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Homes For Sale in Kissimmee 34744 - 363 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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  • 2093 WALNUT CREEK DR, KISSIMMEE, FL 34744

    $398,99097 Days on yellowkey   MLS ID: O6389078

    REDUCED by $3,000 (0.7%) on 05/28/2026

    For Sale O6389078 - 2093 WALNUT CREEK DR, KISSIMMEE, FL 34744 47 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: $2,504 (change assumption)
    Mortgage ($2,186) + Fees ($11) + Taxes in 2025 ($307)


    Taxes:$3,684

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2670 REAGAN LN, KISSIMMEE, FL 34744

    $363,000108 Days on yellowkey   MLS ID: O6385604

    REDUCED by $7,000 (1.9%) on 06/01/2026

    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: $2,083 (change assumption)
    Mortgage ($1,989) + Taxes in 2025 ($94)


    Taxes:$1,125

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1527 GANTS CIR, KISSIMMEE, FL 34744

    $589,00030 Days on yellowkey   MLS ID: O6407722

    REDUCED by $10,000 (1.7%) on 06/07/2026

    For Sale O6407722 - 1527 GANTS CIR, KISSIMMEE, FL 34744 44 photos

    Bed: 5   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2871
       Built: 2002
    Monthly Fee: $75
       Tax: $4,456 (2025)
    Community: Ashley Cove Unit 3
    Single Family


    Estimated Monthly Payment: $3,674 (change assumption)
    Mortgage ($3,227) + Fees ($75) + Taxes in 2025 ($371)


    Taxes:$4,456

    Elementary School: Partin Settlement Elem

    High School: Osceola High School

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 205 OWENSHIRE CIR, KISSIMMEE, FL 34744

    $359,90010 Days on yellowkey   MLS ID: S5151174

    For Sale S5151174 - 205 OWENSHIRE CIR, KISSIMMEE, FL 34744 29 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1560
       Built: 2003
    Monthly Fee: $23
       Tax: $5,644 (2025)
    Community: Remington Prcl K Ph 3
    Single Family


    Estimated Monthly Payment: $2,465 (change assumption)
    Mortgage ($1,972) + Fees ($23) + Taxes in 2025 ($470)


    Taxes:$5,644

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1595 SHADY OAK DR, KISSIMMEE, FL 34744

    $450,000108 Days on yellowkey   MLS ID: S5144261

    REDUCED by $7,000 (1.5%) on 04/30/2026

    For Sale S5144261 - 1595 SHADY OAK DR, KISSIMMEE, FL 34744 39 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2116
       Built: 1981   Tax: $4,757 (2025)
    Community: Regal Oak Shores Unit 6
    Single Family


    Estimated Monthly Payment: $2,862 (change assumption)
    Mortgage ($2,466) + Taxes in 2025 ($396)


    Taxes:$4,757

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1710 WOODSIDE CT, KISSIMMEE, FL 34744

    $550,000173 Days on yellowkey   MLS ID: O6369122

    REDUCED by $50,000 (8.3%) on 05/26/2026

    For Sale O6369122 - 1710 WOODSIDE CT, KISSIMMEE, FL 34744 50 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2369
       Built: 1980
    Monthly Fee: $17
       Tax: $2,230 (2024)
    Community: Harbour Oaks Unit 1
    Single Family


    Estimated Monthly Payment: $3,216 (change assumption)
    Mortgage ($3,014) + Fees ($17) + Taxes in 2024 ($186)


    Taxes:$2,230

    Elementary School: Partin Settlement Elem

    High School: Osceola High School

    Tax Year: 2024

    Middle School: Neptune Middle (6-8)


  • 1979 CACUTTA WAY, KISSIMMEE, FL 34744

    $409,900149 Days on yellowkey   MLS ID: O6374518

    REDUCED by $5,100 (1.2%) on 06/07/2026

    For Sale O6374518 - 1979 CACUTTA WAY, KISSIMMEE, FL 34744 23 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1672
       Built: 2022
    Monthly Fee: $11
       Tax: $6,900 (2025)
    Community: Kindred
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,832 (change assumption)
    Mortgage ($2,246) + Fees ($11) + Taxes in 2025 ($575)


    Taxes:$6,900

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1743 GOOD NEIGHBOR LOOP, KISSIMMEE, FL 34744

    $469,00041 Days on yellowkey   MLS ID: O6403890

    REDUCED by $30,999 (6.2%) on 05/28/2026

    For Sale O6403890 - 1743 GOOD NEIGHBOR LOOP, KISSIMMEE, FL 34744 17 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2133
       Built: 2022
    Monthly Fee: $7
       Tax: $8,696 (2025)
    Community: Tohoqua Ph 2
    Single Family


    Estimated Monthly Payment: $3,301 (change assumption)
    Mortgage ($2,570) + Fees ($7) + Taxes in 2025 ($725)


    Taxes:$8,696

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1489 TWIN VALLEY TER, KISSIMMEE, FL 34744

    $539,90081 Days on yellowkey   MLS ID: O6390966

    0 Days Off yellowkey (back on 6/6/2026)

    REDUCED by $5,000 (0.9%) on 05/23/2026

    For Sale O6390966 - 1489 TWIN VALLEY TER, KISSIMMEE, FL 34744 78 photos

    Bed: 5   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2674
       Built: 2017
    Monthly Fee: $11
       Tax: $7,067 (2025)
    Community: Kindred Ph 1A & 1B
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,558 (change assumption)
    Mortgage ($2,958) + Fees ($11) + Taxes in 2025 ($589)


    Taxes:$7,067

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2739 SUMMER RETREAT LN, KISSIMMEE, FL 34744

    $324,0009 Days on yellowkey   MLS ID: O6412964

    For Sale O6412964 - 2739 SUMMER RETREAT LN, KISSIMMEE, FL 34744 25 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1559
       Built: 2023
    Monthly Fee: $221
       Tax: $5,441 (2025)
    Community: Tohoqua
    Single Family


    Estimated Monthly Payment: $2,450 (change assumption)
    Mortgage ($1,775) + Fees ($221) + Taxes in 2025 ($453)


    Taxes:$5,441

    Elementary School: Island Village Elementary School

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Harmony Middle


  • 162 HARWOOD CIR, KISSIMMEE, FL 34744

    $463,50013 Days on yellowkey   MLS ID: O6412762

    FORECLOSURE O6412762 - 162 HARWOOD CIR, KISSIMMEE, FL 34744 35 photos

    Bed: 4   Bath: 2.5   Gar: 3
    Liv Area Sq Ft: 2516
       Built: 1998
    Monthly Fee: $14
       Tax: $6,859 (2025)
    Community: Remington Ph 1 Tr D
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,125 (change assumption)
    Mortgage ($2,540) + Fees ($14) + Taxes in 2025 ($572)


    Taxes:$6,859

    Elementary School: Partin Settlement Elem

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 3012 VILLA PRECIOSA DR, KISSIMMEE, FL 34744

    $425,000315 Days on yellowkey   MLS ID: O6310848

    For Sale O6310848 - 3012 VILLA PRECIOSA DR, KISSIMMEE, FL 34744 43 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2074
       Built: 2004
    Monthly Fee: $160
       Tax: $4,927 (2024)
    Community: Villa Sol Ph 1 Village 5
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,899 (change assumption)
    Mortgage ($2,329) + Fees ($160) + Taxes in 2024 ($411)


    Taxes:$4,927

    Elementary School: East Lake Elementary-OS

    High School: Tohopekaliga High School

    Tax Year: 2024

    Middle School: Neptune Middle (6-8)


  • 3044 CAMINO REAL DR S, KISSIMMEE, FL 34744

    $479,00038 Days on yellowkey   MLS ID: O6406104

    REDUCED by $10,000 (2.0%) on 05/31/2026

    For Sale O6406104 - 3044 CAMINO REAL DR S, KISSIMMEE, FL 34744 35 photos

    Bed: 5   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2264
       Built: 2005
    Monthly Fee: $160
       Tax: $5,505 (2025)
    Community: Villa Sol Ph 2 Village 3
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,243 (change assumption)
    Mortgage ($2,625) + Fees ($160) + Taxes in 2025 ($459)


    Taxes:$5,505

    Elementary School: Cypress Elem (K 6)

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Parkway Middle


  • 2540 WINNERS CIR, KISSIMMEE, FL 34744

    $699,000115 Days on yellowkey   MLS ID: O6382446

    REDUCED by $26,000 (3.6%) on 05/28/2026

    For Sale O6382446 - 2540 WINNERS CIR, KISSIMMEE, FL 34744 54 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: $4,137 (change assumption)
    Mortgage ($3,830) + 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)


  • 2754 CALLAWAY LN, KISSIMMEE, FL 34744

    $420,000146 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


  • 1636 BARBERRY DR, KISSIMMEE, FL 34744

    $560,000111 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


  • 4424 SILVER CREEK ST, KISSIMMEE, FL 34744

    $470,000142 Days on yellowkey   MLS ID: L4958851

    REDUCED by $9,900 (2.1%) on 05/26/2026

    For Sale L4958851 - 4424 SILVER CREEK ST, KISSIMMEE, FL 34744 27 photos

    Bed: 5   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2370
       Built: 2019
    Monthly Fee: $123
       Tax: $6,332 (2025)
    Community: Creekside At Boggy Creek Ph 1
    Single Family


    Estimated Monthly Payment: $3,226 (change assumption)
    Mortgage ($2,575) + Fees ($123) + Taxes in 2025 ($528)


    Taxes:$6,332

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2850 SPRING BREEZE WAY, KISSIMMEE, FL 34744

    $775,00048 Days on yellowkey   MLS ID: S5147876

    REDUCED by $15,000 (1.9%) on 06/06/2026

    For Sale S5147876 - 2850 SPRING BREEZE WAY, KISSIMMEE, FL 34744 37 photos

    Bed: 6   Bath: 4.5   Gar: 3
    Liv Area Sq Ft: 3899
       Built: 2014
    Monthly Fee: $100
       Tax: $8,635 (2025)
    Community: North Point Ph 2B-2C
    Spa: No

    Single Family


    Estimated Monthly Payment: $5,066 (change assumption)
    Mortgage ($4,246) + Fees ($100) + Taxes in 2025 ($720)


    Taxes:$8,635

    Elementary School: East Lake Elem

    High School: Tohopekaliga High School

    Tax Year: 2025

    Middle School: Narcoossee Middle


  • 1404 DUSTY STONE LN, KISSIMMEE, FL 34744

    $316,990101 Days on yellowkey   MLS ID: O6387862

    REDUCED by $10 (0.0%) on 06/06/2026

    For Sale O6387862 - 1404 DUSTY STONE LN, KISSIMMEE, FL 34744 44 photos

    Bed: 3   Bath: 2.5   Gar: 1
    Liv Area Sq Ft: 1624
       Built: 2017
    Monthly Fee: $95
       Tax: $5,720 (2025)
    Community: Kindred Ph 1A & 1B
    Townhouse


    Estimated Monthly Payment: $2,309 (change assumption)
    Mortgage ($1,737) + Fees ($95) + Taxes in 2025 ($477)


    Taxes:$5,720

    Elementary School: Neptune Elementary

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 1451 TAOS AVE, KISSIMMEE, FL 34744

    $390,00056 Days on yellowkey   MLS ID: S5148136

    REDUCED by $30,000 (7.1%) on 06/05/2026

    For Sale S5148136 - 1451 TAOS AVE, KISSIMMEE, FL 34744 38 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1846
       Built: 2019
    Monthly Fee: $11
       Tax: $6,597 (2025)
    Community: Kindred Ph 1E
    Single Family


    Estimated Monthly Payment: $2,698 (change assumption)
    Mortgage ($2,137) + Fees ($11) + Taxes in 2025 ($550)


    Taxes:$6,597

    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.