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Homes For Sale in Kissimmee 34744 - 286 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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  • 2943 CASABELLA DR, KISSIMMEE, FL 34744

    $399,900131 Days on yellowkey   MLS ID: O6363943

    For Sale O6363943 - 2943 CASABELLA DR, KISSIMMEE, FL 34744 18 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1895
       Built: 2014
    Monthly Fee: $175
       Tax: $7,799 (2024)
    Community: Villa Sol Village
    Single Family


    Estimated Monthly Payment: $3,016 (change assumption)
    Mortgage ($2,191) + Fees ($175) + Taxes in 2024 ($650)


    Taxes:$7,799

    Elementary School: East Lake Elem

    High School: Tohopekaliga High School

    Tax Year: 2024

    Middle School: Neptune Middle (6-8)


  • 2639 CANDIED APPLE ALY, KISSIMMEE, FL 34744

    $449,00016 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)


  • 2195 WIND JAMMER CT, KISSIMMEE, FL 34744

    $300,000187 Days on yellowkey   MLS ID: S5136093

    3 Days Off yellowkey (back on 12/26/2025)

    For Sale S5136093 - 2195 WIND JAMMER CT, KISSIMMEE, FL 34744 36 photos

    Bed: 3   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1216
       Built: 1986
    Monthly Fee: $30
       Tax: $3,478 (2024)
    Community: Windsong
    Single Family


    Estimated Monthly Payment: $1,964 (change assumption)
    Mortgage ($1,644) + Fees ($30) + Taxes in 2024 ($290)


    Taxes:$3,478

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 2629 DIXIE LN, KISSIMMEE, FL 34744

    $342,00022 Days on yellowkey   MLS ID: S5146501

    0 Days Off yellowkey (back on 4/1/2026)

    For Sale S5146501 - 2629 DIXIE LN, KISSIMMEE, FL 34744 18 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1405
       Built: 1985   Tax: $738 (2026)
    Community: Not Applicable
    Single Family


    Estimated Monthly Payment: $1,935 (change assumption)
    Mortgage ($1,874) + Taxes in 2026 ($62)


    Taxes:$738

    Elementary School: Mill Creek Elem (K 5)

    High School: Gateway High School (9 12)

    Tax Year: 2026

    Middle School: Denn John Middle


  • 2640 SERENITY GARDEN DRIVE, KISSIMMEE, FL 34744

    $549,14016 Days on yellowkey   MLS ID: O6393207

    For Sale O6393207 - 2640 SERENITY GARDEN DRIVE, KISSIMMEE, FL 34744 32 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2894
       Built: 2025
    Monthly Fee: $7
       Tax: $1,329 (2025)
    Community: Tohoqua
    Single Family


    Estimated Monthly Payment: $3,127 (change assumption)
    Mortgage ($3,009) + Fees ($7) + Taxes in 2025 ($111)


    Taxes:$1,329

    Elementary School: Neptune Elementary

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 2733 SERENITY MEADOW DRIVE, KISSIMMEE, FL 34744

    $392,01016 Days on yellowkey   MLS ID: O6395315

    For Sale O6395315 - 2733 SERENITY MEADOW DRIVE, KISSIMMEE, FL 34744 33 photos

    Bed: 2   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1670
       Built: 2025
    Monthly Fee: $136
       Tax: $3,086 (2025)
    Community: Tohoqua Reserve
    Single Family


    Estimated Monthly Payment: $2,541 (change assumption)
    Mortgage ($2,148) + Fees ($136) + Taxes in 2025 ($257)


    Taxes:$3,086

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1638 WINDSOR OAK CT, KISSIMMEE, FL 34744

    $265,000223 Days on yellowkey   MLS ID: S5133782

    For Sale S5133782 - 1638 WINDSOR OAK CT, KISSIMMEE, FL 34744 35 photos

    Bed: 3   Bath: 2.5
    Liv Area Sq Ft: 1380
       Built: 1999
    Monthly Fee: $180
       Tax: $2,008 (2024)
    Community: Windsor Oaks
    Townhouse


    Estimated Monthly Payment: $1,799 (change assumption)
    Mortgage ($1,452) + Fees ($180) + Taxes in 2024 ($167)


    Taxes:$2,008

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 1057 UNIVERSAL REST PL, KISSIMMEE, FL 34744

    $280,00042 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


  • 1545 LEAF LN, KISSIMMEE, FL 34744

    $545,00035 Days on yellowkey   MLS ID: O6390201

    For Sale O6390201 - 1545 LEAF LN, KISSIMMEE, FL 34744 39 photos

    Bed: 4   Bath: 2.5
    Liv Area Sq Ft: 2456
       Built: 2022
    Monthly Fee: $134
       Tax: $6,444 (2025)
    Community: Pennyroyal
    Single Family


    Estimated Monthly Payment: $3,657 (change assumption)
    Mortgage ($2,986) + Fees ($134) + Taxes in 2025 ($537)


    Taxes:$6,444

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2780 LAKE VISTA DR, KISSIMMEE, FL 34744

    $580,000203 Days on yellowkey   MLS ID: S5135312

    3 Days Off yellowkey (back on 3/31/2026)

    For Sale S5135312 - 2780 LAKE VISTA DR, KISSIMMEE, FL 34744 36 photos

    Bed: 3   Bath: 3.0
    Liv Area Sq Ft: 1850
       Built: 1994   Tax: $6,077 (2024)
    Community: Acreage & Unrec
    Single Family


    Estimated Monthly Payment: $3,684 (change assumption)
    Mortgage ($3,178) + Taxes in 2024 ($506)


    Taxes:$6,077

    Elementary School: East Lake Elementary-OS

    High School: Tohopekaliga High School

    Tax Year: 2024

    Middle School: Narcoossee Middle


  • 1024 CHALCEDONY ST, KISSIMMEE, FL 34744

    $299,000189 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


  • 1973 SPRING SHOWER CIR, KISSIMMEE, FL 34744

    $405,000174 Days on yellowkey   MLS ID: P4936815

    For Sale P4936815 - 1973 SPRING SHOWER CIR, KISSIMMEE, FL 34744 43 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1701
       Built: 2022
    Monthly Fee: $127
       Tax: $6,547 (2024)
    Community: Tohoqua Ph 5A
    Single Family


    Estimated Monthly Payment: $2,892 (change assumption)
    Mortgage ($2,219) + Fees ($127) + Taxes in 2024 ($546)


    Taxes:$6,547

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 3016 MADELIA LN, KISSIMMEE, FL 34744

    $405,00041 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


  • 1719 FLOURISH AVE, KISSIMMEE, FL 34744

    $459,99960 Days on yellowkey   MLS ID: O6382782

    0 Days Off yellowkey (back on 3/31/2026)

    For Sale O6382782 - 1719 FLOURISH AVE, KISSIMMEE, FL 34744 5 photos

    Bed: 5   Bath: 2.5
    Liv Area Sq Ft: 2450
       Built: 2021
    Monthly Fee: $80
       Tax: $5,605 (2025)
    Community: Tohoqua Ph 1
    Single Family


    Estimated Monthly Payment: $3,068 (change assumption)
    Mortgage ($2,520) + Fees ($80) + Taxes in 2025 ($467)


    Taxes:$5,605

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2093 WALNUT CREEK DR, KISSIMMEE, FL 34744

    $399,99038 Days on yellowkey   MLS ID: O6389078

    2 Days Off yellowkey (back on 3/31/2026)

    For Sale O6389078 - 2093 WALNUT CREEK DR, KISSIMMEE, FL 34744 33 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1614
       Built: 2025
    Monthly Fee: $11
       Tax: $3,684 (2025)
    Community: Kindred Ph 3B 3C & 3D
    Single Family


    Estimated Monthly Payment: $2,510 (change assumption)
    Mortgage ($2,192) + Fees ($11) + Taxes in 2025 ($307)


    Taxes:$3,684

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2097 WALNUT CREEK DR, KISSIMMEE, FL 34744

    $454,99038 Days on yellowkey   MLS ID: O6389060

    2 Days Off yellowkey (back on 3/31/2026)

    For Sale O6389060 - 2097 WALNUT CREEK DR, KISSIMMEE, FL 34744 60 photos

    Bed: 5   Bath: 3.0
    Liv Area Sq Ft: 2447
       Built: 2025
    Monthly Fee: $11
       Tax: $3,684 (2025)
    Community: Kindred Ph 3B 3C & 3D
    Single Family


    Estimated Monthly Payment: $2,811 (change assumption)
    Mortgage ($2,493) + Fees ($11) + Taxes in 2025 ($307)


    Taxes:$3,684

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2905 SUMMER GREEN TRL, KISSIMMEE, FL 34744

    $462,500232 Days on yellowkey   MLS ID: O6339462

    REDUCED by $10,000 (2.1%) on 03/31/2026

    For Sale O6339462 - 2905 SUMMER GREEN TRL, KISSIMMEE, FL 34744 59 photos

    Bed: 4   Bath: 3.0
    Liv Area Sq Ft: 2344
       Built: 2021
    Monthly Fee: $93
       Tax: $4,210 (2024)
    Community: Marbella Ph 2
    Single Family


    Estimated Monthly Payment: $2,978 (change assumption)
    Mortgage ($2,534) + Fees ($93) + Taxes in 2024 ($351)


    Taxes:$4,210

    Elementary School: East Lake Elem

    High School: Tohopekaliga High School

    Tax Year: 2024

    Middle School: Neptune Middle (6-8)


  • 1740 NEPTUNE RD, KISSIMMEE, FL 34744

    $435,00071 Days on yellowkey   MLS ID: O6379685

    For Sale O6379685 - 1740 NEPTUNE RD, KISSIMMEE, FL 34744 51 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 2013
       Built: 1966   Tax: $1,925 (2025)
    Community: Neptune Shores 1
    Single Family


    Estimated Monthly Payment: $2,544 (change assumption)
    Mortgage ($2,384) + Taxes in 2025 ($160)


    Taxes:$1,925

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 215 E LAKE SHORE BLVD, KISSIMMEE, FL 34744

    $625,00094 Days on yellowkey   MLS ID: O6369181

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

    Bed: 4   Bath: 2.5
    Liv Area Sq Ft: 2666
       Built: 1989   Tax: $4,092 (2025)
    Community: East Lake Estates
    Single Family


    Estimated Monthly Payment: $3,766 (change assumption)
    Mortgage ($3,425) + Taxes in 2025 ($341)


    Taxes:$4,092

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 3821 SHOREVIEW DR, KISSIMMEE, FL 34744

    $524,99021 Days on yellowkey   MLS ID: S5146534

    For Sale S5146534 - 3821 SHOREVIEW DR, KISSIMMEE, FL 34744 18 photos

    Bed: 4   Bath: 3.0
    Liv Area Sq Ft: 2458
       Built: 2009
    Monthly Fee: $188
       Tax: $3,749 (2025)
    Community: North Shore Village
    Single Family


    Estimated Monthly Payment: $3,377 (change assumption)
    Mortgage ($2,877) + Fees ($188) + Taxes in 2025 ($312)


    Taxes:$3,749

    Elementary School: East Lake Elem

    High School: Tohopekaliga High School

    Tax Year: 2025

    Middle School: Narcoossee 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.