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Homes For Sale in Kissimmee 34744 - 347 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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  • 3111 TURNBERRY BLVD, KISSIMMEE, FL 34744

    $350,000192 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


  • 1383 LEVY BEND DR, KISSIMMEE, FL 34744

    $494,50036 Days on yellowkey   MLS ID: O6400373

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

    For Sale O6400373 - 1383 LEVY BEND DR, KISSIMMEE, FL 34744 35 photos

    Bed: 4   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 2102
       Built: 2024
    Monthly Fee: $80
       Tax: $6,287 (2025)
    Community: Seasons At Big Sky Ph 2
    Single Family


    Estimated Monthly Payment: $3,313 (change assumption)
    Mortgage ($2,710) + Fees ($80) + Taxes in 2025 ($524)


    Taxes:$6,287

    Elementary School: Partin Settlement Elem

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 130 WESTMORELAND CIR, KISSIMMEE, FL 34744

    $514,90015 Days on yellowkey   MLS ID: O6404741

    For Sale O6404741 - 130 WESTMORELAND CIR, KISSIMMEE, FL 34744 44 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2814
       Built: 1997   Tax: $7,501 (2025)
    Community: Remington
    Single Family


    Estimated Monthly Payment: $3,446 (change assumption)
    Mortgage ($2,821) + Taxes in 2025 ($625)


    Taxes:$7,501

    Elementary School: Partin Settlement Elem

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 2513 CROWN RIDGE CIR, KISSIMMEE, FL 34744

    $379,90020 Days on yellowkey   MLS ID: S5149544

    For Sale S5149544 - 2513 CROWN RIDGE CIR, KISSIMMEE, FL 34744 68 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1766
       Built: 2001
    Monthly Fee: $14
       Tax: $3,026 (2025)
    Community: Remington
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,348 (change assumption)
    Mortgage ($2,082) + Fees ($14) + Taxes in 2025 ($252)


    Taxes:$3,026

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 3878 WOOD THRUSH DR, KISSIMMEE, FL 34744

    $415,00048 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


  • 1838 TOHOQUA BLVD, KISSIMMEE, FL 34744

    $309,90049 Days on yellowkey   MLS ID: S5147475

    REDUCED by $11,090 (3.5%) on 05/14/2026

    For Sale S5147475 - 1838 TOHOQUA BLVD, KISSIMMEE, FL 34744 43 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1600
       Built: 2023
    Monthly Fee: $126
       Tax: $6,276 (2025)
    Community: Tohoqua Ph 6
    Townhouse


    Estimated Monthly Payment: $2,347 (change assumption)
    Mortgage ($1,698) + Fees ($126) + Taxes in 2025 ($523)


    Taxes:$6,276

    Elementary School: Neptune Elementary

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 1795 RANGER HIGHLANDS RD, KISSIMMEE, FL 34744

    $529,00088 Days on yellowkey   MLS ID: O6386466

    1 Days Off yellowkey (back on 5/17/2026)

    For Sale O6386466 - 1795 RANGER HIGHLANDS RD, KISSIMMEE, FL 34744 63 photos

    Bed: 4   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 2374
       Built: 2018
    Monthly Fee: $11
       Tax: $7,274 (2025)
    Community: Kindred Ph 1D
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $3,516 (change assumption)
    Mortgage ($2,899) + Fees ($11) + Taxes in 2025 ($606)


    Taxes:$7,274

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2305 JESSICA LN, KISSIMMEE, FL 34744

    $465,00014 Days on yellowkey   MLS ID: O6407917

    For Sale O6407917 - 2305 JESSICA LN, KISSIMMEE, FL 34744 46 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1820
       Built: 2000
    Monthly Fee: $14
       Tax: $4,461 (2025)
    Community: Woods At Kings Crest The Ph 4
    Single Family


    Estimated Monthly Payment: $2,934 (change assumption)
    Mortgage ($2,548) + Fees ($14) + Taxes in 2025 ($372)


    Taxes:$4,461

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1994 SPRING SHOWER CIR, KISSIMMEE, FL 34744

    $455,00092 Days on yellowkey   MLS ID: S5144463

    REDUCED by $19,000 (4.0%) on 05/09/2026

    For Sale S5144463 - 1994 SPRING SHOWER CIR, KISSIMMEE, FL 34744 32 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2056
       Built: 2022
    Monthly Fee: $128
       Tax: $7,519 (2025)
    Community: Tohoqua Reserve
    Single Family


    Estimated Monthly Payment: $3,248 (change assumption)
    Mortgage ($2,493) + Fees ($128) + Taxes in 2025 ($627)


    Taxes:$7,519

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2825 RUNNING BROOK CIR, KISSIMMEE, FL 34744

    $399,90027 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


  • 2540 WINNERS CIR, KISSIMMEE, FL 34744

    $725,00098 Days on yellowkey   MLS ID: O6382446

    REDUCED by $14,000 (1.9%) on 05/13/2026

    For Sale O6382446 - 2540 WINNERS CIR, KISSIMMEE, FL 34744 54 photos

    Bed: 4   Bath: 4.5   Gar: 4
    Liv Area Sq Ft: 3246
       Built: 2000   Tax: $3,688 (2025)
    Community: Winners Park
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,280 (change assumption)
    Mortgage ($3,973) + Taxes in 2025 ($307)


    Taxes:$3,688

    Elementary School: East Lake Elem

    High School: Tohopekaliga High School

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 1540 GRANDVIEW BLVD, KISSIMMEE, FL 34744

    $924,900104 Days on yellowkey   MLS ID: S5143565

    REDUCED by $25,000 (2.6%) on 05/17/2026

    For Sale S5143565 - 1540 GRANDVIEW BLVD, KISSIMMEE, FL 34744 56 photos

    Bed: 4   Bath: 4.5   Gar: 3
    Liv Area Sq Ft: 5207
       Built: 1981   Tax: $7,032 (2025)
    Community: Regal Oak Shores Unit 1
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $5,654 (change assumption)
    Mortgage ($5,068) + Taxes in 2025 ($586)


    Taxes:$7,032

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1715 HAPPINESS ROW, KISSIMMEE, FL 34744

    $399,000112 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


  • 1103 MARYGON ST, KISSIMMEE, FL 34744

    $320,00062 Days on yellowkey   MLS ID: O6394276

    3 Days Off yellowkey (back on 5/17/2026)

    For Sale O6394276 - 1103 MARYGON ST, KISSIMMEE, FL 34744 20 photos

    Bed: 3   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1192
       Built: 1971   Tax: $635 (2025)
    Community: Johnston Park Rep
    Single Family


    Estimated Monthly Payment: $1,806 (change assumption)
    Mortgage ($1,753) + Taxes in 2025 ($53)


    Taxes:$635

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 215 E LAKE SHORE BLVD, KISSIMMEE, FL 34744

    $599,900136 Days on yellowkey   MLS ID: O6369181

    1 Days Off yellowkey (back on 5/17/2026)

    REDUCED by $25,100 (4.0%) on 04/20/2026

    For Sale O6369181 - 215 E LAKE SHORE BLVD, KISSIMMEE, FL 34744 71 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2666
       Built: 1989   Tax: $4,092 (2025)
    Community: East Lake Estates
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $3,628 (change assumption)
    Mortgage ($3,287) + Taxes in 2025 ($341)


    Taxes:$4,092

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2723 CALLAWAY LN, KISSIMMEE, FL 34744

    $435,00046 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)


  • 1508 JENNI LEE CT, KISSIMMEE, FL 34744

    $474,90012 Days on yellowkey   MLS ID: TB8508177

    For Sale TB8508177 - 1508 JENNI LEE CT, KISSIMMEE, FL 34744 15 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2077
       Built: 1996
    Monthly Fee: $21
       Tax: $1,877 (2025)
    Community: Woods At Kings Crest The Ph 1
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,780 (change assumption)
    Mortgage ($2,602) + Fees ($21) + Taxes in 2025 ($156)


    Taxes:$1,877

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2491 HASSONITE ST, KISSIMMEE, FL 34744

    $299,00012 Days on yellowkey   MLS ID: O6407957

    For Sale O6407957 - 2491 HASSONITE ST, KISSIMMEE, FL 34744 27 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1734
       Built: 2007
    Monthly Fee: $170
       Tax: $3,846 (2025)
    Community: Amber Pointe
    Spa: No

    Townhouse


    Estimated Monthly Payment: $2,129 (change assumption)
    Mortgage ($1,638) + Fees ($170) + Taxes in 2025 ($320)


    Taxes:$3,846

    Elementary School: Partin Settlement Elem

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Denn John Middle


  • 2589 AVENTURINE ST, KISSIMMEE, FL 34744

    $314,90022 Days on yellowkey   MLS ID: S5149368

    0 Days Off yellowkey (back on 5/16/2026)

    For Sale S5149368 - 2589 AVENTURINE ST, KISSIMMEE, FL 34744 36 photos

    Bed: 4   Bath: 2.5   Gar: 1
    Liv Area Sq Ft: 1697
       Built: 2008
    Monthly Fee: $170
       Tax: $2,100 (2025)
    Community: Amber Pointe
    Townhouse


    Estimated Monthly Payment: $2,070 (change assumption)
    Mortgage ($1,725) + Fees ($170) + Taxes in 2025 ($175)


    Taxes:$2,100

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2015 SPRING SHOWER CIR, KISSIMMEE, FL 34744

    $412,000322 Days on yellowkey   MLS ID: S5130256

    For Sale S5130256 - 2015 SPRING SHOWER CIR, KISSIMMEE, FL 34744 49 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2054
       Built: 2022
    Monthly Fee: $128
       Tax: $7,088 (2024)
    Community: Tohoqua Reserve
    Single Family


    Estimated Monthly Payment: $2,976 (change assumption)
    Mortgage ($2,257) + Fees ($128) + Taxes in 2024 ($591)


    Taxes:$7,088

    Elementary School: Neptune Elementary

    High School: Gateway High School (9 12)

    Tax Year: 2024

    Middle School: Neptune Middle (6-8)




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.