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Homes For Sale in Kissimmee 34744 - 372 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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  • 1817 MICHIGAN AVE #D, KISSIMMEE, FL 34744

    $159,900164 Days on yellowkey   MLS ID: S5141290

    For Sale S5141290 - 1817 MICHIGAN AVE #D, KISSIMMEE, FL 34744 9 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1118
       Built: 1973   Tax: $371 (2025)
    Community: Essex Park Villas Condo
    Condo


    Estimated Monthly Payment: $907 (change assumption)
    Mortgage ($876) + Taxes in 2025 ($31)


    Taxes:$371

    Elementary School: Mill Creek Elem (K 5)

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Denn John Middle


  • 1624 WINDSOR OAK CT, KISSIMMEE, FL 34744

    $264,90058 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


  • 1724 RANGER HIGHLANDS RD, KISSIMMEE, FL 34744

    $363,000340 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)


  • 2057 WALNUT CREEK DR, KISSIMMEE, FL 34744

    $456,99065 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

    $565,00082 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

    $395,00064 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

    $329,000135 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

    $335,00066 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


  • 1874 HICKORY BLUFF RD, KISSIMMEE, FL 34744

    $550,00071 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


  • 2937 SLOUGH CREEK DR, KISSIMMEE, FL 34744

    $519,900130 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

    $345,000304 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

    $380,990429 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

    $149,900128 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


  • 2518 BOWMER DR, KISSIMMEE, FL 34744

    $359,900687 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


  • 1791 SMARTS RULE ST, KISSIMMEE, FL 34744

    $510,000143 Days on yellowkey   MLS ID: S5142907

    For Sale S5142907 - 1791 SMARTS RULE ST, KISSIMMEE, FL 34744 50 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2500
       Built: 2021
    Monthly Fee: $7
       Tax: $9,049 (2025)
    Community: Tohoqua Ph 1B
    Single Family


    Estimated Monthly Payment: $3,556 (change assumption)
    Mortgage ($2,794) + Fees ($7) + Taxes in 2025 ($754)


    Taxes:$9,049

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2418 BROOKSIDE AVE, KISSIMMEE, FL 34744

    $220,000100 Days on yellowkey   MLS ID: S5145883

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

    For Sale S5145883 - 2418 BROOKSIDE AVE, KISSIMMEE, FL 34744 1 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1807
       Built: 1979   Tax: $4,934 (2025)
    Community: Whisper Woods
    Single Family


    Estimated Monthly Payment: $1,617 (change assumption)
    Mortgage ($1,205) + Taxes in 2025 ($411)


    Taxes:$4,934

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 4436 AZURE ISLE WAY, KISSIMMEE, FL 34744

    $499,000139 Days on yellowkey   MLS ID: O6379702

    For Sale O6379702 - 4436 AZURE ISLE WAY, KISSIMMEE, FL 34744 35 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2251
       Built: 2013
    Monthly Fee: $108
       Tax: $3,771 (2025)
    Community: North Point Ph 1B
    Single Family


    Estimated Monthly Payment: $3,156 (change assumption)
    Mortgage ($2,734) + Fees ($108) + Taxes in 2025 ($314)


    Taxes:$3,771

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1326 SWEETWOOD BLVD, KISSIMMEE, FL 34744

    $435,00079 Days on yellowkey   MLS ID: S5147282

    For Sale S5147282 - 1326 SWEETWOOD BLVD, KISSIMMEE, FL 34744 20 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1571
       Built: 1978   Tax: $5,280 (2025)
    Community: Sweetwood Estates
    Single Family


    Estimated Monthly Payment: $2,824 (change assumption)
    Mortgage ($2,384) + Taxes in 2025 ($440)


    Taxes:$5,280

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 422 JANICE KAY PL, KISSIMMEE, FL 34744

    $479,000300 Days on yellowkey   MLS ID: S5133405

    REDUCED by $10,000 (2.0%) on 04/06/2026

    For Sale S5133405 - 422 JANICE KAY PL, KISSIMMEE, FL 34744 19 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 3424
       Built: 2004
    Monthly Fee: $13
       Tax: $7,517 (2024)
    Community: Eagles Landing
    Single Family


    Estimated Monthly Payment: $3,264 (change assumption)
    Mortgage ($2,625) + Fees ($13) + Taxes in 2024 ($626)


    Taxes:$7,517

    Elementary School: Partin Settlement Elem

    High School: Gateway High School (9 12)

    Tax Year: 2024

    Middle School: Neptune Middle (6-8)


  • 2575 AVENTURINE ST, KISSIMMEE, FL 34744

    $320,000117 Days on yellowkey   MLS ID: S5144762

    For Sale S5144762 - 2575 AVENTURINE ST, KISSIMMEE, FL 34744 24 photos

    Bed: 3   Bath: 2.5   Gar: 1
    Liv Area Sq Ft: 1758
       Built: 2007
    Monthly Fee: $170
       Tax: $3,934 (2025)
    Community: Amber Pointe Unit 2
    Townhouse


    Estimated Monthly Payment: $2,251 (change assumption)
    Mortgage ($1,753) + Fees ($170) + Taxes in 2025 ($328)


    Taxes:$3,934

    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.