Winter Park began in the 1880s when two New Englanders set out to plan a community that would appeal to other ex-pats from the north. Along with the promise of warm, sunny winters, they established good schools and a lively arts scene to lure wealthy residents. The main commercial district, Park Avenue, was where residents shopped and ate together. The city’s chain of lakes provided endless hours of boating and fishing. Over the years, Winter Park has grown to feel more like a Central Florida city, with shopping centers and access to major highways. However, it still lives up to its “City of Arts and Culture” nickname with its museums and appeal to wealthy residents. Over the years, actors, musicians and athletes have called Winter Park home, and they mingle seamlessly with their lesser-known neighbors. “If you don’t follow sports, you could be sitting next to a famous basketball player at a restaurant and not even know it,” says Jamie Ampel, the owner of All Sellers & Buyers Realty and a Central Florida native. The city’s nearly 30,000 residents often head to Orlando, about 10 miles away, for work or play. While at home, they enjoy highly rated schools, easy lake access, and a lively art scene, just like the residents who came before them.
A mix of home styles from petite bungalows to lakeside mansions
The city is a mix of residential subdivisions and commercial pockets set among the Winter Park Chain of Lakes, six large bodies of water connected by narrow, navigable canals. This proximity to the water means many residents enjoy backyard lake views. Single-family homes sit on landscaped lawns on streets often lined with sidewalks. Sizes and styles include New Traditional homes from the 1990s, midcentury-era ranch homes, early 2000s-era Colonial Revival, New Traditional and Contemporary homes, and renovated historic homes. The median price for single-family homes is about $785,000. Two- to four-bedroom townhouses are available mainly on the city’s west side, with a median price of around $725,000. Condos are also available, ranging from the mid $100,000s for a petite one-bedroom to just over $3 million for a sprawling unit in a luxury building.
Boutiques and bistros line Park Avenue
Park Avenue is still a shopping and dining destination, with high-end boutiques and bistros. A favorite is The Ravenous Pig, a beer garden and gastropub. Its chef, Julie Petrakis, is a multi-time James Beard semi-finalist for Best Restaurant and Chef. Near Park Avenue’s south end sits Rollins College, a private liberal arts school featuring The Rollins Museum of Art, which houses several thousand pieces. The nearby Alfond Inn, a boutique hotel near campus, houses dozens more. Nearby residents often stop into the hotel for coffee or a glass of wine after walking their dogs — with their dogs in tow — or dine at the hotel’s restaurant. “We’re a little like the living room of Winter Park. There’s a big local following here,” says Debbie Potter, Director of Sales & Marketing for The Alfond. Popular chain restaurants and stores are conveniently located in shopping centers throughout the rest of the city. AdventHealth Winter Park Hospital is on the city’s east side, surrounded by additional medical facilities.
Downtown Orlando is less than 10 miles away and offers hundreds more shopping, dining and entertainment options. Walt Disney World is about 23 miles away and Universal Studios Florida is about 16 miles away.
Highly-rated public and private school options
Orange County Public Schools serves the area. The district rates an A-minus on Niche and offers school choice. One of the district’s standout schools is Winter Park High, which rates an A-plus on Niche. Trinity Preparatory School of Florida is the area’s highest-rated private school, with an A-plus on Niche. Graduates who want to stay close to home can attend Rollins College, which offers over 60 majors.
Boating on the Winter Park Chain of Lakes; green space at Central park
Residents enjoy boating, kayaking and paddleboarding in the Winter Park Chain of Lakes. Among the city’s many green spaces, Central Park is the standout. Dubbed “the crown jewel” of all the parks in the city, Central Park sits in the heart and spans 11 acres, with walking paths and a rose garden on its southern border. The Winter Park Country Club and Golf Course is a public nine-hole course that draws locals looking for a quick game.
Annual events revolve around the arts and community
Each March, the Winter Park Sidewalk Arts Festival attracts thousands of visitors who admire paintings and sculptures by global artists. Christmas on Park is a collection of events from mid-November to early January. Park Avenue is illuminated with Christmas lights, and a small carousel is set up for children.
Residents get around by interstate, SunRail and Lynx buses
Interstate 4 runs near the city’s west side and connects residents to Orlando and the rest of Central Florida. Orange Avenue and Colonial Drive offer more options for getting around, though they can back up during rush hour. SunRail, a popular rail service spanning four counties, has a station in Downtown Winter Park. The Lynx bus is another public transportation option, with dozens of stops throughout the city. The Orlando International Airport is about 20 miles away and offers domestic and international flights.
Winter Park's weather and crime rates
Winter Park is often safe from hurricanes, but major storms can cause flooding and wind damage. In 2024, Hurricane Milton brought flooding and even tornadoes. According to FBI statistics for 2022, Winter Park’s violent crime rate is 2.9 per 1,000 people, compared to 8.2 in nearby Orlando. The property crime rate is also lower, at 18.7 per 1,000, compared to 39.6 in Orlando. The city’s police department offers a community crime map tool on its website to help keep residents informed.
When you choose to work with Brad Bess, you are partnering with a REALTOR® that is passionate about helping you transition from one chapter to the next. Brad ensures a smooth transaction by listening to your real estate goals and dreams so he can understand how to make them a reality. Then, he will work tirelessly until he achieves a closing that makes you happy and excited about your future. And he’s more than an agent, he’s your friend in real estate. So, he will begin creating a personal connection with you the moment you contact him and will make the process as enjoyable as possible.
Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. Our sources include: Accuweather, Public Records and Neustar. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.
