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Homes For Sale in Kissimmee 34744 - 376 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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  • 2627 CLEAR NIGHT AVENUE, KISSIMMEE, FL 34744

    $599,11046 Days on yellowkey   MLS ID: O6412075

    REDUCED by $37,000 (5.8%) on 07/13/2026

    For Sale O6412075 - 2627 CLEAR NIGHT AVENUE, KISSIMMEE, FL 34744 43 photos

    Bed: 5   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 3598
       Built: 2026
    Monthly Fee: $42
       Tax: $1,329 (2025)
    Community: Tohoqua
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,435 (change assumption)
    Mortgage ($3,283) + Fees ($42) + Taxes in 2025 ($111)


    Taxes:$1,329

    Elementary School: Neptune Elementary

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 2735 SCARBOROUGH DR, KISSIMMEE, FL 34744

    $515,00092 Days on yellowkey   MLS ID: S5147642

    REDUCED by $15,000 (2.8%) on 05/20/2026

    For Sale S5147642 - 2735 SCARBOROUGH DR, KISSIMMEE, FL 34744 41 photos

    Bed: 5   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 2930
       Built: 1996
    Monthly Fee: $13
       Tax: $6,439 (2025)
    Community: Remington Ph 1 Tr E
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $3,371 (change assumption)
    Mortgage ($2,822) + Fees ($13) + Taxes in 2025 ($537)


    Taxes:$6,439

    Elementary School: Partin Settlement Elem

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 2155 SOUTHBURY DRIVE, KISSIMMEE, FL 34744

    $370,00021 Days on yellowkey   MLS ID: O6419423

    REDUCED by $26,490 (6.7%) on 07/13/2026

    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: $2,314 (change assumption)
    Mortgage ($2,027) + 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

    $339,19021 Days on yellowkey   MLS ID: O6419342

    REDUCED by $20,000 (5.6%) on 07/13/2026

    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: $2,120 (change assumption)
    Mortgage ($1,859) + 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)


  • 2122 SOUTHBURY DR, KISSIMMEE, FL 34744

    $365,49024 Days on yellowkey   MLS ID: O6418725

    REDUCED by $21,000 (5.4%) on 07/13/2026

    For Sale O6418725 - 2122 SOUTHBURY DR, KISSIMMEE, FL 34744 27 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1770
       Built: 2026
    Monthly Fee: $126
       Tax: $1,920 (2025)
    Community: Tohoqua
    Spa: No

    Townhouse


    Estimated Monthly Payment: $2,289 (change assumption)
    Mortgage ($2,003) + Fees ($126) + 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)


  • 2602 LOLA LN, KISSIMMEE, FL 34744

    $487,45132 Days on yellowkey   MLS ID: O6415813

    3 Days Off yellowkey (back on 7/13/2026)

    For Sale O6415813 - 2602 LOLA LN, KISSIMMEE, FL 34744 5 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2059
       Built: 2025
    Monthly Fee: $167
       Tax: $434 (2025)
    Community: Hilliard Ridg
    Single Family


    Estimated Monthly Payment: $2,874 (change assumption)
    Mortgage ($2,671) + Fees ($167) + Taxes in 2025 ($36)


    Taxes:$434

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1422 PATRICIA ST, KISSIMMEE, FL 34744

    $399,00021 Days on yellowkey   MLS ID: O6419136

    REDUCED by $6,000 (1.5%) on 07/13/2026

    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: $2,677 (change assumption)
    Mortgage ($2,186) + Taxes in 2025 ($491)


    Taxes:$5,892

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 3100 CONRAD CT, KISSIMMEE, FL 34744

    $600,0006 Days on yellowkey   MLS ID: O6423286

    For Sale O6423286 - 3100 CONRAD CT, KISSIMMEE, FL 34744 56 photos

    Bed: 4   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 2824
       Built: 2005
    Monthly Fee: $53
       Tax: $6,888 (2025)
    Community: Fells Cove Unit 2 Ph 1
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,915 (change assumption)
    Mortgage ($3,288) + Fees ($53) + Taxes in 2025 ($574)


    Taxes:$6,888

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2728 PORTCHESTER CT, KISSIMMEE, FL 34744

    $389,900426 Days on yellowkey   MLS ID: S5126915

    REDUCED by $5,000 (1.3%) on 07/13/2026

    For Sale S5126915 - 2728 PORTCHESTER CT, KISSIMMEE, FL 34744 16 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 1960
       Built: 2005
    Monthly Fee: $7
       Tax: $6,060 (2024)
    Community: Somerset
    Single Family


    Estimated Monthly Payment: $2,648 (change assumption)
    Mortgage ($2,136) + Fees ($7) + Taxes in 2024 ($505)


    Taxes:$6,060

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 1527 GANTS CIR, KISSIMMEE, FL 34744

    $574,99960 Days on yellowkey   MLS ID: O6407722

    0 Days Off yellowkey (back on 7/13/2026)

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

    For Sale O6407722 - 1527 GANTS CIR, KISSIMMEE, FL 34744 46 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)


  • 1495 SKYLINE DR, KISSIMMEE, FL 34744

    $472,900130 Days on yellowkey   MLS ID: S5145209

    REDUCED by $2,000 (0.4%) on 07/13/2026

    For Sale S5145209 - 1495 SKYLINE DR, KISSIMMEE, FL 34744 50 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2094
       Built: 1973
    Monthly Fee: $16
       Tax: $5,404 (2025)
    Community: Harbour Oaks Unit 1
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,057 (change assumption)
    Mortgage ($2,591) + Fees ($16) + Taxes in 2025 ($450)


    Taxes:$5,404

    Elementary School: Partin Settlement Elem

    High School: Osceola High School

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 1336 E LAKE SHORE BLVD, KISSIMMEE, FL 34744

    $354,99982 Days on yellowkey   MLS ID: A4691089

    0 Days Off yellowkey (back on 7/13/2026)

    REDUCED by $5,000 (1.4%) on 05/06/2026

    For Sale A4691089 - 1336 E LAKE SHORE BLVD, KISSIMMEE, FL 34744 19 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1450
       Built: 1963   Tax: $2,633 (2025)
    Community: Ocean Gulf Estates Sec 1
    Single Family


    Estimated Monthly Payment: $2,165 (change assumption)
    Mortgage ($1,945) + Taxes in 2025 ($219)


    Taxes:$2,633

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1556 HEATHER WAY, KISSIMMEE, FL 34744

    $320,00074 Days on yellowkey   MLS ID: O6404040

    REDUCED by $20,000 (5.9%) on 05/30/2026

    For Sale O6404040 - 1556 HEATHER WAY, KISSIMMEE, FL 34744 5 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1577
       Built: 1976   Tax: $3,121 (2025)
    Community: Heather Oaks
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,013 (change assumption)
    Mortgage ($1,753) + Taxes in 2025 ($260)


    Taxes:$3,121

    Elementary School: Mill Creek Elem (K 5)

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Denn John Middle


  • 3012 VILLA PRECIOSA DR, KISSIMMEE, FL 34744

    $425,000345 Days on yellowkey   MLS ID: O6310848

    For Sale O6310848 - 3012 VILLA PRECIOSA DR, KISSIMMEE, FL 34744 43 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2074
       Built: 2004
    Monthly Fee: $160
       Tax: $4,927 (2024)
    Community: Villa Sol Ph 1 Village 5
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,899 (change assumption)
    Mortgage ($2,329) + Fees ($160) + Taxes in 2024 ($411)


    Taxes:$4,927

    Elementary School: East Lake Elementary-OS

    High School: Tohopekaliga High School

    Tax Year: 2024

    Middle School: Neptune Middle (6-8)


  • 109 E BASS ST, KISSIMMEE, FL 34744

    $234,50025 Days on yellowkey   MLS ID: O6418571

    REDUCED by $2,500 (1.1%) on 07/06/2026

    For Sale O6418571 - 109 E BASS ST, KISSIMMEE, FL 34744 20 photos

    Bed: 2   Bath: 1.0
    Liv Area Sq Ft: 638
       Built: 1910   Tax: $1,667 (2025)
    Community: Nathan C Bryans
    Single Family


    Estimated Monthly Payment: $1,424 (change assumption)
    Mortgage ($1,285) + Taxes in 2025 ($139)


    Taxes:$1,667

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 4424 SILVER CREEK ST, KISSIMMEE, FL 34744

    $449,9905 Days on yellowkey   MLS ID: O6423965

    REDUCED by $20,000 (4.3%) on 07/13/2026

    For Sale O6423965 - 4424 SILVER CREEK ST, KISSIMMEE, FL 34744 29 photos

    Bed: 5   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2370
       Built: 2019
    Monthly Fee: $123
       Tax: $6,332 (2025)
    Community: Creekside At Boggy Creek Ph 1
    Single Family


    Estimated Monthly Payment: $3,116 (change assumption)
    Mortgage ($2,466) + Fees ($123) + Taxes in 2025 ($528)


    Taxes:$6,332

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1002 BELVOIR DR, KISSIMMEE, FL 34744

    $515,00026 Days on yellowkey   MLS ID: O6417742

    1 Days Off yellowkey (back on 7/13/2026)

    REDUCED by $10,000 (1.9%) on 07/08/2026

    For Sale O6417742 - 1002 BELVOIR DR, KISSIMMEE, FL 34744 87 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3460
       Built: 2005
    Monthly Fee: $13
       Tax: $7,923 (2025)
    Community: Somerset
    Single Family


    Estimated Monthly Payment: $3,495 (change assumption)
    Mortgage ($2,822) + Fees ($13) + Taxes in 2025 ($660)


    Taxes:$7,923

    Elementary School: Partin Settlement Elem

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Parkway Middle


  • 1578 CONTENTMENT LOOP, KISSIMMEE, FL 34744

    $511,00056 Days on yellowkey   MLS ID: S5150200

    For Sale S5150200 - 1578 CONTENTMENT LOOP, KISSIMMEE, FL 34744 16 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2113
       Built: 2023
    Monthly Fee: $7
       Tax: $6,094 (2025)
    Community: Tohoqua Ph 3
    Single Family


    Estimated Monthly Payment: $3,315 (change assumption)
    Mortgage ($2,800) + Fees ($7) + Taxes in 2025 ($508)


    Taxes:$6,094

    Elementary School: Island Village Elementary School

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Narcoossee Middle


  • 1957 RED CANYON DR, KISSIMMEE, FL 34744

    $460,00056 Days on yellowkey   MLS ID: O6409138

    For Sale O6409138 - 1957 RED CANYON DR, KISSIMMEE, FL 34744 55 photos

    Bed: 5   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2469
       Built: 2016
    Monthly Fee: $11
       Tax: $8,263 (2025)
    Community: Kindred Ph 1A & 1B
    Single Family


    Estimated Monthly Payment: $3,220 (change assumption)
    Mortgage ($2,520) + Fees ($11) + Taxes in 2025 ($689)


    Taxes:$8,263

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1777 WALNUT CREEK DR, KISSIMMEE, FL 34744

    $444,500113 Days on yellowkey   MLS ID: O6390965

    REDUCED by $5,000 (1.1%) on 07/12/2026

    For Sale O6390965 - 1777 WALNUT CREEK DR, KISSIMMEE, FL 34744 76 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2339
       Built: 2023
    Monthly Fee: $11
       Tax: $3,358 (2025)
    Community: Kindred Ph 3A
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,726 (change assumption)
    Mortgage ($2,436) + Fees ($11) + Taxes in 2025 ($280)


    Taxes:$3,358

    Elementary School: None

    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.