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Homes For Sale in Kissimmee 34744 - 270 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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  • 1330 SWEETWOOD BLVD, KISSIMMEE, FL 34744

    $395,0001 Day on yellowkey   MLS ID: O6396384

    For Sale O6396384 - 1330 SWEETWOOD BLVD, KISSIMMEE, FL 34744 44 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1571
       Built: 1977   Tax: $4,667 (2025)
    Community: Sweetwood Estates
    Single Family


    Estimated Monthly Payment: $2,553 (change assumption)
    Mortgage ($2,164) + Taxes in 2025 ($389)


    Taxes:$4,667

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2501 BALMORAL DR, KISSIMMEE, FL 34744

    $390,00025 Days on yellowkey   MLS ID: S5146190

    REDUCED by $9,900 (2.5%) on 04/13/2026

    For Sale S5146190 - 2501 BALMORAL DR, KISSIMMEE, FL 34744 59 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1994
       Built: 2004
    Monthly Fee: $14
       Tax: $2,652 (2025)
    Community: Remington Prcl G Ph 2
    Single Family


    Estimated Monthly Payment: $2,372 (change assumption)
    Mortgage ($2,137) + Fees ($14) + Taxes in 2025 ($221)


    Taxes:$2,652

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2507 WINNERS CIR, KISSIMMEE, FL 34744

    $549,0004 Days on yellowkey   MLS ID: S5147254

    For Sale S5147254 - 2507 WINNERS CIR, KISSIMMEE, FL 34744 98 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1914
       Built: 1999   Tax: $2,483 (2025)
    Community: D S Estates
    Single Family


    Estimated Monthly Payment: $3,215 (change assumption)
    Mortgage ($3,008) + Taxes in 2025 ($207)


    Taxes:$2,483

    Elementary School: East Lake Elem

    High School: Tohopekaliga High School

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 1214 CHEROKEE CT, KISSIMMEE, FL 34744

    $289,0007 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


  • 15 ADAMS AVE, KISSIMMEE, FL 34744

    $440,000174 Days on yellowkey   MLS ID: OM711923

    For Sale OM711923 - 15 ADAMS AVE, KISSIMMEE, FL 34744 49 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1682
       Built: 1972   Tax: $2,767 (2024)
    Community: Idora Park
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $2,642 (change assumption)
    Mortgage ($2,411) + Taxes in 2024 ($231)


    Taxes:$2,767

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 4371 SUMMER BREEZE WAY, KISSIMMEE, FL 34744

    $899,90063 Days on yellowkey   MLS ID: S5143143

    For Sale S5143143 - 4371 SUMMER BREEZE WAY, KISSIMMEE, FL 34744 65 photos

    Bed: 5   Bath: 4.0   Gar: 3
    Liv Area Sq Ft: 4499
       Built: 2017
    Monthly Fee: $111
       Tax: $7,557 (2025)
    Community: North Point Ph 2B-2C
    Single Family


    Estimated Monthly Payment: $5,672 (change assumption)
    Mortgage ($4,931) + Fees ($111) + Taxes in 2025 ($630)


    Taxes:$7,557

    Elementary School: East Lake Elem

    High School: Tohopekaliga High School

    Tax Year: 2025

    Middle School: Narcoossee Middle


  • 2077 WALNUT CREEK DR, KISSIMMEE, FL 34744

    $454,40026 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

    $309,0006 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


  • 2735 SCARBOROUGH DR, KISSIMMEE, FL 34744

    $530,000Listed 04/13/2026 2:02AM   MLS ID: S5147642

    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: $3,454 (change assumption)
    Mortgage ($2,904) + 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)


  • 1603 BARBERRY DR, KISSIMMEE, FL 34744

    $450,000Listed 04/12/2026 10:36PM   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


  • 2723 CALLAWAY LN, KISSIMMEE, FL 34744

    $435,000Listed 04/12/2026 6:14PM   MLS ID: O6397750

    For Sale O6397750 - 2723 CALLAWAY LN, KISSIMMEE, FL 34744 56 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2513
       Built: 2005
    Monthly Fee: $78
       Tax: $6,939 (2024)
    Community: Remington Prcl M1
    Single Family


    Estimated Monthly Payment: $3,040 (change assumption)
    Mortgage ($2,384) + Fees ($78) + Taxes in 2024 ($578)


    Taxes:$6,939

    Elementary School: Partin Settlement Elem

    High School: Gateway High School (9 12)

    Tax Year: 2024

    Middle School: Neptune Middle (6-8)


  • 1488 SOPHIE WAY, KISSIMMEE, FL 34744

    $399,0001 Day on yellowkey   MLS ID: S5147658

    For Sale S5147658 - 1488 SOPHIE WAY, KISSIMMEE, FL 34744 49 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1552
       Built: 1993
    Monthly Fee: $33
       Tax: $713 (2025)
    Community: Westminster Gardens Ph 1
    Single Family


    Estimated Monthly Payment: $2,279 (change assumption)
    Mortgage ($2,186) + Fees ($33) + Taxes in 2025 ($59)


    Taxes:$713

    Elementary School: Partin Settlement Elem

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 4419 AZURE ISLE WAY, KISSIMMEE, FL 34744

    $479,99038 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


  • 1489 TWIN VALLEY TER, KISSIMMEE, FL 34744

    $560,00019 Days on yellowkey   MLS ID: O6390966

    For Sale O6390966 - 1489 TWIN VALLEY TER, KISSIMMEE, FL 34744 77 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: $3,668 (change assumption)
    Mortgage ($3,068) + Fees ($11) + Taxes in 2025 ($589)


    Taxes:$7,067

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2035 SPRING SHOWER CIR, KISSIMMEE, FL 34744

    $424,39088 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


  • 2320 SOUTHBURY DR, KISSIMMEE, FL 34744

    $339,990209 Days on yellowkey   MLS ID: O6344888

    1 Days Off yellowkey (back on 4/9/2026)

    For Sale O6344888 - 2320 SOUTHBURY DR, KISSIMMEE, FL 34744 21 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1553
       Built: 2025
    Monthly Fee: $130
       Tax: $1,610 (2024)
    Community: Tohoqua
    Spa: No

    Townhouse


    Estimated Monthly Payment: $2,127 (change assumption)
    Mortgage ($1,863) + Fees ($130) + Taxes in 2024 ($134)


    Taxes:$1,610

    Elementary School: Neptune Elementary

    High School: Gateway High School (9 12)

    Tax Year: 2024

    Middle School: Neptune Middle (6-8)


  • 2506 VOLUNTEER AVE, KISSIMMEE, FL 34744

    $520,0003 Days on yellowkey   MLS ID: O6398097

    For Sale O6398097 - 2506 VOLUNTEER AVE, KISSIMMEE, FL 34744 45 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3199
       Built: 2019
    Monthly Fee: $7
       Tax: $9,289 (2025)
    Community: Tohoqua Ph 1
    Single Family


    Estimated Monthly Payment: $3,630 (change assumption)
    Mortgage ($2,849) + Fees ($7) + Taxes in 2025 ($774)


    Taxes:$9,289

    Elementary School: Neptune Elementary

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 429 JANICE KAY PL, KISSIMMEE, FL 34744

    $450,00035 Days on yellowkey   MLS ID: S5145448

    For Sale S5145448 - 429 JANICE KAY PL, KISSIMMEE, FL 34744 20 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2906
       Built: 2004
    Monthly Fee: $14
       Tax: $2,737 (2024)
    Community: Eagle Point
    Single Family


    Estimated Monthly Payment: $2,708 (change assumption)
    Mortgage ($2,466) + Fees ($14) + Taxes in 2024 ($228)


    Taxes:$2,737

    Elementary School: Partin Settlement Elem

    High School: Gateway High School (9 12)

    Tax Year: 2024

    Middle School: Neptune Middle (6-8)


  • 1135 CHEROKEE DR, KISSIMMEE, FL 34744

    $375,99042 Days on yellowkey   MLS ID: S5144943

    For Sale S5144943 - 1135 CHEROKEE DR, KISSIMMEE, FL 34744 12 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1358
       Built: 1964   Tax: $1,014 (2025)
    Community: Osceola Acres
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,145 (change assumption)
    Mortgage ($2,060) + Taxes in 2025 ($85)


    Taxes:$1,014

    Elementary School: Mill Creek Elem (K 5)

    High School: Osceola High School

    Tax Year: 2025

    Middle School: Denn John Middle


  • 4408 BREEZE ISLE LN, KISSIMMEE, FL 34744

    $675,00017 Days on yellowkey   MLS ID: O6393234

    For Sale O6393234 - 4408 BREEZE ISLE LN, KISSIMMEE, FL 34744 47 photos

    Bed: 5   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 3267
       Built: 2014
    Monthly Fee: $111
       Tax: $4,883 (2025)
    Community: North Point Ph Ic
    Single Family


    Estimated Monthly Payment: $4,216 (change assumption)
    Mortgage ($3,699) + Fees ($111) + Taxes in 2025 ($407)


    Taxes:$4,883

    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.