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Homes For Sale in Kissimmee 34744 - 356 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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  • 3013 MANDOLIN DR, KISSIMMEE, FL 34744

    $439,00015 Days on yellowkey   MLS ID: O6411560

    For Sale O6411560 - 3013 MANDOLIN DR, KISSIMMEE, FL 34744 58 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2148
       Built: 2005
    Monthly Fee: $83
       Tax: $5,071 (2025)
    Community: Turnberry Reserve Unit 1
    Single Family


    Estimated Monthly Payment: $2,911 (change assumption)
    Mortgage ($2,405) + Fees ($83) + Taxes in 2025 ($423)


    Taxes:$5,071

    Elementary School: East Lake Elem

    High School: Tohopekaliga High School

    Tax Year: 2025

    Middle School: Narcoossee Middle


  • 1340 SAWDUST TRL, KISSIMMEE, FL 34744

    $239,900147 Days on yellowkey   MLS ID: G5106887

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

    For Sale G5106887 - 1340 SAWDUST TRL, KISSIMMEE, FL 34744 24 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 924
       Built: 1996   Tax: $2,377 (2025)
    Community: Marydia
    Manufactured Home


    Estimated Monthly Payment: $1,513 (change assumption)
    Mortgage ($1,314) + Taxes in 2025 ($198)


    Taxes:$2,377

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1010 VAN LIEU ST, KISSIMMEE, FL 34744

    $324,50024 Days on yellowkey   MLS ID: O6409485

    REDUCED by $25,000 (7.2%) on 06/04/2026

    For Sale O6409485 - 1010 VAN LIEU ST, KISSIMMEE, FL 34744 12 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1062
       Built: 1986   Tax: $3,618 (2025)
    Community: Kissimmee Heights
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,080 (change assumption)
    Mortgage ($1,778) + Taxes in 2025 ($302)


    Taxes:$3,618

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1933 BELLKNOLL LN, KISSIMMEE, FL 34744

    $429,00012 Days on yellowkey   MLS ID: O6411567

    For Sale O6411567 - 1933 BELLKNOLL LN, KISSIMMEE, FL 34744 36 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1846
       Built: 2020
    Monthly Fee: $11
       Tax: $6,080 (2025)
    Community: Kindred
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,868 (change assumption)
    Mortgage ($2,351) + Fees ($11) + Taxes in 2025 ($507)


    Taxes:$6,080

    Elementary School: None

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: None


  • 1601 MOHEGAN BLVD, KISSIMMEE, FL 34744

    $365,00010 Days on yellowkey   MLS ID: O6413325

    For Sale O6413325 - 1601 MOHEGAN BLVD, KISSIMMEE, FL 34744 27 photos

    Bed: 3   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2167
       Built: 2014
    Monthly Fee: $164
       Tax: $3,207 (2025)
    Community: Heritage Run
    Single Family


    Estimated Monthly Payment: $2,431 (change assumption)
    Mortgage ($2,000) + Fees ($164) + Taxes in 2025 ($267)


    Taxes:$3,207

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 4871 FELLS COVE AVE, KISSIMMEE, FL 34744

    $435,00010 Days on yellowkey   MLS ID: A4695870

    For Sale A4695870 - 4871 FELLS COVE AVE, KISSIMMEE, FL 34744 21 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2603
       Built: 2005
    Monthly Fee: $53
       Tax: $6,313 (2025)
    Community: Fells Cove Units 3-4 Ph 2
    Single Family


    Estimated Monthly Payment: $2,963 (change assumption)
    Mortgage ($2,384) + Fees ($53) + Taxes in 2025 ($526)


    Taxes:$6,313

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2905 SUMMER GREEN TRL, KISSIMMEE, FL 34744

    $469,90010 Days 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


  • 2220 EMPEROR DR, KISSIMMEE, FL 34744

    $624,90053 Days on yellowkey   MLS ID: S5148275

    For Sale S5148275 - 2220 EMPEROR DR, KISSIMMEE, FL 34744 36 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


  • 4371 CREEK COVE LN, KISSIMMEE, FL 34744

    $395,00058 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


  • 2507 WINNERS CIR, KISSIMMEE, FL 34744

    $549,00065 Days on yellowkey   MLS ID: S5147254

    REDUCED by $5,000 (0.9%) on 06/03/2026

    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)


  • 4416 SILVER CREEK ST, KISSIMMEE, FL 34744

    $380,00057 Days on yellowkey   MLS ID: O6398907

    REDUCED by $10,000 (2.6%) on 06/03/2026

    For Sale O6398907 - 4416 SILVER CREEK ST, KISSIMMEE, FL 34744 31 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1504
       Built: 2019
    Monthly Fee: $130
       Tax: $4,679 (2025)
    Community: Creekside At Boggy Creek Ph 1
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,602 (change assumption)
    Mortgage ($2,082) + Fees ($130) + Taxes in 2025 ($390)


    Taxes:$4,679

    Elementary School: East Lake Elem

    High School: Tohopekaliga High School

    Tax Year: 2025

    Middle School: Narcoossee Middle


  • 1433 RIVERBOAT DR, KISSIMMEE, FL 34744

    $375,000240 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

    $394,90095 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


  • 14 GLENDALE DR, KISSIMMEE, FL 34744

    $495,00092 Days on yellowkey   MLS ID: S5145799

    REDUCED by $14,900 (2.9%) on 06/03/2026

    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: $3,184 (change assumption)
    Mortgage ($2,712) + Taxes in 2025 ($472)


    Taxes:$5,664

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1709 MICHIGAN AVE #C, KISSIMMEE, FL 34744

    $119,90054 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

    $129,90012 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

    $350,000663 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

    $387,00033 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

    $370,000113 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

    $399,900189 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)




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.