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.
Winter Park still hangs on to old cobblestone roads of Old Flordia.
In Winter Park, Park Avenue is a delightful spot for residents and visitors to shop and dine.
1/2
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.
Winter Park has a variety of home styles to choose from.
Modern luxury homes are a feature in Winter Park.
1/2
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.
Park Ave is a popular area for shopping and dining in Winter Park.
The Briarpatch on Park Avenue, Winter Park, is renowned for street-side dining and breakfast.
1/2
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.
Fraser Valley Elementary School is one of two elementary schools in the East Grand 2 School District.
Winter Park High School is the home of the Wildcats.
1/2
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.
Scenic canals connect Winter Park lakes, delighting boating enthusiasts.
The Scenic Boat Tour in Winter Park is a must-do to appreciate the beautiful architecture.
Winter Park residents relish golfing at the acclaimed Winter Park Golf Course.
Winter Park has tons of walking and biking trails in the community.
1/4
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.
Written By
Sara Huffman
Video By
Matt Ferguson
Interested in learning more about homes in this area?
Reach out to
Carmen Vazquez,
an experienced agent in this area.
On average, homes in Winter Park, FL sell after 63 days on the market compared to the national average of 53 days. The median sale price for homes in Winter Park, FL over the last 12 months is $485,000, up 3% from the median home sale price over the previous 12 months.
Affordable living in Winter Park. This 1-bedroom, 1-bath condo in The Colonies offers an excellent opportunity for investors or first-time buyers. Recently updated, the unit is ready for a new owner. The location is a major draw, just minutes from Full Sail University, Valencia College, UCF, Park Avenue, Downtown Orlando, and Orlando International Airport. With highly rated Winter Park schools,
Wonderful opportunity - homes rarely come available on this street! Located in the heart of Winter Park, this elegantly designed 3-bedroom, 2.5-bathroom residence offers 2,557 square feet of living space and a 2-car garage on a picturesque tree-lined brick street just minutes from Park Avenue. The first level features the living room, bonus/flex space, dining room, kitchen and laundry room with
This beautiful Mediterranean style home offers a rare opportunity for prime waterfront living on Lake Mizell, part of the highly sought out after Winter Park Chain of Lakes. Situated on a 1.32 acre lot, the property is just a short walk or drive to Park Avenue’s restaurants, boutiques, and local attractions. The main home features three bedrooms and five bathrooms, each bedroom offering its own
Welcome home to this beautiful 2-bedroom, 1-bath gem in the heart of Winter Park! Nestled on the ground floor of the Lake Killarney Condominiums, Unit 101 offers a seamless blend of comfort, style, and lakeside living. Bright & open layout that flows from the living space into a modern kitchen with a large center island — perfect for entertaining or casual family meals. Granite countertops,
Welcome home to Lake Waunatta Cove subdivision in Orange County. This attractive, beautifully decorated, very spacious 5 bedrooms, 3 full bathrooms, with a family room, and a very rare Basement. This roomy home is open and airy with vaulted ceilings, skylights, newer lighted ceiling fans in all bedrooms, living room, and family room, a wood burning fireplace in the living room, and a fantastic
Affordable living in Winter Park. This 1-bedroom, 1-bath condo in The Colonies offers an excellent opportunity for investors or first-time buyers. Recently updated, the unit is ready for a new owner. The location is a major draw, just minutes from Full Sail University, Valencia College, UCF, Park Avenue, Downtown Orlando, and Orlando International Airport. With highly rated Winter Park schools,
Completely rebuilt in 2019, this stunning Winter Park residence offers the perfect blend of modern design and refined comfort. Soaring ceilings and an open, split floor plan create a bright, airy living space ideal for both relaxation and entertaining. The chef’s kitchen features gas appliances, quartz counters, and custom cabinetry, flowing seamlessly into the spacious great room. The primary
Discover easy living at 2500 Lee Road, Unit 244, Winter Park, FL 32789. This charming spacious 1 bedroom, 1 full bathroom condo is located in the heart of Winter Park, offering comfort, convenience, and access to everything you need. Bright kitchen with plenty of storageand an Open living area with natural light Community features may include: Swimming pool, Assigned parking, Landscaped
Nestled in the highly sought-after community of Winter Park, this charming 2br/2b property offers an exceptional rental opportunity. Inside you will find an inviting floor plan with gorgeous tiled flooring and fresh paint. The kitchen has plenty of cabinet space with stainless steel appliances. 151 Stefanik Rd is situated in a peaceful neighborhood, offering easy access to Winter Park’s vibrant
Walk Score® measures the walkability of any address. Transit Score® measures access to public transit. Bike Score® measures the bikeability of any address. CAP Index provides objective, accurate, and consistent data to help measure, compare, and mitigate crime risks.
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.
