34744, FL homes for sale & real estate

9 hours on Rocket

$380,000

3 beds • 2 baths • 1,866 sqft

416 Janice Kay Pl, Kissimmee, FL 34744

#O6329548, Monica Perlas, Listing office: COLDWELL BANKER REALTY

10 hours on Rocket

$449,000

4 beds • 3 baths • 1,848 sqft

156 Magic Landings Blvd, Kissimmee, FL 34744

#S5131309, Irena Aistrop, Listing office: LA ROSA REALTY LLC

Room to negotiate?

Median Sold Price

$400K

Avg. Sale Time

51 Days

Based on our June 2025 Market Report.

19 hours on RocketTour

$242,000

2 beds • 2.5 baths • 1,219 sqft

3022 Skyline Loop, Kissimmee, FL 34758

#O6329300, Michelle Campbell, Listing office: TAYLOR MORRISON REALTY OF FLORIDA INC

2907 Willow Oak Ct, Kissimmee, FL 34744 - photo 1

19 hours on Rocket

$314,999

3 beds • 2 baths • 1,360 sqft

2907 Willow Oak Ct, Kissimmee, FL 34744

#O6328663, Jemima Douze Cretu, Listing office: REALTY HUB

19 hours on RocketTour

$235,000

2 beds • 2.5 baths • 1,219 sqft

3034 Skyline Loop, Kissimmee, FL 34758

#O6329294, Michelle Campbell, Listing office: TAYLOR MORRISON REALTY OF FLORIDA INC

20 hours on RocketTour

$237,000

2 beds • 2.5 baths • 1,219 sqft

3030 Skyline Loop, Kissimmee, FL 34758

#O6329287, Michelle Campbell, Listing office: TAYLOR MORRISON REALTY OF FLORIDA INC

23 hours on RocketTour

$459,900

4 beds • 2.5 baths • 2,262 sqft

231 Strathmore Cir, Kissimmee, FL 34744

#S5131280, Kish Munjal, Listing office: CENTURY 21 ALL HOMES & PROPERT

1 day on RocketTour

$548,846

4 beds • 4 baths • 2,722 sqft

1855 Bright Sky Dr, Kissimmee, FL 34744

#O6328998, Ben Goldstein, Listing office: LENNAR REALTY

1 day on RocketTour

$556,090

4 beds • 3 baths • 2,109 sqft

1873 Bright Sky Dr, Kissimmee, FL 34744

#O6329008, Ben Goldstein, Listing office: LENNAR REALTY

1 day on RocketTour

$410,000

3 beds • 2 baths • 1,680 sqft

1560 Gladewater Rd, Kissimmee, FL 34744

#S5131160, Liliana Aranguibel, Listing office: LA ROSA REALTY KISSIMMEE

1 day on RocketTour

$920,000

5 beds • 4.5 baths • 4,964 sqft

1698 Taylor Ridge Loop, Kissimmee, FL 34744

#O6328758, Jaime Carr, Listing office: KNIGHT & DREWS

3 days on RocketTour

$389,900

4 beds • 2 baths • 1,910 sqft

1724 Ranger Highlands Rd, Kissimmee, FL 34744

#TB8408985, Danielle Angel, Listing office: 444 REALTY GROUP LLC

4 days on RocketTour

$520,900

5 beds • 3 baths • 2,709 sqft

2812 Quiet Water Trl, Kissimmee, FL 34744

#O6328120, JRodz Rodriguez, Listing office: HOUSESTAR REALTY GROUP INC

4 days on RocketTour

$364,900

3 beds • 2 baths • 1,342 sqft

305 E Jackson St, Kissimmee, FL 34744

#S5131155, Jonathan Ortiz, Listing office: LPT REALTY, LLC

4 days on RocketTour

$515,000

4 beds • 4 baths • 2,717 sqft

1839 Good Neighbor Loop, Kissimmee, FL 34744

#O6328214, Kerlin Torre Wesson, Listing office: MY REALTY GROUP, LLC.

5 days on RocketTour

$375,000

3 beds • 2 baths • 1,816 sqft

119 Southampton Dr, Kissimmee, FL 34744

#O6327034, Jenny Wemert, Listing office: WEMERT GROUP REALTY LLC

5 days on RocketTour

$449,990

4 beds • 2 baths • 2,259 sqft

3028 Camino Real Dr S, Kissimmee, FL 34744

#O6328104, John Joseph, Listing office: CENTRIC REALTY SERVICES LLC

5 days on RocketTour

$474,990

4 beds • 2.5 baths • 1,883 sqft

2831 Noble Crow Dr, Kissimmee, FL 34744

#O6326852, Claireth Canongo, Listing office: MY REALTY GROUP, LLC.

5 days on RocketTour

$349,900

3 beds • 2 baths • 1,536 sqft

185 Thornbury Dr, Kissimmee, FL 34744

#S5131061, Claudia Martinez, Listing office: LATIN CONNECTION REALTY GROUP

5 days on RocketTour

$543,990

4 beds • 3 baths • 2,361 sqft

2001 Walnut Creek Dr, Kissimmee, FL 34744

#O6327922, Paul King, Listing office: DR HORTON REALTY OF CENTRAL FLORIDA LLC

5 days on Rocket

$469,000

3 beds • 2 baths • 1,844 sqft

1544 Regal Ct, Kissimmee, FL 34744

#S5130684, Melissa Godwin, Listing office: GODWIN REALTY GROUP

6 days on RocketTour

$359,900

3 beds • 2 baths • 1,948 sqft

913 Tramells Trl, Kissimmee, FL 34744

#S5130758, Andy Chen, Listing office: HAPPY HOME REAL ESTATE LLC

6 days on Rocket

$359,000

3 beds • 2 baths • 1,676 sqft

1884 Hickory Bluff Rd, Kissimmee, FL 34744

#O6326853, Angel Ruiz, Listing office: KELLER WILLIAMS ADVANTAGE III

6 days on RocketTour

$409,900

4 beds • 3 baths • 1,993 sqft

223 Westmoreland Cir, Kissimmee, FL 34744

#O6327399, Eliezer Ayala, Listing office: PLATINUM STAR REALTY

6 days on RocketTour

$515,000

4 beds • 3 baths • 2,297 sqft

2822 Sail Breeze Way, Kissimmee, FL 34744

#O6326044, Jay Winston, Listing office: COLDWELL BANKER RESIDENTIAL RE

7 days on RocketTour

$379,900

4 beds • 2 baths • 1,846 sqft

1831 Brockridge Rd, Kissimmee, FL 34744

#L4953976, Heather Stone, Listing office: BHHS FLORIDA PROPERTIES GROUP

7 days on Rocket

$329,900

4 beds • 2 baths • 1,870 sqft

1864 Red Canyon Dr, Kissimmee, FL 34744

#S5130905, Alex Vazquez, Listing office: NONA LEGACY POWERED BY LA ROSA

7 days on RocketTour

$307,000

3 beds • 2.5 baths • 1,380 sqft

1661 Windsor Oak Ct, Kissimmee, FL 34744

#O6327343, Nubia Saenz, Listing office: BETTER HOMES AND GARDENS REAL ESTATE MANN GLOBAL P

7 days on RocketTour

$329,900

2 beds • 2.5 baths • 1,186 sqft

3171 Paradox Cir Unit 102, Kissimmee, FL 34746

#TB8405029, Lori Joy, Listing office: REDFIN CORPORATION

7 days on RocketTour

$285,990

3 beds • 2.5 baths • 1,834 sqft

2664 Skyline Loop, Kissimmee, FL 34758

#O6327135, Ben Goldstein, Listing office: LENNAR REALTY

Tour

$565,000

4 beds • 3.5 baths • 2,851 sqft

1799 Ranger Highlands Rd, Kissimmee, FL 34744

#O6327045, Gregory Woerner, Listing office: WATSON REALTY CORP

Tour

$360,000

3 beds • 2 baths • 1,393 sqft

2529 Colony Ave, Kissimmee, FL 34744

#S5130787, Ramon Francisco, Listing office: AGENT TRUST REALTY CORPORATION

Tour

$390,000

4 beds • 2 baths • 1,442 sqft

Address Not Disclosed, Kissimmee, FL 34744

#S5130785, Jorge Espinosa, Listing office: THE REAL ESTATE GALLERY LLC

Tour

$276,900

3 beds • 2 baths • 1,148 sqft

1150 Jade E Ln, Kissimmee, FL 34744

#TB8406978, Angelo Sepulveda, Listing office: LPT REALTY, LLC

$399,500

3 beds • 2 baths • 1,757 sqft

3003 Bay Laurel, Kissimmee, FL 34744

#TB8400039, Tanner Tillung, Listing office: EXP REALTY LLC

Tour

$410,000

4 beds • 2 baths • 1,846 sqft

1433 Riverboat Dr, Kissimmee, FL 34744

#O6326625, Tara Garkowski, Listing office: KELLER WILLIAMS ADVANTAGE REALTY

$300,000

3 beds • 2 baths • 1,516 sqft

2654 Ann Ave, Kissimmee, FL 34744

#S5130486, Tiffany Licata, Listing office: IRON VALLEY REAL ESTATE OSCEOL

Tour

$394,824

3 beds • 2.5 baths • 1,615 sqft

1865 Fulfillment Dr, Kissimmee, FL 34744

#O6326428, Ben Goldstein, Listing office: LENNAR REALTY

Tour

$379,999

3 beds • 2.5 baths • 2,016 sqft

1608 Mohegan Blvd, Kissimmee, FL 34744

#O6326118, Mesner Belidor, Listing office: KELLER WILLIAMS LEGACY REALTY

$378,690

3 beds • 2.5 baths • 1,553 sqft

2304 Southbury Dr, Kissimmee, FL 34744

#O6326244, Adrienne Escott, Listing office: PULTE REALTY OF NORTH FLORIDA LLC

34744, FL Real Estate Market Overview

There are 408 homes for sale in 34744, FL. The following market insights reflect all property types in the 34744, FL real estate market. The number of homes for sale in 34744, FL decreased by 5.8% between May 2025 and June 2025. In June 2025, listings were on the market for 51 days. During the same period, the median list price in this real estate market was $400,000. While more than 8 listings in 34744, FL in June 2025 were sold above asking price, there were more than 30 listings sold at asking price, and more than 27 were sold below.

From Rocket Homes Real Estate and based on county public records data

What is it like to live in 34744, FL

Overview

34744 is located in Florida. There are roughly 47,060 residents, living in 15,425 households. The average temperature for 34744 this time of the year is low of 72F and high of 92F. On average, 34744 gets about 6.93 inches of precipitation in July. Most residents are home owners (63%), have a post secondary degree (49%) and are single, no kids (30%).

Data provided by Home Junction

Schools near 34744, FL

Elementary Schools

Oakshire Elementary School
14501 Oakshire Blvd
Public District PK-5
Boggy Creek Elementary School
810 Florida Pkwy
Public District PK-5
Partin Settlement Elementary School
2434 Remington Blvd
Public District PK-5

Middle Schools

Kissimmee Charter Academy
2850 Bill Beck Blvd
Public Charter KG-8
Sports Leadership Arts Management (Slam)
611 Line Dr
Public Charter 6-9
P. M. Wells Charter Academy
2426 Remington Blvd
Public Charter KG-8

High Schools

Zenith Accelerated Academy
2218 E Irlo Bronson Memorial Hwy
Public District 8-12
Main Street High School
1100 N Main St
Public Charter 9-12
Neocity Academy
195 Neocity Way
Public District 9-12

Data provided by Great Schools