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Homes For Sale in Kissimmee 34744 - 266 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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  • 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


  • 1595 SHADY OAK DR, KISSIMMEE, FL 34744

    $457,00046 Days on yellowkey   MLS ID: S5144261

    For Sale S5144261 - 1595 SHADY OAK DR, KISSIMMEE, FL 34744 39 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2116
       Built: 1981   Tax: $4,757 (2025)
    Community: Regal Oak Shores Unit 6
    Single Family


    Estimated Monthly Payment: $2,900 (change assumption)
    Mortgage ($2,504) + Taxes in 2025 ($396)


    Taxes:$4,757

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1459 OAK LEAF LN, KISSIMMEE, FL 34744

    $347,7374 Days on yellowkey   MLS ID: O6397026

    For Sale O6397026 - 1459 OAK LEAF LN, KISSIMMEE, FL 34744 31 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1242
       Built: 1979   Tax: $4,859 (2025)
    Community: Heather Oaks Unit 4
    Single Family


    Estimated Monthly Payment: $2,310 (change assumption)
    Mortgage ($1,905) + Taxes in 2025 ($405)


    Taxes:$4,859

    Elementary School: Mill Creek Elem (K 5)

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Denn John Middle


  • 4405 BISCAYNE BREEZE WAY, KISSIMMEE, FL 34744

    $485,0001 Day 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


  • 1519 JADEWOOD WAY, KISSIMMEE, FL 34744

    $539,0003 Days on yellowkey   MLS ID: S5147592

    For Sale S5147592 - 1519 JADEWOOD WAY, KISSIMMEE, FL 34744 27 photos

    Bed: 5   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2601
       Built: 2022
    Monthly Fee: $10
       Tax: $7,660 (2025)
    Community: Kindred Ph 1
    Single Family


    Estimated Monthly Payment: $3,602 (change assumption)
    Mortgage ($2,953) + Fees ($10) + Taxes in 2025 ($638)


    Taxes:$7,660

    Elementary School: Mill Creek Elem (K 5)

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 1838 TOHOQUA BLVD, KISSIMMEE, FL 34744

    $339,9004 Days on yellowkey   MLS ID: S5147475

    For Sale S5147475 - 1838 TOHOQUA BLVD, KISSIMMEE, FL 34744 1 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1600
       Built: 2023
    Monthly Fee: $126
       Tax: $6,276 (2025)
    Community: Tohoqua Ph 6
    Townhouse


    Estimated Monthly Payment: $2,511 (change assumption)
    Mortgage ($1,862) + Fees ($126) + Taxes in 2025 ($523)


    Taxes:$6,276

    Elementary School: Neptune Elementary

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 2672 DEBANY RD, KISSIMMEE, FL 34744

    $400,00060 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

    $710,00068 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


  • 7 WESTCHESTER DR, KISSIMMEE, FL 34744

    $439,000330 Days on yellowkey   MLS ID: O6309992

    REDUCED by $5,500 (1.2%) on 04/01/2026

    For Sale O6309992 - 7 WESTCHESTER DR, KISSIMMEE, FL 34744 45 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1786
       Built: 1962   Tax: $1,988 (2024)
    Community: Fairlawn Manor
    Single Family


    Estimated Monthly Payment: $2,571 (change assumption)
    Mortgage ($2,405) + Taxes in 2024 ($166)


    Taxes:$1,988

    Elementary School: Partin Settlement Elem

    High School: Osceola High School

    Tax Year: 2024

    Middle School: Neptune Middle (6-8)


  • 1807 GOOD NEIGHBOR LOOP, KISSIMMEE, FL 34744

    $440,00011 Days on yellowkey   MLS ID: O6395467

    For Sale O6395467 - 1807 GOOD NEIGHBOR LOOP, KISSIMMEE, FL 34744 33 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2151
       Built: 2022
    Monthly Fee: $30
       Tax: $1,907 (2025)
    Community: Tohoqua Ph 2
    Single Family


    Estimated Monthly Payment: $2,600 (change assumption)
    Mortgage ($2,411) + Fees ($30) + Taxes in 2025 ($159)


    Taxes:$1,907

    Elementary School: None

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: None


  • 2963 SERA BELLA WAY, KISSIMMEE, FL 34744

    $515,00035 Days on yellowkey   MLS ID: S5144389

    For Sale S5144389 - 2963 SERA BELLA WAY, KISSIMMEE, FL 34744 74 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2416
       Built: 2016
    Monthly Fee: $120
       Tax: $5,072 (2025)
    Community: Sera Bella
    Single Family


    Estimated Monthly Payment: $3,365 (change assumption)
    Mortgage ($2,822) + Fees ($120) + Taxes in 2025 ($423)


    Taxes:$5,072

    Elementary School: Ventura Elem

    High School: Tohopekaliga High School

    Tax Year: 2025

    Middle School: Parkway Middle


  • 1495 SKYLINE DR, KISSIMMEE, FL 34744

    $524,90038 Days on yellowkey   MLS ID: S5145209

    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: $3,342 (change assumption)
    Mortgage ($2,876) + 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)


  • 2661 AMES HAVEN RD, KISSIMMEE, FL 34744

    $439,00040 Days on yellowkey   MLS ID: S5145125

    REDUCED by $6,000 (1.3%) on 03/31/2026

    For Sale S5145125 - 2661 AMES HAVEN RD, KISSIMMEE, FL 34744 51 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1666
       Built: 1984   Tax: $4,502 (2025)
    Community: Emerald Lake Colony Unit 1
    Single Family


    Estimated Monthly Payment: $2,781 (change assumption)
    Mortgage ($2,405) + Taxes in 2025 ($375)


    Taxes:$4,502

    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.