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Homes For Sale in Kissimmee 34744 - 290 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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  • 1765 BROCKRIDGE RD, KISSIMMEE, FL 34744

    $364,990217 Days on yellowkey   MLS ID: S5134833

    For Sale S5134833 - 1765 BROCKRIDGE RD, KISSIMMEE, FL 34744 45 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1690
       Built: 2018
    Monthly Fee: $11
       Tax: $5,653 (2024)
    Community: Kindred Ph 1D
    Single Family


    Estimated Monthly Payment: $2,482 (change assumption)
    Mortgage ($2,000) + Fees ($11) + Taxes in 2024 ($471)


    Taxes:$5,653

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 2744 SERENITY MEADOW DRIVE, KISSIMMEE, FL 34744

    $439,89029 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


  • 2396 VOLUNTEER AVE, KISSIMMEE, FL 34744

    $530,000230 Days on yellowkey   MLS ID: O6341462

    For Sale O6341462 - 2396 VOLUNTEER AVE, KISSIMMEE, FL 34744 36 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2133
       Built: 2021
    Monthly Fee: $10
       Tax: $8,606 (2024)
    Community: Tohoqua Ph 2
    Single Family


    Estimated Monthly Payment: $3,631 (change assumption)
    Mortgage ($2,904) + Fees ($10) + Taxes in 2024 ($717)


    Taxes:$8,606

    Elementary School: Neptune Elementary

    High School: Gateway High School (9 12)

    Tax Year: 2024

    Middle School: Neptune Middle (6-8)


  • 1945 SPRING SHOWER CIRCLE, KISSIMMEE, FL 34744

    $419,98023 Days on yellowkey   MLS ID: O6395124

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

    For Sale O6395124 - 1945 SPRING SHOWER CIRCLE, KISSIMMEE, FL 34744 23 photos

    Bed: 2   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2185
       Built: 2026
    Monthly Fee: $136
       Tax: $3,427 (2025)
    Community: Tohoqua Reserve
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,723 (change assumption)
    Mortgage ($2,301) + Fees ($136) + Taxes in 2025 ($286)


    Taxes:$3,427

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1510 GANTS CIR, KISSIMMEE, FL 34744

    $511,50090 Days on yellowkey   MLS ID: O6376374

    REDUCED by $2,500 (0.5%) on 04/13/2026

    For Sale O6376374 - 1510 GANTS CIR, KISSIMMEE, FL 34744 54 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2025
       Built: 2002
    Monthly Fee: $75
       Tax: $3,603 (2025)
    Community: Ashley Cove Unit 3
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,178 (change assumption)
    Mortgage ($2,803) + Fees ($75) + Taxes in 2025 ($300)


    Taxes:$3,603

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1214 CHEROKEE CT, KISSIMMEE, FL 34744

    $289,00017 Days on yellowkey   MLS ID: O6390987

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

    For Sale O6390987 - 1214 CHEROKEE CT, KISSIMMEE, FL 34744 9 photos

    Bed: 2   Bath: 1.0
    Liv Area Sq Ft: 1600
       Built: 1976   Tax: $3,877 (2025)
    Community: Oak Grove East
    Single Family


    Estimated Monthly Payment: $1,907 (change assumption)
    Mortgage ($1,584) + Taxes in 2025 ($323)


    Taxes:$3,877

    Elementary School: Mill Creek Elem (K 5)

    High School: Osceola County School for Arts

    Tax Year: 2025

    Middle School: Denn John Middle


  • 2077 WALNUT CREEK DR, KISSIMMEE, FL 34744

    $454,40036 Days on yellowkey   MLS ID: O6391693

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

    REDUCED by $4,590 (1.0%) on 04/08/2026

    For Sale O6391693 - 2077 WALNUT CREEK DR, KISSIMMEE, FL 34744 60 photos

    Bed: 5   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2447
       Built: 2025
    Monthly Fee: $11
       Tax: $3,684 (2025)
    Community: Kindred Ph 3B 3C & 3D
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,808 (change assumption)
    Mortgage ($2,490) + Fees ($11) + Taxes in 2025 ($307)


    Taxes:$3,684

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1914 DAMON AVE, KISSIMMEE, FL 34744

    $309,00016 Days on yellowkey   MLS ID: O6396516

    For Sale O6396516 - 1914 DAMON AVE, KISSIMMEE, FL 34744 25 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1385
       Built: 1972   Tax: $3,300 (2025)
    Community: Kissimmee Heights
    Single Family


    Estimated Monthly Payment: $1,968 (change assumption)
    Mortgage ($1,693) + Taxes in 2025 ($275)


    Taxes:$3,300

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1603 BARBERRY DR, KISSIMMEE, FL 34744

    $450,00011 Days on yellowkey   MLS ID: O6398483

    For Sale O6398483 - 1603 BARBERRY DR, KISSIMMEE, FL 34744 18 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1846
       Built: 2023
    Monthly Fee: $11
       Tax: $7,712 (2025)
    Community: Kindred Ph 2C & 2D
    Single Family


    Estimated Monthly Payment: $3,119 (change assumption)
    Mortgage ($2,466) + Fees ($11) + Taxes in 2025 ($643)


    Taxes:$7,712

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 4419 AZURE ISLE WAY, KISSIMMEE, FL 34744

    $479,99048 Days on yellowkey   MLS ID: O6387844

    For Sale O6387844 - 4419 AZURE ISLE WAY, KISSIMMEE, FL 34744 39 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1941
       Built: 2013
    Monthly Fee: $110
       Tax: $3,787 (2025)
    Community: North Point Ph 1B
    Single Family


    Estimated Monthly Payment: $3,056 (change assumption)
    Mortgage ($2,630) + Fees ($110) + Taxes in 2025 ($316)


    Taxes:$3,787

    Elementary School: East Lake Elem

    High School: Tohopekaliga High School

    Tax Year: 2025

    Middle School: Narcoossee Middle


  • 4405 BISCAYNE BREEZE WAY, KISSIMMEE, FL 34744

    $485,00012 Days on yellowkey   MLS ID: O6398072

    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: $3,123 (change assumption)
    Mortgage ($2,657) + 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


  • 2672 DEBANY RD, KISSIMMEE, FL 34744

    $400,00070 Days on yellowkey   MLS ID: S5143538

    REDUCED by $15,000 (3.6%) on 04/04/2026

    For Sale S5143538 - 2672 DEBANY RD, KISSIMMEE, FL 34744 19 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1599
       Built: 1989   Tax: $1,423 (2025)
    Community: Mill Run Unit 6
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,310 (change assumption)
    Mortgage ($2,192) + Taxes in 2025 ($119)


    Taxes:$1,423

    Elementary School: Mill Creek Elem (K 5)

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Denn John Middle


  • 219 STRATHMORE CIR, KISSIMMEE, FL 34744

    $710,00078 Days on yellowkey   MLS ID: O6379060

    REDUCED by $19,999 (2.7%) on 04/06/2026

    For Sale O6379060 - 219 STRATHMORE CIR, KISSIMMEE, FL 34744 57 photos

    Bed: 5   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 3897
       Built: 1997
    Monthly Fee: $15
       Tax: $3,216 (2025)
    Community: Remington Ph 1 Tr B
    Single Family


    Estimated Monthly Payment: $4,173 (change assumption)
    Mortgage ($3,890) + Fees ($15) + Taxes in 2025 ($268)


    Taxes:$3,216

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1278 ASHER MASON AVE, KISSIMMEE, FL 34744

    $455,00060 Days on yellowkey   MLS ID: S5144373

    For Sale S5144373 - 1278 ASHER MASON AVE, KISSIMMEE, FL 34744 29 photos

    Bed: 4   Bath: 2.0   Gar: 3
    Liv Area Sq Ft: 1824
       Built: 2023
    Monthly Fee: $80
       Tax: $5,409 (2024)
    Community: Seasons At Big Sky Ph 2
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,024 (change assumption)
    Mortgage ($2,493) + Fees ($80) + Taxes in 2024 ($451)


    Taxes:$5,409

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 2540 WINNERS CIR, KISSIMMEE, FL 34744

    $739,00063 Days on yellowkey   MLS ID: O6382446

    For Sale O6382446 - 2540 WINNERS CIR, KISSIMMEE, FL 34744 37 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: $4,357 (change assumption)
    Mortgage ($4,049) + 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)


  • 1791 SMARTS RULE ST, KISSIMMEE, FL 34744

    $510,00081 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


  • 1636 BARBERRY DR, KISSIMMEE, FL 34744

    $560,00059 Days on yellowkey   MLS ID: S5144068

    For Sale S5144068 - 1636 BARBERRY DR, KISSIMMEE, FL 34744 65 photos

    Bed: 4   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 2851
       Built: 2023
    Monthly Fee: $11
       Tax: $7,432 (2025)
    Community: Kindred Ph 2C & 2D
    Single Family


    Estimated Monthly Payment: $3,699 (change assumption)
    Mortgage ($3,068) + Fees ($11) + Taxes in 2025 ($619)


    Taxes:$7,432

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2352 ROSS ST, KISSIMMEE, FL 34744

    $315,000308 Days on yellowkey   MLS ID: O6320029

    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


  • 2418 BROOKSIDE AVE, KISSIMMEE, FL 34744

    $220,00038 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


  • 2568 AVENTURINE ST, KISSIMMEE, FL 34744

    $305,000135 Days on yellowkey   MLS ID: O6365441

    For Sale O6365441 - 2568 AVENTURINE ST, KISSIMMEE, FL 34744 37 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1734
       Built: 2008
    Monthly Fee: $170
       Tax: $631 (2024)
    Community: Amber Pointe Unit 2
    Townhouse


    Estimated Monthly Payment: $1,894 (change assumption)
    Mortgage ($1,671) + Fees ($170) + Taxes in 2024 ($53)


    Taxes:$631

    Elementary School: None

    High School: None

    Tax Year: 2024

    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.