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Homes For Sale in Kissimmee 34744 - 365 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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  • 2503 HASSONITE ST, KISSIMMEE, FL 34744

    $345,000232 Days on yellowkey   MLS ID: S5137504

    For Sale S5137504 - 2503 HASSONITE ST, KISSIMMEE, FL 34744 22 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2018
       Built: 2007
    Monthly Fee: $170
       Tax: $1,559 (2024)
    Community: Amber Pointe
    Townhouse


    Estimated Monthly Payment: $2,190 (change assumption)
    Mortgage ($1,890) + Fees ($170) + Taxes in 2024 ($130)


    Taxes:$1,559

    Elementary School: Partin Settlement Elem

    High School: Gateway High School (9 12)

    Tax Year: 2024

    Middle School: Denn John Middle


  • 2937 SLOUGH CREEK DR, KISSIMMEE, FL 34744

    $519,900129 Days on yellowkey   MLS ID: S5143801

    For Sale S5143801 - 2937 SLOUGH CREEK DR, KISSIMMEE, FL 34744 21 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2727
       Built: 2023
    Monthly Fee: $130
       Tax: $7,208 (2025)
    Community: Creekside At Boggy Creek Ph 3
    Single Family


    Estimated Monthly Payment: $3,579 (change assumption)
    Mortgage ($2,849) + Fees ($130) + Taxes in 2025 ($601)


    Taxes:$7,208

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1873 SPRING SHOWER CIR, KISSIMMEE, FL 34744

    $345,000303 Days on yellowkey   MLS ID: S5133310

    For Sale S5133310 - 1873 SPRING SHOWER CIR, KISSIMMEE, FL 34744 18 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1559
       Built: 2023
    Monthly Fee: $212
       Tax: $5,457 (2024)
    Community: Tohoqua Ph 5B
    Villa


    Estimated Monthly Payment: $2,557 (change assumption)
    Mortgage ($1,890) + Fees ($212) + Taxes in 2024 ($455)


    Taxes:$5,457

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 1648 HEART BAR RD, KISSIMMEE, FL 34744

    $380,990428 Days on yellowkey   MLS ID: S5125282

    For Sale S5125282 - 1648 HEART BAR RD, KISSIMMEE, FL 34744 77 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1516
       Built: 2023   Tax: $5,045 (2025)
    Community: Kindred Ph 2C & 2D
    Single Family


    Estimated Monthly Payment: $2,508 (change assumption)
    Mortgage ($2,088) + Taxes in 2025 ($420)


    Taxes:$5,045

    Elementary School: Neptune Elementary

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 1703 MICHIGAN AVE #A, KISSIMMEE, FL 34744

    $149,900127 Days on yellowkey   MLS ID: S5143470

    For Sale S5143470 - 1703 MICHIGAN AVE #A, KISSIMMEE, FL 34744 6 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1118
       Built: 1973
    Monthly Fee: $345
       Tax: $2,561 (2025)
    Community: Essex Park Villas Condo
    Condo


    Estimated Monthly Payment: $1,380 (change assumption)
    Mortgage ($821) + Fees ($345) + Taxes in 2025 ($213)


    Taxes:$2,561

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1491 AUGUST GRAY DR, KISSIMMEE, FL 34744

    $430,00075 Days on yellowkey   MLS ID: O6397176

    SHORT SALE O6397176 - 1491 AUGUST GRAY DR, KISSIMMEE, FL 34744 34 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2070
       Built: 2025
    Monthly Fee: $80
       Tax: $1,748 (2025)
    Community: Seasons At Big Sky Ph 1
    Single Family


    Estimated Monthly Payment: $2,582 (change assumption)
    Mortgage ($2,356) + Fees ($80) + Taxes in 2025 ($146)


    Taxes:$1,748

    Elementary School: Partin Settlement Elem

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 2518 BOWMER DR, KISSIMMEE, FL 34744

    $359,900686 Days on yellowkey   MLS ID: S5109889

    For Sale S5109889 - 2518 BOWMER DR, KISSIMMEE, FL 34744 21 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1523
       Built: 1982   Tax: $1,246 (2025)
    Community: Mill Run Unit 3
    Single Family


    Estimated Monthly Payment: $2,076 (change assumption)
    Mortgage ($1,972) + Taxes in 2025 ($104)


    Taxes:$1,246

    Elementary School: Mill Creek Elem (K 5)

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Denn John Middle


  • 1791 SMARTS RULE ST, KISSIMMEE, FL 34744

    $510,000142 Days on yellowkey   MLS ID: S5142907

    For Sale S5142907 - 1791 SMARTS RULE ST, KISSIMMEE, FL 34744 50 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2500
       Built: 2021
    Monthly Fee: $7
       Tax: $9,049 (2025)
    Community: Tohoqua Ph 1B
    Single Family


    Estimated Monthly Payment: $3,556 (change assumption)
    Mortgage ($2,794) + Fees ($7) + Taxes in 2025 ($754)


    Taxes:$9,049

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2418 BROOKSIDE AVE, KISSIMMEE, FL 34744

    $220,00099 Days on yellowkey   MLS ID: S5145883

    0 Days Off yellowkey (back on 3/16/2026)

    For Sale S5145883 - 2418 BROOKSIDE AVE, KISSIMMEE, FL 34744 1 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1807
       Built: 1979   Tax: $4,934 (2025)
    Community: Whisper Woods
    Single Family


    Estimated Monthly Payment: $1,617 (change assumption)
    Mortgage ($1,205) + Taxes in 2025 ($411)


    Taxes:$4,934

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 4436 AZURE ISLE WAY, KISSIMMEE, FL 34744

    $499,000138 Days on yellowkey   MLS ID: O6379702

    For Sale O6379702 - 4436 AZURE ISLE WAY, KISSIMMEE, FL 34744 35 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2251
       Built: 2013
    Monthly Fee: $108
       Tax: $3,771 (2025)
    Community: North Point Ph 1B
    Single Family


    Estimated Monthly Payment: $3,156 (change assumption)
    Mortgage ($2,734) + Fees ($108) + Taxes in 2025 ($314)


    Taxes:$3,771

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1326 SWEETWOOD BLVD, KISSIMMEE, FL 34744

    $435,00078 Days on yellowkey   MLS ID: S5147282

    For Sale S5147282 - 1326 SWEETWOOD BLVD, KISSIMMEE, FL 34744 20 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1571
       Built: 1978   Tax: $5,280 (2025)
    Community: Sweetwood Estates
    Single Family


    Estimated Monthly Payment: $2,824 (change assumption)
    Mortgage ($2,384) + Taxes in 2025 ($440)


    Taxes:$5,280

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 422 JANICE KAY PL, KISSIMMEE, FL 34744

    $479,000299 Days on yellowkey   MLS ID: S5133405

    REDUCED by $10,000 (2.0%) on 04/06/2026

    For Sale S5133405 - 422 JANICE KAY PL, KISSIMMEE, FL 34744 19 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 3424
       Built: 2004
    Monthly Fee: $13
       Tax: $7,517 (2024)
    Community: Eagles Landing
    Single Family


    Estimated Monthly Payment: $3,264 (change assumption)
    Mortgage ($2,625) + Fees ($13) + Taxes in 2024 ($626)


    Taxes:$7,517

    Elementary School: Partin Settlement Elem

    High School: Gateway High School (9 12)

    Tax Year: 2024

    Middle School: Neptune Middle (6-8)


  • 2575 AVENTURINE ST, KISSIMMEE, FL 34744

    $320,000116 Days on yellowkey   MLS ID: S5144762

    For Sale S5144762 - 2575 AVENTURINE ST, KISSIMMEE, FL 34744 24 photos

    Bed: 3   Bath: 2.5   Gar: 1
    Liv Area Sq Ft: 1758
       Built: 2007
    Monthly Fee: $170
       Tax: $3,934 (2025)
    Community: Amber Pointe Unit 2
    Townhouse


    Estimated Monthly Payment: $2,251 (change assumption)
    Mortgage ($1,753) + Fees ($170) + Taxes in 2025 ($328)


    Taxes:$3,934

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1989 SPRING SHOWER CIR, KISSIMMEE, FL 34744

    $415,000159 Days on yellowkey   MLS ID: O6371277

    REDUCED by $5,000 (1.2%) on 04/02/2026

    For Sale O6371277 - 1989 SPRING SHOWER CIR, KISSIMMEE, FL 34744 63 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2087
       Built: 2023
    Monthly Fee: $136
       Tax: $7,473 (2025)
    Community: Tohoqua Reserve
    Single Family


    Estimated Monthly Payment: $3,033 (change assumption)
    Mortgage ($2,274) + Fees ($136) + Taxes in 2025 ($623)


    Taxes:$7,473

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2639 CANDIED APPLE ALY, KISSIMMEE, FL 34744

    $449,00084 Days on yellowkey   MLS ID: O6394670

    For Sale O6394670 - 2639 CANDIED APPLE ALY, KISSIMMEE, FL 34744 33 photos

    Bed: 3   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 1755
       Built: 2024
    Monthly Fee: $154
       Tax: $2,218 (2025)
    Community: Tohoqua Ph 7
    Townhouse


    Estimated Monthly Payment: $2,799 (change assumption)
    Mortgage ($2,460) + Fees ($154) + Taxes in 2025 ($185)


    Taxes:$2,218

    Elementary School: Neptune Elementary

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 1057 UNIVERSAL REST PL, KISSIMMEE, FL 34744

    $280,000110 Days on yellowkey   MLS ID: S5143478

    For Sale S5143478 - 1057 UNIVERSAL REST PL, KISSIMMEE, FL 34744 36 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1728
       Built: 1998
    Monthly Fee: $200
       Tax: $3,278 (2025)
    Community: Eric Estates
    Townhouse


    Estimated Monthly Payment: $2,007 (change assumption)
    Mortgage ($1,534) + Fees ($200) + Taxes in 2025 ($273)


    Taxes:$3,278

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1024 CHALCEDONY ST, KISSIMMEE, FL 34744

    $299,000257 Days on yellowkey   MLS ID: S5136346

    REDUCED by $11,000 (3.5%) on 03/31/2026

    For Sale S5136346 - 1024 CHALCEDONY ST, KISSIMMEE, FL 34744 37 photos

    Bed: 3   Bath: 2.5
    Liv Area Sq Ft: 1562
       Built: 2009
    Monthly Fee: $170
       Tax: $3,773 (2024)
    Community: Amber Pointe Unit 2
    Townhouse


    Estimated Monthly Payment: $2,123 (change assumption)
    Mortgage ($1,638) + Fees ($170) + Taxes in 2024 ($314)


    Taxes:$3,773

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 3016 MADELIA LN, KISSIMMEE, FL 34744

    $405,000109 Days on yellowkey   MLS ID: O6387128

    REDUCED by $10,000 (2.4%) on 03/31/2026

    For Sale O6387128 - 3016 MADELIA LN, KISSIMMEE, FL 34744 9 photos

    Bed: 4   Bath: 2.0
    Liv Area Sq Ft: 1784
       Built: 2016
    Monthly Fee: $83
       Tax: $5,256 (2025)
    Community: Legacy Park Ph 3
    Single Family


    Estimated Monthly Payment: $2,740 (change assumption)
    Mortgage ($2,219) + Fees ($83) + Taxes in 2025 ($438)


    Taxes:$5,256

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1974 SPRING SHOWER CIR, KISSIMMEE, FL 34744

    $463,999187 Days on yellowkey   MLS ID: O6367917

    For Sale O6367917 - 1974 SPRING SHOWER CIR, KISSIMMEE, FL 34744 27 photos

    Bed: 3   Bath: 3.0
    Liv Area Sq Ft: 2175
       Built: 2023
    Monthly Fee: $128
       Tax: $2,980 (2024)
    Community: Tohoqua Ph 5A
    Single Family


    Estimated Monthly Payment: $2,919 (change assumption)
    Mortgage ($2,542) + Fees ($128) + Taxes in 2024 ($248)


    Taxes:$2,980

    Elementary School: Neptune Elementary

    High School: Gateway High School (9 12)

    Tax Year: 2024

    Middle School: Neptune Middle (6-8)


  • 3166 ARMSTRONG SPRING DR, KISSIMMEE, FL 34744

    $550,000266 Days on yellowkey   MLS ID: S5135636

    For Sale S5135636 - 3166 ARMSTRONG SPRING DR, KISSIMMEE, FL 34744 31 photos

    Bed: 4   Bath: 3.0
    Liv Area Sq Ft: 2378
       Built: 2023
    Community: Creekside At Boggy Creek
    Single Family


    Estimated Monthly Payment: $3,014 (change assumption)
    Mortgage ($3,014)


    Taxes:

    Elementary School: None

    High School: None

    Tax Year:

    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.