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Homes For Sale in Kissimmee 34744 - 360 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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  • 1433 RIVERBOAT DR, KISSIMMEE, FL 34744

    $375,000243 Days on yellowkey   MLS ID: G5103345

    REDUCED by $5,000 (1.3%) on 06/03/2026

    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: $2,659 (change assumption)
    Mortgage ($2,055) + 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)


  • 1823 SPRING SHOWER CIR, KISSIMMEE, FL 34744

    $394,90098 Days on yellowkey   MLS ID: O6389198

    REDUCED by $4,100 (1.0%) on 06/03/2026

    For Sale O6389198 - 1823 SPRING SHOWER CIR, KISSIMMEE, FL 34744 38 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1579
       Built: 2022
    Monthly Fee: $220
       Tax: $5,193 (2025)
    Community: Tohoqua Reserve
    Spa: No

    Half Duplex


    Estimated Monthly Payment: $2,817 (change assumption)
    Mortgage ($2,164) + Fees ($220) + Taxes in 2025 ($433)


    Taxes:$5,193

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1709 MICHIGAN AVE #C, KISSIMMEE, FL 34744

    $119,90057 Days on yellowkey   MLS ID: S5148282

    REDUCED by $10,000 (7.7%) on 06/03/2026

    For Sale S5148282 - 1709 MICHIGAN AVE #C, KISSIMMEE, FL 34744 14 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1118
       Built: 1973
    Monthly Fee: $298
       Tax: $2,400 (2025)
    Community: Essex Park Villas
    Condo


    Estimated Monthly Payment: $1,155 (change assumption)
    Mortgage ($657) + Fees ($298) + Taxes in 2025 ($200)


    Taxes:$2,400

    Elementary School: Deerwood Elem (Osceola Cty)

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Denn John Middle


  • 1805 MICHIGAN AVE #D, KISSIMMEE, FL 34744

    $129,90015 Days on yellowkey   MLS ID: S5150908

    REDUCED by $9,100 (6.5%) on 06/03/2026

    For Sale S5150908 - 1805 MICHIGAN AVE #D, KISSIMMEE, FL 34744 9 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1118
       Built: 1973
    Monthly Fee: $345
       Tax: $2,118 (2025)
    Community: Essex Park Villas Condo
    Condo


    Estimated Monthly Payment: $1,233 (change assumption)
    Mortgage ($712) + Fees ($345) + Taxes in 2025 ($176)


    Taxes:$2,118

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1502 JADEWOOD WAY, KISSIMMEE, FL 34744

    $350,000666 Days on yellowkey   MLS ID: O6233314

    SHORT SALE O6233314 - 1502 JADEWOOD WAY, KISSIMMEE, FL 34744 35 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1846
       Built: 2022
    Monthly Fee: $11
       Tax: $7,144 (2025)
    Community: Kindred Ph 2C & 2D Pb 30 Pgs 74-80 Lot 323
    Single Family


    Estimated Monthly Payment: $2,524 (change assumption)
    Mortgage ($1,918) + Fees ($11) + Taxes in 2025 ($595)


    Taxes:$7,144

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2708 PRESTWICK LN, KISSIMMEE, FL 34744

    $387,00036 Days on yellowkey   MLS ID: S5149647

    2 Days Off yellowkey (back on 6/3/2026)

    INCREASED by $7,000 (1.8%) on 05/22/2026

    For Sale S5149647 - 2708 PRESTWICK LN, KISSIMMEE, FL 34744 26 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2513
       Built: 2004
    Monthly Fee: $92
       Tax: $7,102 (2025)
    Community: Remington Prcl M1
    Single Family


    Estimated Monthly Payment: $2,804 (change assumption)
    Mortgage ($2,120) + Fees ($92) + Taxes in 2025 ($592)


    Taxes:$7,102

    Elementary School: Partin Settlement Elem

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 170 THORNBURY DR, KISSIMMEE, FL 34744

    $370,000116 Days on yellowkey   MLS ID: O6383967

    0 Days Off yellowkey (back on 5/15/2026)

    REDUCED by $15,000 (3.9%) on 05/12/2026

    For Sale O6383967 - 170 THORNBURY DR, KISSIMMEE, FL 34744 34 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1766
       Built: 2002
    Monthly Fee: $13
       Tax: $3,058 (2025)
    Community: Remington Prcl H Ph 2
    Single Family


    Estimated Monthly Payment: $2,295 (change assumption)
    Mortgage ($2,027) + Fees ($13) + Taxes in 2025 ($255)


    Taxes:$3,058

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2943 CASABELLA DR, KISSIMMEE, FL 34744

    $399,900192 Days on yellowkey   MLS ID: O6363943

    For Sale O6363943 - 2943 CASABELLA DR, KISSIMMEE, FL 34744 18 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1895
       Built: 2014
    Monthly Fee: $175
       Tax: $7,799 (2024)
    Community: Villa Sol Village
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,016 (change assumption)
    Mortgage ($2,191) + Fees ($175) + Taxes in 2024 ($650)


    Taxes:$7,799

    Elementary School: East Lake Elem

    High School: Tohopekaliga High School

    Tax Year: 2024

    Middle School: Neptune Middle (6-8)


  • 4461 INDIGO SKY LN, KISSIMMEE, FL 34744

    $524,00014 Days on yellowkey   MLS ID: S5151142

    For Sale S5151142 - 4461 INDIGO SKY LN, KISSIMMEE, FL 34744 43 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1941
       Built: 2013
    Monthly Fee: $111
       Tax: $3,837 (2025)
    Community: North Point Ph 1B
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,302 (change assumption)
    Mortgage ($2,871) + Fees ($111) + Taxes in 2025 ($320)


    Taxes:$3,837

    Elementary School: East Lake Elementary-OS

    High School: Tohopekaliga High School

    Tax Year: 2025

    Middle School: Narcoossee Middle


  • 1502 BITTEROOT ST, KISSIMMEE, FL 34744

    $449,99014 Days on yellowkey   MLS ID: O6413239

    For Sale O6413239 - 1502 BITTEROOT ST, KISSIMMEE, FL 34744 29 photos

    Bed: 5   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2674
       Built: 2024
    Monthly Fee: $11
       Tax: $8,691 (2025)
    Community: Kindred Ph 3B 3C & 3D
    Single Family


    Estimated Monthly Payment: $3,201 (change assumption)
    Mortgage ($2,466) + Fees ($11) + Taxes in 2025 ($724)


    Taxes:$8,691

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1577 STARFISH ST, KISSIMMEE, FL 34744

    $598,99914 Days on yellowkey   MLS ID: O6412641

    For Sale O6412641 - 1577 STARFISH ST, KISSIMMEE, FL 34744 36 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1733
       Built: 1979   Tax: $4,214 (2025)
    Community: Neptune Shores 3 Add
    Single Family


    Estimated Monthly Payment: $3,633 (change assumption)
    Mortgage ($3,282) + Taxes in 2025 ($351)


    Taxes:$4,214

    Elementary School: None

    High School: Osceola High School

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 2609 MILL RUN BLVD, KISSIMMEE, FL 34744

    $394,99014 Days on yellowkey   MLS ID: S5150924

    For Sale S5150924 - 2609 MILL RUN BLVD, KISSIMMEE, FL 34744 21 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1280
       Built: 1986   Tax: $5,034 (2024)
    Community: Mill Run Unit 5
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $2,584 (change assumption)
    Mortgage ($2,164) + Taxes in 2024 ($420)


    Taxes:$5,034

    Elementary School: Michigan Avenue Elem (K 5)

    High School: Gateway High School (9 12)

    Tax Year: 2024

    Middle School: Denn John Middle


  • 1069 UNIVERSAL REST PL, KISSIMMEE, FL 34744

    $250,000105 Days on yellowkey   MLS ID: TB8482410

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

    For Sale TB8482410 - 1069 UNIVERSAL REST PL, KISSIMMEE, FL 34744 17 photos

    Bed: 4   Bath: 2.5
    Liv Area Sq Ft: 2176
       Built: 1999
    Monthly Fee: $200
       Tax: $2,147 (2024)
    Community: Universal Place
    Townhouse


    Estimated Monthly Payment: $1,749 (change assumption)
    Mortgage ($1,370) + Fees ($200) + Taxes in 2024 ($179)


    Taxes:$2,147

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 1844 BRIGHT SKY DR, KISSIMMEE, FL 34744

    $385,00049 Days on yellowkey   MLS ID: S5148768

    REDUCED by $4,900 (1.3%) on 06/02/2026

    SHORT SALE S5148768 - 1844 BRIGHT SKY DR, KISSIMMEE, FL 34744 35 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1795
       Built: 2025
    Monthly Fee: $7
       Tax: $2,686 (2025)
    Community: Tohoqua Ph 7
    Single Family


    Estimated Monthly Payment: $2,340 (change assumption)
    Mortgage ($2,110) + Fees ($7) + Taxes in 2025 ($224)


    Taxes:$2,686

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1350 ROCKY RD, KISSIMMEE, FL 34744

    $325,00039 Days on yellowkey   MLS ID: O6405639

    For Sale O6405639 - 1350 ROCKY RD, KISSIMMEE, FL 34744 25 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1108
       Built: 1983   Tax: $4,613 (2025)
    Community: Pebble Creek
    Single Family


    Estimated Monthly Payment: $2,165 (change assumption)
    Mortgage ($1,781) + Taxes in 2025 ($384)


    Taxes:$4,613

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 636 ADRIANE PARK CIR, KISSIMMEE, FL 34744

    $474,90022 Days on yellowkey   MLS ID: S5150339

    0 Days Off yellowkey (back on 5/27/2026)

    For Sale S5150339 - 636 ADRIANE PARK CIR, KISSIMMEE, FL 34744 49 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2444
       Built: 1992
    Monthly Fee: $37
       Tax: $3,345 (2025)
    Community: Adriane Park
    Single Family


    Estimated Monthly Payment: $2,918 (change assumption)
    Mortgage ($2,602) + Fees ($37) + Taxes in 2025 ($279)


    Taxes:$3,345

    Elementary School: Partin Settlement Elem

    High School: Osceola High School

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 2356 VALLEY AVE, KISSIMMEE, FL 34744

    $360,00095 Days on yellowkey   MLS ID: O6390430

    4 Days Off yellowkey (back on 6/2/2026)

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

    For Sale O6390430 - 2356 VALLEY AVE, KISSIMMEE, FL 34744 16 photos

    Bed: 4   Bath: 2.0
    Liv Area Sq Ft: 1855
       Built: 1973   Tax: $671 (2025)
    Community: Town & Country Estates Unit 1
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,028 (change assumption)
    Mortgage ($1,973) + Taxes in 2025 ($56)


    Taxes:$671

    Elementary School: Mill Creek Elem (K 5)

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Denn John Middle


  • 2735 SCARBOROUGH DR, KISSIMMEE, FL 34744

    $515,00064 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)


  • 429 JANICE KAY PL, KISSIMMEE, FL 34744

    $450,00099 Days on yellowkey   MLS ID: S5145448

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

    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)


  • 1800 HOWARD MESA DR, KISSIMMEE, FL 34744

    $421,99043 Days on yellowkey   MLS ID: O6404555

    2 Days Off yellowkey (back on 6/2/2026)

    INCREASED by $2,000 (0.5%) on 05/12/2026

    For Sale O6404555 - 1800 HOWARD MESA DR, KISSIMMEE, FL 34744 50 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1665
       Built: 2025
    Monthly Fee: $11
       Tax: $3,684 (2025)
    Community: Kindred Ph 3B 3C & 3D
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,630 (change assumption)
    Mortgage ($2,312) + Fees ($11) + Taxes in 2025 ($307)


    Taxes:$3,684

    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.