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Homes For Sale in Kissimmee 34744 - 354 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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  • 2627 CLEAR NIGHT AVENUE, KISSIMMEE, FL 34744

    $636,11043 Days on yellowkey   MLS ID: O6412075

    REDUCED by $10,000 (1.5%) on 06/30/2026

    For Sale O6412075 - 2627 CLEAR NIGHT AVENUE, KISSIMMEE, FL 34744 43 photos

    Bed: 5   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 3598
       Built: 2026
    Monthly Fee: $42
       Tax: $1,329 (2025)
    Community: Tohoqua
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,638 (change assumption)
    Mortgage ($3,485) + Fees ($42) + Taxes in 2025 ($111)


    Taxes:$1,329

    Elementary School: Neptune Elementary

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 2462 MILL RUN BLVD, KISSIMMEE, FL 34744

    $429,90019 Days on yellowkey   MLS ID: O6418912

    0 Days Off yellowkey (back on 6/30/2026)

    REDUCED by $10,000 (2.3%) on 06/24/2026

    For Sale O6418912 - 2462 MILL RUN BLVD, KISSIMMEE, FL 34744 46 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1538
       Built: 1980   Tax: $1,698 (2025)
    Community: Mill Run
    Single Family


    Estimated Monthly Payment: $2,497 (change assumption)
    Mortgage ($2,356) + Taxes in 2025 ($141)


    Taxes:$1,698

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2559 RELAXING LN, KISSIMMEE, FL 34744

    $335,00029 Days on yellowkey   MLS ID: O6416641

    3 Days Off yellowkey (back on 6/30/2026)

    For Sale O6416641 - 2559 RELAXING LN, KISSIMMEE, FL 34744 45 photos

    Bed: 3   Bath: 2.5   Gar: 1
    Liv Area Sq Ft: 1603
       Built: 2023
    Monthly Fee: $147
       Tax: $6,276 (2025)
    Community: Tohoqua Ph 3
    Townhouse


    Estimated Monthly Payment: $2,506 (change assumption)
    Mortgage ($1,836) + Fees ($147) + Taxes in 2025 ($523)


    Taxes:$6,276

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 3190 MORNING LIGHT WAY, KISSIMMEE, FL 34744

    $235,000137 Days on yellowkey   MLS ID: S5144407

    0 Days Off yellowkey (back on 6/30/2026)

    REDUCED by $24,000 (9.3%) on 04/20/2026

    For Sale S5144407 - 3190 MORNING LIGHT WAY, KISSIMMEE, FL 34744 58 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1288
       Built: 1989   Tax: $3,325 (2025)
    Community: Morningside Village Unit 3
    Manufactured Home


    Estimated Monthly Payment: $1,565 (change assumption)
    Mortgage ($1,288) + Taxes in 2025 ($277)


    Taxes:$3,325

    Elementary School: East Lake Elem

    High School: Tohopekaliga High School

    Tax Year: 2025

    Middle School: Narcoossee Middle


  • 3837 SPRINGLAKE VILLAGE CT, KISSIMMEE, FL 34744

    $360,00061 Days on yellowkey   MLS ID: S5149674

    REDUCED by $10,000 (2.7%) on 06/30/2026

    For Sale S5149674 - 3837 SPRINGLAKE VILLAGE CT, KISSIMMEE, FL 34744 21 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1766
       Built: 1999
    Monthly Fee: $106
       Tax: $1,233 (2025)
    Community: Springlake Village
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,181 (change assumption)
    Mortgage ($1,973) + Fees ($106) + Taxes in 2025 ($103)


    Taxes:$1,233

    Elementary School: East Lake Elem

    High School: Tohopekaliga High School

    Tax Year: 2025

    Middle School: Narcoossee Middle


  • 1895 SPRING SHOWER CIR, KISSIMMEE, FL 34744

    $319,00083 Days on yellowkey   MLS ID: S5148149

    REDUCED by $1,000 (0.3%) on 06/30/2026

    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: $2,125 (change assumption)
    Mortgage ($1,748) + 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)


  • 2890 FRONTIER DR, KISSIMMEE, FL 34744

    $1,375,00012 Days on yellowkey   MLS ID: O6420732

    For Sale O6420732 - 2890 FRONTIER DR, KISSIMMEE, FL 34744 57 photos

    Bed: 3   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 2250
       Built: 1998   Tax: $8,809 (2025)
    Community: Pine Oaks
    Single Family


    Estimated Monthly Payment: $8,268 (change assumption)
    Mortgage ($7,534) + Taxes in 2025 ($734)


    Taxes:$8,809

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 417 BENITA ST, KISSIMMEE, FL 34744

    $284,000514 Days on yellowkey   MLS ID: O6275736

    For Sale O6275736 - 417 BENITA ST, KISSIMMEE, FL 34744 9 photos

    Bed: 3   Bath: 1.5
    Liv Area Sq Ft: 1186
       Built: 1971   Tax: $380 (2023)
    Community: Benita Park
    Single Family


    Estimated Monthly Payment: $1,588 (change assumption)
    Mortgage ($1,556) + Taxes in 2023 ($32)


    Taxes:$380

    Elementary School: None

    High School: None

    Tax Year: 2023

    Middle School: None


  • 1839 GOOD NEIGHBOR LOOP, KISSIMMEE, FL 34744

    $470,000358 Days on yellowkey   MLS ID: O6328214

    REDUCED by $5,000 (1.1%) on 06/13/2026

    For Sale O6328214 - 1839 GOOD NEIGHBOR LOOP, KISSIMMEE, FL 34744 42 photos

    Bed: 4   Bath: 4.0
    Liv Area Sq Ft: 2717
       Built: 2021
    Monthly Fee: $10
       Tax: $7,387 (2025)
    Community: Tohoqua Ph 2
    Single Family


    Estimated Monthly Payment: $3,201 (change assumption)
    Mortgage ($2,575) + Fees ($10) + Taxes in 2025 ($616)


    Taxes:$7,387

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 3504 SOUTHERN CROSS LOOP, KISSIMMEE, FL 34744

    $473,90075 Days on yellowkey   MLS ID: O6402309

    REDUCED by $1,100 (0.2%) on 06/29/2026

    For Sale O6402309 - 3504 SOUTHERN CROSS LOOP, KISSIMMEE, FL 34744 31 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2463
       Built: 2018
    Monthly Fee: $110
       Tax: $5,942 (2025)
    Community: East Lk Preserve-Ph 1
    Single Family


    Estimated Monthly Payment: $3,202 (change assumption)
    Mortgage ($2,597) + Fees ($110) + Taxes in 2025 ($495)


    Taxes:$5,942

    Elementary School: East Lake Elem

    High School: Tohopekaliga High School

    Tax Year: 2025

    Middle School: Narcoossee Middle


  • 1714 CHERYL LN, KISSIMMEE, FL 34744

    $674,90099 Days on yellowkey   MLS ID: O6395426

    REDUCED by $25,000 (3.6%) on 06/29/2026

    For Sale O6395426 - 1714 CHERYL LN, KISSIMMEE, FL 34744 31 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3609
       Built: 1989   Tax: $3,559 (2025)
    Community: Regal Oak Shores Unit 8
    Single Family


    Estimated Monthly Payment: $3,995 (change assumption)
    Mortgage ($3,698) + Taxes in 2025 ($297)


    Taxes:$3,559

    Elementary School: Partin Settlement Elem

    High School: Osceola High School

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 202 WOODSON CT, KISSIMMEE, FL 34744

    $610,50033 Days on yellowkey   MLS ID: O6414003

    REDUCED by $12,500 (2.0%) on 06/29/2026

    For Sale O6414003 - 202 WOODSON CT, KISSIMMEE, FL 34744 72 photos

    Bed: 5   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 3744
       Built: 2000
    Monthly Fee: $92
       Tax: $4,485 (2025)
    Community: Remington Ph 01 Tr C
    Single Family


    Estimated Monthly Payment: $3,811 (change assumption)
    Mortgage ($3,345) + Fees ($92) + Taxes in 2025 ($374)


    Taxes:$4,485

    Elementary School: Partin Settlement Elem

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 3824 BLUE DASHER DR, KISSIMMEE, FL 34744

    $499,990404 Days on yellowkey   MLS ID: O6314514

    For Sale O6314514 - 3824 BLUE DASHER DR, KISSIMMEE, FL 34744 48 photos

    Bed: 5   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 3783
       Built: 2004
    Monthly Fee: $106
       Tax: $6,729 (2024)
    Community: Springlake Village Ph 03
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $3,406 (change assumption)
    Mortgage ($2,740) + Fees ($106) + Taxes in 2024 ($561)


    Taxes:$6,729

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 1380 E LAKE SHORE BLVD, KISSIMMEE, FL 34744

    $649,900659 Days on yellowkey   MLS ID: S5112666

    REDUCED by $20,000 (3.0%) on 06/20/2026

    For Sale S5112666 - 1380 E LAKE SHORE BLVD, KISSIMMEE, FL 34744 99 photos

    Bed: 4   Bath: 4.0   Gar: 3
    Liv Area Sq Ft: 3637
       Built: 2006   Tax: $4,833 (2023)
    Community: East Lake Shores
    Single Family


    Estimated Monthly Payment: $3,964 (change assumption)
    Mortgage ($3,561) + Taxes in 2023 ($403)


    Taxes:$4,833

    Elementary School: None

    High School: None

    Tax Year: 2023

    Middle School: None


  • 2604 SERENITY GARDEN DRIVE, KISSIMMEE, FL 34744

    $498,12044 Days on yellowkey   MLS ID: O6411675

    For Sale O6411675 - 2604 SERENITY GARDEN DRIVE, KISSIMMEE, FL 34744 25 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1850
       Built: 2025
    Monthly Fee: $20
       Tax: $1,329 (2025)
    Community: Tohoqua
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,860 (change assumption)
    Mortgage ($2,729) + Fees ($20) + Taxes in 2025 ($111)


    Taxes:$1,329

    Elementary School: Neptune Elementary

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 2733 SERENITY MEADOW DRIVE, KISSIMMEE, FL 34744

    $392,010102 Days on yellowkey   MLS ID: O6395315

    1 Days Off yellowkey (back on 6/24/2026)

    For Sale O6395315 - 2733 SERENITY MEADOW DRIVE, KISSIMMEE, FL 34744 33 photos

    Bed: 2   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1670
       Built: 2025
    Monthly Fee: $136
       Tax: $3,086 (2025)
    Community: Tohoqua Reserve
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,541 (change assumption)
    Mortgage ($2,148) + Fees ($136) + Taxes in 2025 ($257)


    Taxes:$3,086

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2015 SPRING SHOWER CIR, KISSIMMEE, FL 34744

    $412,000366 Days on yellowkey   MLS ID: S5130256

    For Sale S5130256 - 2015 SPRING SHOWER CIR, KISSIMMEE, FL 34744 49 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2054
       Built: 2022
    Monthly Fee: $128
       Tax: $7,088 (2024)
    Community: Tohoqua Reserve
    Single Family


    Estimated Monthly Payment: $2,976 (change assumption)
    Mortgage ($2,257) + Fees ($128) + Taxes in 2024 ($591)


    Taxes:$7,088

    Elementary School: Neptune Elementary

    High School: Gateway High School (9 12)

    Tax Year: 2024

    Middle School: Neptune Middle (6-8)


  • 205 OWENSHIRE CIR, KISSIMMEE, FL 34744

    $359,90037 Days on yellowkey   MLS ID: S5151174

    For Sale S5151174 - 205 OWENSHIRE CIR, KISSIMMEE, FL 34744 29 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1560
       Built: 2003
    Monthly Fee: $23
       Tax: $5,644 (2025)
    Community: Remington Prcl K Ph 3
    Single Family


    Estimated Monthly Payment: $2,465 (change assumption)
    Mortgage ($1,972) + Fees ($23) + Taxes in 2025 ($470)


    Taxes:$5,644

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2747 KISSIMMEE BAY CIR, KISSIMMEE, FL 34744

    $599,900150 Days on yellowkey   MLS ID: S5143367

    For Sale S5143367 - 2747 KISSIMMEE BAY CIR, KISSIMMEE, FL 34744 62 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3177
       Built: 1991
    Monthly Fee: $195
       Tax: $4,193 (2025)
    Community: Kissimmee Bay
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,831 (change assumption)
    Mortgage ($3,287) + Fees ($195) + Taxes in 2025 ($349)


    Taxes:$4,193

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 3044 CAMINO REAL DR S, KISSIMMEE, FL 34744

    $479,00065 Days on yellowkey   MLS ID: O6406104

    REDUCED by $10,000 (2.0%) on 05/31/2026

    For Sale O6406104 - 3044 CAMINO REAL DR S, KISSIMMEE, FL 34744 35 photos

    Bed: 5   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2264
       Built: 2005
    Monthly Fee: $160
       Tax: $5,505 (2025)
    Community: Villa Sol Ph 2 Village 3
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,243 (change assumption)
    Mortgage ($2,625) + Fees ($160) + Taxes in 2025 ($459)


    Taxes:$5,505

    Elementary School: Cypress Elem (K 6)

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Parkway Middle




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.