Kissimmee flourished with orange groves and cattle ranches until 1971 when Walt Disney World opened in nearby Orlando, transforming the city’s farmland into shopping centers and sprawling residential neighborhoods. Residents arrived in droves as more theme parks and attractions opened nearby and Kissimmee became a convenient, affordable place to call home for thousands of employees.
Today, a few cattle ranches still operate in Kissimmee, but this city’s main employers are the Walt Disney Company and AdventHealth, a massive healthcare company headquartered in nearby Altamonte Springs. “There are so many hotels opening up, and so many clinics and hospitals opening up,” says Daniel Araque, an associate broker at Keller William Legacy Realty in Kissimmee who has worked in local real estate for more than a decade. “We’re going from cattle and citrus to mixed-use, residential and commercial development.” The historic Downtown Kissimmee offers waterfront views and a buzzing restaurant district.
The city of 80,000 is a mix of retirees, seasonal residents and the entertainers and technicians who keep the parks and hospitals running. They all benefit from Kissimmee’s real estate prices, among the lowest in metro Orlando.
Kissimmee flourished with orange groves and cattle ranches until 1971 when Walt Disney opened in nearby Orlando.
Walt Disney World opened in 1971, just minutes from Kissimmee.
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New residents, investors in the housing market
Kissimmee has been dubbed the “Vacation Homes Capital of the World.” That is, in part, because Osceola County has a large short-term rental market where buyers scoop up homes and rent them out, often with plans of retiring to Florida. “I’d say roughly 40% of our sales in Kissimmee are short-term rental investments,” Araque says.
Osceola County tends to be one of the lower-cost housing markets in metro Orlando, with buyers paying an average of $440,000, compared to $545,000 in Orange County, according to the Orlando Regional Realtor Association. Kissimmee’s median home price is about $395,000, though newcomers can find anything from two-bedroom manufactured homes priced at $50,000 to six-bedroom estates spanning 5,000 square feet for about $2 million.
Gated, HOA neighborhoods are common. With names like Flora Ridge, Tapestry and Remington , these communities offer amenities galore, including community pools, fitness centers and guarded entrances. Communities on the more expensive side tend to offer golf course access and private boat docks.F
Condos and townhouses are also available throughout the city. Prices range from $135,000 for one bedroom to $425,000 for three bedrooms. Townhouses range from $195,000 for one bedroom to around $400,000 for three bedrooms. Osceola County also has several large master-planned communities for homebuyers aged 55-plus.
Whether full-time or part-time, residents are drawn to Kissimmee for the weather. June through September are hot, averaging about 92 degrees with high humidity and frequent afternoon thunderstorms. The rest of the year ranges from the high 70s to low 80s. Despite being in the middle of the state, Kissimmee can be affected by hurricanes and flooding. In 2024, the city experienced some destruction due to Hurricane Helene and Hurricane Milton.
Kissimmee has been dubbed the “Vacation Homes Capital of the World.”
Osceola County is one of the lower-cost housing markets in metro Orlando, with traditional homes starting at 440,000.
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At Disney World’s doorstep
Residents here live within 20 miles of Central Florida’s most-visited attractions, including Walt Disney World Resort, Universal Orlando Resort and SeaWorld Orlando. Special and discounts are available for Florida residents.
The tourism economy plays a major role here. The county brings in more than $75 million a year in taxes from hotel and vacation rental guests. This money funds events held in Kissimmee, programs for public schools and local chambers of commerce. Theme parks are home to some of the most popular events in the region. Highlights include the EPCOT International Flower & Garden Festival at Walt Disney World and Halloween Horror Nights at Universal Orlando.
In February, restaurants across the city take part in the Taste of Kissimmee. And in March, the Kowtown Festival celebrates the city’s birthday with food vendors, live music and mechanical bull riding.
Kissimmee residents are fortunate to live only 20 minutes from Walt Disney World.
Kissimmee residents are within 20 miles of Universal Studios.
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Outdoor recreation at Lake Toho and the Kissimmee Chain of Lakes Area
The city oversees nearly 20 parks and recreational facilities, with another 40 owned by Osceola County. With much of Kissimmee covered by lakes, water recreation is a big deal. Slips downtown let boaters cruise across Lake Tohopekaliga, nicknamed Lake Toho by locals. Outdoor enthusiasts can hunt hogs, hook bass or camp among the 21,000 acres of the Kissimmee Chain of Lakes Area. Swimming typically isn’t advisable in Florida’s alligator- and snake-filled lakes, but locals can splash and slide from May through September at Bob Makinson Aquatic Center in Mill Slough . Golf legends Jack Nicklaus, Arnold Palmer and Tom Watson designed courses at Reunion Resort & Golf Club, a private club in the Reunion area.
Water recreation is popular for Kissimmee residents with easy access to Lake Toho.
A Campbell City resident enjoys swimming at Bob Makinson Aquatic Center, minutes away.
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Public and private schools in Osceola County prep for growth
The School District of Osceola County serves Kissimmee. The district, which rates a B-minus from Niche, operates 49 campuses, but growth in the city is driving the need for more facilities.
The district offers school choice. One popular option is NeoCity Academy, a STEM-focused magnet school that Niche rates as the best public high school in the Orlando area. Only about 10% of students in the county attend private schools. The highest-rated private schools are typically faith-based, such as Heritage Christian School and Osceola Christian Preparatory School. Niche rates both schools an A-minus.
Valencia College operates two campuses where students can earn associate degrees in education, health care and information technology, among other disciplines. Osceola Technical College’s three local campuses award certificates in architecture, audiovisual communication and more. The metro’s biggest university, the University of Central Florida, is 35 miles away in Orlando.
NeoCity Academy is a STEM-focused magnet school in Kissimmee, FL.
Osceola Christian Prep Academy receives ab A minus score from niche.
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Lakeside dining in downtown Kissimmee, more amenities in nearby Orlando
Downtown Kissimmee serves as the center of the local restaurant and shopping scenes. The 150-year-old town center features tapas bars, cafes and antique shops along Broadway, the area’s main drag. Residents run errands at the big-name retailers along Osceola Parkway and Vine Street and catch the latest blockbuster at Regal Cinemas located at The Loop, a sprawling outdoor shopping center in the city’s north end.
In nearby Orlando, shoppers head to Orlando Vineland Premium Outlets, which has more than 160 stores, while Walt Disney World Resort is home to eight restaurants in the Michelin Guide. Parking is free at Disney Springs, Disney World’s retail and dining complex, so anyone can drop by for a meal or to catch a movie at the shopping district's AMC cinema. South of Disney Springs, residents find supermarkets and hardware stores mixed with kitschy tourist attractions along U.S. Route 192.
Many medical offices and facilities are within Kissimmee’s city limits. AdventHealth Kissimmee and HCA Florida Osceola Hospital provide emergency care and are conveniently located near U.S. Route 441.
Downtown Kissimmee is the heart of the local restaurant scene, with 3 Sisters Speakeasy a resident favorite.
Shoppers admire the artwork at Casa Del Artesan in Downtown Kissimmee.
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A look at crime in Kissimmee
In 2023, Kissimmee’s violent crime rate was higher than the U.S. and Florida averages, according to FBI statistics. Kissimmee’s property crime rate is on par with the national average. The Kissimmee Police Department created the Vacation Watch program to deter break-ins while homeowners are out of town. Residents who will be gone for three to 31 days can apply for the program before they leave, and officers will monitor their homes.
Busy roadways can bedevil Kissimmee drivers
Several key highways and toll roads run through Kissimmee, with Florida’s Turnpike used to reach Orlando. Traffic can become backed up in the growing community and getting in and out of town can be a slow process, Araque says. Indeed, the average one-way commute time in Kissimmee is 35 minutes, nearly 10 minutes longer than the national average, per the Census Bureau. Improvements may be on the way, as the state has dedicated $3 billion to fund highway improvements meant to alleviate congestion in Osceola County.
Residents who commute to Orlando may be able to skip traffic by taking SunRail, the regional commuter rail system with a station in Kissimmee. The system stretches as far as the city of DeBary on the north end of the Orlando metro. The Lynx bus system covers Osceola County, with stops in the Kissimmee, St. Cloud and Poinciana communities.
While the city has an airport, it doesn’t offer commercial flights. Instead, residents fly out of Orlando International Airport, located 15 miles away. The bustling airport offers 150 domestic and international destinations. In 2022, Orlando International Airport opened Terminal C, a $2.8 billion addition capable of handling an additional 10 million passengers annually.
Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. Our sources include: Accuweather, Public Records and Neustar. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.
