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Winter Park feels like a world of its own. One minute, you’re on the buzzing stretch of Park Avenue—lined with boutique shops, gourmet restaurants, and art galleries—and the next, you’re in a serene neighborhood that reminds you of Old Florida. It’s easy to see why so many people fall head over heels for this place.
Park Avenue is probably the most iconic part of town. You’ll find gorgeous storefronts, seasonal festivals, and a vibe that’s equal parts trendy and timeless. Stroll around on any given weekend, and you’ll see families pushing strollers, students from Rollins College sipping coffee, and retirees enjoying a leisurely brunch with friends. Venture just a bit off the main drag, and you’ll hit the Winter Park Chain of Lakes—a must for anyone who loves kayaking, paddleboarding, or just staring at the water with a cup of joe in hand.
Each corner of Winter Park offers something slightly different. You’ve got neighborhoods like Via Tuscany, known for upscale estates and that quintessential Florida luxury. Then there’s Orwin Manor, bridging Winter Park and Orlando, which is full of mid-century homes and a walkable feel. And let’s not forget College Quarter, close to Rollins, where you’ll find both students and longtime residents mingling over local brews.
In terms of the people, Winter Park is a melting pot—professionals who commute into downtown Orlando, snowbirds who escape harsh winters up north, and families who’ve lived here for generations. Everyone shares an appreciation for the area’s natural beauty and cultural flair. Speaking of culture, the SunRail stop in nearby Maitland or AdventHealth station offers convenient rides into downtown Orlando if you’re looking to avoid I-4 traffic. Plus, local roads are well-maintained, and there’s usually parking aplenty—though Park Avenue on a Saturday can be a bit of a circus.
Amenities? Oh, where to start. The Winter Park Farmers’ Market on Saturdays is a local favorite, where you can grab fresh produce, a latte, and maybe even adopt a rescue pup. There’s also Mead Botanical Garden, a tranquil oasis perfect for a morning jog or afternoon picnic. Living in Winter Park means you’re never far from top-notch healthcare, entertainment, and, of course, that never-ending lineup of culinary spots that’ll keep your palate guessing.
Bottom line: Winter Park is a place where history meets modern-day flair. You’ll find a corner that fits your style, no doubt about it. Once you settle in, you’ll see why so many people say they can’t imagine living anywhere else.
Winter Park is part of Orange County Public Schools, and the local schools here have a reputation that’s hard to beat. The standout name you’ll hear again and again is Winter Park High School, known for its solid academics, top-tier performing arts programs, and a sports scene that turns heads year after year. The Wildcats (that’s their mascot) are fierce on the football field, but they also dominate in soccer, basketball, and even cross country. If your kid’s a sports junkie, they’ll have plenty of opportunities to flex their skills.
For parents of younger students, Audubon Park School (K–8) has gained quite a following for its innovative approaches and high-achieving student body. There’s also Brookshire Elementary, often praised for its strong community involvement and friendly staff who know each child by name (or so it feels). And if private education is more your speed, Lake Highland Preparatory School is just a short drive away in Orlando, attracting families seeking smaller class sizes and specialized programs.
Performance stats are generally impressive. Orange County Public Schools tout a graduation rate hovering around 90%, with many Winter Park schools specifically ranking higher than the state average in test scores. Beyond academics, these schools put a big emphasis on extracurriculars—everything from robotics clubs to drama troupes to student-run publications.
It’s not just about reading, writing, and arithmetic around here (although they’re pretty good at those, too). The culture is supportive, and teachers often go the extra mile, whether it’s staying after school to tutor or coaching a little league team on weekends. That sense of community pride is palpable, and it makes Winter Park a prime spot for families who want the best for their kids—both in and out of the classroom.
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Winter Park’s leisure scene is all about balancing refined culture with good old Florida fun. Let’s talk shopping first: Park Avenue is basically a shopper’s dream. You’ve got boutiques like Tuni for stylish threads, The Ancient Olive for artisanal goodies, and gift shops galore—there’s always something to find. If you’re more into mainstream retail therapy, Winter Park Village is right around the corner with big-name stores, a movie theater, and eateries that range from fast-casual to date-night fancy.
On the food front, Winter Park’s got you covered. Craving a juicy burger? Check out The Ravenous Pig—locally famous for its gastropub vibe. If upscale Italian is your thing, Prato on Park Avenue is a must-try (their pizza is next-level). And for brunch that’ll blow your mind, Briarpatch has been the local go-to for ages. Just be prepared to wait if you roll in late on a weekend—the line can get ridiculous.
When it comes to fitness, you’ll see runners hitting the pavement around Lake Baldwin and cyclists everywhere, because this area is surprisingly bike-friendly compared to other parts of Central Florida. Gyms like Orangetheory Fitness and LA Fitness are easy to find, and there are smaller yoga studios and personal training spots tucked away in every neighborhood. Sports teams? Well, if you love rowing, Winter Park is a hotbed for crew teams, thanks to the chain of lakes that’s perfect for early morning practice sessions.
If you’re looking for a quick outing, Rollins College campus is a stunner, especially if you want to catch a theatrical performance at the Annie Russell Theatre or a cozy concert at the Knowles Memorial Chapel. Art lovers, don’t miss the Morse Museum of American Art, home to the world’s most comprehensive collection of Louis Comfort Tiffany’s works. Trust me, even if you’re not an art buff, that place will wow you.
Sure, Winter Park can be upscale, but it’s not pretentious. It’s more about enjoying the good life, whether that means sipping coffee on Park Avenue while people-watching or kayaking through the city’s lakes and canals with friends. There’s always something to keep you entertained without the hustle-bustle of a major city.
Ask any local, and they’ll tell you: Winter Park’s community spirit is on another level. Events here range from artsy to downright fun, kicking off early in the year with the Winter Park Sidewalk Art Festival, one of the nation’s top outdoor art fests. It’s a weekend packed with colorful exhibits, live music, and enough food trucks to make your head spin. Then there’s the Taste of Winter Park, where area restaurants show off their best bites—get ready to loosen that belt a notch.
If you’re looking for something more laid-back, Popcorn Flicks in the Park is a monthly staple, where families spread out on blankets in Central Park to watch classic movies under the stars. And when the holiday season rolls around, Winter Park goes all out. The Winter on the Avenue celebration lights up Park Avenue with a tree lighting ceremony, live entertainment, and the kind of festive energy that reminds you why this town is so special.
Population-wise, Winter Park is home to around 30,000 residents. But don’t let that number fool you—it feels both intimate and buzzing at the same time. Part of that comes from Rollins College bringing in students from around the globe, injecting fresh ideas and cultural diversity. Another factor is the steady influx of professionals who appreciate that they’re only minutes from downtown Orlando yet living in a place where you can actually hear the birds chirp in the morning.
One of the big highlights of living here is how everything’s so well-maintained. The city invests in keeping parks clean, roads smooth, and public spaces inviting. That sense of pride filters down to the residents, who tend to be pretty active in community affairs—think local committees, charity events, and neighborhood watch groups that keep everyone safe and informed.
It’s this blend of cultural events, natural beauty, and tight-knit community vibes that make Winter Park more than just a suburb. It’s a place where you can thrive, whether you’re raising a family or just seeking a lifestyle that balances sophistication with down-to-earth charm. And if you’re ready to explore the Winter Park real estate market, the Todd Schroth Home Selling Team brokered by eXp Realty is here to make the journey smooth, personal, and genuinely unforgettable. With over 2,000 homes sold and two decades of experience, we’ve seen firsthand how Winter Park can steal your heart in no time flat. Let’s find the home that does the same.
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Todd Schroth has spent the last 20 years vested in the Orlando Real Estate market by helping others buy, sell, and invest while standing alongside the investing himself. Todd's passionate in serving the community, sharing knowledge he has during his real estate career, and providing the best experiences for everyone he has the opportunity to work with. His overall goal is to better serve and elevate real estate standards. He has found having a strong team made up of different strengths is the best way to provide top notch experiences.
Founder of Todd Schroth Home Selling Team brokered by eXp Realty, his team has sold over 2,000+ homes in the last 20 years and are committed to making every experience exceptional.
As a result of his extensive expertise and dedication to Real Estate, Todd has felt compelled to help other agents and brokers grow their business to the fullest potential. With that passion, he created Agents Who Win, a collaborative platform for agents all over the US to share their successes and learn and grow from one another. In just one year, this Private Group has grown to almost 1,000 members. Todd strives to believe “no one can have true success without strong support systems”. We’re looking forward to this group growing and hosting in-person events to continue our contribution to agents’ success.
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