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Homes For Sale in Kissimmee 34744 - 282 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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  • 310 E MAGNOLIA ST, KISSIMMEE, FL 34744

    $250,00070 Days on yellowkey   MLS ID: O6379567

    For Sale O6379567 - 310 E MAGNOLIA ST, KISSIMMEE, FL 34744 13 photos

    Bed: 4   Bath: 2.5   Gar: 1
    Liv Area Sq Ft: 1312
       Built: 1940   Tax: $3,382 (2025)
    Community: Robert Bass Add
    Single Family


    Estimated Monthly Payment: $1,652 (change assumption)
    Mortgage ($1,370) + Taxes in 2025 ($282)


    Taxes:$3,382

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1698 TAYLOR RIDGE LOOP, KISSIMMEE, FL 34744

    $715,00063 Days on yellowkey   MLS ID: O6366703

    REDUCED by $20,000 (2.7%) on 04/16/2026

    FORECLOSURE O6366703 - 1698 TAYLOR RIDGE LOOP, KISSIMMEE, FL 34744 60 photos

    Bed: 5   Bath: 4.5   Gar: 3
    Liv Area Sq Ft: 4964
       Built: 2005
    Monthly Fee: $150
       Tax: $5,492 (2025)
    Community: Taylor Ridge
    Single Family


    Estimated Monthly Payment: $4,525 (change assumption)
    Mortgage ($3,918) + Fees ($150) + Taxes in 2025 ($458)


    Taxes:$5,492

    Elementary School: Partin Settlement Elem

    High School: Osceola High School

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 1715 HAPPINESS ROW, KISSIMMEE, FL 34744

    $399,00070 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


  • 1967 RANKIN ST, KISSIMMEE, FL 34744

    $510,0007 Days on yellowkey   MLS ID: O6397893

    For Sale O6397893 - 1967 RANKIN ST, KISSIMMEE, FL 34744 44 photos

    Bed: 4   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 2142
       Built: 2023
    Monthly Fee: $11

    Community: Kindred
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $2,805 (change assumption)
    Mortgage ($2,794) + Fees ($11) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1703 MICHIGAN AVE #A, KISSIMMEE, FL 34744

    $149,90059 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

    $320,00020 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


  • 2735 SCARBOROUGH DR, KISSIMMEE, FL 34744

    $530,0003 Days on yellowkey   MLS ID: S5147642

    For Sale S5147642 - 2735 SCARBOROUGH DR, KISSIMMEE, FL 34744 41 photos

    Bed: 5   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 2930
       Built: 1996
    Monthly Fee: $13
       Tax: $6,439 (2025)
    Community: Remington Ph 1 Tr E
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $3,454 (change assumption)
    Mortgage ($2,904) + Fees ($13) + Taxes in 2025 ($537)


    Taxes:$6,439

    Elementary School: Partin Settlement Elem

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 1491 AUGUST GRAY DR, KISSIMMEE, FL 34744

    $430,0007 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)


  • 2695 HOLIDAY WOODS DR, KISSIMMEE, FL 34744

    $299,500Listed 04/16/2026 9:44AM   MLS ID: S5147602

    For Sale S5147602 - 2695 HOLIDAY WOODS DR, KISSIMMEE, FL 34744 55 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1100
       Built: 1981   Tax: $1,429 (2025)
    Community: Holiday Woods
    Single Family


    Estimated Monthly Payment: $1,760 (change assumption)
    Mortgage ($1,641) + Taxes in 2025 ($119)


    Taxes:$1,429

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 651 CORNERSTONE DR, KISSIMMEE, FL 34744

    $267,00033 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

    $365,000146 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

    $464,00080 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


  • 1127 LINDSAY WAY, KISSIMMEE, FL 34744

    $490,00079 Days on yellowkey   MLS ID: O6377189

    1 Days Off yellowkey (back on 3/23/2026)

    For Sale O6377189 - 1127 LINDSAY WAY, KISSIMMEE, FL 34744 7 photos

    Bed: 5   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 2032
       Built: 2026   Tax: $990 (2025)
    Community: Elizabeth Estates
    Single Family


    Estimated Monthly Payment: $2,767 (change assumption)
    Mortgage ($2,685) + Taxes in 2025 ($83)


    Taxes:$990

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1752 LEE JANZEN DR, KISSIMMEE, FL 34744

    $599,90012 Days on yellowkey   MLS ID: S5145877

    For Sale S5145877 - 1752 LEE JANZEN DR, KISSIMMEE, FL 34744 57 photos

    Bed: 5   Bath: 4.0   Gar: 3
    Liv Area Sq Ft: 3376
       Built: 2005
    Monthly Fee: $190
       Tax: $8,834 (2025)
    Community: Kissimmee Bay
    Single Family


    Estimated Monthly Payment: $4,213 (change assumption)
    Mortgage ($3,287) + Fees ($190) + Taxes in 2025 ($736)


    Taxes:$8,834

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1772 STAMEN DR, KISSIMMEE, FL 34744

    $495,5001 Day 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

    $269,9001 Day 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


  • 1325 CYPRESS ARBOR, KISSIMMEE, FL 34744

    $275,0001 Day on yellowkey   MLS ID: O6398060

    For Sale O6398060 - 1325 CYPRESS ARBOR, KISSIMMEE, FL 34744 15 photos

    Bed: 2   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 957
       Built: 1986   Tax: $806 (2025)
    Community: Cypress Arbor
    Single Family


    Estimated Monthly Payment: $1,574 (change assumption)
    Mortgage ($1,507) + Taxes in 2025 ($67)


    Taxes:$806

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1859 RED CANYON DR, KISSIMMEE, FL 34744

    $324,9906 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

    $525,000167 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

    $340,00080 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




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.