


4051 PLEASANT HILL Road
Kissimmee, FL
Courtesy of DREAM BUILDERS 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.
2,967 homes



4051 PLEASANT HILL Road
Kissimmee, FL
Courtesy of DREAM BUILDERS REALTY



7532 SUNVILLE Avenue
Kissimmee, FL
Courtesy of AMERICAN HORIZONS REALTY









4210 CARDINAL Lane
Kissimmee, FL



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.
2609 BRIGHT JEWEL Street #2909
Kissimmee, FL
Courtesy of TALENT REALTY SOLUTIONS
2178 COOPER BELL Place
Kissimmee, FL
Courtesy of REALTY ONE GROUP INSPIRATION
Courtesy of FAITH AND FAMILY REALTY LLC
2429 DUBAI Street
Kissimmee, FL
Courtesy of CELEBRITY GLOBAL REALTY LLC
8826 DUNES Court #207
Kissimmee, FL
Courtesy of CENTURY 21 NEXT LEVEL REALTY
LAUREL Avenue
Kissimmee, FL
Courtesy of ROYAL REALTY REAL ESTATE, LLC
2430 TANGIER Drive
Kissimmee, FL
Courtesy of AMERICAN HORIZONS REALTY
4830 MEMORIES Lane
Kissimmee, FL
Courtesy of REALTY ONE GROUP INSPIRATION
2200 SAN ZANOBI Drive #108
Kissimmee, FL
Courtesy of TEAM DONOVAN
2732 OAKWATER Drive #101
Kissimmee, FL
Courtesy of PREFERRED SHORE LLC
4151 BOGGY CREEK Road
Kissimmee, FL
Courtesy of FAITH AND FAMILY REALTY LLC
4421 LE REVE Court
Kissimmee, FL
Courtesy of FLORIDA CONNEXION PROPERTIES
2010 SPRING SHOWER Circle
Kissimmee, FL
Courtesy of REMAX PREMIER PROPERTIES
4539 PHILADELPHIA Circle
Kissimmee, FL
Courtesy of PREFERRED REAL ESTATE BROKERS
7546 SUNVILLE Avenue
Kissimmee, FL
Courtesy of LA ROSA REALTY, LLC
Active listings set the median price and the count. Recently sold homes set days on market and price per square foot. Refreshed hourly.