If you’re considering a move to Orlando, you’re not alone. Thousands of families, professionals, and retirees relocate to Central Florida every year, drawn by its sunshine, diversity, and sense of community. But just south of the city lies one of the area’s most beloved gems: Kissimmee, Florida.
Known for its small-town warmth and big-city convenience, Kissimmee offers the perfect blend of family-friendly living, exciting recreation, and close proximity to Orlando’s world-class attractions. It’s where neighbors still wave hello, local restaurants feel like home, and the beauty of Florida’s natural landscapes unfolds right outside your door.
At Wemert Group Realty, we’ve helped countless clients find their dream homes in and around Kissimmee, and we can confidently say this area captures the best of Living in Orlando. Whether you’re drawn by the vibrant community, affordable homes, or easy access to major employers, Kissimmee might just be the place where you’ll feel right at home.
Lifestyle & Community
Kissimmee has a unique charm that sets it apart from other parts of Greater Orlando. It’s a city where local culture thrives, where weekend farmers markets bring neighbors together, and where family-friendly festivals fill the calendar year-round.
Downtown Kissimmee has experienced a revitalization in recent years, bringing new restaurants, shops, and gathering spots while maintaining its historic, welcoming feel. Stroll along Broadway Street and you’ll find cozy cafés, boutique stores, and family-owned eateries like 3 Sisters Speakeasy and Matador Tacos + Tapas Bar, local favorites that reflect the community’s friendly and diverse spirit.
Kissimmee’s location also means you’re just minutes from some of Central Florida’s best outdoor escapes. Lakefront Park on the shores of Lake Tohopekaliga (known as Lake Toho to locals) is a go-to for morning jogs, fishing, or evening walks with stunning sunset views.
They said “Kissimmee is one of those places that feels alive. Everywhere you go, people are outside enjoying the weather, the water, and the company of their neighbors.”
At Wemert Group Realty, we love that Kissimmee offers both community and connection—qualities that make Moving to Orlando not just about relocating, but about belonging.
Economy & Job Market
Kissimmee’s proximity to Orlando makes it a fantastic choice for professionals and entrepreneurs alike. The area benefits from Orlando’s strong and diverse economy, which continues to grow in industries like technology, healthcare, aerospace, and hospitality.
Major employers such as AdventHealth, Lockheed Martin, Disney, and Orlando Health all have campuses or offices within an easy commute. The area’s convenient access to major highways like Florida’s Turnpike and I-4 ensures that getting to work or heading to one of the nearby business hubs is quick and stress-free.
For those who dream of starting or growing a business, Kissimmee’s supportive local economy and ongoing development projects make it an ideal place to invest. The city is seeing exciting growth in commercial real estate, new mixed-use developments, and small business initiatives.
Whether you’re a young professional seeking opportunity, a family putting down roots, or a retiree looking for a vibrant yet peaceful community, Kissimmee provides stability, connection, and growth key ingredients for a fulfilling life in Central Florida.
Education & Family Life
For families, Kissimmee offers an incredible range of educational opportunities. The School District of Osceola County is one of the fastest-growing in Florida, with specialized programs in STEM, performing arts, and dual language immersion. Schools like Celebration K-8 and Osceola County School for the Arts are well-known for their academic excellence and creativity-driven programs.
Higher education is also within easy reach. Valencia College and the University of Central Florida (UCF) are nearby, offering continuing education and career development programs.
Families will also appreciate the city’s focus on community living. Parks, youth sports, local libraries, and recreational centers all play a major role in everyday life. From weekend baseball games at Fortune Road Athletic Complex to hands-on science fun at the Kissimmee Lakefront Park splash pad, there’s always something for kids and parents to enjoy.
As one of our team members shared, “Kissimmee feels like a place built for families. You see it in the schools, the parks, and the people. It’s a place that helps kids grow and parents feel supported.”
Recreation & Lifestyle Perks
One of Kissimmee’s biggest draws is its unbeatable access to both outdoor adventure and world-famous attractions. You’re only minutes from Walt Disney World, Universal Orlando, and SeaWorld, but it’s not all theme parks. Locals know that some of the best weekends are spent exploring closer to home.
Nature lovers can kayak along Shingle Creek, known as the northernmost headwaters of the Everglades, or enjoy hiking and birdwatching at Kissimmee Prairie Preserve State Park. The abundance of lakes means boating and fishing are practically a way of life here.
Foodies will love the growing dining scene. Locals rave about Woodsby’s Café for breakfast and Big John’s Rockin’ BBQ for classic southern comfort food. In the evenings, head to Sunset Walk at Margaritaville Resort for live music, great restaurants, and community events under the Florida stars.
Sports fans and outdoor enthusiasts also find plenty to do—from golf courses and soccer fields to fitness trails and community races. And when you want a quick escape, Cocoa Beach and Tampa Bay are both less than two hours away.
Kissimmee offers the best of both worlds: the excitement of a vacation destination with the everyday comfort of home.
Real Estate & Cost of Living
Compared to other major metro areas in Florida, Kissimmee offers incredible value, especially for buyers seeking space, amenities, and proximity to Orlando. The local real estate market features a diverse range of options: from charming single-family homes and modern townhouses to luxury golf community residences and lakefront properties.
Many neighborhoods, like Bellalago, Kindred, and Celebration, offer resort-style amenities such as pools, walking trails, fitness centers, and community events while maintaining a true neighborhood feel.
At Wemert Group Realty, our team has guided countless buyers and sellers through the Kissimmee market. Whether you’re searching for a starter home, a family retreat, or an investment property, we’ll help you navigate current trends and make confident decisions.
The cost of living here remains lower than many other Florida metros, making it a great option for those who want to be close to Orlando without the higher price tag. Plus, with Florida’s tax advantages no state income tax and homestead exemptions your money goes further when you invest in a home here.
We’d love to help you explore what’s available and find a neighborhood that truly feels like home.
Insider Tips & Local Voices
We believe the best way to understand Kissimmee is to hear from the people who live here.
“What surprised me most about Kissimmee was how connected the community feels,” says one of our clients, a recent Orlando relocation buyer. “I expected to find convenience, but I found friendships too.”
Our agents echo that sentiment. “We love spending Sunday mornings at the Kissimmee Farmers Market and grabbing coffee from Downtown Grounds,” shares Raheem, one of our team members. “It’s the kind of place where you run into your neighbors and end up staying to chat.”
Local hangouts like Abracadabra Ice Cream Factory and Big John’s Rockin’ BBQ are long-time favorites, while new additions like The Wharf at Sunset Walk keep the energy fresh and fun.
These personal connections are what make Kissimmee more than a place to live—it’s a community to grow in, explore, and call home.
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Whether you’re moving to Orlando for work, family, or a fresh start, Kissimmee offers the perfect balance of opportunity, comfort, and community. From its welcoming neighborhoods to its thriving local scene, this city has something special for everyone.
At Wemert Group Realty, we’d love to help you feel at home here. Our team lives and works in Central Florida we know these streets, these schools, and these communities because they’re part of our everyday lives.
If you’re ready to explore homes for sale in Kissimmee or want a personalized Orlando relocation guide or neighborhood tour, we’d be honored to help. Let’s make your move not just a transition, but a beginning.
Contact Wemert Group Realty to start your journey today.
