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Homes For Sale in Kissimmee 34744 - 371 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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  • 2418 BROOKSIDE AVE, KISSIMMEE, FL 34744

    $375,00015 Days on yellowkey   MLS ID: O6415743

    0 Days Off yellowkey (back on 6/24/2026)

    For Sale O6415743 - 2418 BROOKSIDE AVE, KISSIMMEE, FL 34744 36 photos

    Bed: 4   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1807
       Built: 1979   Tax: $4,934 (2025)
    Community: Whisper Woods
    Single Family


    Estimated Monthly Payment: $2,466 (change assumption)
    Mortgage ($2,055) + Taxes in 2025 ($411)


    Taxes:$4,934

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1895 SPRING SHOWER CIR, KISSIMMEE, FL 34744

    $320,00067 Days on yellowkey   MLS ID: S5148149

    3 Days Off yellowkey (back on 5/22/2026)

    REDUCED by $19,000 (5.6%) on 05/16/2026

    For Sale S5148149 - 1895 SPRING SHOWER CIR, KISSIMMEE, FL 34744 29 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1559
       Built: 2023
    Monthly Fee: $213
       Tax: $1,967 (2025)
    Community: Tohoqua Ph 5B
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,130 (change assumption)
    Mortgage ($1,753) + Fees ($213) + Taxes in 2025 ($164)


    Taxes:$1,967

    Elementary School: Neptune Elementary

    High School: St. Cloud High School

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 1009 CHALCEDONY ST, KISSIMMEE, FL 34744

    $325,00019 Days on yellowkey   MLS ID: O6412394

    For Sale O6412394 - 1009 CHALCEDONY ST, KISSIMMEE, FL 34744 49 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1683
       Built: 2010
    Monthly Fee: $170
       Tax: $3,128 (2025)
    Community: Amber Pointe
    Spa: No

    Townhouse


    Estimated Monthly Payment: $2,211 (change assumption)
    Mortgage ($1,781) + Fees ($170) + Taxes in 2025 ($261)


    Taxes:$3,128

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1340 SAWDUST TRL, KISSIMMEE, FL 34744

    $235,900159 Days on yellowkey   MLS ID: G5106887

    REDUCED by $4,000 (1.7%) on 06/24/2026

    For Sale G5106887 - 1340 SAWDUST TRL, KISSIMMEE, FL 34744 24 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 924
       Built: 1996   Tax: $2,377 (2025)
    Community: Marydia
    Manufactured Home


    Estimated Monthly Payment: $1,491 (change assumption)
    Mortgage ($1,293) + Taxes in 2025 ($198)


    Taxes:$2,377

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2739 SUMMER RETREAT LN, KISSIMMEE, FL 34744

    $315,00020 Days on yellowkey   MLS ID: O6412964

    0 Days Off yellowkey (back on 6/24/2026)

    REDUCED by $9,000 (2.8%) on 06/17/2026

    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: $2,400 (change assumption)
    Mortgage ($1,726) + 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


  • 1710 WOODSIDE CT, KISSIMMEE, FL 34744

    $534,900184 Days on yellowkey   MLS ID: O6369122

    REDUCED by $15,100 (2.7%) on 06/24/2026

    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: $3,134 (change assumption)
    Mortgage ($2,931) + 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)


  • 2503 HASSONITE ST, KISSIMMEE, FL 34744

    $345,000234 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


  • 1320 MILL CREEK PL, KISSIMMEE, FL 34744

    $349,0002 Days on yellowkey   MLS ID: O6419178

    For Sale O6419178 - 1320 MILL CREEK PL, KISSIMMEE, FL 34744 30 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1363
       Built: 1979   Tax: $1,731 (2025)
    Community: Sweetwood Cove
    Single Family


    Estimated Monthly Payment: $2,057 (change assumption)
    Mortgage ($1,912) + Taxes in 2025 ($144)


    Taxes:$1,731

    Elementary School: Mill Creek Elem (K 5)

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Denn John Middle


  • 1422 PATRICIA ST, KISSIMMEE, FL 34744

    $415,0002 Days on yellowkey   MLS ID: O6419136

    For Sale O6419136 - 1422 PATRICIA ST, KISSIMMEE, FL 34744 44 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1578
       Built: 2015   Tax: $5,892 (2025)
    Community: Emerald Lake Colony Unit 3
    Single Family


    Estimated Monthly Payment: $2,765 (change assumption)
    Mortgage ($2,274) + Taxes in 2025 ($491)


    Taxes:$5,892

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2155 SOUTHBURY DRIVE, KISSIMMEE, FL 34744

    $359,1902 Days on yellowkey   MLS ID: O6419423

    For Sale O6419423 - 2155 SOUTHBURY DRIVE, KISSIMMEE, FL 34744 28 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1770
       Built: 2026
    Monthly Fee: $127
       Tax: $1,920 (2025)
    Community: Tohoqua
    Spa: No

    Townhouse


    Estimated Monthly Payment: $2,255 (change assumption)
    Mortgage ($1,968) + Fees ($127) + Taxes in 2025 ($160)


    Taxes:$1,920

    Elementary School: Neptune Elementary

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 2153 SOUTHBURY DRIVE, KISSIMMEE, FL 34744

    $359,1902 Days on yellowkey   MLS ID: O6419342

    For Sale O6419342 - 2153 SOUTHBURY DRIVE, KISSIMMEE, FL 34744 24 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1553
       Built: 2026
    Monthly Fee: $127
       Tax: $1,610 (2025)
    Community: Tohoqua
    Spa: No

    Townhouse


    Estimated Monthly Payment: $2,229 (change assumption)
    Mortgage ($1,968) + Fees ($127) + 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)


  • 107 E CYPRESS ST, KISSIMMEE, FL 34744

    $154,00042 Days on yellowkey   MLS ID: S5149938

    REDUCED by $15,900 (9.4%) on 06/24/2026

    For Sale S5149938 - 107 E CYPRESS ST, KISSIMMEE, FL 34744 19 photos

    Bed: 2   Bath: 1.0
    Liv Area Sq Ft: 576
       Built: 1966   Tax: $2,111 (2025)
    Community: Robert Bass Add
    Single Family


    Estimated Monthly Payment: $1,020 (change assumption)
    Mortgage ($844) + Taxes in 2025 ($176)


    Taxes:$2,111

    Elementary School: Central Avenue Elem

    High School: Osceola High School

    Tax Year: 2025

    Middle School: Denn John Middle


  • 1624 BARBERRY DR, KISSIMMEE, FL 34744

    $559,9902 Days on yellowkey   MLS ID: S5152366

    For Sale S5152366 - 1624 BARBERRY DR, KISSIMMEE, FL 34744 30 photos

    Bed: 4   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 2851
       Built: 2023
    Monthly Fee: $11
       Tax: $6,483 (2025)
    Community: Kindred Ph 2C & 2D
    Single Family


    Estimated Monthly Payment: $3,620 (change assumption)
    Mortgage ($3,068) + Fees ($11) + Taxes in 2025 ($540)


    Taxes:$6,483

    Elementary School: Neptune Elementary

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 1652 CROSS PRAIRIE PKWY, KISSIMMEE, FL 34744

    $399,900328 Days on yellowkey   MLS ID: O6326699

    For Sale O6326699 - 1652 CROSS PRAIRIE PKWY, KISSIMMEE, FL 34744 10 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2537
       Built: 2022
    Monthly Fee: $10
       Tax: $7,997 (2024)
    Community: Tohoqua Ph 2
    Single Family


    Estimated Monthly Payment: $2,868 (change assumption)
    Mortgage ($2,191) + Fees ($10) + Taxes in 2024 ($666)


    Taxes:$7,997

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 2605 PLAY HARD ALY, KISSIMMEE, FL 34744

    $355,000129 Days on yellowkey   MLS ID: S5143916

    REDUCED by $14,999 (4.1%) on 06/23/2026

    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: $2,451 (change assumption)
    Mortgage ($1,945) + 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)


  • 2604 SUMMER CLOUDS WAY, KISSIMMEE, FL 34744

    $429,50062 Days on yellowkey   MLS ID: O6401673

    REDUCED by $490 (0.1%) on 06/23/2026

    For Sale O6401673 - 2604 SUMMER CLOUDS WAY, KISSIMMEE, FL 34744 75 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2214
       Built: 2022
    Monthly Fee: $10
       Tax: $7,753 (2025)
    Community: Tohoqua Ph 4A
    Single Family


    Estimated Monthly Payment: $3,009 (change assumption)
    Mortgage ($2,353) + Fees ($10) + Taxes in 2025 ($646)


    Taxes:$7,753

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1200 TETON DR, KISSIMMEE, FL 34744

    $319,000138 Days on yellowkey   MLS ID: O6380571

    REDUCED by $10,900 (3.3%) on 06/23/2026

    For Sale O6380571 - 1200 TETON DR, KISSIMMEE, FL 34744 43 photos

    Bed: 4   Bath: 2.5
    Liv Area Sq Ft: 1969
       Built: 2008
    Monthly Fee: $164
       Tax: $2,796 (2025)
    Community: Heritage Run
    Townhouse


    Estimated Monthly Payment: $2,145 (change assumption)
    Mortgage ($1,748) + Fees ($164) + Taxes in 2025 ($233)


    Taxes:$2,796

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1542 COLONY AVE, KISSIMMEE, FL 34744

    $320,000500 Days on yellowkey   MLS ID: O6279065

    0 Days Off yellowkey (back on 6/23/2026)

    SHORT SALE O6279065 - 1542 COLONY AVE, KISSIMMEE, FL 34744 6 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1185
       Built: 1986   Tax: $3,348 (2023)
    Community: Oak Hollow Ph 3
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,032 (change assumption)
    Mortgage ($1,753) + Taxes in 2023 ($279)


    Taxes:$3,348

    Elementary School: None

    High School: None

    Tax Year: 2023

    Middle School: None


  • 2761 MICHIGAN AVE, KISSIMMEE, FL 34744

    $449,000154 Days on yellowkey   MLS ID: O6375128

    REDUCED by $10,000 (2.2%) on 04/30/2026

    For Sale O6375128 - 2761 MICHIGAN AVE, KISSIMMEE, FL 34744 27 photos

    Bed: 4   Bath: 0.0
    Liv Area Sq Ft: 1869
       Built: 1979   Tax: $7,282 (2025)
    Community: Lee Bel Park
    Apartment


    Estimated Monthly Payment: $3,067 (change assumption)
    Mortgage ($2,460) + Taxes in 2025 ($607)


    Taxes:$7,282

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1527 GANTS CIR, KISSIMMEE, FL 34744

    $574,99941 Days on yellowkey   MLS ID: O6407722

    REDUCED by $14,001 (2.4%) on 06/23/2026

    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: $3,597 (change assumption)
    Mortgage ($3,151) + 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)




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.