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Homes For Sale in Kissimmee 34744 - 370 homes

34744 zip code is located in Osceola County, Florida. Find homes for sale in Kissimmee 34744 from the Multiple Listing Service (MLS). Our REALTORS® can assist you in your search for Kissimmee 34744 homes for sale.

Location: Kissimmee , 34744

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  • 1150 STROUPE RD, KISSIMMEE, FL 34744

    $450,00039 Days on yellowkey   MLS ID: S5149769

    1 Days Off yellowkey (back on 5/22/2026)

    For Sale S5149769 - 1150 STROUPE RD, KISSIMMEE, FL 34744 65 photos

    Bed: 3   Bath: 3.0
    Liv Area Sq Ft: 2128
       Built: 1973   Tax: $2,257 (2025)
    Community: Midway City Townsite
    Single Family


    Estimated Monthly Payment: $2,654 (change assumption)
    Mortgage ($2,466) + Taxes in 2025 ($188)


    Taxes:$2,257

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1772 STAMEN DR, KISSIMMEE, FL 34744

    $495,50070 Days on yellowkey   MLS ID: S5147865

    For Sale S5147865 - 1772 STAMEN DR, KISSIMMEE, FL 34744 28 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1965
       Built: 2023
    Monthly Fee: $160
       Tax: $5,861 (2025)
    Community: Pennyroyal
    Single Family


    Estimated Monthly Payment: $3,363 (change assumption)
    Mortgage ($2,715) + Fees ($160) + Taxes in 2025 ($488)


    Taxes:$5,861

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 4424 SILVER CREEK ST, KISSIMMEE, FL 34744

    $470,000152 Days on yellowkey   MLS ID: L4958851

    REDUCED by $9,900 (2.1%) on 05/26/2026

    For Sale L4958851 - 4424 SILVER CREEK ST, KISSIMMEE, FL 34744 27 photos

    Bed: 5   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2370
       Built: 2019
    Monthly Fee: $123
       Tax: $6,332 (2025)
    Community: Creekside At Boggy Creek Ph 1
    Single Family


    Estimated Monthly Payment: $3,226 (change assumption)
    Mortgage ($2,575) + Fees ($123) + Taxes in 2025 ($528)


    Taxes:$6,332

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 3013 MANDOLIN DR, KISSIMMEE, FL 34744

    $434,00026 Days on yellowkey   MLS ID: O6411560

    REDUCED by $5,000 (1.1%) on 06/17/2026

    For Sale O6411560 - 3013 MANDOLIN DR, KISSIMMEE, FL 34744 58 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2148
       Built: 2005
    Monthly Fee: $83
       Tax: $5,071 (2025)
    Community: Turnberry Reserve Unit 1
    Single Family


    Estimated Monthly Payment: $2,884 (change assumption)
    Mortgage ($2,378) + Fees ($83) + Taxes in 2025 ($423)


    Taxes:$5,071

    Elementary School: East Lake Elem

    High School: Tohopekaliga High School

    Tax Year: 2025

    Middle School: Narcoossee Middle


  • 3044 CAMINO REAL DR S, KISSIMMEE, FL 34744

    $479,00048 Days on yellowkey   MLS ID: O6406104

    REDUCED by $10,000 (2.0%) on 05/31/2026

    For Sale O6406104 - 3044 CAMINO REAL DR S, KISSIMMEE, FL 34744 35 photos

    Bed: 5   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2264
       Built: 2005
    Monthly Fee: $160
       Tax: $5,505 (2025)
    Community: Villa Sol Ph 2 Village 3
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,243 (change assumption)
    Mortgage ($2,625) + Fees ($160) + Taxes in 2025 ($459)


    Taxes:$5,505

    Elementary School: Cypress Elem (K 6)

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Parkway Middle


  • 1340 SAWDUST TRL, KISSIMMEE, FL 34744

    $239,900158 Days on yellowkey   MLS ID: G5106887

    0 Days Off yellowkey (back on 5/13/2026)

    For Sale G5106887 - 1340 SAWDUST TRL, KISSIMMEE, FL 34744 24 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 924
       Built: 1996   Tax: $2,377 (2025)
    Community: Marydia
    Manufactured Home


    Estimated Monthly Payment: $1,513 (change assumption)
    Mortgage ($1,314) + Taxes in 2025 ($198)


    Taxes:$2,377

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1624 BARBERRY DR, KISSIMMEE, FL 34744

    $559,9901 Day on yellowkey   MLS ID: S5152366

    For Sale S5152366 - 1624 BARBERRY DR, KISSIMMEE, FL 34744 30 photos

    Bed: 4   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 2851
       Built: 2023
    Monthly Fee: $11
       Tax: $6,483 (2025)
    Community: Kindred Ph 2C & 2D
    Single Family


    Estimated Monthly Payment: $3,620 (change assumption)
    Mortgage ($3,068) + Fees ($11) + Taxes in 2025 ($540)


    Taxes:$6,483

    Elementary School: Neptune Elementary

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 1213 CHEROKEE DR, KISSIMMEE, FL 34744

    $325,0001 Day on yellowkey   MLS ID: K4903584

    For Sale K4903584 - 1213 CHEROKEE DR, KISSIMMEE, FL 34744 5 photos

    Bed: 3   Bath: 1.0
    Liv Area Sq Ft: 1715
       Built: 1965   Tax: $4,057 (2025)
    Community: Osceola Acres
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,119 (change assumption)
    Mortgage ($1,781) + Taxes in 2025 ($338)


    Taxes:$4,057

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2127 SOUTHBURY DR, KISSIMMEE, FL 34744

    $381,4901 Day on yellowkey   MLS ID: O6419027

    For Sale O6419027 - 2127 SOUTHBURY DR, KISSIMMEE, FL 34744 28 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1770
       Built: 2026
    Monthly Fee: $126
       Tax: $1,920 (2025)
    Community: Tohoqua
    Spa: No

    Townhouse


    Estimated Monthly Payment: $2,376 (change assumption)
    Mortgage ($2,090) + Fees ($126) + Taxes in 2025 ($160)


    Taxes:$1,920

    Elementary School: Neptune Elementary

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 2462 MILL RUN BLVD, KISSIMMEE, FL 34744

    $439,9001 Day on yellowkey   MLS ID: O6418912

    For Sale O6418912 - 2462 MILL RUN BLVD, KISSIMMEE, FL 34744 46 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1538
       Built: 1980   Tax: $1,698 (2025)
    Community: Mill Run
    Single Family


    Estimated Monthly Payment: $2,552 (change assumption)
    Mortgage ($2,410) + Taxes in 2025 ($141)


    Taxes:$1,698

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2122 SOUTHBURY DR, KISSIMMEE, FL 34744

    $386,4904 Days on yellowkey   MLS ID: O6418725

    For Sale O6418725 - 2122 SOUTHBURY DR, KISSIMMEE, FL 34744 27 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1770
       Built: 2026
    Monthly Fee: $126
       Tax: $1,920 (2025)
    Community: Tohoqua
    Spa: No

    Townhouse


    Estimated Monthly Payment: $2,404 (change assumption)
    Mortgage ($2,118) + Fees ($126) + Taxes in 2025 ($160)


    Taxes:$1,920

    Elementary School: Neptune Elementary

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 1502 JADEWOOD WAY, KISSIMMEE, FL 34744

    $350,000674 Days on yellowkey   MLS ID: O6233314

    0 Days Off yellowkey (back on 6/18/2026)

    SHORT SALE O6233314 - 1502 JADEWOOD WAY, KISSIMMEE, FL 34744 35 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1846
       Built: 2022
    Monthly Fee: $11
       Tax: $7,144 (2025)
    Community: Kindred Ph 2C & 2D Pb 30 Pgs 74-80 Lot 323
    Single Family


    Estimated Monthly Payment: $2,524 (change assumption)
    Mortgage ($1,918) + Fees ($11) + Taxes in 2025 ($595)


    Taxes:$7,144

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1205 TETON DR, KISSIMMEE, FL 34744

    $342,99042 Days on yellowkey   MLS ID: S5148840

    REDUCED by $11,000 (3.1%) on 05/29/2026

    For Sale S5148840 - 1205 TETON DR, KISSIMMEE, FL 34744 40 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1935
       Built: 2018
    Monthly Fee: $158
       Tax: $3,699 (2025)
    Community: Heritage Run
    Townhouse


    Estimated Monthly Payment: $2,346 (change assumption)
    Mortgage ($1,879) + Fees ($158) + Taxes in 2025 ($308)


    Taxes:$3,699

    Elementary School: Mill Creek Elem (K 5)

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Denn John Middle


  • 3504 SOUTHERN CROSS LOOP, KISSIMMEE, FL 34744

    $475,00058 Days on yellowkey   MLS ID: O6402309

    REDUCED by $5,000 (1.0%) on 05/27/2026

    For Sale O6402309 - 3504 SOUTHERN CROSS LOOP, KISSIMMEE, FL 34744 31 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2463
       Built: 2018
    Monthly Fee: $110
       Tax: $5,942 (2025)
    Community: East Lk Preserve-Ph 1
    Single Family


    Estimated Monthly Payment: $3,208 (change assumption)
    Mortgage ($2,603) + Fees ($110) + Taxes in 2025 ($495)


    Taxes:$5,942

    Elementary School: East Lake Elem

    High School: Tohopekaliga High School

    Tax Year: 2025

    Middle School: Narcoossee Middle


  • 1777 WALNUT CREEK DR, KISSIMMEE, FL 34744

    $449,50093 Days on yellowkey   MLS ID: O6390965

    INCREASED by $14,600 (3.4%) on 06/22/2026

    For Sale O6390965 - 1777 WALNUT CREEK DR, KISSIMMEE, FL 34744 75 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2339
       Built: 2023
    Monthly Fee: $11
       Tax: $3,358 (2025)
    Community: Kindred Ph 3A
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,754 (change assumption)
    Mortgage ($2,463) + Fees ($11) + Taxes in 2025 ($280)


    Taxes:$3,358

    Elementary School: None

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 1973 SPRING SHOWER CIR, KISSIMMEE, FL 34744

    $432,00012 Days on yellowkey   MLS ID: O6416082

    For Sale O6416082 - 1973 SPRING SHOWER CIR, KISSIMMEE, FL 34744 35 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1701
       Built: 2022
    Monthly Fee: $136
       Tax: $6,439 (2025)
    Community: Tohoqua Ph 5A
    Single Family


    Estimated Monthly Payment: $3,040 (change assumption)
    Mortgage ($2,367) + Fees ($136) + Taxes in 2025 ($537)


    Taxes:$6,439

    Elementary School: None

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 1620 MARINA LAKE DR, KISSIMMEE, FL 34744

    $790,00035 Days on yellowkey   MLS ID: S5150329

    For Sale S5150329 - 1620 MARINA LAKE DR, KISSIMMEE, FL 34744 95 photos

    Bed: 5   Bath: 4.0   Gar: 3
    Liv Area Sq Ft: 3643
       Built: 2000
    Monthly Fee: $75
       Tax: $5,686 (2025)
    Community: Ashley Cove Unit 1
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $4,877 (change assumption)
    Mortgage ($4,329) + Fees ($75) + Taxes in 2025 ($474)


    Taxes:$5,686

    Elementary School: Partin Settlement Elem

    High School: None

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 2705 PRESTWICK LN, KISSIMMEE, FL 34744

    $410,000120 Days on yellowkey   MLS ID: O6384546

    For Sale O6384546 - 2705 PRESTWICK LN, KISSIMMEE, FL 34744 43 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 1719
       Built: 2005
    Monthly Fee: $73
       Tax: $6,174 (2025)
    Community: Remington Prcl M1
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,834 (change assumption)
    Mortgage ($2,247) + Fees ($73) + Taxes in 2025 ($515)


    Taxes:$6,174

    Elementary School: Partin Settlement Elem

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 1660 CROSS PRAIRIE PKWY, KISSIMMEE, FL 34744

    $435,00021 Days on yellowkey   MLS ID: R4911380

    REDUCED by $10,000 (2.2%) on 06/22/2026

    For Sale R4911380 - 1660 CROSS PRAIRIE PKWY, KISSIMMEE, FL 34744 30 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1802
       Built: 2022
    Monthly Fee: $20
       Tax: $6,147 (2025)
    Community: Tohoqua Ph 2
    Single Family


    Estimated Monthly Payment: $2,916 (change assumption)
    Mortgage ($2,384) + Fees ($20) + Taxes in 2025 ($512)


    Taxes:$6,147

    Elementary School: Neptune Elementary

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 2093 WALNUT CREEK DR, KISSIMMEE, FL 34744

    $398,990107 Days on yellowkey   MLS ID: O6389078

    2 Days Off yellowkey (back on 6/16/2026)

    REDUCED by $3,000 (0.7%) on 05/28/2026

    For Sale O6389078 - 2093 WALNUT CREEK DR, KISSIMMEE, FL 34744 47 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1614
       Built: 2025
    Monthly Fee: $11
       Tax: $3,684 (2025)
    Community: Kindred Ph 3B 3C & 3D
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,504 (change assumption)
    Mortgage ($2,186) + Fees ($11) + Taxes in 2025 ($307)


    Taxes:$3,684

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None




Why Bother Searching Elsewhere for 34744 Homes for Sale and Other Kissimmee Real Estate?

34744, Kissimmee home, townhome, condo, villa, and other listing rental data is continuously updated on yellowkeyrealty.com. yellowkeyrealty.com offers one of the most exhaustive, current, and relevant set of data you can find on houses for sale in the 34744 zip code. You can use our website to view Multiple Listing Service (MLS) data on 34744, Kissimmee real estate. Feel free to reach out to a REALTOR ® at 1-954-369-1486 if you are unable to find specific information on any of our 34744, Kissimmee listings.



Data is updated at least once a week by Sunday nights. Some properties that appear for sale on this web site may subsequently have been sold and may no longer be available. The data relating to real estate for sale/lease on this web site come in part from a cooperative data exchange program of the multiple listing service (MLS) in which this real estate firm (Broker) participates. Data can be retrieved from any one of the following MLS’s: Greater Fort Lauderdale REALTORS®, Space Coast Association of REALTORS®, My Florida Regional MLS, Florida Gulf Coast MLS, "©2024 Northeast Florida Multiple Listing Service, Inc. All rights reserved." The properties displayed may not be all of the properties in the MLS’s database, or all of the properties listed with Brokers participating in the cooperative data exchange program. Properties listed by Brokers other than this Broker are marked with either the listing Broker’s logo or name or the MLS name or a logo provided by the MLS. Detailed information about such properties includes the name of the listing Brokers. Information provided is thought to be reliable but is not guaranteed to be accurate; you are advised to verify facts that are important to you. No warranties, expressed or implied, are provided for the data herein, or for their use or interpretation by the user. The Florida Association of Realtors® and its cooperating MLSs do not create, control or review the property data displayed herein and take no responsibility for the content of such records. Federal law prohibits discrimination on the basis of race, color, religion, sex, handicap, familial status or national origin in the sale, rental or financing of housing.