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Homes For Sale in Kissimmee 34744 - 245 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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  • 417 BENITA ST, KISSIMMEE, FL 34744

    $284,000418 Days on yellowkey   MLS ID: O6275736

    For Sale O6275736 - 417 BENITA ST, KISSIMMEE, FL 34744 9 photos

    Bed: 3   Bath: 1.5
    Liv Area Sq Ft: 1186
       Built: 1971   Tax: $380 (2023)
    Community: Benita Park
    Single Family


    Estimated Monthly Payment: $1,588 (change assumption)
    Mortgage ($1,556) + Taxes in 2023 ($32)


    Taxes:$380

    Elementary School: None

    High School: None

    Tax Year: 2023

    Middle School: None


  • 1831 BRIGHT SKY DR, KISSIMMEE, FL 34744

    $467,201125 Days on yellowkey   MLS ID: O6364329

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

    REDUCED by $30,000 (6.0%) on 03/31/2026

    For Sale O6364329 - 1831 BRIGHT SKY DR, KISSIMMEE, FL 34744 29 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2139
       Built: 2025
    Monthly Fee: $10

    Community: Tohoqua 50S
    Single Family


    Estimated Monthly Payment: $2,570 (change assumption)
    Mortgage ($2,560) + Fees ($10) + Taxes in 2024 ($0)


    Taxes:$0

    Elementary School: Neptune Elementary

    High School: Gateway High School (9 12)

    Tax Year: 2024

    Middle School: Neptune Middle (6-8)


  • 3193 TOHO CT, KISSIMMEE, FL 34744

    $529,900180 Days on yellowkey   MLS ID: O6350540

    For Sale O6350540 - 3193 TOHO CT, KISSIMMEE, FL 34744 24 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2420
       Built: 2004
    Monthly Fee: $53
       Tax: $3,082 (2024)
    Community: Fells Cove Unit 1 Ph 1
    Single Family


    Estimated Monthly Payment: $3,213 (change assumption)
    Mortgage ($2,903) + Fees ($53) + Taxes in 2024 ($257)


    Taxes:$3,082

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 2624 BLOWING BREEZE AVE, KISSIMMEE, FL 34744

    $499,90053 Days on yellowkey   MLS ID: O6381066

    For Sale O6381066 - 2624 BLOWING BREEZE AVE, KISSIMMEE, FL 34744 35 photos

    Bed: 5   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2590
       Built: 2022
    Monthly Fee: $10
       Tax: $8,564 (2025)
    Community: Tohoqua Ph 4A
    Single Family


    Estimated Monthly Payment: $3,463 (change assumption)
    Mortgage ($2,739) + Fees ($10) + Taxes in 2025 ($714)


    Taxes:$8,564

    Elementary School: Neptune Elementary

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 2512 BLOWING BREEZE AVE, KISSIMMEE, FL 34744

    $340,00040 Days on yellowkey   MLS ID: S5144271

    REDUCED by $10,000 (2.9%) on 04/05/2026

    For Sale S5144271 - 2512 BLOWING BREEZE AVE, KISSIMMEE, FL 34744 40 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1528
       Built: 2021
    Monthly Fee: $154
       Tax: $5,017 (2025)
    Community: Tohoqua Ph 1B
    Townhouse


    Estimated Monthly Payment: $2,435 (change assumption)
    Mortgage ($1,863) + Fees ($154) + Taxes in 2025 ($418)


    Taxes:$5,017

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1752 LEE JANZEN DR, KISSIMMEE, FL 34744

    $599,9001 Day on yellowkey   MLS ID: S5145877

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

    Bed: 5   Bath: 4.5   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


  • 2035 SPRING SHOWER CIR, KISSIMMEE, FL 34744

    $450,54081 Days on yellowkey   MLS ID: O6374311

    For Sale O6374311 - 2035 SPRING SHOWER CIR, KISSIMMEE, FL 34744 23 photos

    Bed: 2   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2018
       Built: 2026
    Monthly Fee: $128
       Tax: $3,007 (2025)
    Community: Tohoqua Reserve
    Single Family


    Estimated Monthly Payment: $2,847 (change assumption)
    Mortgage ($2,469) + Fees ($128) + Taxes in 2025 ($251)


    Taxes:$3,007

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2320 SOUTHBURY DR, KISSIMMEE, FL 34744

    $339,990202 Days on yellowkey   MLS ID: O6344888

    For Sale O6344888 - 2320 SOUTHBURY DR, KISSIMMEE, FL 34744 21 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1553
       Built: 2025
    Monthly Fee: $130
       Tax: $1,610 (2024)
    Community: Tohoqua
    Townhouse


    Estimated Monthly Payment: $2,127 (change assumption)
    Mortgage ($1,863) + Fees ($130) + Taxes in 2024 ($134)


    Taxes:$1,610

    Elementary School: Neptune Elementary

    High School: Gateway High School (9 12)

    Tax Year: 2024

    Middle School: Neptune Middle (6-8)


  • 2672 DEBANY RD, KISSIMMEE, FL 34744

    $400,00053 Days on yellowkey   MLS ID: S5143538

    REDUCED by $15,000 (3.6%) on 04/04/2026

    For Sale S5143538 - 2672 DEBANY RD, KISSIMMEE, FL 34744 19 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1599
       Built: 1989   Tax: $1,423 (2025)
    Community: Mill Run Unit 6
    Single Family


    Estimated Monthly Payment: $2,310 (change assumption)
    Mortgage ($2,192) + Taxes in 2025 ($119)


    Taxes:$1,423

    Elementary School: Mill Creek Elem (K 5)

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Denn John Middle


  • 627 WOODLAND CREEK BLVD, KISSIMMEE, FL 34744

    $469,90018 Days on yellowkey   MLS ID: O6392189

    For Sale O6392189 - 627 WOODLAND CREEK BLVD, KISSIMMEE, FL 34744 47 photos

    Bed: 4   Bath: 2.5   Gar: 3
    Liv Area Sq Ft: 2846
       Built: 2005
    Monthly Fee: $41
       Tax: $3,538 (2025)
    Community: Woodland Creek
    Single Family


    Estimated Monthly Payment: $2,911 (change assumption)
    Mortgage ($2,575) + Fees ($41) + Taxes in 2025 ($295)


    Taxes:$3,538

    Elementary School: Mill Creek Elem (K 5)

    High School: Osceola High School

    Tax Year: 2025

    Middle School: Denn John Middle


  • 1595 SHADY OAK DR, KISSIMMEE, FL 34744

    $457,00039 Days on yellowkey   MLS ID: S5144261

    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: $2,900 (change assumption)
    Mortgage ($2,504) + Taxes in 2025 ($396)


    Taxes:$4,757

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1839 GOOD NEIGHBOR LOOP, KISSIMMEE, FL 34744

    $475,000262 Days on yellowkey   MLS ID: O6328214

    For Sale O6328214 - 1839 GOOD NEIGHBOR LOOP, KISSIMMEE, FL 34744 44 photos

    Bed: 4   Bath: 4.0
    Liv Area Sq Ft: 2717
       Built: 2021
    Monthly Fee: $10
       Tax: $9,250 (2024)
    Community: Tohoqua Ph 2
    Single Family


    Estimated Monthly Payment: $3,384 (change assumption)
    Mortgage ($2,603) + Fees ($10) + Taxes in 2024 ($771)


    Taxes:$9,250

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 1135 CHEROKEE DR, KISSIMMEE, FL 34744

    $375,99035 Days on yellowkey   MLS ID: S5144943

    For Sale S5144943 - 1135 CHEROKEE DR, KISSIMMEE, FL 34744 12 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1358
       Built: 1964   Tax: $1,014 (2025)
    Community: Osceola Acres
    Single Family


    Estimated Monthly Payment: $2,145 (change assumption)
    Mortgage ($2,060) + Taxes in 2025 ($85)


    Taxes:$1,014

    Elementary School: Mill Creek Elem (K 5)

    High School: Osceola High School

    Tax Year: 2025

    Middle School: Denn John Middle


  • 1889 RUSTIC FALLS DR, KISSIMMEE, FL 34744

    $525,000138 Days on yellowkey   MLS ID: S5138827

    For Sale S5138827 - 1889 RUSTIC FALLS DR, KISSIMMEE, FL 34744 69 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3099
       Built: 2017
    Monthly Fee: $11
       Tax: $5,957 (2024)
    Community: Kindred Ph 1C
    Single Family


    Estimated Monthly Payment: $3,384 (change assumption)
    Mortgage ($2,877) + Fees ($11) + Taxes in 2024 ($496)


    Taxes:$5,957

    Elementary School: Neptune Elementary

    High School: Gateway High School (9 12)

    Tax Year: 2024

    Middle School: Neptune Middle (6-8)


  • 1872 RUSTIC FALLS DR, KISSIMMEE, FL 34744

    $565,0003 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


  • 2602 BIRCHWOOD AVE, KISSIMMEE, FL 34744

    $467,00045 Days on yellowkey   MLS ID: O6383961

    For Sale O6383961 - 2602 BIRCHWOOD AVE, KISSIMMEE, FL 34744 34 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1393
       Built: 1989   Tax: $5,428 (2025)
    Community: Oak Hollow Ph 4
    Single Family


    Estimated Monthly Payment: $3,011 (change assumption)
    Mortgage ($2,559) + Taxes in 2025 ($452)


    Taxes:$5,428

    Elementary School: Mill Creek Elem (K 5)

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Denn John Middle


  • 2609 CLEAR NIGHT AVE, KISSIMMEE, FL 34744

    $495,140307 Days on yellowkey   MLS ID: O6314894

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

    For Sale O6314894 - 2609 CLEAR NIGHT AVE, KISSIMMEE, FL 34744 25 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1850
       Built: 2025
    Monthly Fee: $10
       Tax: $917 (2024)
    Community: Tohoqua
    Single Family


    Estimated Monthly Payment: $2,799 (change assumption)
    Mortgage ($2,713) + Fees ($10) + Taxes in 2024 ($76)


    Taxes:$917

    Elementary School: Neptune Elementary

    High School: Gateway High School (9 12)

    Tax Year: 2024

    Middle School: Neptune Middle (6-8)


  • 1714 CHERYL LN, KISSIMMEE, FL 34744

    $749,0003 Days on yellowkey   MLS ID: O6395426

    For Sale O6395426 - 1714 CHERYL LN, KISSIMMEE, FL 34744 33 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3609
       Built: 1989   Tax: $3,559 (2025)
    Community: Regal Oak Shores Unit 8
    Single Family


    Estimated Monthly Payment: $4,401 (change assumption)
    Mortgage ($4,104) + Taxes in 2025 ($297)


    Taxes:$3,559

    Elementary School: Partin Settlement Elem

    High School: Osceola High School

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 2747 KISSIMMEE BAY CIR, KISSIMMEE, FL 34744

    $599,90054 Days on yellowkey   MLS ID: S5143367

    For Sale S5143367 - 2747 KISSIMMEE BAY CIR, KISSIMMEE, FL 34744 61 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3177
       Built: 1991
    Monthly Fee: $195
       Tax: $4,193 (2025)
    Community: Kissimmee Bay
    Single Family


    Estimated Monthly Payment: $3,831 (change assumption)
    Mortgage ($3,287) + Fees ($195) + Taxes in 2025 ($349)


    Taxes:$4,193

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1941 PARTIN TERRACE RD, KISSIMMEE, FL 34744

    $520,00038 Days on yellowkey   MLS ID: O6386096

    REDUCED by $9,000 (1.7%) on 04/03/2026

    For Sale O6386096 - 1941 PARTIN TERRACE RD, KISSIMMEE, FL 34744 35 photos

    Bed: 4   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 2787
       Built: 2019
    Monthly Fee: $11
       Tax: $3,624 (2025)
    Community: Kindred 100 Rep
    Single Family


    Estimated Monthly Payment: $3,162 (change assumption)
    Mortgage ($2,849) + Fees ($11) + Taxes in 2025 ($302)


    Taxes:$3,624

    Elementary School: Neptune Elementary

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)




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.