34744 Homes for Sale — Kissimmee, FL

Every active MLS listing in Kissimmee’s 34744 ZIP code, refreshed nightly, with the price bands, the property mix and the communities that have the most homes for sale. For the whole city see homes for sale in Kissimmee, FL (3,104 listings); for the ZIP’s values, taxes and growth see the 34744 housing scorecard.

34744 at a glance

ZIP 34744 is Kissimmee, Osceola County, FL. The numbers below are computed from MLS closings and live listings for every community in the ZIP and refresh with each data pull.

Where it isKissimmee, Osceola County, FL
Communities278 MLS communities, 87 with 12-month sales data
Median sold price, 12 months$406K (+1.3% year over year)
Price per square foot$215
For sale / under contract now128 / 26
Homes sold, 12 months296
Days to contract (median)33
Months of supply6.7
New construction share of sales36%
Sale-to-original-list97.3%
By price band (for sale / sold 12 mo / months)Under $300K: 26 / 39 / 8.0; $300K–$500K: 97 / 230 / 5.1
FEMA flood zone (SFHA) shareabout 11% of 124 sampled homes in the ZIP's largest communities sit in a Special Flood Hazard Area
Communities with the most salesTOHOQUA ($406K), KINDRED ($390K), ORANGE GARDENS SEC 04 ($320K), mill run unit 6 ($349K), Oak Run Unit 9 ($350K), Heather Oaks ($390K)

34744 housing market tracker · all homes for sale in Kissimmee, FL · Osceola County property tax

337 homes are for sale in ZIP 34744 (Kissimmee, FL) right now, from $274,900 to $633,500 for the middle 80%, at a median asking price of $400,000 and $215 per square foot. The typical listing is 1,846 sq ft, built 2016; 30 came on the market in the last 7 days and 14% are new construction.

Newest homes for sale in 34744

Kissimmee
$389,999 New
3 bd · 2 ba · 1,682 sq ft · built 1989
2609 Birchwood Avenue
Listing courtesy of MDZ REALTY, LLC.
Kissimmee
$399,999 New
4 bd · 2 ba · 1,822 sq ft · built 1992
1451 Kingston Way
Listing courtesy of EXP REALTY LLC
Tohoqua
$399,000 New
3 bd · 2.5 ba · 1,802 sq ft · built 2023
1543 Cross Prairie Parkway
Tohoqua
Listing courtesy of KELLER WILLIAMS LEGACY REALTY
2925 Siesta View Drive, home for sale in Kissimmee 34744
$465,000 New
4 bd · 3 ba · 2,296 sq ft · built 2017
2925 Siesta View Drive
Listing courtesy of LPT REALTY, LLC
gleneagles
$399,900 New
4 bd · 2.5 ba · 2,415 sq ft · built 2000
2602 Brandywine Court
gleneagles
Listing courtesy of ALL STAR PROPERTIES OF CENTRAL
4375 Silver Creek Street, home for sale in Kissimmee 34744
$599,900 New
5 bd · 2.5 ba · 3,092 sq ft · built 2019
4375 Silver Creek Street
Creekside At Boggy Creek
Listing courtesy of REAL BROKER, LLC
1785 Petiole Place, home for sale in Kissimmee 34744
$525,000 New
4 bd · 3 ba · 2,384 sq ft · built 2023
1785 Petiole Place
Pennyroyal
Listing courtesy of WEMERT GROUP REALTY LLC
2579 Clear Night Avenue, home for sale in Kissimmee 34744
$516,100 New
3 bd · 2 ba · 1,943 sq ft · built 2027
2579 Clear Night Avenue
Tohoqua
Listing courtesy of PULTE REALTY OF NORTH FLORIDA LLC
2514 Serenity Garden Drive, home for sale in Kissimmee 34744
$486,860 New
5 bd · 3 ba · 2,615 sq ft · built 2026
2514 Serenity Garden Drive
Tohoqua
Listing courtesy of PULTE REALTY OF NORTH FLORIDA LLC
1739 Good Neighbor Loop, home for sale in Kissimmee 34744
$436,000 New
3 bd · 2 ba · 2,068 sq ft · built 2022
1739 Good Neighbor Loop
Tohoqua
Listing courtesy of GLOBAL SAPPHIRE REALTY
3557 Rock Creek Lane, home for sale in Kissimmee 34744
$419,900 New
4 bd · 3 ba · 2,128 sq ft · built 2020
3557 Rock Creek Lane
East Lake Preserve
Listing courtesy of NONA LEGACY POWERED BY LA ROSA
1895 Cassidy Knoll Drive, home for sale in Kissimmee 34744
$375,000 New
3 bd · 2 ba · 1,676 sq ft · built 2019
1895 Cassidy Knoll Drive
Kindred
Listing courtesy of REMAX PREMIER PROPERTIES
1872 Cross Prairie Parkway, home for sale in Kissimmee 34744
$335,000 New
3 bd · 2.5 ba · 1,528 sq ft · built 2022
1872 Cross Prairie Parkway
Tohoqua
Listing courtesy of PM ELITE REALTY LLC
2621 Gold Dust Circle, home for sale in Kissimmee 34744
$359,900 New
3 bd · 2 ba · 1,745 sq ft · built 2001
2621 Gold Dust Circle
Fortune Lakes
Listing courtesy of ODRY VARGAS REALTY GROUP
3113 Conrad Court, home for sale in Kissimmee 34744
$730,000 New
5 bd · 5.5 ba · 2,821 sq ft · built 2005
3113 Conrad Court
Listing courtesy of REALTY OF AMERICA
2855 N Point Blvd, home for sale in Kissimmee 34744
$595,000 New
5 bd · 3.5 ba · 3,475 sq ft · built 2014
2855 N Point Blvd
Listing courtesy of ONE TEAM REALTY
1869 Kings Point Boulevard, home for sale in Kissimmee 34744
$350,000 New
3 bd · 3 ba · 1,704 sq ft · built 1983
1869 Kings Point Boulevard
Kings Point
Listing courtesy of COLDWELL BANKER REALTY
4106 Longworth Loop, home for sale in Kissimmee 34744
$420,000
4 bd · 2 ba · 1,945 sq ft · built 2006
4106 Longworth Loop
Turnberry Reserve
Listing courtesy of AGENT TRUST REALTY CORPORATION
1520 Shady Oak Drive, home for sale in Kissimmee 34744
$485,000
3 bd · 2 ba · 2,468 sq ft · built 1987
1520 Shady Oak Drive
Listing courtesy of LPT REALTY, LLC
4406 Silver Creek Street, home for sale in Kissimmee 34744
$439,000
3 bd · 2.5 ba · 1,878 sq ft · built 2019
4406 Silver Creek Street
Creekside At Boggy Creek
Listing courtesy of VECTOR REALTY
1485 Rylee Rock Way, home for sale in Kissimmee 34744
$320,000
3 bd · 2.5 ba · 1,870 sq ft · built 2016
1485 Rylee Rock Way
Listing courtesy of CHARLES RUTENBERG REALTY ORLANDO
3150 Morning Light Way, home for sale in Kissimmee 34744
$215,000
3 bd · 2 ba · 1,216 sq ft · built 1998
3150 Morning Light Way
Listing courtesy of WEMERT GROUP REALTY LLC
1311 Carson Avenue, home for sale in Kissimmee 34744
$295,000
2 bd · 1 ba · 1,103 sq ft · built 1939
1311 Carson Avenue
Listing courtesy of EXP REALTY LLC
3145 Twisted Oak Loop, home for sale in Kissimmee 34744
$640,000
5 bd · 3.5 ba · 3,183 sq ft · built 2005
3145 Twisted Oak Loop
Listing courtesy of MUTTER REALTY
1805 Lee Janzen Drive, home for sale in Kissimmee 34744
$550,000
3 bd · 3 ba · 2,155 sq ft · built 1994
1805 Lee Janzen Drive
Kissimmee Bay
Listing courtesy of MARK SPAIN REAL ESTATE
2921 Casabella Drive, home for sale in Kissimmee 34744
$455,000
4 bd · 4 ba · 2,392 sq ft · built 2013
2921 Casabella Drive
Listing courtesy of MOSAIC PARTNERS GROUP
1744 Quail Ridge Loop, home for sale in Kissimmee 34744
$425,000
3 bd · 2.5 ba · 1,260 sq ft · built 1991
1744 Quail Ridge Loop
Listing courtesy of COLDWELL BANKER REALTY

Every home for sale in 34744 right now (298)

All 298 active listings in ZIP 34744 with a detail page, newest first, refreshed twice a day from the MLS.

Homes for sale in 34744 by price

Price bandFor saleShare
Under $200K216%
$200K–$300K237%
$300K–$400K12437%
$400K–$500K9528%
$500K–$750K5115%
$750K+237%

Communities in 34744 with the most homes for sale

How to read this

Counts and medians are from active MLS listings with a 34744 mailing ZIP as of October 24, 2026; property mix Single-family 73%, Townhouse 16%, Condo 1%. Prices are asking prices. Listings are shown with the courtesy of the listing brokerage under IDX rules; information deemed reliable but not guaranteed. Other Kissimmee ZIP codes: 34747, 34746, 34758, 34741, 34759, 34743. See also homes for sale in Osceola County. More: Kissimmee condos, Kissimmee townhomes, luxury homes in Kissimmee, new listings this week in Kissimmee, Kissimmee homes by street.

Hiring an agent in Kissimmee, FL?

Get matched with the right local expert.

Tell us your goal in Kissimmee, FL and we’ll connect you with the Momentum agent who knows it best — backed by a RealTrends 500 brokerage. No pressure, no obligation.

Prefer to talk now? Call (904) 351-6461.

Work with a local Kissimmee, FL expert

A real conversation with a local specialist, usually within one business day.

or call (904) 351-6461