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Homes For Sale in Kissimmee 34744 - 340 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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  • 1519 JADEWOOD WAY, KISSIMMEE, FL 34744

    $549,00056 Days on yellowkey   MLS ID: S5147592

    INCREASED by $10,000 (1.9%) on 04/20/2026

    For Sale S5147592 - 1519 JADEWOOD WAY, KISSIMMEE, FL 34744 27 photos

    Bed: 5   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2601
       Built: 2022
    Monthly Fee: $10
       Tax: $7,660 (2025)
    Community: Kindred Ph 1
    Single Family


    Estimated Monthly Payment: $3,656 (change assumption)
    Mortgage ($3,008) + Fees ($10) + Taxes in 2025 ($638)


    Taxes:$7,660

    Elementary School: Mill Creek Elem (K 5)

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 1708 NEBRASKA AVE, KISSIMMEE, FL 34744

    $335,00047 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


  • 2275 SOUTHBURY DR, KISSIMMEE, FL 34744

    $348,79095 Days on yellowkey   MLS ID: O6386802

    For Sale O6386802 - 2275 SOUTHBURY DR, KISSIMMEE, FL 34744 24 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1553
       Built: 2026
    Monthly Fee: $130
       Tax: $1,610 (2025)
    Community: Tohoqua
    Spa: No

    Townhouse


    Estimated Monthly Payment: $2,175 (change assumption)
    Mortgage ($1,911) + Fees ($130) + Taxes in 2025 ($134)


    Taxes:$1,610

    Elementary School: Neptune Elementary

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 2213 SOUTHBURY DR, KISSIMMEE, FL 34744

    $404,990207 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

    $550,00052 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

    $345,000214 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

    $519,900111 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

    $345,000285 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

    $380,990410 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

    $149,900109 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

    $430,00057 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

    $495,50051 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


  • 2604 BLOWING BREEZE AVE, KISSIMMEE, FL 34744

    $507,000200 Days on yellowkey   MLS ID: O6360718

    2 Days Off yellowkey (back on 4/15/2026)

    For Sale O6360718 - 2604 BLOWING BREEZE AVE, KISSIMMEE, FL 34744 64 photos

    Bed: 5   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2590
       Built: 2022
    Monthly Fee: $10
       Tax: $8,552 (2024)
    Community: Tohoqua Ph 4A
    Single Family


    Estimated Monthly Payment: $3,501 (change assumption)
    Mortgage ($2,778) + Fees ($10) + Taxes in 2024 ($713)


    Taxes:$8,552

    Elementary School: Neptune Elementary

    High School: Gateway High School (9 12)

    Tax Year: 2024

    Middle School: Neptune Middle (6-8)


  • 2518 BOWMER DR, KISSIMMEE, FL 34744

    $359,900668 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


  • 1705 BRIDGETS CT, KISSIMMEE, FL 34744

    $565,00088 Days on yellowkey   MLS ID: S5145159

    REDUCED by $10,000 (1.7%) on 04/14/2026

    For Sale S5145159 - 1705 BRIDGETS CT, KISSIMMEE, FL 34744 57 photos

    Bed: 4   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 2994
       Built: 2004
    Monthly Fee: $190
       Tax: $5,502 (2025)
    Community: M3 At Kissimmee Bay
    Single Family


    Estimated Monthly Payment: $3,744 (change assumption)
    Mortgage ($3,096) + Fees ($190) + Taxes in 2025 ($459)


    Taxes:$5,502

    Elementary School: Partin Settlement Elem

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 2744 SERENITY MEADOW DRIVE, KISSIMMEE, FL 34744

    $439,89072 Days on yellowkey   MLS ID: O6393758

    0 Days Off yellowkey (back on 4/13/2026)

    For Sale O6393758 - 2744 SERENITY MEADOW DRIVE, KISSIMMEE, FL 34744 23 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2056
       Built: 2026
    Monthly Fee: $136
       Tax: $3,212 (2025)
    Community: Tohoqua Reserve
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,814 (change assumption)
    Mortgage ($2,410) + Fees ($136) + Taxes in 2025 ($268)


    Taxes:$3,212

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1791 SMARTS RULE ST, KISSIMMEE, FL 34744

    $510,000124 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

    $220,00081 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

    $499,000120 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

    $435,00060 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




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.