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 Florida.
In Winter Park, Park Avenue is a delightful spot for residents and visitors to shop and dine.
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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.
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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 Avenue is a popular area for shopping and dining in Winter Park.
The Briarpatch on Park Avenue in Winter Park is renowned for street-side dining and breakfast.
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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.
Hillcrest Elementary School serves Winter Park students and receives an overall Niche grade of A.
Howard Middle School is proud to offer Magnet and Stem programs for the students of Winter Park.
Winter Park High School is the home of the Wildcats.
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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.
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.
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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
Jamie Ampel,
an experienced agent in this area.
GreatSchools:
The GreatSchools Rating helps parents compare schools within a state based on a variety of school quality indicators and provides a helpful picture of how effectively each school serves all of its students. Ratings are on a scale of 1 (below average) to 10 (above average) and can include test scores, college readiness, academic progress, advanced courses, equity, discipline and attendance data. We also advise parents to visit schools, consider other information on school performance and programs, and consider family needs as part of the school selection process.
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On average, homes in Winter Park, FL sell after 67 days on the market compared to the national average of 55 days. The median sale price for homes in Winter Park, FL over the last 12 months is $480,000, up 2% from the median home sale price over the previous 12 months.
Your pool home in Winter Park. This home offers three bedrooms plus a versatile bonus room, approximately 1,770 sq ft of living space, built in 1967, along with a two-car garage and extended driveway for additional parking. Located in the established Eastbrook community with no HOA. Key updates include a roof replaced in 2018, solar panels installed in 2020 (fully paid off), water heater replaced
One or more photo(s) has been virtually staged. This luxurious Modern Style home epitomizes maintenance-free living, featuring a premium solar system you own outright, paying for your electricity. (Ask to see the bill.) Imagine relaxing on your private, expanded lanai, soaking in the breathtaking sunsets. Your spacious 4-bedroom, 3.5-bathroom home offers premium views of nature, and is just steps
Welcome to 1174 Wildmeadow Run in Winter Park’s gated Hawk’s Crest community. Located on a quiet, non-thru street, this SINGLE-STORY residence offers modern construction, refined finishes, and a comfortable, well-designed layout in the heart of Winter Park. Built in 2021, the home was thoughtfully planned for everyday living and easy entertaining. The open-concept design feels light and
Beautifully updated condo in a prime Winter Park location! This move-in ready unit features a beautifully renovated kitchen, updated bathrooms, and tile flooring throughout, offering a modern and low-maintenance living space. Ideally situated on South Semoran Blvd, you’ll love the convenience of being just minutes to Baldwin Park, Full Sail University, UCF, and Downtown Winter Park, with easy
Your pool home in Winter Park. This home offers three bedrooms plus a versatile bonus room, approximately 1,770 sq ft of living space, built in 1967, along with a two-car garage and extended driveway for additional parking. Located in the established Eastbrook community with no HOA. Key updates include a roof replaced in 2018, solar panels installed in 2020 (fully paid off), water heater replaced
One or more photo(s) has been virtually staged. Experience refined living in this exquisitely renovated custom home, positioned on an oversized corner lot in one of the area’s most peaceful and private neighborhoods. Tucked away at the end of a quiet dead-end street, this residence offers an exceptional blend of craftsmanship, sophistication, and modern comfort. Inside, soaring 10-foot ceilings
DRAMATIC PRICE ADJUSTMENT! Million Dollar Lakefront View of Lake Killarney from Private Balcony and multiple Rooms in the Unit and View of Courtyard with it's Gracious Old Tree and Meandering Walkways from second Private Balcony. Once in a lifetime opportunity to own this meticulously maintained and updated Mid-Century Modern Character that says "Home" when you walk through the Door! Kitchen has
Welcome to your Florida retreat.Whether you’re searching for the perfect first home or looking to downsize into a low-maintenance lifestyle, this single-story end-unit villa offers the ideal blend of comfort, convenience, and charm. With only one shared wall, it lives and feels like a single-family home.The HOA handles all exterior maintenance—including the roof, which was replaced just a
One or more photo(s) has been virtually staged. This luxurious Modern Style home epitomizes maintenance-free living, featuring a premium solar system you own outright, paying for your electricity. (Ask to see the bill.) Imagine relaxing on your private, expanded lanai, soaking in the breathtaking sunsets. Your spacious 4-bedroom, 3.5-bathroom home offers premium views of nature, and is just steps
One or more photo(s) has been virtually staged. Welcome to 1036 Aragon Avenue, a charming Winter Park bungalow perfectly positioned in one of Central Florida’s most sought-after locations. Nestled along picturesque cobblestone roads and surrounded by mature, tree-lined streets, this move-in ready home captures the character and warmth that make Winter Park real estate so desirable. Located just
Discover the opportunity to own in Winter Park at 1952 Spring Street—a well loved 3-bedroom, 2-bath townhouse offering charm, functionality, and a private yard, a rare find in this desirable area. Nestled in a well-established neighborhood, this home provides a peaceful residential feel and tranquility while remaining just minutes from everything Winter Park has in store.The interior features
Located on a quiet cul-de-sac in the heart of Winter Park, this traditional two-story home offers a functional, well-designed floorplan for both everyday living and entertaining. From the moment you step inside, the home has an inviting warmth that you can immediately feel. The main level features a spacious primary suite along with connected living spaces that flow easily from room to room. The
One or more photo(s) has been virtually staged. This home can be purchased with NO INCOME VERIFICATION needed! Welcome to 720 W Webster Avenue, a beautifully renovated home in the heart of historic Carver Town in Winter Park—one of the most sought-after locations in Central Florida. Just a short walk to downtown Winter Park, this charming residence blends modern updates with timeless character
LAKEFRONT COMMUNITY WITH SPECTACULAR SUNSETS OVER BEAUTIFUL LAKE KILLARNEY. LOCATED IN THE CHARMING AND ELLEGANT NEIGHBORHOOD OF WINTER PARK, IN A FULLY REVITALIZED AREA.CONVENIENT TO I-4, PARK AVENUE, FARMER'S MARKETS, TRADER JOE'S, AS WELL AS A MOVIE THEATER, BOUTIQUE SHOPS, RENOWNED RESTAURANTS AND A NATIONALLY RATED ART FESTIVAL - ALL WITHIN A SHORT WALKING DISTANCE.BRIGHT SUN-FILLED
Welcome to this original-owner residence in The Meadows at Hawk’s Crest, where thoughtful design and exceptional privacy come together—featuring two true primary suites, one on the first floor and one on the second. Set on an oversized fenced homesite along a quiet non-thru street with no neighbor to the east, this beautifully maintained 4-bedroom, 3.5-bath home offers over 3,020 sq.ft. of living
Welcome home to this beautiful 2-bedroom, 1-bath gem in the heart of Winter Park! Nestled on the ground floor of theLake Killarney Condominiums, Unit 101 offers a seamless blend of comfort, style, and lakeside living. Bright & openlayout that flows from the living space into a modern kitchen with a large center island — perfect for entertaining orcasual family meals. Granite
FULLY FURNISHED 5br/4b +bonus loft GEM! Welcome to 2075 Jewel Avenue, an exceptional residence nestled in the heart of Winter Park, 32789—one of Central Florida’s most sought-after communities. Ideally situated just minutes from the vibrant shops and dining along Park Avenue and the scenic beauty of Rollins College, this home offers the perfect blend of charm, convenience, and lifestyle. Set on a
Beautifully maintained home in the highly desirable Winter Park 32789 neighborhood. This charming property offers an inviting floor plan with abundant natural light, spacious living and dining areas, and a well-appointed kitchen with generous counter space and modern finishes. Comfortable bedrooms provide ample storage, and the primary suite offers a private and peaceful retreat. Flexible bonus
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
Winter Park Lakefront Community. Lakefront Deck, Dock, Grill, Community Building, Heated Pool and Sauna. Immaculate 2 Bedroom 2 Bath First Floor Unit. Upgraded Kitchen with Raised Ceiling, Maple Cabinets and Granite Counters. Cabinets (matching Kitchen Cabinets) and Counters built in Dining Room for extra Storage. Recently Painted. New Carpets in Bedrooms. Bathroom Vanities and Commodes have been
Welcome home to Oak Reserve at Winter Park Apartments, a quiet community where your needs and wishes are our priority. Covering all the bases for a comfortable living experience, our apartments in Winter Park, FL, are completed by lifestyle-oriented amenities, fantastic services, and a well-connected location within walking distance of Full Sail University. Short-term leases are available,
Newly Renovated | Prime Winter Park Location | Move-In Ready Opportunity Positioned in one of Central Florida’s most desirable and high-demand areas, this newly renovated residence at 540 W Comstock Ave offers a rare opportunity for tenants seeking both location and lifestyle in the heart of Winter Park. Thoughtfully updated with modern finishes, the home features a clean, refreshed interior
Fredrick JacobsKELLER WILLIAMS GAINESVILLE REALTY PARTNERS
Celebrate the power of possibilities. Signature details enhance grand features in expansive homes, all a promise to your heightened prosperity at Bainbridge Winter Park. In the heart of Winter Park, Florida’s lush parks and gardens, museums, festivals, and events - you’re central to the finer things in life.
Bring your boat and discover this charming Winter Park gem, perfectly nestled on a quiet, desirable brick-lined street. This inviting 2-bedroom, 1-bath home features beautiful hardwood floors and a warm, welcoming feel throughout. Enjoy a lakefront yard feet from the house that offers peaceful water views and the perfect setting for outdoor living. Step outside to an amazing backyard complete
Welcome to Elon Winter Park Apartments in Winter Park, Florida, where chic meets serenity in the heart of Winter Park's vibrant tapestry. Nestled within this charming community, our boutique one-bedroom apartments redefine urban living with spacious interiors, a contemporary aesthetic, and designer accents that elevate every moment. Immerse yourself in the allure of Winter Park's entertainment
Welcome home to the heart of Winter Park's coveted Tree Streets. This beautifully remodeled single-family home sits on an oversized lot just moments from Interlachen Country Club and Winter Park Racquet Club, and is zoned for Lakemont Elementary, Maitland Middle, and Winter Park High School. Inside, natural light pours through windows in every room, giving the home a bright, airy feel throughout.
Situated in Winter Park near Harry P Leu Gardens, Juno Winter Park brings you urban living at its height. Featuring exquisite studio, one, two, and three-bedroom apartments along with a variety of enviable amenities, our vibrant community invites you to elevate your everyday life. Plus, our prime location just six miles north of downtown Orlando puts you within arm's reach of top-notch shopping,
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