


5521 WILLOW BEND Trail
Kissimmee, FL
Courtesy of COLDWELL BANKER REALTY
Where a short-term rental and a family home can both make sense. Highway 192 runs the rental communities near the parks, and downtown holds the older lakefront blocks. I live and work this market, so I know which streets hold value.
2,907 homes



5521 WILLOW BEND Trail
Kissimmee, FL
Courtesy of COLDWELL BANKER REALTY



47 LAS PALMAS Way #47
Kissimmee, FL
Courtesy of MARLAND REALTY GROUP INC


0 HERALDO CT.
Kissimmee, FL
Courtesy of KELLER WILLIAMS ADVANTAGE III









Where a short-term rental and a family home can both make sense. Highway 192 runs the rental communities near the parks, and downtown holds the older lakefront blocks. I live and work this market, so I know which streets hold value.
Kissimmee sits on the south side of Orlando, wrapped around the theme-park corridor and stretched along US-192. New builds, resale subdivisions, and short-term rental zones all live here, and each one runs on its own rules.
Es un mercado activo, todos los días. I read the zoning, the HOA, and the short-term rental maps with you before you fall for a floor plan. First-time buyer, vacation home, or rental investor: same broker, same process, in English or Spanish.
The count on this page is live from the MLS and changes through the day, so the number above the grid is the current one. To narrow it, filter by price and bedrooms, or call or text me at 414.712.6275 and tell me what you need in Kissimmee. I will send you a shorter, better list than any filter produces.
I hear about homes before they reach the feed, from agents I close with every month. Send me your budget and must-haves and I will go find it, in English or Spanish.
2165 THE OAKS Boulevard
Kissimmee, FL
Courtesy of OUTLET REALTY
7770 SANDY RIDGE Drive #238
Kissimmee, FL
Courtesy of LA ROSA REALTY LLC
7770 SANDY RIDGE Drive #236
Kissimmee, FL
Courtesy of LA ROSA REALTY LLC
7770 SANDY RIDGE Drive #138
Kissimmee, FL
Courtesy of LA ROSA REALTY LLC
1852 ANCESTRY Trail
Kissimmee, FL
Courtesy of COLDWELL BANKER REALTY
3008 RED GINGER Road
Kissimmee, FL
Courtesy of BELMONT REALTY
4021 VENETIAN BAY Drive #103
Kissimmee, FL
Courtesy of VS INTERNATIONAL PROPERTIES
1098 JUNE Street
Kissimmee, FL
Courtesy of VP REALTY
1102 JUNE Street
Kissimmee, FL
Courtesy of VP REALTY
1106 JUNE Street
Kissimmee, FL
Courtesy of VP REALTY
1814 STARGAZER Trail
Kissimmee, FL
Courtesy of EXP REALTY LLC
2007 FORAGE Drive
Kissimmee, FL
Courtesy of PREMIER SOTHEBYS INT'L REALTY
327 MARQUEE Drive
Kissimmee, FL
Courtesy of ELITE REALTY, LLC
9009 EGRET MILLS Terrace
Kissimmee, FL
Courtesy of GLOBAL SAPPHIRE REALTY
1739 GOOD NEIGHBOR Loop
Kissimmee, FL
Courtesy of GLOBAL SAPPHIRE REALTY
1583 BARBERRY Drive
Kissimmee, FL
Courtesy of GLOBAL SAPPHIRE REALTY
2514 SERENITY GARDEN DRIVE
Kissimmee, FL
Courtesy of PULTE REALTY OF NORTH FLORIDA LLC
9009 EGRET MILLS Terrace
Kissimmee, FL
Courtesy of GLOBAL SAPPHIRE REALTY
148 DORCHESTER Court
Kissimmee, FL
Courtesy of NOVA REAL ESTATE SERVICES INC
4615 EAGLET Lane
Kissimmee, FL
Courtesy of OPENDOOR BROKERAGE LLC
3275 AMBERLEY PARK Circle
Kissimmee, FL
Courtesy of EMPIRE REALTY & MANAGEMENT SERVICES
Active listings set the median price and the count. Recently sold homes set days on market and price per square foot. Refreshed hourly.