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Homes For Sale in Kissimmee 34744 - 294 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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  • 1135 CHEROKEE DR, KISSIMMEE, FL 34744

    $368,90052 Days on yellowkey   MLS ID: S5144943

    REDUCED by $7,090 (1.9%) on 04/23/2026

    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: $2,106 (change assumption)
    Mortgage ($2,021) + 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


  • 14 GLENDALE DR, KISSIMMEE, FL 34744

    $528,90041 Days on yellowkey   MLS ID: S5145799

    REDUCED by $6,000 (1.1%) on 04/23/2026

    For Sale S5145799 - 14 GLENDALE DR, KISSIMMEE, FL 34744 22 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2510
       Built: 1970   Tax: $5,664 (2025)
    Community: Fairlawn Manor
    Single Family


    Estimated Monthly Payment: $3,370 (change assumption)
    Mortgage ($2,898) + Taxes in 2025 ($472)


    Taxes:$5,664

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2220 EMPEROR DR, KISSIMMEE, FL 34744

    $624,9002 Days on yellowkey   MLS ID: S5148275

    For Sale S5148275 - 2220 EMPEROR DR, KISSIMMEE, FL 34744 35 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2502
       Built: 1991   Tax: $3,970 (2025)
    Community: Cane Brake Ph 2
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,755 (change assumption)
    Mortgage ($3,424) + Taxes in 2025 ($331)


    Taxes:$3,970

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1709 MICHIGAN AVE #C, KISSIMMEE, FL 34744

    $134,9003 Days on yellowkey   MLS ID: S5148282

    REDUCED by $10,100 (7.0%) on 04/23/2026

    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: $1,237 (change assumption)
    Mortgage ($739) + 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


  • 1489 TWIN VALLEY TER, KISSIMMEE, FL 34744

    $549,90029 Days on yellowkey   MLS ID: O6390966

    REDUCED by $10,100 (1.8%) on 04/18/2026

    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: $3,613 (change assumption)
    Mortgage ($3,013) + Fees ($11) + Taxes in 2025 ($589)


    Taxes:$7,067

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1777 WALNUT CREEK DR, KISSIMMEE, FL 34744

    $449,90031 Days on yellowkey   MLS ID: O6390965

    REDUCED by $9,100 (2.0%) on 04/20/2026

    For Sale O6390965 - 1777 WALNUT CREEK DR, KISSIMMEE, FL 34744 73 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2339
       Built: 2023
    Monthly Fee: $11
       Tax: $3,358 (2025)
    Community: Kindred Ph 3A
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,756 (change assumption)
    Mortgage ($2,465) + Fees ($11) + Taxes in 2025 ($280)


    Taxes:$3,358

    Elementary School: None

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 1805 MICHIGAN AVE #D, KISSIMMEE, FL 34744

    $139,0002 Days on yellowkey   MLS ID: S5148360

    For Sale S5148360 - 1805 MICHIGAN AVE #D, KISSIMMEE, FL 34744 9 photos

    Bed: 2   Bath: 0.0
    Liv Area Sq Ft: 1118
       Built: 1973
    Monthly Fee: $345
       Tax: $2,118 (2025)
    Community: Essex Park Villas Condo
    Apartment


    Estimated Monthly Payment: $1,283 (change assumption)
    Mortgage ($762) + Fees ($345) + Taxes in 2025 ($176)


    Taxes:$2,118

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2988 MARBELLA DR, KISSIMMEE, FL 34744

    $485,000Listed 04/23/2026 4:41PM   MLS ID: S5148494

    For Sale S5148494 - 2988 MARBELLA DR, KISSIMMEE, FL 34744 37 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2160
       Built: 2004
    Monthly Fee: $167
       Tax: $5,357 (2025)
    Community: Villa Sol Ph 2 Village 3
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $3,271 (change assumption)
    Mortgage ($2,657) + Fees ($167) + Taxes in 2025 ($446)


    Taxes:$5,357

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1720 FULFILLMENT DR, KISSIMMEE, FL 34744

    $425,000Listed 04/23/2026 4:16PM   MLS ID: O6401021

    For Sale O6401021 - 1720 FULFILLMENT DR, KISSIMMEE, FL 34744 41 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2044
       Built: 2022
    Monthly Fee: $10
       Tax: $7,447 (2025)
    Community: Tohoqua Ph 2
    Single Family


    Estimated Monthly Payment: $2,959 (change assumption)
    Mortgage ($2,329) + Fees ($10) + Taxes in 2025 ($621)


    Taxes:$7,447

    Elementary School: None

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 1895 SPRING SHOWER CIR, KISSIMMEE, FL 34744

    $339,0004 Days on yellowkey   MLS ID: S5148149

    For Sale S5148149 - 1895 SPRING SHOWER CIR, KISSIMMEE, FL 34744 29 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1559
       Built: 2023
    Monthly Fee: $213
       Tax: $1,967 (2025)
    Community: Tohoqua Ph 5B
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,234 (change assumption)
    Mortgage ($1,857) + Fees ($213) + Taxes in 2025 ($164)


    Taxes:$1,967

    Elementary School: Neptune Elementary

    High School: St. Cloud High School

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 1980 SUMMER CT, KISSIMMEE, FL 34744

    $535,00029 Days on yellowkey   MLS ID: O6392643

    REDUCED by $14,000 (2.6%) on 04/23/2026

    For Sale O6392643 - 1980 SUMMER CT, KISSIMMEE, FL 34744 39 photos

    Bed: 3   Bath: 3.0   Gar: 4
    Liv Area Sq Ft: 2687
       Built: 2005   Tax: $6,583 (2025)
    Community: Meadow Spgs
    Single Family


    Estimated Monthly Payment: $3,480 (change assumption)
    Mortgage ($2,931) + Taxes in 2025 ($549)


    Taxes:$6,583

    Elementary School: Partin Settlement Elem

    High School: Osceola High School

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 3589 ROCK CREEK LN, KISSIMMEE, FL 34744

    $359,00079 Days on yellowkey   MLS ID: S5143035

    REDUCED by $5,999 (1.6%) on 04/23/2026

    For Sale S5143035 - 3589 ROCK CREEK LN, KISSIMMEE, FL 34744 28 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1554
       Built: 2019
    Monthly Fee: $138
       Tax: $3,593 (2025)
    Community: East Lake Preserve Ph 3
    Single Family


    Estimated Monthly Payment: $2,405 (change assumption)
    Mortgage ($1,967) + Fees ($138) + Taxes in 2025 ($299)


    Taxes:$3,593

    Elementary School: East Lake Elem

    High School: Tohopekaliga High School

    Tax Year: 2025

    Middle School: Narcoossee Middle


  • 1516 PINE ISLAND RD, KISSIMMEE, FL 34744

    $875,00028 Days on yellowkey   MLS ID: S5145674

    For Sale S5145674 - 1516 PINE ISLAND RD, KISSIMMEE, FL 34744 59 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2613
       Built: 2026   Tax: $1,385 (2025)
    Community: Regal Point Estates Unit 1
    Single Family


    Estimated Monthly Payment: $4,910 (change assumption)
    Mortgage ($4,794) + Taxes in 2025 ($115)


    Taxes:$1,385

    Elementary School: None

    High School: None

    Tax Year: 2025

    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)


  • 1895 HICKORY BLUFF RD, KISSIMMEE, FL 34744

    $349,90093 Days on yellowkey   MLS ID: S5142089

    For Sale S5142089 - 1895 HICKORY BLUFF RD, KISSIMMEE, FL 34744 17 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1676
       Built: 2017
    Monthly Fee: $11
       Tax: $6,019 (2025)
    Community: Kindred Ph 1C Pb 25 Pgs 127-134 Lot 373
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,430 (change assumption)
    Mortgage ($1,917) + Fees ($11) + Taxes in 2025 ($502)


    Taxes:$6,019

    Elementary School: Neptune Elementary

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 100 THORNBURY LN, KISSIMMEE, FL 34744

    $440,000226 Days on yellowkey   MLS ID: O6342537

    For Sale O6342537 - 100 THORNBURY LN, KISSIMMEE, FL 34744 50 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2379
       Built: 2002
    Monthly Fee: $13
       Tax: $3,689 (2024)
    Community: Remington Prcl H Ph 2
    Single Family


    Estimated Monthly Payment: $2,731 (change assumption)
    Mortgage ($2,411) + Fees ($13) + Taxes in 2024 ($307)


    Taxes:$3,689

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 2533 OAK RUN BLVD, KISSIMMEE, FL 34744

    $397,00070 Days on yellowkey   MLS ID: S5143776

    0 Days Off yellowkey (back on 3/16/2026)

    For Sale S5143776 - 2533 OAK RUN BLVD, KISSIMMEE, FL 34744 59 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1661
       Built: 1986   Tax: $5,386 (2025)
    Community: Oak Run Unit 3
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,624 (change assumption)
    Mortgage ($2,175) + Taxes in 2025 ($449)


    Taxes:$5,386

    Elementary School: Mill Creek Elem (K 5)

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Denn John Middle


  • 107 BENITA STREET, KISSIMMEE, FL 34744

    $150,000533 Days on yellowkey   MLS ID: O6255238

    For Sale O6255238 - 107 BENITA STREET, KISSIMMEE, FL 34744 13 photos

    Bed: 3   Bath: 1.0
    Liv Area Sq Ft: 1010
       Built: 1965   Tax: $1,221 (2024)
    Community: Roy Wells
    Mobile Home


    Estimated Monthly Payment: $924 (change assumption)
    Mortgage ($822) + Taxes in 2024 ($102)


    Taxes:$1,221

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 1336 E LAKE SHORE BLVD, KISSIMMEE, FL 34744

    $359,999Listed 04/23/2026 9:26AM   MLS ID: A4691089

    For Sale A4691089 - 1336 E LAKE SHORE BLVD, KISSIMMEE, FL 34744 19 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1450
       Built: 1963   Tax: $2,633 (2025)
    Community: Ocean Gulf Estates Sec 1
    Single Family


    Estimated Monthly Payment: $2,192 (change assumption)
    Mortgage ($1,973) + Taxes in 2025 ($219)


    Taxes:$2,633

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2605 PLAY HARD ALY, KISSIMMEE, FL 34744

    $375,00066 Days on yellowkey   MLS ID: S5143916

    For Sale S5143916 - 2605 PLAY HARD ALY, KISSIMMEE, FL 34744 40 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1603
       Built: 2019
    Monthly Fee: $154
       Tax: $4,220 (2025)
    Community: Tohoqua Ph 1
    Townhouse


    Estimated Monthly Payment: $2,560 (change assumption)
    Mortgage ($2,055) + Fees ($154) + Taxes in 2025 ($352)


    Taxes:$4,220

    Elementary School: Neptune Elementary

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)




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.