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Homes For Sale in Kissimmee 34744 - 360 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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  • 1495 SKYLINE DR, KISSIMMEE, FL 34744

    $474,900107 Days on yellowkey   MLS ID: S5145209

    REDUCED by $19,600 (4.0%) on 05/20/2026

    For Sale S5145209 - 1495 SKYLINE DR, KISSIMMEE, FL 34744 50 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2094
       Built: 1973
    Monthly Fee: $16
       Tax: $5,404 (2025)
    Community: Harbour Oaks Unit 1
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,068 (change assumption)
    Mortgage ($2,602) + Fees ($16) + Taxes in 2025 ($450)


    Taxes:$5,404

    Elementary School: Partin Settlement Elem

    High School: Osceola High School

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 2540 BLOWING BREEZE AVE, KISSIMMEE, FL 34744

    $370,000164 Days on yellowkey   MLS ID: S5141277

    For Sale S5141277 - 2540 BLOWING BREEZE AVE, KISSIMMEE, FL 34744 29 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1700
       Built: 2021
    Monthly Fee: $154
       Tax: $6,407 (2025)
    Community: Tohoqua Ph 1B
    Townhouse


    Estimated Monthly Payment: $2,715 (change assumption)
    Mortgage ($2,027) + Fees ($154) + Taxes in 2025 ($534)


    Taxes:$6,407

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2789 WOODLAND CREEK LOOP, KISSIMMEE, FL 34744

    $550,00033 Days on yellowkey   MLS ID: O6409086

    For Sale O6409086 - 2789 WOODLAND CREEK LOOP, KISSIMMEE, FL 34744 25 photos

    Bed: 4   Bath: 2.5   Gar: 3
    Liv Area Sq Ft: 2419
       Built: 2004
    Monthly Fee: $41
       Tax: $2,204 (2025)
    Community: Woodland Creek
    Single Family


    Estimated Monthly Payment: $3,238 (change assumption)
    Mortgage ($3,014) + Fees ($41) + Taxes in 2025 ($184)


    Taxes:$2,204

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2821 SCENIC LN, KISSIMMEE, FL 34744

    $499,900138 Days on yellowkey   MLS ID: O6379416

    For Sale O6379416 - 2821 SCENIC LN, KISSIMMEE, FL 34744 30 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2538
       Built: 2009
    Monthly Fee: $169
       Tax: $6,468 (2025)
    Community: North Shore Village
    Single Family


    Estimated Monthly Payment: $3,447 (change assumption)
    Mortgage ($2,739) + Fees ($169) + Taxes in 2025 ($539)


    Taxes:$6,468

    Elementary School: East Lake Elem

    High School: Tohopekaliga High School

    Tax Year: 2025

    Middle School: Narcoossee Middle


  • 3837 WOOD THRUSH DR, KISSIMMEE, FL 34744

    $397,900269 Days on yellowkey   MLS ID: O6347371

    REDUCED by $99 (0.0%) on 05/19/2026

    For Sale O6347371 - 3837 WOOD THRUSH DR, KISSIMMEE, FL 34744 29 photos

    Bed: 5   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2065
       Built: 2006
    Monthly Fee: $120
       Tax: $4,848 (2024)
    Community: Springlake Vlg Ph 5A
    Single Family


    Estimated Monthly Payment: $2,704 (change assumption)
    Mortgage ($2,180) + Fees ($120) + Taxes in 2024 ($404)


    Taxes:$4,848

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 4450 SMALL CREEK RD, KISSIMMEE, FL 34744

    $375,000287 Days on yellowkey   MLS ID: S5134233

    For Sale S5134233 - 4450 SMALL CREEK RD, KISSIMMEE, FL 34744 25 photos

    Bed: 3   Bath: 2.5   Gar: 1
    Liv Area Sq Ft: 1534
       Built: 2023
    Monthly Fee: $229
       Tax: $5,169 (2024)
    Community: Creekside Twnhms
    Townhouse


    Estimated Monthly Payment: $2,714 (change assumption)
    Mortgage ($2,055) + Fees ($229) + Taxes in 2024 ($431)


    Taxes:$5,169

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 1617 MOHEGAN BLVD, KISSIMMEE, FL 34744

    $339,000260 Days on yellowkey   MLS ID: O6349369

    For Sale O6349369 - 1617 MOHEGAN BLVD, KISSIMMEE, FL 34744 50 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1896
       Built: 2018
    Monthly Fee: $140
       Tax: $631 (2024)
    Community: Heritage Run
    Townhouse


    Estimated Monthly Payment: $2,050 (change assumption)
    Mortgage ($1,857) + Fees ($140) + Taxes in 2024 ($53)


    Taxes:$631

    Elementary School: Mill Creek Elem (K 5)

    High School: Gateway High School (9 12)

    Tax Year: 2024

    Middle School: Denn John Middle


  • 2501 BALMORAL DR, KISSIMMEE, FL 34744

    $390,00094 Days on yellowkey   MLS ID: S5146190

    1 Days Off yellowkey (back on 5/18/2026)

    REDUCED by $9,900 (2.5%) on 04/13/2026

    For Sale S5146190 - 2501 BALMORAL DR, KISSIMMEE, FL 34744 59 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1994
       Built: 2004
    Monthly Fee: $14
       Tax: $4,485 (2025)
    Community: Remington Prcl G Ph 2
    Single Family


    Estimated Monthly Payment: $2,525 (change assumption)
    Mortgage ($2,137) + Fees ($14) + Taxes in 2025 ($374)


    Taxes:$4,485

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2374 ROSS ST, KISSIMMEE, FL 34744

    $167,000484 Days on yellowkey   MLS ID: O6275526

    0 Days Off yellowkey (back on 2/22/2025)

    For Sale O6275526 - 2374 ROSS ST, KISSIMMEE, FL 34744 1 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1382
       Built: 1920   Tax: $1,430 (2023)
    Community: Gilchrist 2Nd Add
    Single Family


    Estimated Monthly Payment: $1,034 (change assumption)
    Mortgage ($915) + Taxes in 2023 ($119)


    Taxes:$1,430

    Elementary School: None

    High School: None

    Tax Year: 2023

    Middle School: None


  • 3111 TURNBERRY BLVD, KISSIMMEE, FL 34744

    $350,000216 Days on yellowkey   MLS ID: S5138322

    129 Days Off yellowkey (back on 5/18/2026)

    SHORT SALE S5138322 - 3111 TURNBERRY BLVD, KISSIMMEE, FL 34744 51 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1400
       Built: 2007
    Monthly Fee: $76
       Tax: $4,633 (2024)
    Community: Turnberry Reserve Unit 2
    Single Family


    Estimated Monthly Payment: $2,380 (change assumption)
    Mortgage ($1,918) + Fees ($76) + Taxes in 2024 ($386)


    Taxes:$4,633

    Elementary School: East Lake Elem

    High School: Tohopekaliga High School

    Tax Year: 2024

    Middle School: Narcoossee Middle


  • 3878 WOOD THRUSH DR, KISSIMMEE, FL 34744

    $415,00072 Days on yellowkey   MLS ID: O6396827

    REDUCED by $10,000 (2.4%) on 05/18/2026

    For Sale O6396827 - 3878 WOOD THRUSH DR, KISSIMMEE, FL 34744 40 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2061
       Built: 2006
    Monthly Fee: $140
       Tax: $3,745 (2025)
    Community: Springlake Village Ph 5B
    Single Family


    Estimated Monthly Payment: $2,726 (change assumption)
    Mortgage ($2,274) + Fees ($140) + Taxes in 2025 ($312)


    Taxes:$3,745

    Elementary School: East Lake Elem

    High School: Tohopekaliga High School

    Tax Year: 2025

    Middle School: Narcoossee Middle


  • 2825 RUNNING BROOK CIR, KISSIMMEE, FL 34744

    $399,90051 Days on yellowkey   MLS ID: O6401962

    For Sale O6401962 - 2825 RUNNING BROOK CIR, KISSIMMEE, FL 34744 34 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1839
       Built: 2011
    Monthly Fee: $178
       Tax: $3,276 (2025)
    Community: North Shore Village Ph 2
    Single Family


    Estimated Monthly Payment: $2,642 (change assumption)
    Mortgage ($2,191) + Fees ($178) + Taxes in 2025 ($273)


    Taxes:$3,276

    Elementary School: East Lake Elem

    High School: Tohopekaliga High School

    Tax Year: 2025

    Middle School: Narcoossee Middle


  • 1715 HAPPINESS ROW, KISSIMMEE, FL 34744

    $399,000136 Days on yellowkey   MLS ID: S5142449

    For Sale S5142449 - 1715 HAPPINESS ROW, KISSIMMEE, FL 34744 52 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2044
       Built: 2022
    Monthly Fee: $10
       Tax: $6,675 (2025)
    Community: Tohoqua Ph 2
    Single Family


    Estimated Monthly Payment: $2,753 (change assumption)
    Mortgage ($2,186) + Fees ($10) + Taxes in 2025 ($556)


    Taxes:$6,675

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2723 CALLAWAY LN, KISSIMMEE, FL 34744

    $435,00070 Days on yellowkey   MLS ID: O6397750

    For Sale O6397750 - 2723 CALLAWAY LN, KISSIMMEE, FL 34744 56 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2513
       Built: 2005
    Monthly Fee: $78
       Tax: $6,939 (2024)
    Community: Remington Prcl M1
    Single Family


    Estimated Monthly Payment: $3,040 (change assumption)
    Mortgage ($2,384) + Fees ($78) + Taxes in 2024 ($578)


    Taxes:$6,939

    Elementary School: Partin Settlement Elem

    High School: Gateway High School (9 12)

    Tax Year: 2024

    Middle School: Neptune Middle (6-8)


  • 107 E CYPRESS ST, KISSIMMEE, FL 34744

    $169,90038 Days on yellowkey   MLS ID: S5149938

    For Sale S5149938 - 107 E CYPRESS ST, KISSIMMEE, FL 34744 19 photos

    Bed: 2   Bath: 1.0
    Liv Area Sq Ft: 576
       Built: 1966   Tax: $2,111 (2025)
    Community: Robert Bass Add
    Single Family


    Estimated Monthly Payment: $1,107 (change assumption)
    Mortgage ($931) + Taxes in 2025 ($176)


    Taxes:$2,111

    Elementary School: Central Avenue Elem

    High School: Osceola High School

    Tax Year: 2025

    Middle School: Denn John Middle


  • 2519 PEACE OF MIND AVE, KISSIMMEE, FL 34744

    $495,00043 Days on yellowkey   MLS ID: S5149191

    For Sale S5149191 - 2519 PEACE OF MIND AVE, KISSIMMEE, FL 34744 16 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2539
       Built: 2025   Tax: $3,691 (2025)
    Community: Tohoqua Ph 7
    Single Family


    Estimated Monthly Payment: $3,020 (change assumption)
    Mortgage ($2,712) + Taxes in 2025 ($308)


    Taxes:$3,691

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 417 BENITA ST, KISSIMMEE, FL 34744

    $284,000494 Days on yellowkey   MLS ID: O6275736

    For Sale O6275736 - 417 BENITA ST, KISSIMMEE, FL 34744 9 photos

    Bed: 3   Bath: 1.5
    Liv Area Sq Ft: 1186
       Built: 1971   Tax: $380 (2023)
    Community: Benita Park
    Single Family


    Estimated Monthly Payment: $1,588 (change assumption)
    Mortgage ($1,556) + Taxes in 2023 ($32)


    Taxes:$380

    Elementary School: None

    High School: None

    Tax Year: 2023

    Middle School: None


  • 1714 CHERYL LN, KISSIMMEE, FL 34744

    $699,90079 Days on yellowkey   MLS ID: O6395426

    REDUCED by $49,100 (6.6%) on 05/14/2026

    For Sale O6395426 - 1714 CHERYL LN, KISSIMMEE, FL 34744 31 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3609
       Built: 1989   Tax: $3,559 (2025)
    Community: Regal Oak Shores Unit 8
    Single Family


    Estimated Monthly Payment: $4,132 (change assumption)
    Mortgage ($3,835) + Taxes in 2025 ($297)


    Taxes:$3,559

    Elementary School: Partin Settlement Elem

    High School: Osceola High School

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 3589 ROCK CREEK LN, KISSIMMEE, FL 34744

    $354,000138 Days on yellowkey   MLS ID: S5143035

    REDUCED by $5,000 (1.4%) on 05/14/2026

    For Sale S5143035 - 3589 ROCK CREEK LN, KISSIMMEE, FL 34744 28 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1554
       Built: 2019
    Monthly Fee: $138
       Tax: $3,593 (2025)
    Community: East Lake Preserve Ph 3
    Single Family


    Estimated Monthly Payment: $2,377 (change assumption)
    Mortgage ($1,940) + Fees ($138) + Taxes in 2025 ($299)


    Taxes:$3,593

    Elementary School: East Lake Elem

    High School: Tohopekaliga High School

    Tax Year: 2025

    Middle School: Narcoossee Middle


  • 1736 FULFILLMENT DR, KISSIMMEE, FL 34744

    $410,00044 Days on yellowkey   MLS ID: S5149578

    For Sale S5149578 - 1736 FULFILLMENT DR, KISSIMMEE, FL 34744 24 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1802
       Built: 2022
    Monthly Fee: $10
       Tax: $6,619 (2025)
    Community: Tohoqua Ph 2 Pb 29 Pgs 187-192 Lot 38
    Single Family


    Estimated Monthly Payment: $2,808 (change assumption)
    Mortgage ($2,247) + Fees ($10) + Taxes in 2025 ($552)


    Taxes:$6,619

    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.