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Homes For Sale in Kissimmee 34744 - 337 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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  • 1709 MICHIGAN AVE #C, KISSIMMEE, FL 34744

    $119,90045 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


  • 1956 EGRET MEADOWS AVE, KISSIMMEE, FL 34744

    $379,99014 Days on yellowkey   MLS ID: O6409425

    REDUCED by $15,000 (3.8%) on 06/01/2026

    For Sale O6409425 - 1956 EGRET MEADOWS AVE, KISSIMMEE, FL 34744 21 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1516
       Built: 2020
    Monthly Fee: $11
       Tax: $6,661 (2025)
    Community: Kindred Ph 2A
    Single Family


    Estimated Monthly Payment: $2,648 (change assumption)
    Mortgage ($2,082) + Fees ($11) + Taxes in 2025 ($555)


    Taxes:$6,661

    Elementary School: Neptune Elementary

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 1211 LEHIGH ST, KISSIMMEE, FL 34744

    $364,90059 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


  • 1805 MICHIGAN AVE #D, KISSIMMEE, FL 34744

    $129,9003 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

    $350,000654 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

    $387,00024 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

    $370,000104 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

    $399,900180 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)


  • 4371 CREEK COVE LN, KISSIMMEE, FL 34744

    $395,00049 Days on yellowkey   MLS ID: S5147262

    REDUCED by $20,000 (4.8%) on 05/26/2026

    SHORT SALE S5147262 - 4371 CREEK COVE LN, KISSIMMEE, FL 34744 27 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 1867
       Built: 2023
    Monthly Fee: $242
       Tax: $3,773 (2025)
    Community: The Towns At Creekside
    Spa: No

    Townhouse


    Estimated Monthly Payment: $2,721 (change assumption)
    Mortgage ($2,164) + Fees ($242) + Taxes in 2025 ($314)


    Taxes:$3,773

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2905 SUMMER GREEN TRL, KISSIMMEE, FL 34744

    $469,9001 Day on yellowkey   MLS ID: O6413243

    For Sale O6413243 - 2905 SUMMER GREEN TRL, KISSIMMEE, FL 34744 50 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2344
       Built: 2021
    Monthly Fee: $93
       Tax: $4,418 (2025)
    Community: Marbella Ph 2
    Single Family


    Estimated Monthly Payment: $3,036 (change assumption)
    Mortgage ($2,575) + Fees ($93) + Taxes in 2025 ($368)


    Taxes:$4,418

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 4461 INDIGO SKY LN, KISSIMMEE, FL 34744

    $524,0001 Day 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

    $449,9901 Day 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

    $598,9991 Day 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)


  • 302 E DRURY AVE, KISSIMMEE, FL 34744

    $368,0002 Days on yellowkey   MLS ID: O6411839

    For Sale O6411839 - 302 E DRURY AVE, KISSIMMEE, FL 34744 41 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1528
       Built: 1950   Tax: $778 (2025)
    Community: Cape Breeze
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,081 (change assumption)
    Mortgage ($2,016) + Taxes in 2025 ($65)


    Taxes:$778

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2609 MILL RUN BLVD, KISSIMMEE, FL 34744

    $394,9902 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


  • 109 THORNBURY DR, KISSIMMEE, FL 34744

    $349,90062 Days on yellowkey   MLS ID: O6395896

    2 Days Off yellowkey (back on 5/13/2026)

    REDUCED by $10,100 (2.8%) on 05/05/2026

    For Sale O6395896 - 109 THORNBURY DR, KISSIMMEE, FL 34744 18 photos

    Bed: 5   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1622
       Built: 2003
    Monthly Fee: $14
       Tax: $6,074 (2025)
    Community: Remington Prcl H Ph 1
    Single Family


    Estimated Monthly Payment: $2,437 (change assumption)
    Mortgage ($1,917) + Fees ($14) + Taxes in 2025 ($506)


    Taxes:$6,074

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1719 CROSS PRAIRIE PKWY, KISSIMMEE, FL 34744

    $415,000204 Days on yellowkey   MLS ID: O6355766

    For Sale O6355766 - 1719 CROSS PRAIRIE PKWY, KISSIMMEE, FL 34744 29 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2000
       Built: 2023
    Monthly Fee: $138
       Tax: $5,872 (2024)
    Community: Tohoqua Ii 25 Th
    Townhouse


    Estimated Monthly Payment: $2,901 (change assumption)
    Mortgage ($2,274) + Fees ($138) + Taxes in 2024 ($489)


    Taxes:$5,872

    Elementary School: Neptune Elementary

    High School: Gateway High School (9 12)

    Tax Year: 2024

    Middle School: Neptune Middle (6-8)


  • 1488 SOPHIE WAY, KISSIMMEE, FL 34744

    $399,00053 Days on yellowkey   MLS ID: S5147658

    1 Days Off yellowkey (back on 4/15/2026)

    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)


  • 162 HARWOOD CIR, KISSIMMEE, FL 34744

    $463,5003 Days on yellowkey   MLS ID: O6412762

    FORECLOSURE O6412762 - 162 HARWOOD CIR, KISSIMMEE, FL 34744 35 photos

    Bed: 4   Bath: 2.5   Gar: 3
    Liv Area Sq Ft: 2516
       Built: 1998
    Monthly Fee: $14
       Tax: $6,859 (2025)
    Community: Remington Ph 1 Tr D
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,125 (change assumption)
    Mortgage ($2,540) + Fees ($14) + Taxes in 2025 ($572)


    Taxes:$6,859

    Elementary School: Partin Settlement Elem

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 1069 UNIVERSAL REST PL, KISSIMMEE, FL 34744

    $250,00093 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




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.