If you’re considering a move to Orlando, you’re not alone. Thousands of families and professionals relocate here every year, and for good reason. At Wemert Group Realty, we often hear the same mix of emotions: excitement about the sunshine, opportunity, and lifestyle, along with the natural hesitation that comes with finding the right place to call home.
That’s why we want to share one of Central Florida’s most loved communities: Winter Garden. Just a few miles west of downtown Orlando, this charming city blends small-town warmth with modern convenience. Whether you’re moving for work, family, or a fresh start, Winter Garden offers a vibrant, connected, and welcoming lifestyle.
Think of this as your personal Orlando relocation guide — a closer look at what makes Winter Garden one of the best places to live in Central Florida. We’d love to help you feel at home here.
Lifestyle & Community
Living in Orlando means enjoying diversity, sunshine, and a strong sense of community. Winter Garden captures that spirit perfectly. The city’s walkable, brick-lined downtown feels like something out of a movie, filled with boutique shops, cafes, and friendly faces.
Start your weekend at the Winter Garden Farmers Market, one of Central Florida’s best-loved markets, where you can browse fresh produce, baked goods, and handmade crafts while live music fills the air. Locals gather here every Saturday morning to sip coffee, meet friends, and catch up on neighborhood news.
Nearby, you’ll find the West Orange Trail, a 22-mile scenic path that weaves through lush greenery, connecting Winter Garden with neighboring communities. It’s perfect for biking, jogging, or simply taking in the Florida sunshine.
Our team loves how Winter Garden feels alive all year long. The Downtown Winter Garden events calendar is filled with art festivals, outdoor concerts, and holiday celebrations that keep the community close. From the annual Blues & BBQ Festival to classic car shows, there’s always something happening.
Here’s what we love most about living here:
- You can grab brunch at Rosallie Le French Café or coffee from Axum Coffee, stroll the farmers market, and still enjoy a quiet afternoon at home.
- You’ll find neighbors who greet you by name and local shop owners who remember your order.
- There’s a true sense of belonging — a small-town heartbeat just minutes from big-city Orlando.
For those moving to Orlando in search of connection, Winter Garden is a community that truly feels like home.
Economy & Job Market
Winter Garden’s location makes it ideal for professionals who want proximity to Orlando’s growing industries. The region is booming with opportunities in technology, healthcare, aerospace, and hospitality — four of the city’s strongest economic pillars.
Orlando was recently ranked among the fastest-growing tech hubs in the U.S., attracting both startups and established companies. (Nucamp’s Orlando Tech Guide) The nearby Medical City at Lake Nona is another major employment center, focused on health innovation and research.
Within Winter Garden itself, local entrepreneurship thrives. The city encourages small business growth through its Economic Development Department, which provides resources for local startups and commercial investors. The result is a balanced mix of professionals, remote workers, and family-run businesses that keep the local economy vibrant.
If you’re moving to Orlando for work, Winter Garden lets you enjoy the best of both worlds — a peaceful, family-friendly home base within easy reach of downtown job opportunities.
Education & Family Life
For families relocating to Orlando, education is often a top priority — and Winter Garden delivers. The area is served by top-rated public and charter schools within Orange County Public Schools, as well as several private and magnet programs.
Nearby, you’ll also find specialized academies with strong STEM and arts programs, plus easy access to colleges and universities like Valencia College, Rollins College, and the University of Central Florida. Families appreciate the variety of after-school options, from sports to robotics to theater.
One of Winter Garden’s best assets for families is its design neighborhoods are built with parks, green spaces, and safe walking paths. From splash pads to playgrounds, everything encourages outdoor living. It’s easy to see why so many parents call it one of Orlando’s most family-friendly suburbs.
We help families not only find the right home but also understand the local resources available to them, from nearby schools to summer programs and family-friendly dining.
Recreation & Lifestyle Perks
Winter Garden has something for everyone. You can enjoy world-class attractions within minutes, yet still unwind in a community that feels peaceful and local.
Spend a Saturday exploring Plant Street Market, a popular indoor marketplace filled with artisan food stalls, breweries, and local shops. It’s home to favorites like Crooked Can Brewing Company, a local craft brewery beloved by residents and visitors alike.
Outdoor lovers can kayak on Lake Apopka, one of Florida’s largest lakes, or take a drive through the scenic Lake Apopka Wildlife Drive, where you might spot alligators, herons, and eagles. For those who prefer structured recreation, the Winter Garden Recreation Department offers everything from youth sports to adult fitness classes.
And of course, you’re just a short drive from Orlando’s world-famous attractions — Walt Disney World, Universal Orlando, and SeaWorld. The beaches on both coasts are only about an hour away, making weekend getaways easy.
Living here truly offers the best of both worlds: the magic of Orlando paired with the everyday ease of small-town life.
Real Estate & Cost of Living
As Orlando continues to grow, Winter Garden stands out for its beautiful neighborhoods, modern amenities, and lasting value.
The cost of living in Winter Garden is about 5% lower than the national average, while housing remains slightly above the Orlando metro median due to high demand. According to Zillow, the median home price in 2025 is approximately $568,000, while Redfin reports that most homes sell within 44 days on the market.
Homebuyers will find a wide range of styles here:
- Historic homes near downtown with unique architectural details.
- New master-planned communities like Horizon West offering resort-style amenities and top-rated schools.
- Townhomes, condos, and single-family homes with modern designs and energy-efficient features.
At Wemert Group Realty, our agents know how to match your lifestyle and budget with the right neighborhood. Whether you’re a first-time buyer, a growing family, or an investor, we’ll help you navigate the Orlando housing market with confidence.
Insider Tips & Local Voices
We believe that the best insights come from the people who live here. Here’s what some locals and our team have to say about Winter Garden:
“Downtown Winter Garden feels like a storybook town — walkable, friendly, and full of local pride.”
“Plant Street Market is my go-to spot for meeting friends and grabbing dinner. The community vibe here is unbeatable.”
Our agents often recommend visiting on a weekend to get the full feel of the area. Stop by the farmers market, grab lunch at The Chef’s Table at the Edgewater, or catch a show at the beautifully restored Garden Theatre. These are the moments that show what living in Orlando can truly feel like when you’re part of a connected community.
For families, check out Newton Park for a peaceful picnic by the lake, or the Winter Garden Heritage Museum for a dose of local history. Each of these spots tells part of the story that makes this city so special.
If you’re moving to Orlando and searching for the right place to call home, Winter Garden deserves to be at the top of your list. It combines everything people love about Central Florida — sunshine, opportunity, community, and charm.
At Wemert Group Realty, we know that moving is about more than just finding a house. It’s about discovering where you’ll build your life. We’d love to help you feel at home here.
Connect with us today for your personalized Orlando relocation guide or to schedule a neighborhood tour of Winter Garden. Let’s find the place that feels right for you — where your next chapter begins.
Welcome home!
