for a sweet treat.


Not to be overshadowed by the restaurants that call Park Avenue home, a variety of stores line the street and are also waiting to be explored. These range from international brands such as Lululemon and Pottery Barn to local boutiques such as Adjectives Market and the Writer’s Block Bookstore. There’s no doubt that what you’re looking for (and maybe even something you’re not) lives somewhere on Park Ave.


It’s location north of downtown makes Winter Park an easy drive to several of Florida’s east coast beaches. Daytona, New Smyrna and Cocoa beaches are all around an hour’s driving distance, while Universal Studios and the Disney Parks are a quick 30 minute trip down the I-4 corridor. If beaches and theme parks aren’t your thing, the Cornell Fine Arts Museum is located right in the heart of Winter Park on the Rollins College campus! The Orlando Science Center, Leu Gardens and more are all on your doorstep as a Winter Park resident.

Final Thoughts

While the area is known for its pricey real estate, there is something for everyone within the boundaries of Winter Park. Affordable homes are out there but can take some time and effort to come across and could require repairs and remodeling. If you’re looking to be in a safe neighborhood that is in close proximity to great schools and minutes from downtown, this could easily top the list as one of the best places to live around Orlando.

If Winter Park doesn’t sound like a great fit for you, check out our other posts on the best places to live in and around Central Florida. 

Posted by The Orlando Real on
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