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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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  • 1624 BARBERRY DR, KISSIMMEE, FL 34744

    $559,9901 Day 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

    $399,900327 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

    $355,000128 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

    $429,50061 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

    $319,000137 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

    $320,000499 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

    $449,000153 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

    $574,99940 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)


  • 1001 LA MIRADA CT, KISSIMMEE, FL 34744

    $363,000100 Days on yellowkey   MLS ID: O6391089

    For Sale O6391089 - 1001 LA MIRADA CT, KISSIMMEE, FL 34744 16 photos

    Bed: 4   Bath: 2.5   Gar: 1
    Liv Area Sq Ft: 1626
       Built: 2021   Tax: $3,315 (2025)
    Community: Lago Buendia Ph 1
    Townhouse


    Estimated Monthly Payment: $2,265 (change assumption)
    Mortgage ($1,989) + Taxes in 2025 ($276)


    Taxes:$3,315

    Elementary School: Partin Settlement Elem

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 2058 WALNUT CREEK DR, KISSIMMEE, FL 34744

    $399,99013 Days on yellowkey   MLS ID: O6416156

    For Sale O6416156 - 2058 WALNUT CREEK DR, KISSIMMEE, FL 34744 48 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1614
       Built: 2025
    Monthly Fee: $11
       Tax: $3,684 (2025)
    Community: Kindred Ph 3B 3C & 3D
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,510 (change assumption)
    Mortgage ($2,192) + Fees ($11) + Taxes in 2025 ($307)


    Taxes:$3,684

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 4020 SUNNY DAY WAY, KISSIMMEE, FL 34744

    $419,90043 Days on yellowkey   MLS ID: S5149650

    REDUCED by $10,000 (2.3%) on 06/23/2026

    For Sale S5149650 - 4020 SUNNY DAY WAY, KISSIMMEE, FL 34744 34 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2148
       Built: 2006
    Monthly Fee: $83
       Tax: $5,436 (2025)
    Community: Turnberry Reserve Unit 1
    Single Family


    Estimated Monthly Payment: $2,837 (change assumption)
    Mortgage ($2,301) + Fees ($83) + Taxes in 2025 ($453)


    Taxes:$5,436

    Elementary School: East Lake Elementary-OS

    High School: Tohopekaliga High School

    Tax Year: 2025

    Middle School: Narcoossee Middle


  • 1491 AUGUST GRAY DR, KISSIMMEE, FL 34744

    $419,90076 Days on yellowkey   MLS ID: O6397176

    REDUCED by $10,100 (2.3%) on 06/23/2026

    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: $2,526 (change assumption)
    Mortgage ($2,301) + 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)


  • 2352 ROSS ST, KISSIMMEE, FL 34744

    $315,000370 Days on yellowkey   MLS ID: O6320029

    4 Days Off yellowkey (back on 6/1/2026)

    For Sale O6320029 - 2352 ROSS ST, KISSIMMEE, FL 34744 5 photos

    Bed: 3   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1330
       Built: 2025   Tax: $608 (2024)
    Community: Gilchrist Add To Kissimmee
    Single Family


    Estimated Monthly Payment: $1,777 (change assumption)
    Mortgage ($1,726) + Taxes in 2024 ($51)


    Taxes:$608

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 945 TRAMELLS TRL, KISSIMMEE, FL 34744

    $398,90034 Days on yellowkey   MLS ID: S5150165

    REDUCED by $1,000 (0.3%) on 06/17/2026

    For Sale S5150165 - 945 TRAMELLS TRL, KISSIMMEE, FL 34744 36 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2014
       Built: 2006
    Monthly Fee: $14
       Tax: $3,991 (2025)
    Community: Remington Prcl O
    Single Family


    Estimated Monthly Payment: $2,532 (change assumption)
    Mortgage ($2,186) + Fees ($14) + Taxes in 2025 ($333)


    Taxes:$3,991

    Elementary School: Partin Settlement Elem

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 104 CLUB VILLAS LN #N/A, KISSIMMEE, FL 34744

    $299,0002 Days on yellowkey   MLS ID: G5114128

    For Sale G5114128 - 104 CLUB VILLAS LN #N/A, KISSIMMEE, FL 34744 30 photos

    Bed: 2   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1417
       Built: 2003
    Monthly Fee: $312
       Tax: $2,867 (2025)
    Community: Remington Ph 1 Tr A
    Condo


    Estimated Monthly Payment: $2,189 (change assumption)
    Mortgage ($1,638) + Fees ($312) + Taxes in 2025 ($239)


    Taxes:$2,867

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 3193 TOHO CT, KISSIMMEE, FL 34744

    $529,900259 Days on yellowkey   MLS ID: O6350540

    For Sale O6350540 - 3193 TOHO CT, KISSIMMEE, FL 34744 33 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


  • 2540 WINNERS CIR, KISSIMMEE, FL 34744

    $689,000125 Days on yellowkey   MLS ID: O6382446

    REDUCED by $10,000 (1.4%) on 06/23/2026

    For Sale O6382446 - 2540 WINNERS CIR, KISSIMMEE, FL 34744 52 photos

    Bed: 4   Bath: 4.5   Gar: 4
    Liv Area Sq Ft: 3246
       Built: 2000   Tax: $3,688 (2025)
    Community: Winners Park
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,083 (change assumption)
    Mortgage ($3,775) + Taxes in 2025 ($307)


    Taxes:$3,688

    Elementary School: East Lake Elem

    High School: Tohopekaliga High School

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 2602 BIRCHWOOD AVE, KISSIMMEE, FL 34744

    $400,000124 Days on yellowkey   MLS ID: O6383961

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

    REDUCED by $35,000 (8.0%) on 05/14/2026

    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: $2,644 (change assumption)
    Mortgage ($2,192) + 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


  • 1778 GOOD NEIGHBOR LOOP, KISSIMMEE, FL 34744

    $470,000122 Days on yellowkey   MLS ID: O6384377

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

    For Sale O6384377 - 1778 GOOD NEIGHBOR LOOP, KISSIMMEE, FL 34744 32 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2133
       Built: 2022
    Monthly Fee: $7
       Tax: $7,640 (2025)
    Community: Tohoqua Ph 2
    Single Family


    Estimated Monthly Payment: $3,219 (change assumption)
    Mortgage ($2,575) + Fees ($7) + Taxes in 2025 ($637)


    Taxes:$7,640

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1150 STROUPE RD, KISSIMMEE, FL 34744

    $450,00039 Days on yellowkey   MLS ID: S5149769

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

    For Sale S5149769 - 1150 STROUPE RD, KISSIMMEE, FL 34744 65 photos

    Bed: 3   Bath: 3.0
    Liv Area Sq Ft: 2128
       Built: 1973   Tax: $2,257 (2025)
    Community: Midway City Townsite
    Single Family


    Estimated Monthly Payment: $2,654 (change assumption)
    Mortgage ($2,466) + Taxes in 2025 ($188)


    Taxes:$2,257

    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.