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Homes For Sale in Kissimmee 34744 - 372 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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  • 4416 SILVER CREEK ST, KISSIMMEE, FL 34744

    $380,00068 Days on yellowkey   MLS ID: O6398907

    1 Days Off yellowkey (back on 6/24/2026)

    REDUCED by $10,000 (2.6%) on 06/03/2026

    For Sale O6398907 - 4416 SILVER CREEK ST, KISSIMMEE, FL 34744 31 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1504
       Built: 2019
    Monthly Fee: $130
       Tax: $4,679 (2025)
    Community: Creekside At Boggy Creek Ph 1
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,602 (change assumption)
    Mortgage ($2,082) + Fees ($130) + Taxes in 2025 ($390)


    Taxes:$4,679

    Elementary School: East Lake Elem

    High School: Tohopekaliga High School

    Tax Year: 2025

    Middle School: Narcoossee Middle


  • 2405 CEDARFIELD LN, KISSIMMEE, FL 34744

    $289,000Listed 06/24/2026 10:14AM   MLS ID: S5152134

    For Sale S5152134 - 2405 CEDARFIELD LN, KISSIMMEE, FL 34744 37 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1523
       Built: 2001
    Monthly Fee: $14
       Tax: $5,348 (2025)
    Community: Remington Prcl J
    Single Family


    Estimated Monthly Payment: $2,043 (change assumption)
    Mortgage ($1,584) + Fees ($14) + Taxes in 2025 ($446)


    Taxes:$5,348

    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


  • 3557 ROCK CREEK LN, KISSIMMEE, FL 34744

    $520,000Listed 06/24/2026 1:38PM   MLS ID: S5152410

    For Sale S5152410 - 3557 ROCK CREEK LN, KISSIMMEE, FL 34744 57 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2128
       Built: 2020
    Monthly Fee: $105
       Tax: $4,593 (2025)
    Community: East Lake Preserve Ph 3
    Single Family


    Estimated Monthly Payment: $3,337 (change assumption)
    Mortgage ($2,849) + Fees ($105) + Taxes in 2025 ($383)


    Taxes:$4,593

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2723 CALLAWAY LN, KISSIMMEE, FL 34744

    $435,00073 Days on yellowkey   MLS ID: O6397750

    1 Days Off yellowkey (back on 6/24/2026)

    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)


  • 3837 WOOD THRUSH DR, KISSIMMEE, FL 34744

    $397,750272 Days on yellowkey   MLS ID: O6347371

    REDUCED by $150 (0.0%) on 06/24/2026

    For Sale O6347371 - 3837 WOOD THRUSH DR, KISSIMMEE, FL 34744 28 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: $2,703 (change assumption)
    Mortgage ($2,179) + Fees ($120) + Taxes in 2024 ($404)


    Taxes:$4,848

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 2418 BROOKSIDE AVE, KISSIMMEE, FL 34744

    $375,00014 Days on yellowkey   MLS ID: O6415743

    0 Days Off yellowkey (back on 6/24/2026)

    For Sale O6415743 - 2418 BROOKSIDE AVE, KISSIMMEE, FL 34744 36 photos

    Bed: 4   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1807
       Built: 1979   Tax: $4,934 (2025)
    Community: Whisper Woods
    Single Family


    Estimated Monthly Payment: $2,466 (change assumption)
    Mortgage ($2,055) + Taxes in 2025 ($411)


    Taxes:$4,934

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1895 SPRING SHOWER CIR, KISSIMMEE, FL 34744

    $320,00066 Days on yellowkey   MLS ID: S5148149

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

    REDUCED by $19,000 (5.6%) on 05/16/2026

    For Sale S5148149 - 1895 SPRING SHOWER CIR, KISSIMMEE, FL 34744 29 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1559
       Built: 2023
    Monthly Fee: $213
       Tax: $1,967 (2025)
    Community: Tohoqua Ph 5B
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,130 (change assumption)
    Mortgage ($1,753) + Fees ($213) + Taxes in 2025 ($164)


    Taxes:$1,967

    Elementary School: Neptune Elementary

    High School: St. Cloud High School

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 1720 FULFILLMENT DR, KISSIMMEE, FL 34744

    $400,00062 Days on yellowkey   MLS ID: O6401021

    1 Days Off yellowkey (back on 6/24/2026)

    REDUCED by $20,000 (4.8%) on 05/27/2026

    For Sale O6401021 - 1720 FULFILLMENT DR, KISSIMMEE, FL 34744 41 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2044
       Built: 2022
    Monthly Fee: $10
       Tax: $7,447 (2025)
    Community: Tohoqua Ph 2
    Single Family


    Estimated Monthly Payment: $2,822 (change assumption)
    Mortgage ($2,192) + Fees ($10) + Taxes in 2025 ($621)


    Taxes:$7,447

    Elementary School: None

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 1009 CHALCEDONY ST, KISSIMMEE, FL 34744

    $325,00018 Days on yellowkey   MLS ID: O6412394

    For Sale O6412394 - 1009 CHALCEDONY ST, KISSIMMEE, FL 34744 49 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1683
       Built: 2010
    Monthly Fee: $170
       Tax: $3,128 (2025)
    Community: Amber Pointe
    Spa: No

    Townhouse


    Estimated Monthly Payment: $2,211 (change assumption)
    Mortgage ($1,781) + Fees ($170) + Taxes in 2025 ($261)


    Taxes:$3,128

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1340 SAWDUST TRL, KISSIMMEE, FL 34744

    $235,900158 Days on yellowkey   MLS ID: G5106887

    REDUCED by $4,000 (1.7%) on 06/24/2026

    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: $1,491 (change assumption)
    Mortgage ($1,293) + Taxes in 2025 ($198)


    Taxes:$2,377

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2739 SUMMER RETREAT LN, KISSIMMEE, FL 34744

    $315,00019 Days on yellowkey   MLS ID: O6412964

    0 Days Off yellowkey (back on 6/24/2026)

    REDUCED by $9,000 (2.8%) on 06/17/2026

    For Sale O6412964 - 2739 SUMMER RETREAT LN, KISSIMMEE, FL 34744 25 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1559
       Built: 2023
    Monthly Fee: $221
       Tax: $5,441 (2025)
    Community: Tohoqua
    Single Family


    Estimated Monthly Payment: $2,400 (change assumption)
    Mortgage ($1,726) + Fees ($221) + Taxes in 2025 ($453)


    Taxes:$5,441

    Elementary School: Island Village Elementary School

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Harmony Middle


  • 1710 WOODSIDE CT, KISSIMMEE, FL 34744

    $534,900183 Days on yellowkey   MLS ID: O6369122

    REDUCED by $15,100 (2.7%) on 06/24/2026

    For Sale O6369122 - 1710 WOODSIDE CT, KISSIMMEE, FL 34744 50 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2369
       Built: 1980
    Monthly Fee: $17
       Tax: $2,230 (2024)
    Community: Harbour Oaks Unit 1
    Single Family


    Estimated Monthly Payment: $3,134 (change assumption)
    Mortgage ($2,931) + Fees ($17) + Taxes in 2024 ($186)


    Taxes:$2,230

    Elementary School: Partin Settlement Elem

    High School: Osceola High School

    Tax Year: 2024

    Middle School: Neptune Middle (6-8)


  • 1974 SPRING SHOWER CIR, KISSIMMEE, FL 34744

    $450,000Listed 06/24/2026 8:36AM   MLS ID: O6418282

    For Sale O6418282 - 1974 SPRING SHOWER CIR, KISSIMMEE, FL 34744 69 photos

    Bed: 3   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2175
       Built: 2023
    Monthly Fee: $136
       Tax: $2,980 (2024)
    Community: Tohoqua Ph 5A
    Single Family


    Estimated Monthly Payment: $2,850 (change assumption)
    Mortgage ($2,466) + Fees ($136) + 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)


  • 2503 HASSONITE ST, KISSIMMEE, FL 34744

    $345,000233 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


  • 1320 MILL CREEK PL, KISSIMMEE, FL 34744

    $349,000Listed 06/23/2026 10:13PM   MLS ID: O6419178

    For Sale O6419178 - 1320 MILL CREEK PL, KISSIMMEE, FL 34744 30 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1363
       Built: 1979   Tax: $1,731 (2025)
    Community: Sweetwood Cove
    Single Family


    Estimated Monthly Payment: $2,057 (change assumption)
    Mortgage ($1,912) + Taxes in 2025 ($144)


    Taxes:$1,731

    Elementary School: Mill Creek Elem (K 5)

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Denn John Middle


  • 1422 PATRICIA ST, KISSIMMEE, FL 34744

    $415,000Listed 06/23/2026 10:03PM   MLS ID: O6419136

    For Sale O6419136 - 1422 PATRICIA ST, KISSIMMEE, FL 34744 44 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1578
       Built: 2015   Tax: $5,892 (2025)
    Community: Emerald Lake Colony Unit 3
    Single Family


    Estimated Monthly Payment: $2,765 (change assumption)
    Mortgage ($2,274) + Taxes in 2025 ($491)


    Taxes:$5,892

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2155 SOUTHBURY DRIVE, KISSIMMEE, FL 34744

    $359,1901 Day on yellowkey   MLS ID: O6419423

    For Sale O6419423 - 2155 SOUTHBURY DRIVE, KISSIMMEE, FL 34744 28 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1770
       Built: 2026
    Monthly Fee: $127
       Tax: $1,920 (2025)
    Community: Tohoqua
    Spa: No

    Townhouse


    Estimated Monthly Payment: $2,255 (change assumption)
    Mortgage ($1,968) + Fees ($127) + 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)


  • 2153 SOUTHBURY DRIVE, KISSIMMEE, FL 34744

    $359,1901 Day on yellowkey   MLS ID: O6419342

    For Sale O6419342 - 2153 SOUTHBURY DRIVE, KISSIMMEE, FL 34744 24 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1553
       Built: 2026
    Monthly Fee: $127
       Tax: $1,610 (2025)
    Community: Tohoqua
    Spa: No

    Townhouse


    Estimated Monthly Payment: $2,229 (change assumption)
    Mortgage ($1,968) + Fees ($127) + Taxes in 2025 ($134)


    Taxes:$1,610

    Elementary School: Neptune Elementary

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 107 E CYPRESS ST, KISSIMMEE, FL 34744

    $154,00041 Days on yellowkey   MLS ID: S5149938

    REDUCED by $15,900 (9.4%) on 06/24/2026

    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: $1,020 (change assumption)
    Mortgage ($844) + 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




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.