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
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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 66 days on the market compared to the national average of 56 days. The median sale price for homes in Winter Park, FL over the last 12 months is $485,000, up 2% from the median home sale price over the previous 12 months.
Virtually Staged. Temporarily Off the Market to replace driveway and sidewalks. PRICE IMPROVEMENT! NO HOA! Experience refined living in this renovated custom designed home on a 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.
Welcome to this beautifully maintained 3-bedroom, 2-bathroom home nestled in the highly desirable Winter Park area. Combining comfort, style, and an unbeatable location, this charming residence offers the perfect opportunity for homeowners seeking a move-in-ready property in one of Central Florida's most sought-after communities. Step inside to discover a bright and inviting floor plan designed
Built by Clarkson Concepts and ideally located in the heart of Winter Park just moments from Park Avenue, this sophisticated modern residence blends luxury design, smart-home innovation, and effortless indoor-outdoor living across three thoughtfully designed levels. From the moment you arrive, the striking foyer makes a memorable first impression with its bold geometric detailing, designer
**This house comes with a REDUCED RATE through the seller's preferred lender. This is a lender-paid rate buydown that reduces the buyer's interest rate and monthly payment.** Welcome to 2500 Lee Road, Unit 220, in Winter Park, a beautifully maintained condominium offering stylish, low-maintenance living in one of Central Florida's most convenient locations. Inside, the condo features 2 bedrooms
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
Tucked inside a quiet Winter Park neighborhood, this three-bedroom, two-bath home offers a comfortable layout and a sense of privacy that’s hard to find. No rear neighbors and a tree-lined backyard create a peaceful setting you’ll appreciate every day. The main living area is open and versatile, allowing you to arrange the space in a way that truly fits your lifestyle. The living room and dining
One or more photo(s) has been virtually staged. **This house comes with a REDUCED RATE through the seller's preferred lender. This is a lender-paid rate buy-down that reduces the buyer's interest rate and monthly payment.**This luxurious Modern Style home epitomizes maintenance-free living, featuring a premium, state of the art solar system YOU OWN OUTRIGHT, nearly eliminating your cost of
**This house comes with a REDUCED RATE through the seller's preferred lender. This is a lender-paid rate buydown that reduces the buyer's interest rate and monthly payment.** Welcome to 1287 Verdant Glade Place in Winter Park, a spacious two-story home offering 4 bedrooms, 3 full baths, 1 half bath, and a dedicated office, all thoughtfully arranged within an open floorplan designed for both
Rare Two-Story 2BR/2.5BA Condo with Two Private Suites in Winter Park. Highlights: Two-story floor plan condominium with a townhome-style layout, 2 spacious bedrooms, each with its own private ensuite bathroom, 2.5 bathrooms, Functional kitchen with stainless steel appliances, Open-concept living and dining area, Private fenced patio – perfect for relaxing, grilling, or entertaining, Covered
**This house comes with a REDUCED RATE through the seller's preferred lender. This is a lender-paid rate buydown that reduces the buyer's interest rate and monthly payment.** Welcome to 440 Cambridge Blvd in Winter Park, a charming 2-bedroom, 1-bath home featuring an open floorplan, an additional family room, and inviting indoor-outdoor spaces that offer both comfort and flexibility. Thoughtfully
Virtually Staged. Temporarily Off the Market to replace driveway and sidewalks. PRICE IMPROVEMENT! NO HOA! Experience refined living in this renovated custom designed home on a 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.
Virtually Staged. Virtually Staged. Waterfall Cove, where urban convenience meets tranquil living. This charming 2-bedroom, 1-bathroom condo offers a cozy retreat with all the perks of modern living. Located in the heart of Orlando, this condo is perfect for those looking for a blend of city life and natural beauty. As you step into the condo, you're greeted by a bright and spacious living area,
MAJOR PRICE ADJUSTMENT!Fantastic Winter Park Location on Lake Killarney. This 2 Bedroom 2 Bath Upstairs Unit has Lake and Pool Views. Spacious Living Spaces and Generously-sized Bedrooms. Unique Updated Kitchen has Sub Zero Refrigerator, Bosch Dishwasher, Solid Surface Counters, unbelievable amount of Storage with Corner Cabinets, Drawers, pull-out Shelving and 3 Tiers of Lighting! Updates
Turnkey Living in the Heart of Winter Park!Welcome to this beautifully maintained 2-bedroom, 2-bath townhome offering the perfect blend of comfort, convenience, and low-maintenance living. Vacant and move-in ready, this home has been freshly painted and features a recently replaced air conditioning system, providing peace of mind for its next owner.Inside, you'll find a thoughtfully
Lakefront Community! Enjoy Glorious Sunsets, Cocktails on the Deck and the Peace of Water and the Amazing Joy of Nature! All this near the heart of Winter Park and walking distance to all kinds of Shopping!One of few 1 Bedrooms and an Upstairs End Unit! Enjoy Spacious Room Sizes for easy Furniture Placement, Compact Kitchen, Bright Master Bedroom with additional Built-in Closets, Vanity and
Gorgeous FULLY FURNISHED 1 Bedroom/1 Bath apartment with private entrance, in Winter Park. This attached apartment has been thoughtfully renovated with beautiful Luxury European Design. This apartment features a private courtyard and private entrance. Upon entering you will be greeted by a spacious living room fitted with a sofa chase, 55” Flat Screen Television, a small dining table/desk, modern
The Seabrook Apartment community is located near the 408 Expressway, close to shopping and dining areas 1/4 mile away, just minutes away from the downtown areas of Orlando and Winter Park. Several renowned schools such as Brookshire Elementary, Glenridge Middle School and Winter Park High School are nearby as well. We offer spacious one and two-bedroom apartments. All of our homes have been
Be careful of scams. Only talk to a license agent. This is 2 bedroom not a 4 bedroom.Welcome to your new 2 bedrm+ office/ 2 bath/ 2 car garage home in charming Winter Park, FL. This inviting property offers an ideal location surrounded by lakes and green space, restaurants and grocery stores, making everyday conveniences just a short drive away. Your commute to work or school is easy with
Dwell well with us. Welcome to quintessential Vintage Winter Park, a residential community featuring One, Two & Three bedroom apartments in Winter Park, FL. Spacious layouts and amenities welcome you home, along with exceptional service and an ideal location within walking distance to shopping, dining and entertainment options.
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
Experience the perfect blend of comfort and convenience at Cranes Landing Apartments in Winter Park, Florida. Our beautifully designed one-, two-, and three-bedroom apartment homes feature open-concept layouts, modern finishes, and premium appliances to complement your lifestyle.Enjoy a community that’s built around connection and comfort. Relax by the resort-style pool, challenge friends
Charming 3-bedroom, 2-bath bungalow located in the highly desirable, well-established Orwin Manor neighborhood in the City of Winter Park. Ideally situated between Downtown Orlando and Park Avenue, this home is just minutes from AdventHealth Hospital, Rollins College, and offers convenient access to I-4. The spacious retreat is located just across the hall from a beautifully renovated bathroom.
Central Place at Winter Park, where contemporary living meets convenience in a vibrant locale in Winter Park, FL. Our one, two, and three-bedroom apartment community offers a prime location on University Blvd. near Full Sail University and just moments away from the charming downtown Winter Park area. Experience the essence of modern living in our thoughtfully designed residences, featuring
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,
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.
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
Calibre Bend Apartments offers a wide variety of apartment styles designed to accommodate the demands of today's sophisticated professional, while offering the setting and charm of yesteryear. You can expect unsurpassed amenities that will delight your senses, and a cozy community that makes coming home a breeze. Imagine your meals coming together perfectly in your gourmet kitchen, relaxing on
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