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Homes For Sale in Kissimmee 34744 - 343 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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  • 1783 SMARTS RULE ST, KISSIMMEE, FL 34744

    $525,0005 Days on yellowkey   MLS ID: S5150485

    For Sale S5150485 - 1783 SMARTS RULE ST, KISSIMMEE, FL 34744 38 photos

    Bed: 5   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2500
       Built: 2022
    Monthly Fee: $10
       Tax: $9,191 (2025)
    Community: Tohoqua Ph 1B
    Single Family


    Estimated Monthly Payment: $3,653 (change assumption)
    Mortgage ($2,877) + Fees ($10) + Taxes in 2025 ($766)


    Taxes:$9,191

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2668 WILLOW GLEN CIR, KISSIMMEE, FL 34744

    $395,0005 Days on yellowkey   MLS ID: S5150227

    For Sale S5150227 - 2668 WILLOW GLEN CIR, KISSIMMEE, FL 34744 29 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1676
       Built: 2003
    Monthly Fee: $23
       Tax: $6,164 (2025)
    Community: Gleneagles
    Single Family


    Estimated Monthly Payment: $2,701 (change assumption)
    Mortgage ($2,164) + Fees ($23) + Taxes in 2025 ($514)


    Taxes:$6,164

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1489 TWIN VALLEY TER, KISSIMMEE, FL 34744

    $539,90066 Days on yellowkey   MLS ID: O6390966

    REDUCED by $5,000 (0.9%) on 05/23/2026

    For Sale O6390966 - 1489 TWIN VALLEY TER, KISSIMMEE, FL 34744 78 photos

    Bed: 5   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2674
       Built: 2017
    Monthly Fee: $11
       Tax: $7,067 (2025)
    Community: Kindred Ph 1A & 1B
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,558 (change assumption)
    Mortgage ($2,958) + Fees ($11) + Taxes in 2025 ($589)


    Taxes:$7,067

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 3044 CAMINO REAL DR S, KISSIMMEE, FL 34744

    $489,00023 Days on yellowkey   MLS ID: O6406104

    For Sale O6406104 - 3044 CAMINO REAL DR S, KISSIMMEE, FL 34744 35 photos

    Bed: 5   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2264
       Built: 2005
    Monthly Fee: $160
       Tax: $5,505 (2025)
    Community: Villa Sol Ph 2 Village 3
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,298 (change assumption)
    Mortgage ($2,679) + Fees ($160) + Taxes in 2025 ($459)


    Taxes:$5,505

    Elementary School: Cypress Elem (K 6)

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Parkway Middle


  • 1740 NEPTUNE RD, KISSIMMEE, FL 34744

    $435,000115 Days on yellowkey   MLS ID: O6379685

    For Sale O6379685 - 1740 NEPTUNE RD, KISSIMMEE, FL 34744 49 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 2013
       Built: 1966   Tax: $1,925 (2025)
    Community: Neptune Shores 1
    Single Family


    Estimated Monthly Payment: $2,544 (change assumption)
    Mortgage ($2,384) + Taxes in 2025 ($160)


    Taxes:$1,925

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 237 STRATHMORE CIR, KISSIMMEE, FL 34744

    $435,00026 Days on yellowkey   MLS ID: O6403214

    For Sale O6403214 - 237 STRATHMORE CIR, KISSIMMEE, FL 34744 55 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2278
       Built: 1999
    Monthly Fee: $18
       Tax: $4,632 (2025)
    Community: Remington Ph 1 Tr B
    Single Family


    Estimated Monthly Payment: $2,787 (change assumption)
    Mortgage ($2,384) + Fees ($18) + Taxes in 2025 ($386)


    Taxes:$4,632

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2754 CALLAWAY LN, KISSIMMEE, FL 34744

    $420,000131 Days on yellowkey   MLS ID: S5141838

    0 Days Off yellowkey (back on 5/7/2026)

    For Sale S5141838 - 2754 CALLAWAY LN, KISSIMMEE, FL 34744 50 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2513
       Built: 2004
    Monthly Fee: $78
       Tax: $6,917 (2025)
    Community: Remington Prcl M1
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,956 (change assumption)
    Mortgage ($2,301) + Fees ($78) + Taxes in 2025 ($576)


    Taxes:$6,917

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 3570 SOUTHERN CROSS LOOP, KISSIMMEE, FL 34744

    $400,000296 Days on yellowkey   MLS ID: O6333789

    INCREASED by $1,000 (0.3%) on 04/08/2026

    For Sale O6333789 - 3570 SOUTHERN CROSS LOOP, KISSIMMEE, FL 34744 36 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1554
       Built: 2018
    Monthly Fee: $118
       Tax: $3,192 (2024)
    Community: East Lake Preserve
    Single Family


    Estimated Monthly Payment: $2,576 (change assumption)
    Mortgage ($2,192) + Fees ($118) + Taxes in 2024 ($266)


    Taxes:$3,192

    Elementary School: East Lake Elementary-OS

    High School: Tohopekaliga High School

    Tax Year: 2024

    Middle School: Narcoossee Middle


  • 1503 OAK RESERVE DR, KISSIMMEE, FL 34744

    $440,000100 Days on yellowkey   MLS ID: S5144250

    REDUCED by $5,000 (1.1%) on 04/22/2026

    For Sale S5144250 - 1503 OAK RESERVE DR, KISSIMMEE, FL 34744 34 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1846
       Built: 2022   Tax: $7,738 (2025)
    Community: Kindred Ph 2C & 2D
    Single Family


    Estimated Monthly Payment: $3,056 (change assumption)
    Mortgage ($2,411) + Taxes in 2025 ($645)


    Taxes:$7,738

    Elementary School: Neptune Elementary

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: St. Cloud Middle (6-8)


  • 1767 SMARTS RULE ST, KISSIMMEE, FL 34744

    $509,90020 Days on yellowkey   MLS ID: S5149626

    For Sale S5149626 - 1767 SMARTS RULE ST, KISSIMMEE, FL 34744 38 photos

    Bed: 5   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2764
       Built: 2022
    Monthly Fee: $1
       Tax: $7,949 (2024)
    Community: Tohoqua Ph 1B
    Single Family


    Estimated Monthly Payment: $3,457 (change assumption)
    Mortgage ($2,794) + Fees ($1) + Taxes in 2024 ($662)


    Taxes:$7,949

    Elementary School: Neptune Elementary

    High School: Gateway High School (9 12)

    Tax Year: 2024

    Middle School: Neptune Middle (6-8)


  • 710 E JACKSON ST, KISSIMMEE, FL 34744

    $320,00015 Days on yellowkey   MLS ID: S5149877

    For Sale S5149877 - 710 E JACKSON ST, KISSIMMEE, FL 34744 31 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1338
       Built: 1957   Tax: $2,295 (2025)
    Community: Michigan Terrace
    Single Family


    Estimated Monthly Payment: $1,945 (change assumption)
    Mortgage ($1,753) + Taxes in 2025 ($191)


    Taxes:$2,295

    Elementary School: Kissimmee Elem

    High School: Osceola High School

    Tax Year: 2025

    Middle School: Denn John Middle


  • KISSIMMEE, FL 34744

    $327,00078 Days on yellowkey   MLS ID: O6388756

    2 Days Off yellowkey (back on 5/24/2026)

    REDUCED by $22,000 (6.3%) on 04/22/2026

    For Sale O6388756 - KISSIMMEE, FL 34744 1 photos

    Bed: 4   Bath: 2.0
    Liv Area Sq Ft: 1792
       Built: 1982   Tax: $3,556 (2025)
    Community: Kissimmee Heights
    Single Family


    Estimated Monthly Payment: $2,088 (change assumption)
    Mortgage ($1,792) + Taxes in 2025 ($296)


    Taxes:$3,556

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1211 LEHIGH ST, KISSIMMEE, FL 34744

    $364,90054 Days on yellowkey   MLS ID: S5147242

    REDUCED by $5,000 (1.4%) on 05/07/2026

    For Sale S5147242 - 1211 LEHIGH ST, KISSIMMEE, FL 34744 22 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1685
       Built: 1960   Tax: $5,105 (2025)
    Community: Johnston Park Rep
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,425 (change assumption)
    Mortgage ($1,999) + Taxes in 2025 ($425)


    Taxes:$5,105

    Elementary School: Mill Creek Elem (K 5)

    High School: Osceola High School

    Tax Year: 2025

    Middle School: Parkway Middle


  • 2733 SERENITY MEADOW DRIVE, KISSIMMEE, FL 34744

    $392,01060 Days on yellowkey   MLS ID: O6395315

    For Sale O6395315 - 2733 SERENITY MEADOW DRIVE, KISSIMMEE, FL 34744 33 photos

    Bed: 2   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1670
       Built: 2025
    Monthly Fee: $136
       Tax: $3,086 (2025)
    Community: Tohoqua Reserve
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,541 (change assumption)
    Mortgage ($2,148) + Fees ($136) + Taxes in 2025 ($257)


    Taxes:$3,086

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2035 SPRING SHOWER CIR, KISSIMMEE, FL 34744

    $424,390135 Days on yellowkey   MLS ID: O6374311

    REDUCED by $26,150 (5.8%) on 04/08/2026

    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
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,704 (change assumption)
    Mortgage ($2,325) + Fees ($128) + Taxes in 2025 ($251)


    Taxes:$3,007

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1433 RIVERBOAT DR, KISSIMMEE, FL 34744

    $380,000226 Days on yellowkey   MLS ID: G5103345

    INCREASED by $5,000 (1.3%) on 04/15/2026

    For Sale G5103345 - 1433 RIVERBOAT DR, KISSIMMEE, FL 34744 44 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1846
       Built: 2021
    Monthly Fee: $11
       Tax: $7,119 (2024)
    Community: Kindred Ph 1
    Single Family


    Estimated Monthly Payment: $2,686 (change assumption)
    Mortgage ($2,082) + Fees ($11) + Taxes in 2024 ($593)


    Taxes:$7,119

    Elementary School: Neptune Elementary

    High School: Gateway High School (9 12)

    Tax Year: 2024

    Middle School: Neptune Middle (6-8)


  • 155 THORNBURY DR, KISSIMMEE, FL 34744

    $375,00016 Days on yellowkey   MLS ID: L4961841

    1 Days Off yellowkey (back on 5/17/2026)

    For Sale L4961841 - 155 THORNBURY DR, KISSIMMEE, FL 34744 43 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1642
       Built: 2002
    Monthly Fee: $14
       Tax: $6,077 (2025)
    Community: Remington Prcl H Ph 2
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $2,575 (change assumption)
    Mortgage ($2,055) + Fees ($14) + Taxes in 2025 ($506)


    Taxes:$6,077

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1541 AMHERST LN, KISSIMMEE, FL 34744

    $405,000222 Days on yellowkey   MLS ID: O6354005

    REDUCED by $25,000 (5.8%) on 05/21/2026

    For Sale O6354005 - 1541 AMHERST LN, KISSIMMEE, FL 34744 26 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2002
       Built: 1989   Tax: $1,317 (2024)
    Community: Oak Hollow Ph 4
    Single Family


    Estimated Monthly Payment: $2,329 (change assumption)
    Mortgage ($2,219) + Taxes in 2024 ($110)


    Taxes:$1,317

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 4405 BISCAYNE BREEZE WAY, KISSIMMEE, FL 34744

    $475,00049 Days on yellowkey   MLS ID: O6398072

    REDUCED by $10,000 (2.1%) on 04/28/2026

    For Sale O6398072 - 4405 BISCAYNE BREEZE WAY, KISSIMMEE, FL 34744 24 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2601
       Built: 2011
    Monthly Fee: $111
       Tax: $4,260 (2025)
    Community: North Point Ph 1A
    Single Family


    Estimated Monthly Payment: $3,069 (change assumption)
    Mortgage ($2,603) + Fees ($111) + Taxes in 2025 ($355)


    Taxes:$4,260

    Elementary School: East Lake Elem

    High School: Tohopekaliga High School

    Tax Year: 2025

    Middle School: Narcoossee Middle


  • 2579 RELAXING LN, KISSIMMEE, FL 34744

    $394,90023 Days on yellowkey   MLS ID: S5149255

    REDUCED by $5,000 (1.3%) on 05/21/2026

    For Sale S5149255 - 2579 RELAXING LN, KISSIMMEE, FL 34744 37 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1755
       Built: 2023
    Monthly Fee: $147
       Tax: $5,861 (2025)
    Community: Tohoqua Ph 3
    Townhouse


    Estimated Monthly Payment: $2,799 (change assumption)
    Mortgage ($2,164) + Fees ($147) + Taxes in 2025 ($488)


    Taxes:$5,861

    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.