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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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  • 1491 AUGUST GRAY DR, KISSIMMEE, FL 34744

    $430,00048 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)


  • 1772 STAMEN DR, KISSIMMEE, FL 34744

    $495,50042 Days on yellowkey   MLS ID: S5147865

    For Sale S5147865 - 1772 STAMEN DR, KISSIMMEE, FL 34744 28 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1965
       Built: 2023
    Monthly Fee: $160
       Tax: $5,861 (2025)
    Community: Pennyroyal
    Single Family


    Estimated Monthly Payment: $3,363 (change assumption)
    Mortgage ($2,715) + Fees ($160) + Taxes in 2025 ($488)


    Taxes:$5,861

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 609 CORNERSTONE DR, KISSIMMEE, FL 34744

    $269,90042 Days on yellowkey   MLS ID: O6398322

    For Sale O6398322 - 609 CORNERSTONE DR, KISSIMMEE, FL 34744 23 photos

    Bed: 3   Bath: 2.5
    Liv Area Sq Ft: 1512
       Built: 2007
    Monthly Fee: $284
       Tax: $3,237 (2025)
    Community: Heritage Key Villas
    Townhouse


    Estimated Monthly Payment: $2,033 (change assumption)
    Mortgage ($1,479) + Fees ($284) + Taxes in 2025 ($270)


    Taxes:$3,237

    Elementary School: Mill Creek Elem (K 5)

    High School: Osceola High School

    Tax Year: 2025

    Middle School: Denn John Middle


  • 1859 RED CANYON DR, KISSIMMEE, FL 34744

    $324,99047 Days on yellowkey   MLS ID: O6396176

    For Sale O6396176 - 1859 RED CANYON DR, KISSIMMEE, FL 34744 29 photos

    Bed: 3   Bath: 2.5   Gar: 1
    Liv Area Sq Ft: 1624
       Built: 2019
    Monthly Fee: $94
       Tax: $5,866 (2025)
    Community: Kindred Ph 1E
    Townhouse


    Estimated Monthly Payment: $2,364 (change assumption)
    Mortgage ($1,781) + Fees ($94) + Taxes in 2025 ($489)


    Taxes:$5,866

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2664 WILLOW GLEN CIR, KISSIMMEE, FL 34744

    $429,00048 Days on yellowkey   MLS ID: S5147485

    2 Days Off yellowkey (back on 4/15/2026)

    For Sale S5147485 - 2664 WILLOW GLEN CIR, KISSIMMEE, FL 34744 36 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2415
       Built: 2000
    Monthly Fee: $23
       Tax: $4,509 (2025)
    Community: Gleneagles
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $2,749 (change assumption)
    Mortgage ($2,351) + Fees ($23) + Taxes in 2025 ($376)


    Taxes:$4,509

    Elementary School: Partin Settlement Elem

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 2604 BLOWING BREEZE AVE, KISSIMMEE, FL 34744

    $507,000191 Days on yellowkey   MLS ID: O6360718

    2 Days Off yellowkey (back on 4/15/2026)

    For Sale O6360718 - 2604 BLOWING BREEZE AVE, KISSIMMEE, FL 34744 64 photos

    Bed: 5   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2590
       Built: 2022
    Monthly Fee: $10
       Tax: $8,552 (2024)
    Community: Tohoqua Ph 4A
    Single Family


    Estimated Monthly Payment: $3,501 (change assumption)
    Mortgage ($2,778) + Fees ($10) + Taxes in 2024 ($713)


    Taxes:$8,552

    Elementary School: Neptune Elementary

    High School: Gateway High School (9 12)

    Tax Year: 2024

    Middle School: Neptune Middle (6-8)


  • 1488 SOPHIE WAY, KISSIMMEE, FL 34744

    $399,00045 Days on yellowkey   MLS ID: S5147658

    1 Days Off yellowkey (back on 4/15/2026)

    For Sale S5147658 - 1488 SOPHIE WAY, KISSIMMEE, FL 34744 49 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1552
       Built: 1993
    Monthly Fee: $33
       Tax: $713 (2025)
    Community: Westminster Gardens Ph 1
    Single Family


    Estimated Monthly Payment: $2,279 (change assumption)
    Mortgage ($2,186) + Fees ($33) + Taxes in 2025 ($59)


    Taxes:$713

    Elementary School: Partin Settlement Elem

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 1906 DAMON AVE, KISSIMMEE, FL 34744

    $199,000267 Days on yellowkey   MLS ID: O6337678

    0 Days Off yellowkey (back on 9/10/2025)

    For Sale O6337678 - 1906 DAMON AVE, KISSIMMEE, FL 34744 8 photos

    Bed: 4   Bath: 2.0
    Liv Area Sq Ft: 1224
       Built: 1972   Tax: $1,376 (2024)
    Community: Kissimmee Heights
    Single Family


    Estimated Monthly Payment: $1,205 (change assumption)
    Mortgage ($1,090) + Taxes in 2024 ($115)


    Taxes:$1,376

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 2518 BOWMER DR, KISSIMMEE, FL 34744

    $359,900659 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


  • 1705 BRIDGETS CT, KISSIMMEE, FL 34744

    $565,00079 Days on yellowkey   MLS ID: S5145159

    REDUCED by $10,000 (1.7%) on 04/14/2026

    For Sale S5145159 - 1705 BRIDGETS CT, KISSIMMEE, FL 34744 57 photos

    Bed: 4   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 2994
       Built: 2004
    Monthly Fee: $190
       Tax: $5,502 (2025)
    Community: M3 At Kissimmee Bay
    Single Family


    Estimated Monthly Payment: $3,744 (change assumption)
    Mortgage ($3,096) + Fees ($190) + Taxes in 2025 ($459)


    Taxes:$5,502

    Elementary School: Partin Settlement Elem

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 1563 CROSS PRAIRIE PKWY, KISSIMMEE, FL 34744

    $360,00044 Days on yellowkey   MLS ID: S5147463

    SHORT SALE S5147463 - 1563 CROSS PRAIRIE PKWY, KISSIMMEE, FL 34744 54 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1802
       Built: 2023
    Monthly Fee: $10
       Tax: $7,403 (2025)
    Community: Tohoqua Ph 3
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,599 (change assumption)
    Mortgage ($1,973) + Fees ($10) + Taxes in 2025 ($617)


    Taxes:$7,403

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1765 BROCKRIDGE RD, KISSIMMEE, FL 34744

    $364,990251 Days on yellowkey   MLS ID: S5134833

    For Sale S5134833 - 1765 BROCKRIDGE RD, KISSIMMEE, FL 34744 45 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1690
       Built: 2018
    Monthly Fee: $11
       Tax: $5,653 (2024)
    Community: Kindred Ph 1D
    Single Family


    Estimated Monthly Payment: $2,482 (change assumption)
    Mortgage ($2,000) + Fees ($11) + Taxes in 2024 ($471)


    Taxes:$5,653

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 2744 SERENITY MEADOW DRIVE, KISSIMMEE, FL 34744

    $439,89063 Days on yellowkey   MLS ID: O6393758

    0 Days Off yellowkey (back on 4/13/2026)

    For Sale O6393758 - 2744 SERENITY MEADOW DRIVE, KISSIMMEE, FL 34744 23 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2056
       Built: 2026
    Monthly Fee: $136
       Tax: $3,212 (2025)
    Community: Tohoqua Reserve
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,814 (change assumption)
    Mortgage ($2,410) + Fees ($136) + Taxes in 2025 ($268)


    Taxes:$3,212

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2077 WALNUT CREEK DR, KISSIMMEE, FL 34744

    $454,40070 Days on yellowkey   MLS ID: O6391693

    3 Days Off yellowkey (back on 4/13/2026)

    REDUCED by $4,590 (1.0%) on 04/08/2026

    For Sale O6391693 - 2077 WALNUT CREEK DR, KISSIMMEE, FL 34744 60 photos

    Bed: 5   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2447
       Built: 2025
    Monthly Fee: $11
       Tax: $3,684 (2025)
    Community: Kindred Ph 3B 3C & 3D
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,808 (change assumption)
    Mortgage ($2,490) + Fees ($11) + Taxes in 2025 ($307)


    Taxes:$3,684

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 4419 AZURE ISLE WAY, KISSIMMEE, FL 34744

    $479,99082 Days on yellowkey   MLS ID: O6387844

    For Sale O6387844 - 4419 AZURE ISLE WAY, KISSIMMEE, FL 34744 39 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1941
       Built: 2013
    Monthly Fee: $110
       Tax: $3,787 (2025)
    Community: North Point Ph 1B
    Single Family


    Estimated Monthly Payment: $3,056 (change assumption)
    Mortgage ($2,630) + Fees ($110) + Taxes in 2025 ($316)


    Taxes:$3,787

    Elementary School: East Lake Elem

    High School: Tohopekaliga High School

    Tax Year: 2025

    Middle School: Narcoossee Middle


  • 1791 SMARTS RULE ST, KISSIMMEE, FL 34744

    $510,000115 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


  • 2352 ROSS ST, KISSIMMEE, FL 34744

    $315,000342 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


  • 2418 BROOKSIDE AVE, KISSIMMEE, FL 34744

    $220,00072 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

    $499,000111 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


  • 2670 REAGAN LN, KISSIMMEE, FL 34744

    $370,00090 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.