If you’re considering a move to Orlando, you’re not alone. Every year, thousands of families, young professionals, and retirees relocate here drawn by the sunshine, vibrant culture, and sense of community that makes Central Florida feel like home. But among the many places that make up Greater Orlando, there’s one city that stands out for its charm, elegance, and welcoming atmosphere: Winter Park, Florida.
Known for its tree-lined streets, stunning lakes, and rich history, Winter Park offers a blend of small-town warmth and big-city access. Whether you’re exploring the scenic Park Avenue, attending a local art festival, or enjoying a quiet afternoon by the water, life here feels both peaceful and full of possibility. At Wemert Group Realty, we love helping families discover this beautiful pocket of Central Florida and we’d love to help you feel at home here too.
Lifestyle & Community
Living in Orlando means having access to incredible diversity, culture, and entertainment, but Winter Park adds its own unique flavor. The community is known for its rich arts scene, walkable downtown, and welcoming atmosphere. Locals gather every Saturday morning at the Winter Park Farmers’ Market for fresh produce, homemade treats, and friendly conversation. It’s more than just a market—it’s a tradition that brings the community together week after week.
On Park Avenue, you’ll find some of the best boutique shopping and dining in Central Florida. Enjoy brunch at Briarpatch Restaurant, treat yourself to a glass of wine at The Wine Room, or unwind with a latte at New General Café all local favorites where the staff know your name. For art lovers, the Charles Hosmer Morse Museum of American Art is a must-see, featuring the world’s most comprehensive collection of works by Louis Comfort Tiffany.
Our team loves Winter Park because it truly has a heartbeat of its own. It’s a city where families gather at Central Park for movie nights under the stars, where local business owners greet regulars by name, and where seasonal events like the Winter Park Sidewalk Art Festival bring everyone together to celebrate creativity and community.
Economy & Job Market
When moving to Orlando, you’re not just choosing a place to liveyou’re choosing a place to grow. Winter Park’s proximity to Downtown Orlando makes it an excellent location for professionals in industries like technology, healthcare, hospitality, and aerospace. Major employers such as AdventHealth, Lockheed Martin, and EA Sports are all within a short commute, and Orlando’s booming startup scene continues to attract entrepreneurs from across the country.
The local economy is diverse, resilient, and future-focused. Whether you’re looking to advance your career, start a business, or transition into a new field, you’ll find opportunity here. With a lower cost of living compared to other major U.S. metros and no state income tax, it’s easy to see why so many professionals choose Orlando and Winter Park as their home base.
Education & Family Life
For families considering a relocation, education is often a top priority and Winter Park delivers. The area is home to some of the most highly rated public and private schools in the region, such as Winter Park High School and Trinity Preparatory School. Families also love the area’s access to enrichment programs, from STEM and robotics to performing arts and athletics.
Higher education opportunities abound too. Rollins College located right in the heart of Winter Park is one of the top liberal arts colleges in the nation, offering beautiful lakefront views and a vibrant campus culture. For younger children, the city’s many parks, recreation centers, and libraries provide safe, engaging spaces to play and learn.
Families moving to Orlando often mention how quickly they feel settled in Winter Park. Between the friendly neighbors, strong school systems, and endless family activities, it’s easy to see why so many people choose to plant roots here.
Recreation & Lifestyle Perks
Life in Winter Park offers the best of both worlds a relaxed, scenic lifestyle with access to world-class entertainment. Outdoor enthusiasts can kayak across the Winter Park Chain of Lakes, explore the Mead Botanical Garden, or bike through tree-canopied neighborhoods that feel straight out of a postcard.
Sports fans can catch an Orlando Magic game downtown or cheer on the Orlando City Soccer Club just a short drive away. And of course, you’re only 30 minutes from Walt Disney World Resort, Universal Orlando Resort, and SeaWorld Orlando making spontaneous weekend adventures easy and exciting.
The city’s park system and lakes also make outdoor living a natural part of everyday life. Residents enjoy paddleboarding at sunset, picnics by the water, or attending seasonal festivals. For food lovers, local favorites like Prato, Hillstone, and Boca Winter Park offer everything from Italian classics to farm-to-table dining, all set against charming backdrops.
Real Estate & Cost of Living
Winter Park’s real estate market offers a wide range of options, from historic bungalows shaded by oak trees to modern lakefront estates. Whether you’re looking for a cozy condo near Park Avenue or a family home with space to grow, our team can help you find the perfect fit.
Compared to other metro areas, living in Orlando remains remarkably affordable for the quality of life it offers. While Winter Park is one of the area’s more sought-after communities, many families find that their investment here pays off in lifestyle, stability, and long-term value. The blend of character, location, and convenience makes Winter Park one of the most desirable markets in Central Florida.
At Wemert Group Realty, we’ve helped countless families navigate the process of buying and selling homes in Winter Park. We understand that moving isn’t just about finding a house, it’s about finding your place. Our team will guide you through every step, from exploring neighborhoods to connecting you with trusted local resources.
Insider Tips & Our Local Voices
What truly sets Winter Park apart is its people. Locals describe it as “the perfect mix of small-town warmth and city sophistication.” One of our clients recently shared, “What surprised me most about moving to Orlando was how connected Winter Park feels. It’s like everyone genuinely cares about this community it’s easy to build relationships here.”
Our agents love recommending their favorite hidden gems around town. For coffee, Foxtail Coffee Co. is a must-visit spot that started right here in Central Florida. For date night, try the romantic lakeside views at Hillstone Restaurant or live jazz at Blue Bamboo Center for the Arts. And if you’re looking for something truly local, don’t miss the Scenic Boat Tour—a guided cruise through the city’s chain of lakes that showcases Winter Park’s history, architecture, and beauty.
These personal touches are what make this area so special. Every street, café, and park tells a story and every person who moves here becomes part of that story too.
If you’re thinking about moving to Orlando and want a place that blends beauty, connection, and opportunity, Winter Park might be exactly what you’re looking for. With its walkable charm, welcoming people, and unbeatable lifestyle, it’s easy to understand why so many call it home.
At Wemert Group Realty, we’d love to help you discover what makes this community so special. Whether you’re relocating from across town or across the country, our team can create a personalized Orlando relocation guide, answer your questions, and even arrange a private Winter Park neighborhood tour to help you find the perfect fit.
Your next chapter starts here and we’d love to help you feel at home in Winter Park.
