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 Kissimmee homes for sale (3,127 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
Communities243 MLS communities, 38 with 12-month sales data
Median sold price, 12 months$390K (+5.3% year over year)
Price per square foot$212
Homes sold, 12 months271
Days to contract (median)36
New construction share of sales25%
Sale-to-original-list97.6%
By price band (for sale / sold 12 mo / months)Under $300K: 5 / 21 / 2.9; $300K–$500K: 10 / 26 / 4.6
FEMA flood zone (SFHA) shareabout 31% of 26 sampled homes in the ZIP's largest communities sit in a Special Flood Hazard Area
Schools listings report mostOsceola County Public Schools (verify by address); Confirm zoned elementary, middle, and high; Magnet and choice options may apply
Communities with the most salesORANGE GARDENS SEC 04 ($320K), Legacy Park Ph 3 ($375K), mill run unit 6 ($285K), SPRINGLAKE VILLAGE PH 03 ($375K), Creekside At Boggy Creek Kissimmee ($435K), SEASONS AT BIG SKY ($557K)

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

329 homes are for sale in ZIP 34744 (Kissimmee, FL) right now, from $309,900 to $590,000 for the middle 80%, at a median asking price of $410,000 and $215 per square foot. The typical listing is 1,869 sq ft, built 2018; 27 came on the market in the last 7 days and 18% are new construction.

Newest homes for sale in 34744

3064 Slough Creek Drive, home for sale in Kissimmee 34744
$435,000 New
5 bd · 2.5 ba · 2,370 sq ft · built 2020
3064 Slough Creek Drive
Creekside At Boggy Creek
Listing courtesy of BLOOM HOME GROUP REALTY LLC
1550 Diamond Loop Drive, home for sale in Kissimmee 34744
$430,000 New
5 bd · 3 ba · 2,674 sq ft · built 2017
1550 Diamond Loop Drive
Listing courtesy of MY REALTY GROUP, LLC.
1862 Flourish Avenue, home for sale in Kissimmee 34744
$525,000 New
4 bd · 4 ba · 2,717 sq ft · built 2024
1862 Flourish Avenue
Tohoqua
Listing courtesy of LEGACY PLUS REALTY INC
1900 Southbury Drive, home for sale in Kissimmee 34744
$514,335 New
5 bd · 3 ba · 2,605 sq ft · built 2026
1900 Southbury Drive
Kindred
Listing courtesy of DR HORTON REALTY OF CENTRAL FLORIDA LLC
4561 Gadwall Drive, home for sale in Kissimmee 34744
$385,000 New
3 bd · 2 ba · 1,501 sq ft · built 2019
4561 Gadwall Drive
Osprey Ridge
Listing courtesy of RE/MAX ASSURED
1952 Southbury Drive, home for sale in Kissimmee 34744
$380,990 New
3 bd · 2 ba · 1,593 sq ft · built 2026
1952 Southbury Drive
Kindred
Listing courtesy of DR HORTON REALTY OF CENTRAL FLORIDA LLC
742 Country Woods Circle, home for sale in Kissimmee 34744
$335,000 New
3 bd · 2 ba · 1,766 sq ft · built 1991
742 Country Woods Circle
Listing courtesy of THE WILKINS WAY LLC
1306 Axel Graeson Avenue, home for sale in Kissimmee 34744
$490,000 New
4 bd · 3 ba · 2,102 sq ft · built 2024
1306 Axel Graeson Avenue
Seasons At Big Sky
Listing courtesy of BEST INTERNATIONAL REALTY
2508 Serenity Garden Drive, home for sale in Kissimmee 34744
$481,560 New
4 bd · 3 ba · 2,207 sq ft · built 2026
2508 Serenity Garden Drive
Tohoqua
Listing courtesy of PULTE REALTY OF NORTH FLORIDA LLC
2944 Oak Run Boulevard, home for sale in Kissimmee 34744
$384,990 New
3 bd · 2 ba · 1,334 sq ft · built 1996
2944 Oak Run Boulevard
Westwood Forest
Listing courtesy of NEXTHOME SUNSHINE REALTY
2215 Rita Lane, home for sale in Kissimmee 34744
$347,990 New
3 bd · 2.5 ba · 1,484 sq ft · built 2026
2215 Rita Lane
Listing courtesy of DR HORTON REALTY OF CENTRAL FLORIDA LLC
3833 Siskin Drive, home for sale in Kissimmee 34744
$480,000 New
5 bd · 3 ba · 2,800 sq ft · built 2006
3833 Siskin Drive
Listing courtesy of REAL BROKER, LLC
3043 Slough Creek Drive, home for sale in Kissimmee 34744
$489,990 New
3 bd · 2 ba · 2,022 sq ft · built 2021
3043 Slough Creek Drive
Creekside At Boggy Creek
Listing courtesy of NONA LEGACY POWERED BY LA ROSA
3820 Springlake Village Court, home for sale in Kissimmee 34744
$480,000 New
4 bd · 3 ba · 2,135 sq ft · built 2000
3820 Springlake Village Court
Listing courtesy of RE/MAX TOWN & COUNTRY REALTY
1573 Park Side Avenue, home for sale in Kissimmee 34744
$465,000 New
4 bd · 2 ba · 2,034 sq ft · built 2021
1573 Park Side Avenue
Kindred
Listing courtesy of RE/MAX DOWNTOWN
3012 Villa Preciosa Drive, home for sale in Kissimmee 34744
$420,000 New
4 bd · 2 ba · 2,074 sq ft · built 2004
3012 Villa Preciosa Drive
Listing courtesy of RE/MAX SELECT GROUP
1012 Whirlaway Drive, home for sale in Kissimmee 34744
$419,900 New
4 bd · 3.5 ba · 2,614 sq ft · built 2006
1012 Whirlaway Drive
Listing courtesy of 407 PROPERTIES
1850 Walnut Creek Drive, home for sale in Kissimmee 34744
$389,990 New
4 bd · 2 ba · 1,846 sq ft · built 2024
1850 Walnut Creek Drive
Listing courtesy of KELLER WILLIAMS LEGACY REALTY
1043 La Mirada Court, home for sale in Kissimmee 34744
$365,000 New
4 bd · 3 ba · 1,626 sq ft · built 2020
1043 La Mirada Court
Lago Buendia
Listing courtesy of DALTON WADE INC
1571 Dawnview Way, home for sale in Kissimmee 34744
$309,900 New
3 bd · 2.5 ba · 1,870 sq ft · built 2020
1571 Dawnview Way
Kindred
Listing courtesy of CREEGAN GROUP
1949 Blissful Drive, home for sale in Kissimmee 34744
$520,000 New
5 bd · 3 ba · 2,538 sq ft · built 2025
1949 Blissful Drive
Tohoqua
Listing courtesy of KELLER WILLIAMS ADVANTAGE III
1606 Lund Ave, home for sale in Kissimmee 34744
$389,000 New
3 bd · 2 ba · 1,530 sq ft · built 1993
1606 Lund Ave
Listing courtesy of REPETTO REALTY GROUP LLC
2214 Rolling Hills Road, home for sale in Kissimmee 34744
$365,990 New
3 bd · 2.5 ba · 1,551 sq ft · built 2026
2214 Rolling Hills Road
Listing courtesy of DR HORTON REALTY OF CENTRAL FLORIDA LLC
2220 Rolling Hills Road, home for sale in Kissimmee 34744
$361,990 New
3 bd · 2.5 ba · 1,553 sq ft · built 2026
2220 Rolling Hills Road
Listing courtesy of DR HORTON REALTY OF CENTRAL FLORIDA LLC
2454 Quail Run Boulevard, home for sale in Kissimmee 34744
$355,000 New
3 bd · 2 ba · 1,172 sq ft · built 1998
2454 Quail Run Boulevard
Listing courtesy of PREFERRED REAL ESTATE BROKERS
2216 Rolling Hilld Road, home for sale in Kissimmee 34744
$347,990 New
3 bd · 2.5 ba · 1,553 sq ft · built 2026
2216 Rolling Hilld Road
Listing courtesy of DR HORTON REALTY OF CENTRAL FLORIDA LLC
2218 Rolling Hills Road, home for sale in Kissimmee 34744
$347,990 New
3 bd · 2.5 ba · 1,553 sq ft · built 2026
2218 Rolling Hills Road
Listing courtesy of DR HORTON REALTY OF CENTRAL FLORIDA LLC
1920 Southbury Drive, home for sale in Kissimmee 34744
$496,490
5 bd · 3 ba · 2,601 sq ft · built 2026
1920 Southbury Drive
Kindred
Listing courtesy of DR HORTON REALTY OF CENTRAL FLORIDA LLC
1916 Southbury Drive, home for sale in Kissimmee 34744
$489,790
5 bd · 3 ba · 2,077 sq ft · built 2026
1916 Southbury Drive
Kindred
Listing courtesy of DR HORTON REALTY OF CENTRAL FLORIDA LLC
1944 Southbury Drive, home for sale in Kissimmee 34744
$397,990
4 bd · 2 ba · 1,720 sq ft · built 2026
1944 Southbury Drive
Kindred
Listing courtesy of DR HORTON REALTY OF CENTRAL FLORIDA LLC

Every home for sale in 34744 right now (316)

All 316 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 $200K62%
$200K–$300K237%
$300K–$400K12638%
$400K–$500K10733%
$500K–$750K5416%
$750K+134%

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 November 14, 2026; property mix Single-family 78%, Townhouse 17%, 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.

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