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Homes For Sale in Kissimmee 34744 - 290 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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  • 1703 MICHIGAN AVE #A, KISSIMMEE, FL 34744

    $149,90062 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


  • 1103 MARYGON ST, KISSIMMEE, FL 34744

    $320,00023 Days on yellowkey   MLS ID: O6394276

    0 Days Off yellowkey (back on 4/16/2026)

    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


  • 1491 AUGUST GRAY DR, KISSIMMEE, FL 34744

    $430,00010 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)


  • 651 CORNERSTONE DR, KISSIMMEE, FL 34744

    $267,00036 Days on yellowkey   MLS ID: S5145831

    0 Days Off yellowkey (back on 3/25/2026)

    For Sale S5145831 - 651 CORNERSTONE DR, KISSIMMEE, FL 34744 55 photos

    Bed: 3   Bath: 2.5
    Liv Area Sq Ft: 1408
       Built: 2007
    Monthly Fee: $284
       Tax: $3,037 (2025)
    Community: Heritage Key Villas Ph 1 & 2
    Townhouse


    Estimated Monthly Payment: $2,000 (change assumption)
    Mortgage ($1,463) + Fees ($284) + Taxes in 2025 ($253)


    Taxes:$3,037

    Elementary School: Mill Creek Elem (K 5)

    High School: Osceola High School

    Tax Year: 2025

    Middle School: Denn John Middle


  • 1855 SPRING SHOWER CIR, KISSIMMEE, FL 34744

    $365,000149 Days on yellowkey   MLS ID: O6360691

    For Sale O6360691 - 1855 SPRING SHOWER CIR, KISSIMMEE, FL 34744 50 photos

    Bed: 2   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1559
       Built: 2023
    Monthly Fee: $212
       Tax: $5,060 (2025)
    Community: Tohoqua Reserve
    Villa


    Estimated Monthly Payment: $2,634 (change assumption)
    Mortgage ($2,000) + Fees ($212) + Taxes in 2025 ($422)


    Taxes:$5,060

    Elementary School: Neptune Elementary

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Harmony Middle


  • 1568 E OAK LEAF LN, KISSIMMEE, FL 34744

    $464,00083 Days on yellowkey   MLS ID: O6376960

    For Sale O6376960 - 1568 E OAK LEAF LN, KISSIMMEE, FL 34744 32 photos

    Bed: 4   Bath: 2.0
    Liv Area Sq Ft: 1845
       Built: 1975   Tax: $4,836 (2025)
    Community: Heather Oaks
    Single Family


    Estimated Monthly Payment: $2,945 (change assumption)
    Mortgage ($2,542) + Taxes in 2025 ($403)


    Taxes:$4,836

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1772 STAMEN DR, KISSIMMEE, FL 34744

    $495,5004 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

    $269,9004 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

    $324,9909 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


  • 2958 SERA BELLA WAY, KISSIMMEE, FL 34744

    $525,000170 Days on yellowkey   MLS ID: OM712701

    For Sale OM712701 - 2958 SERA BELLA WAY, KISSIMMEE, FL 34744 51 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2280
       Built: 2016
    Monthly Fee: $84
       Tax: $3,670 (2024)
    Community: Sera Bella
    Single Family


    Estimated Monthly Payment: $3,266 (change assumption)
    Mortgage ($2,877) + Fees ($84) + Taxes in 2024 ($306)


    Taxes:$3,670

    Elementary School: East Lake Elem

    High School: Tohopekaliga High School

    Tax Year: 2024

    Middle School: Neptune Middle (6-8)


  • 1779 RED CANYON DR, KISSIMMEE, FL 34744

    $340,00083 Days on yellowkey   MLS ID: S5142388

    For Sale S5142388 - 1779 RED CANYON DR, KISSIMMEE, FL 34744 35 photos

    Bed: 3   Bath: 2.5   Gar: 1
    Liv Area Sq Ft: 1624
       Built: 2021
    Monthly Fee: $84
       Tax: $5,092 (2025)
    Community: Kindred Ph 1Fb
    Townhouse


    Estimated Monthly Payment: $2,371 (change assumption)
    Mortgage ($1,863) + Fees ($84) + Taxes in 2025 ($424)


    Taxes:$5,092

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1838 TOHOQUA BLVD, KISSIMMEE, FL 34744

    $339,90010 Days on yellowkey   MLS ID: S5147475

    For Sale S5147475 - 1838 TOHOQUA BLVD, KISSIMMEE, FL 34744 43 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1600
       Built: 2023
    Monthly Fee: $126
       Tax: $6,276 (2025)
    Community: Tohoqua Ph 6
    Townhouse


    Estimated Monthly Payment: $2,511 (change assumption)
    Mortgage ($1,862) + Fees ($126) + Taxes in 2025 ($523)


    Taxes:$6,276

    Elementary School: Neptune Elementary

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 2506 VOLUNTEER AVE, KISSIMMEE, FL 34744

    $520,0009 Days on yellowkey   MLS ID: O6398097

    For Sale O6398097 - 2506 VOLUNTEER AVE, KISSIMMEE, FL 34744 45 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3199
       Built: 2019
    Monthly Fee: $7
       Tax: $9,289 (2025)
    Community: Tohoqua Ph 1
    Single Family


    Estimated Monthly Payment: $3,630 (change assumption)
    Mortgage ($2,849) + Fees ($7) + Taxes in 2025 ($774)


    Taxes:$9,289

    Elementary School: Neptune Elementary

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 2571 AMES HAVEN RD, KISSIMMEE, FL 34744

    $749,900303 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


  • 1495 SKYLINE DR, KISSIMMEE, FL 34744

    $499,90044 Days on yellowkey   MLS ID: S5145209

    REDUCED by $25,000 (4.8%) on 04/15/2026

    For Sale S5145209 - 1495 SKYLINE DR, KISSIMMEE, FL 34744 50 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2094
       Built: 1973
    Monthly Fee: $16
       Tax: $5,404 (2025)
    Community: Harbour Oaks Unit 1
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,205 (change assumption)
    Mortgage ($2,739) + Fees ($16) + Taxes in 2025 ($450)


    Taxes:$5,404

    Elementary School: Partin Settlement Elem

    High School: Osceola High School

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 2664 WILLOW GLEN CIR, KISSIMMEE, FL 34744

    $429,00010 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)


  • 2961 BIG SKY BLVD, KISSIMMEE, FL 34744

    $390,99017 Days on yellowkey   MLS ID: S5147103

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

    For Sale S5147103 - 2961 BIG SKY BLVD, KISSIMMEE, FL 34744 22 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1860
       Built: 1986   Tax: $5,305 (2025)
    Community: Big Sky Unit 1
    Single Family


    Estimated Monthly Payment: $2,584 (change assumption)
    Mortgage ($2,142) + Taxes in 2025 ($442)


    Taxes:$5,305

    Elementary School: Partin Settlement Elem

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 2970 SERA BELLA WAY, KISSIMMEE, FL 34744

    $529,00045 Days on yellowkey   MLS ID: S5145092

    REDUCED by $11,000 (2.0%) on 04/15/2026

    For Sale S5145092 - 2970 SERA BELLA WAY, KISSIMMEE, FL 34744 96 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2427
       Built: 2016
    Monthly Fee: $120
       Tax: $4,789 (2025)
    Community: Sera Bella
    Single Family


    Estimated Monthly Payment: $3,418 (change assumption)
    Mortgage ($2,899) + Fees ($120) + Taxes in 2025 ($399)


    Taxes:$4,789

    Elementary School: East Lake Elem

    High School: Tohopekaliga High School

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 2533 OAK RUN BLVD, KISSIMMEE, FL 34744

    $397,00066 Days on yellowkey   MLS ID: S5143776

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

    For Sale S5143776 - 2533 OAK RUN BLVD, KISSIMMEE, FL 34744 59 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1661
       Built: 1986   Tax: $5,386 (2025)
    Community: Oak Run Unit 3
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,624 (change assumption)
    Mortgage ($2,175) + Taxes in 2025 ($449)


    Taxes:$5,386

    Elementary School: Mill Creek Elem (K 5)

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Denn John Middle


  • 2661 AMES HAVEN RD, KISSIMMEE, FL 34744

    $439,00046 Days on yellowkey   MLS ID: S5145125

    REDUCED by $6,000 (1.3%) on 03/31/2026

    For Sale S5145125 - 2661 AMES HAVEN RD, KISSIMMEE, FL 34744 51 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1666
       Built: 1984   Tax: $4,502 (2025)
    Community: Emerald Lake Colony Unit 1
    Single Family


    Estimated Monthly Payment: $2,781 (change assumption)
    Mortgage ($2,405) + Taxes in 2025 ($375)


    Taxes:$4,502

    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.