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Homes For Sale in Kissimmee 34744 - 270 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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  • 1278 ASHER MASON AVE, KISSIMMEE, FL 34744

    $455,00051 Days on yellowkey   MLS ID: S5144373

    For Sale S5144373 - 1278 ASHER MASON AVE, KISSIMMEE, FL 34744 29 photos

    Bed: 4   Bath: 2.0   Gar: 3
    Liv Area Sq Ft: 1824
       Built: 2023
    Monthly Fee: $80
       Tax: $5,409 (2024)
    Community: Seasons At Big Sky Ph 2
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,024 (change assumption)
    Mortgage ($2,493) + Fees ($80) + Taxes in 2024 ($451)


    Taxes:$5,409

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 2540 WINNERS CIR, KISSIMMEE, FL 34744

    $739,00054 Days on yellowkey   MLS ID: O6382446

    For Sale O6382446 - 2540 WINNERS CIR, KISSIMMEE, FL 34744 37 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: $4,357 (change assumption)
    Mortgage ($4,049) + 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)


  • 1791 SMARTS RULE ST, KISSIMMEE, FL 34744

    $510,00072 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


  • 1889 RUSTIC FALLS DR, KISSIMMEE, FL 34744

    $525,000146 Days on yellowkey   MLS ID: S5138827

    For Sale S5138827 - 1889 RUSTIC FALLS DR, KISSIMMEE, FL 34744 69 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3099
       Built: 2017
    Monthly Fee: $11
       Tax: $5,957 (2024)
    Community: Kindred Ph 1C
    Single Family


    Estimated Monthly Payment: $3,384 (change assumption)
    Mortgage ($2,877) + Fees ($11) + Taxes in 2024 ($496)


    Taxes:$5,957

    Elementary School: Neptune Elementary

    High School: Gateway High School (9 12)

    Tax Year: 2024

    Middle School: Neptune Middle (6-8)


  • 1715 HAPPINESS ROW, KISSIMMEE, FL 34744

    $399,00068 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

    $320,00018 Days on yellowkey   MLS ID: O6394276

    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


  • 3050 MENORCA CT, KISSIMMEE, FL 34744

    $469,90047 Days on yellowkey   MLS ID: S5144709

    For Sale S5144709 - 3050 MENORCA CT, KISSIMMEE, FL 34744 59 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2453
       Built: 2015
    Monthly Fee: $160
       Tax: $3,185 (2025)
    Community: Villa Sol Village 4
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,000 (change assumption)
    Mortgage ($2,575) + Fees ($160) + Taxes in 2025 ($265)


    Taxes:$3,185

    Elementary School: East Lake Elem

    High School: Tohopekaliga High School

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 1636 BARBERRY DR, KISSIMMEE, FL 34744

    $560,00050 Days on yellowkey   MLS ID: S5144068

    For Sale S5144068 - 1636 BARBERRY DR, KISSIMMEE, FL 34744 65 photos

    Bed: 4   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 2851
       Built: 2023
    Monthly Fee: $11
       Tax: $7,432 (2025)
    Community: Kindred Ph 2C & 2D
    Single Family


    Estimated Monthly Payment: $3,699 (change assumption)
    Mortgage ($3,068) + Fees ($11) + Taxes in 2025 ($619)


    Taxes:$7,432

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1503 OAK RESERVE DR, KISSIMMEE, FL 34744

    $445,00054 Days on yellowkey   MLS ID: S5144250

    REDUCED by $5,000 (1.1%) on 04/08/2026

    For Sale S5144250 - 1503 OAK RESERVE DR, KISSIMMEE, FL 34744 34 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1846
       Built: 2022   Tax: $7,738 (2025)
    Community: Kindred Ph 2C & 2D
    Single Family


    Estimated Monthly Payment: $3,083 (change assumption)
    Mortgage ($2,438) + Taxes in 2025 ($645)


    Taxes:$7,738

    Elementary School: Neptune Elementary

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: St. Cloud Middle (6-8)


  • 2352 ROSS ST, KISSIMMEE, FL 34744

    $315,000299 Days on yellowkey   MLS ID: O6320029

    For Sale O6320029 - 2352 ROSS ST, KISSIMMEE, FL 34744 5 photos

    Bed: 3   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1330
       Built: 2025   Tax: $608 (2024)
    Community: Gilchrist Add To Kissimmee
    Single Family


    Estimated Monthly Payment: $1,777 (change assumption)
    Mortgage ($1,726) + Taxes in 2024 ($51)


    Taxes:$608

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 1819 BROCKRIDGE RD, KISSIMMEE, FL 34744

    $400,00053 Days on yellowkey   MLS ID: O6383806

    0 Days Off yellowkey (back on 2/25/2026)

    For Sale O6383806 - 1819 BROCKRIDGE RD, KISSIMMEE, FL 34744 58 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1846
       Built: 2017
    Monthly Fee: $133
       Tax: $6,383 (2025)
    Community: Kindred Ph 1C
    Single Family


    Estimated Monthly Payment: $2,857 (change assumption)
    Mortgage ($2,192) + Fees ($133) + Taxes in 2025 ($532)


    Taxes:$6,383

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2418 BROOKSIDE AVE, KISSIMMEE, FL 34744

    $220,00029 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


  • 2568 AVENTURINE ST, KISSIMMEE, FL 34744

    $305,000126 Days on yellowkey   MLS ID: O6365441

    For Sale O6365441 - 2568 AVENTURINE ST, KISSIMMEE, FL 34744 37 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1734
       Built: 2008
    Monthly Fee: $170
       Tax: $631 (2024)
    Community: Amber Pointe Unit 2
    Townhouse


    Estimated Monthly Payment: $1,894 (change assumption)
    Mortgage ($1,671) + Fees ($170) + Taxes in 2024 ($53)


    Taxes:$631

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 2394 OLD DIXIE HWY, KISSIMMEE, FL 34744

    $289,99933 Days on yellowkey   MLS ID: O6366826

    0 Days Off yellowkey (back on 3/12/2026)

    For Sale O6366826 - 2394 OLD DIXIE HWY, KISSIMMEE, FL 34744 3 photos

    Bed: 4   Bath: 3.0
    Liv Area Sq Ft: 1567
       Built: 1958   Tax: $3,253 (2024)
    Community: Colonial Estates
    Single Family


    Estimated Monthly Payment: $1,860 (change assumption)
    Mortgage ($1,589) + Taxes in 2024 ($271)


    Taxes:$3,253

    Elementary School: Central Avenue Elem

    High School: Osceola High School

    Tax Year: 2024

    Middle School: Denn John Middle


  • 229 STRATHMORE CIR, KISSIMMEE, FL 34744

    $489,900123 Days on yellowkey   MLS ID: O6367119

    REDUCED by $10,000 (2.0%) on 04/08/2026

    For Sale O6367119 - 229 STRATHMORE CIR, KISSIMMEE, FL 34744 74 photos

    Bed: 5   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2606
       Built: 1996
    Monthly Fee: $14
       Tax: $4,408 (2024)
    Community: Remington Ph 1 Tr B
    Single Family


    Estimated Monthly Payment: $3,066 (change assumption)
    Mortgage ($2,684) + Fees ($14) + Taxes in 2024 ($367)


    Taxes:$4,408

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 4436 AZURE ISLE WAY, KISSIMMEE, FL 34744

    $499,00068 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


  • 2705 WILLOW GLEN CIR, KISSIMMEE, FL 34744

    $390,00077 Days on yellowkey   MLS ID: G5107373

    0 Days Off yellowkey (back on 4/8/2026)

    For Sale G5107373 - 2705 WILLOW GLEN CIR, KISSIMMEE, FL 34744 14 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 1679
       Built: 2001
    Monthly Fee: $19
       Tax: $6,110 (2025)
    Community: Gleneagles
    Single Family


    Estimated Monthly Payment: $2,665 (change assumption)
    Mortgage ($2,137) + Fees ($19) + Taxes in 2025 ($509)


    Taxes:$6,110

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 305 POINCIANA CIR, KISSIMMEE, FL 34744

    $360,00078 Days on yellowkey   MLS ID: S5142338

    0 Days Off yellowkey (back on 1/26/2026)

    For Sale S5142338 - 305 POINCIANA CIR, KISSIMMEE, FL 34744 1 photos

    Bed: 4   Bath: 2.0
    Liv Area Sq Ft: 1361
       Built: 1955   Tax: $521 (2025)
    Community: Dellwood Park
    Single Family


    Estimated Monthly Payment: $2,016 (change assumption)
    Mortgage ($1,973) + Taxes in 2025 ($43)


    Taxes:$521

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2571 AMES HAVEN RD, KISSIMMEE, FL 34744

    $749,900298 Days on yellowkey   MLS ID: S5129375

    4 Days Off yellowkey (back on 2/18/2026)

    For Sale S5129375 - 2571 AMES HAVEN RD, KISSIMMEE, FL 34744 86 photos

    Bed: 4   Bath: 3.0   Gar: 4
    Liv Area Sq Ft: 2556
       Built: 1920   Tax: $4,045 (2024)
    Community: None
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $4,446 (change assumption)
    Mortgage ($4,109) + Taxes in 2024 ($337)


    Taxes:$4,045

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 2670 REAGAN LN, KISSIMMEE, FL 34744

    $370,00047 Days on yellowkey   MLS ID: O6385604

    For Sale O6385604 - 2670 REAGAN LN, KISSIMMEE, FL 34744 65 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1294
       Built: 1981   Tax: $1,125 (2025)
    Community: Gehrett Gardens
    Single Family


    Estimated Monthly Payment: $2,121 (change assumption)
    Mortgage ($2,027) + Taxes in 2025 ($94)


    Taxes:$1,125

    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.