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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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  • 1624 WINDSOR OAK CT, KISSIMMEE, FL 34744

    $264,90048 Days on yellowkey   MLS ID: O6402513

    For Sale O6402513 - 1624 WINDSOR OAK CT, KISSIMMEE, FL 34744 53 photos

    Bed: 3   Bath: 2.5
    Liv Area Sq Ft: 1380
       Built: 1998
    Monthly Fee: $180
       Tax: $2,775 (2025)
    Community: Windsor Oaks
    Townhouse


    Estimated Monthly Payment: $1,863 (change assumption)
    Mortgage ($1,451) + Fees ($180) + Taxes in 2025 ($231)


    Taxes:$2,775

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1380 E LAKE SHORE BLVD, KISSIMMEE, FL 34744

    $669,900632 Days on yellowkey   MLS ID: S5112666

    REDUCED by $30,000 (4.3%) on 04/27/2026

    For Sale S5112666 - 1380 E LAKE SHORE BLVD, KISSIMMEE, FL 34744 99 photos

    Bed: 4   Bath: 4.0   Gar: 3
    Liv Area Sq Ft: 3637
       Built: 2006   Tax: $4,833 (2023)
    Community: East Lake Shores
    Single Family


    Estimated Monthly Payment: $4,073 (change assumption)
    Mortgage ($3,671) + Taxes in 2023 ($403)


    Taxes:$4,833

    Elementary School: None

    High School: None

    Tax Year: 2023

    Middle School: None


  • 2605 PLAY HARD ALY, KISSIMMEE, FL 34744

    $369,999118 Days on yellowkey   MLS ID: S5143916

    REDUCED by $5,001 (1.3%) on 04/27/2026

    For Sale S5143916 - 2605 PLAY HARD ALY, KISSIMMEE, FL 34744 40 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1603
       Built: 2019
    Monthly Fee: $154
       Tax: $4,220 (2025)
    Community: Tohoqua Ph 1
    Townhouse


    Estimated Monthly Payment: $2,533 (change assumption)
    Mortgage ($2,027) + Fees ($154) + Taxes in 2025 ($352)


    Taxes:$4,220

    Elementary School: Neptune Elementary

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 1724 RANGER HIGHLANDS RD, KISSIMMEE, FL 34744

    $363,000330 Days on yellowkey   MLS ID: TB8408985

    REDUCED by $4,000 (1.1%) on 04/24/2026

    For Sale TB8408985 - 1724 RANGER HIGHLANDS RD, KISSIMMEE, FL 34744 53 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1910
       Built: 2018
    Monthly Fee: $11
       Tax: $5,835 (2024)
    Community: Kindred Ph 1D
    Single Family


    Estimated Monthly Payment: $2,486 (change assumption)
    Mortgage ($1,989) + Fees ($11) + Taxes in 2024 ($486)


    Taxes:$5,835

    Elementary School: Neptune Elementary

    High School: Gateway High School (9 12)

    Tax Year: 2024

    Middle School: Neptune Middle (6-8)


  • 107 THORNBURY LN, KISSIMMEE, FL 34744

    $400,00065 Days on yellowkey   MLS ID: S5147435

    3 Days Off yellowkey (back on 4/24/2026)

    For Sale S5147435 - 107 THORNBURY LN, KISSIMMEE, FL 34744 31 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1766
       Built: 2002
    Monthly Fee: $13
       Tax: $3,290 (2025)
    Community: Remington Prcl H Ph 2
    Single Family


    Estimated Monthly Payment: $2,479 (change assumption)
    Mortgage ($2,192) + Fees ($13) + Taxes in 2025 ($274)


    Taxes:$3,290

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2057 WALNUT CREEK DR, KISSIMMEE, FL 34744

    $456,99055 Days on yellowkey   MLS ID: O6400629

    1 Days Off yellowkey (back on 4/23/2026)

    For Sale O6400629 - 2057 WALNUT CREEK DR, KISSIMMEE, FL 34744 51 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: $2,822 (change assumption)
    Mortgage ($2,504) + Fees ($11) + Taxes in 2025 ($307)


    Taxes:$3,684

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1872 RUSTIC FALLS DR, KISSIMMEE, FL 34744

    $565,00072 Days on yellowkey   MLS ID: O6396038

    For Sale O6396038 - 1872 RUSTIC FALLS DR, KISSIMMEE, FL 34744 31 photos

    Bed: 8   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2824
       Built: 2020
    Monthly Fee: $125
       Tax: $8,846 (2025)
    Community: Kindred Ph 1Fa
    Single Family


    Estimated Monthly Payment: $3,958 (change assumption)
    Mortgage ($3,096) + Fees ($125) + Taxes in 2025 ($737)


    Taxes:$8,846

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1776 FULFILLMENT DR, KISSIMMEE, FL 34744

    $395,00054 Days on yellowkey   MLS ID: S5148323

    For Sale S5148323 - 1776 FULFILLMENT DR, KISSIMMEE, FL 34744 24 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1620
       Built: 2020
    Monthly Fee: $55
       Tax: $5,091 (2025)
    Community: Tohoqua Ph 1
    Townhouse


    Estimated Monthly Payment: $2,644 (change assumption)
    Mortgage ($2,164) + Fees ($55) + Taxes in 2025 ($424)


    Taxes:$5,091

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 103 DELLWOOD DR, KISSIMMEE, FL 34744

    $329,000125 Days on yellowkey   MLS ID: S5143443

    For Sale S5143443 - 103 DELLWOOD DR, KISSIMMEE, FL 34744 20 photos

    Bed: 3   Bath: 1.0
    Liv Area Sq Ft: 1368
       Built: 1955   Tax: $5,415 (2025)
    Community: Dellwood Park
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,254 (change assumption)
    Mortgage ($1,803) + Taxes in 2025 ($451)


    Taxes:$5,415

    Elementary School: Central Avenue Elem

    High School: Osceola High School

    Tax Year: 2025

    Middle School: Denn John Middle


  • 1708 NEBRASKA AVE, KISSIMMEE, FL 34744

    $335,00056 Days on yellowkey   MLS ID: O6400560

    For Sale O6400560 - 1708 NEBRASKA AVE, KISSIMMEE, FL 34744 10 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1008
       Built: 1971   Tax: $3,138 (2025)
    Community: Johnston Park
    Single Family


    Estimated Monthly Payment: $2,097 (change assumption)
    Mortgage ($1,836) + Taxes in 2025 ($262)


    Taxes:$3,138

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2213 SOUTHBURY DR, KISSIMMEE, FL 34744

    $404,990216 Days on yellowkey   MLS ID: O6359460

    0 Days Off yellowkey (back on 4/19/2026)

    REDUCED by $5,000 (1.2%) on 04/16/2026

    For Sale O6359460 - 2213 SOUTHBURY DR, KISSIMMEE, FL 34744 25 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1913
       Built: 2025
    Monthly Fee: $10
       Tax: $967 (2025)
    Community: Tohoqua
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,310 (change assumption)
    Mortgage ($2,219) + Fees ($10) + Taxes in 2025 ($81)


    Taxes:$967

    Elementary School: Neptune Elementary

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 1874 HICKORY BLUFF RD, KISSIMMEE, FL 34744

    $550,00061 Days on yellowkey   MLS ID: O6398896

    For Sale O6398896 - 1874 HICKORY BLUFF RD, KISSIMMEE, FL 34744 20 photos

    Bed: 5   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2674
       Built: 2017
    Monthly Fee: $12
       Tax: $15,385 (2025)
    Community: Kindred
    Single Family


    Estimated Monthly Payment: $4,308 (change assumption)
    Mortgage ($3,014) + Fees ($12) + Taxes in 2025 ($1,282)


    Taxes:$15,385

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2503 HASSONITE ST, KISSIMMEE, FL 34744

    $345,000223 Days on yellowkey   MLS ID: S5137504

    For Sale S5137504 - 2503 HASSONITE ST, KISSIMMEE, FL 34744 22 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2018
       Built: 2007
    Monthly Fee: $170
       Tax: $1,559 (2024)
    Community: Amber Pointe
    Townhouse


    Estimated Monthly Payment: $2,190 (change assumption)
    Mortgage ($1,890) + Fees ($170) + Taxes in 2024 ($130)


    Taxes:$1,559

    Elementary School: Partin Settlement Elem

    High School: Gateway High School (9 12)

    Tax Year: 2024

    Middle School: Denn John Middle


  • 2937 SLOUGH CREEK DR, KISSIMMEE, FL 34744

    $519,900120 Days on yellowkey   MLS ID: S5143801

    For Sale S5143801 - 2937 SLOUGH CREEK DR, KISSIMMEE, FL 34744 21 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2727
       Built: 2023
    Monthly Fee: $130
       Tax: $7,208 (2025)
    Community: Creekside At Boggy Creek Ph 3
    Single Family


    Estimated Monthly Payment: $3,579 (change assumption)
    Mortgage ($2,849) + Fees ($130) + Taxes in 2025 ($601)


    Taxes:$7,208

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1873 SPRING SHOWER CIR, KISSIMMEE, FL 34744

    $345,000294 Days on yellowkey   MLS ID: S5133310

    For Sale S5133310 - 1873 SPRING SHOWER CIR, KISSIMMEE, FL 34744 18 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1559
       Built: 2023
    Monthly Fee: $212
       Tax: $5,457 (2024)
    Community: Tohoqua Ph 5B
    Villa


    Estimated Monthly Payment: $2,557 (change assumption)
    Mortgage ($1,890) + Fees ($212) + Taxes in 2024 ($455)


    Taxes:$5,457

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 1648 HEART BAR RD, KISSIMMEE, FL 34744

    $380,990419 Days on yellowkey   MLS ID: S5125282

    For Sale S5125282 - 1648 HEART BAR RD, KISSIMMEE, FL 34744 77 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1516
       Built: 2023   Tax: $5,045 (2025)
    Community: Kindred Ph 2C & 2D
    Single Family


    Estimated Monthly Payment: $2,508 (change assumption)
    Mortgage ($2,088) + Taxes in 2025 ($420)


    Taxes:$5,045

    Elementary School: Neptune Elementary

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 1703 MICHIGAN AVE #A, KISSIMMEE, FL 34744

    $149,900118 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


  • 1491 AUGUST GRAY DR, KISSIMMEE, FL 34744

    $430,00066 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

    $495,50060 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


  • 2518 BOWMER DR, KISSIMMEE, FL 34744

    $359,900677 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




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.