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Homes For Sale in Kissimmee 34744 - 376 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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  • 2754 CALLAWAY LN, KISSIMMEE, FL 34744

    $420,000176 Days on yellowkey   MLS ID: S5141838

    0 Days Off yellowkey (back on 5/7/2026)

    For Sale S5141838 - 2754 CALLAWAY LN, KISSIMMEE, FL 34744 50 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2513
       Built: 2004
    Monthly Fee: $78
       Tax: $6,917 (2025)
    Community: Remington Prcl M1
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,956 (change assumption)
    Mortgage ($2,301) + Fees ($78) + Taxes in 2025 ($576)


    Taxes:$6,917

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1701 BULL HILL RD, KISSIMMEE, FL 34744

    $579,99078 Days on yellowkey   MLS ID: S5148728

    For Sale S5148728 - 1701 BULL HILL RD, KISSIMMEE, FL 34744 24 photos

    Bed: 4   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 2852
       Built: 2024
    Monthly Fee: $16
       Tax: $7,143 (2025)
    Community: Kindred Ph 3B 3C & 3D
    Single Family


    Estimated Monthly Payment: $3,789 (change assumption)
    Mortgage ($3,178) + Fees ($16) + Taxes in 2025 ($595)


    Taxes:$7,143

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 3210 QUEEN ALEXANDRIA DR, KISSIMMEE, FL 34744

    $369,900123 Days on yellowkey   MLS ID: O6389027

    1 Days Off yellowkey (back on 7/8/2026)

    REDUCED by $12,100 (3.2%) on 06/01/2026

    For Sale O6389027 - 3210 QUEEN ALEXANDRIA DR, KISSIMMEE, FL 34744 26 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1541
       Built: 2011
    Monthly Fee: $136
       Tax: $4,861 (2025)
    Community: Raintree At Springlake Village Ph 2
    Single Family


    Estimated Monthly Payment: $2,568 (change assumption)
    Mortgage ($2,027) + Fees ($136) + Taxes in 2025 ($405)


    Taxes:$4,861

    Elementary School: East Lake Elem

    High School: Tohopekaliga High School

    Tax Year: 2025

    Middle School: Narcoossee Middle


  • 2823 SAIL BREEZE WAY, KISSIMMEE, FL 34744

    $474,999378 Days on yellowkey   MLS ID: S5130069

    1 Days Off yellowkey (back on 7/8/2026)

    REDUCED by $14,001 (2.9%) on 05/26/2026

    For Sale S5130069 - 2823 SAIL BREEZE WAY, KISSIMMEE, FL 34744 50 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2251
       Built: 2012
    Monthly Fee: $112
       Tax: $4,907 (2024)
    Community: North Point Ph 1A
    Single Family


    Estimated Monthly Payment: $3,124 (change assumption)
    Mortgage ($2,603) + Fees ($112) + Taxes in 2024 ($409)


    Taxes:$4,907

    Elementary School: East Lake Elem

    High School: Tohopekaliga High School

    Tax Year: 2024

    Middle School: Narcoossee Middle


  • 1508 JENNI LEE CT, KISSIMMEE, FL 34744

    $444,90059 Days on yellowkey   MLS ID: TB8508177

    REDUCED by $15,000 (3.3%) on 07/08/2026

    For Sale TB8508177 - 1508 JENNI LEE CT, KISSIMMEE, FL 34744 15 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2077
       Built: 1996
    Monthly Fee: $21
       Tax: $1,877 (2025)
    Community: Woods At Kings Crest The Ph 1
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,615 (change assumption)
    Mortgage ($2,438) + Fees ($21) + Taxes in 2025 ($156)


    Taxes:$1,877

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2601 GOLD DUST CIR, KISSIMMEE, FL 34744

    $479,000110 Days on yellowkey   MLS ID: S5146084

    REDUCED by $5,999 (1.2%) on 07/08/2026

    For Sale S5146084 - 2601 GOLD DUST CIR, KISSIMMEE, FL 34744 23 photos

    Bed: 4   Bath: 3.5   Gar: 18
    Liv Area Sq Ft: 2691
       Built: 2001
    Monthly Fee: $47
       Tax: $4,131 (2025)
    Community: Fortune Lakes
    Single Family


    Estimated Monthly Payment: $3,016 (change assumption)
    Mortgage ($2,625) + Fees ($47) + Taxes in 2025 ($344)


    Taxes:$4,131

    Elementary School: Partin Settlement Elem

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 2716 WORTHAM LN, KISSIMMEE, FL 34744

    $410,000137 Days on yellowkey   MLS ID: O6385986

    REDUCED by $5,000 (1.2%) on 07/08/2026

    For Sale O6385986 - 2716 WORTHAM LN, KISSIMMEE, FL 34744 29 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2341
       Built: 1998
    Monthly Fee: $13
       Tax: $6,364 (2025)
    Community: Remington Ph 1 Tr E
    Single Family


    Estimated Monthly Payment: $2,790 (change assumption)
    Mortgage ($2,247) + Fees ($13) + Taxes in 2025 ($530)


    Taxes:$6,364

    Elementary School: Partin Settlement Elem

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 604 CHADBURY WAY, KISSIMMEE, FL 34744

    $439,00015 Days on yellowkey   MLS ID: O6420445

    For Sale O6420445 - 604 CHADBURY WAY, KISSIMMEE, FL 34744 39 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 1719
       Built: 2005
    Monthly Fee: $78
       Tax: $5,214 (2025)
    Community: Remington Prcl M1
    Single Family


    Estimated Monthly Payment: $2,918 (change assumption)
    Mortgage ($2,405) + Fees ($78) + Taxes in 2025 ($434)


    Taxes:$5,214

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 4421 JIM BRANCH RD, KISSIMMEE, FL 34744

    $849,9007 Days on yellowkey   MLS ID: S5153225

    For Sale S5153225 - 4421 JIM BRANCH RD, KISSIMMEE, FL 34744 46 photos

    Bed: 3   Bath: 2.0   Gar: 3
    Liv Area Sq Ft: 2000
       Built: 2020   Tax: $5,348 (2025)
    Community: N/A
    Single Family


    Estimated Monthly Payment: $5,103 (change assumption)
    Mortgage ($4,657) + Taxes in 2025 ($446)


    Taxes:$5,348

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1909 HOWARD MESA DR, KISSIMMEE, FL 34744

    $389,9907 Days on yellowkey   MLS ID: O6422957

    For Sale O6422957 - 1909 HOWARD MESA DR, KISSIMMEE, FL 34744 67 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1614
       Built: 2025
    Monthly Fee: $11
       Tax: $3,684 (2025)
    Community: Kindred Ph 3B 3C & 3D
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,455 (change assumption)
    Mortgage ($2,137) + Fees ($11) + Taxes in 2025 ($307)


    Taxes:$3,684

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2042 WALNUT CREEK DR, KISSIMMEE, FL 34744

    $399,9907 Days on yellowkey   MLS ID: O6422932

    For Sale O6422932 - 2042 WALNUT CREEK DR, KISSIMMEE, FL 34744 67 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1614
       Built: 2025
    Monthly Fee: $11
       Tax: $3,684 (2025)
    Community: Kindred Ph 3B 3C & 3D
    Spa: No

    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


  • 3821 SHOREVIEW DR, KISSIMMEE, FL 34744

    $523,000110 Days on yellowkey   MLS ID: S5146534

    REDUCED by $1,994 (0.4%) on 07/07/2026

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

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2458
       Built: 2009
    Monthly Fee: $188
       Tax: $3,749 (2025)
    Community: North Shore Village
    Single Family


    Estimated Monthly Payment: $3,366 (change assumption)
    Mortgage ($2,866) + 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


  • 1057 UNIVERSAL REST PL, KISSIMMEE, FL 34744

    $260,000131 Days on yellowkey   MLS ID: S5143478

    REDUCED by $20,000 (7.1%) on 07/07/2026

    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: $1,898 (change assumption)
    Mortgage ($1,425) + Fees ($200) + Taxes in 2025 ($273)


    Taxes:$3,278

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2356 VALLEY AVE, KISSIMMEE, FL 34744

    $360,000123 Days on yellowkey   MLS ID: O6390430

    4 Days Off yellowkey (back on 6/2/2026)

    REDUCED by $5,000 (1.4%) on 05/05/2026

    For Sale O6390430 - 2356 VALLEY AVE, KISSIMMEE, FL 34744 16 photos

    Bed: 4   Bath: 2.0
    Liv Area Sq Ft: 1855
       Built: 1973   Tax: $671 (2025)
    Community: Town & Country Estates Unit 1
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,028 (change assumption)
    Mortgage ($1,973) + Taxes in 2025 ($56)


    Taxes:$671

    Elementary School: Mill Creek Elem (K 5)

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Denn John Middle


  • 1137 SHAWNEE DR, KISSIMMEE, FL 34744

    $234,700308 Days on yellowkey   MLS ID: O6342706

    For Sale O6342706 - 1137 SHAWNEE DR, KISSIMMEE, FL 34744 37 photos

    Bed: 2   Bath: 1.0
    Liv Area Sq Ft: 684
       Built: 1920   Tax: $2,343 (2024)
    Community: Osceola Acres
    Single Family


    Estimated Monthly Payment: $1,481 (change assumption)
    Mortgage ($1,286) + Taxes in 2024 ($195)


    Taxes:$2,343

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 2943 CASABELLA DR, KISSIMMEE, FL 34744

    $399,900220 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
    Spa: No

    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)


  • 1528 ERIN BREEZE LN, KISSIMMEE, FL 34744

    $375,000102 Days on yellowkey   MLS ID: S5147056

    REDUCED by $4,000 (1.1%) on 06/15/2026

    For Sale S5147056 - 1528 ERIN BREEZE LN, KISSIMMEE, FL 34744 44 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1509
       Built: 2024
    Monthly Fee: $280
       Tax: $4,867 (2025)
    Community: Seasons At Big Sky Ph 1
    Townhouse


    Estimated Monthly Payment: $2,740 (change assumption)
    Mortgage ($2,055) + Fees ($280) + Taxes in 2025 ($406)


    Taxes:$4,867

    Elementary School: Partin Settlement Elem

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 1550 REGAL OAK DR, KISSIMMEE, FL 34744

    $460,00060 Days on yellowkey   MLS ID: S5150034

    1 Days Off yellowkey (back on 7/7/2026)

    REDUCED by $10,000 (2.1%) on 06/29/2026

    For Sale S5150034 - 1550 REGAL OAK DR, KISSIMMEE, FL 34744 44 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2312
       Built: 1983   Tax: $3,426 (2025)
    Community: Regal Oak Shores Unit 4
    Single Family


    Estimated Monthly Payment: $2,806 (change assumption)
    Mortgage ($2,520) + Taxes in 2025 ($286)


    Taxes:$3,426

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1826 HOWARD MESA DR, KISSIMMEE, FL 34744

    $419,99033 Days on yellowkey   MLS ID: O6416048

    2 Days Off yellowkey (back on 7/7/2026)

    REDUCED by $5,000 (1.2%) on 07/02/2026

    For Sale O6416048 - 1826 HOWARD MESA DR, KISSIMMEE, FL 34744 48 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1665
       Built: 2025
    Monthly Fee: $11
       Tax: $3,684 (2025)
    Community: Kindred Ph 3B 3C & 3D
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,619 (change assumption)
    Mortgage ($2,301) + Fees ($11) + Taxes in 2025 ($307)


    Taxes:$3,684

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1808 HOWARD MESA DR, KISSIMMEE, FL 34744

    $412,99071 Days on yellowkey   MLS ID: O6404608

    2 Days Off yellowkey (back on 7/7/2026)

    REDUCED by $6,000 (1.4%) on 07/02/2026

    For Sale O6404608 - 1808 HOWARD MESA DR, KISSIMMEE, FL 34744 50 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1665
       Built: 2025
    Monthly Fee: $11
       Tax: $3,684 (2025)
    Community: Kindred Ph 3B 3C & 3D
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,581 (change assumption)
    Mortgage ($2,263) + Fees ($11) + Taxes in 2025 ($307)


    Taxes:$3,684

    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.