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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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  • 4020 SUNNY DAY WAY, KISSIMMEE, FL 34744

    $419,90060 Days on yellowkey   MLS ID: S5149650

    REDUCED by $10,000 (2.3%) on 06/23/2026

    For Sale S5149650 - 4020 SUNNY DAY WAY, KISSIMMEE, FL 34744 34 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2148
       Built: 2006
    Monthly Fee: $83
       Tax: $5,436 (2025)
    Community: Turnberry Reserve Unit 1
    Single Family


    Estimated Monthly Payment: $2,837 (change assumption)
    Mortgage ($2,301) + Fees ($83) + Taxes in 2025 ($453)


    Taxes:$5,436

    Elementary School: East Lake Elementary-OS

    High School: Tohopekaliga High School

    Tax Year: 2025

    Middle School: Narcoossee Middle


  • 1491 AUGUST GRAY DR, KISSIMMEE, FL 34744

    $419,90093 Days on yellowkey   MLS ID: O6397176

    REDUCED by $10,100 (2.3%) on 06/23/2026

    SHORT SALE O6397176 - 1491 AUGUST GRAY DR, KISSIMMEE, FL 34744 34 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2070
       Built: 2025
    Monthly Fee: $80
       Tax: $1,748 (2025)
    Community: Seasons At Big Sky Ph 1
    Single Family


    Estimated Monthly Payment: $2,526 (change assumption)
    Mortgage ($2,301) + Fees ($80) + Taxes in 2025 ($146)


    Taxes:$1,748

    Elementary School: Partin Settlement Elem

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 1778 GOOD NEIGHBOR LOOP, KISSIMMEE, FL 34744

    $470,000139 Days on yellowkey   MLS ID: O6384377

    1 Days Off yellowkey (back on 6/23/2026)

    For Sale O6384377 - 1778 GOOD NEIGHBOR LOOP, KISSIMMEE, FL 34744 32 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2133
       Built: 2022
    Monthly Fee: $7
       Tax: $7,640 (2025)
    Community: Tohoqua Ph 2
    Single Family


    Estimated Monthly Payment: $3,219 (change assumption)
    Mortgage ($2,575) + Fees ($7) + Taxes in 2025 ($637)


    Taxes:$7,640

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1772 STAMEN DR, KISSIMMEE, FL 34744

    $495,50087 Days on yellowkey   MLS ID: S5147865

    For Sale S5147865 - 1772 STAMEN DR, KISSIMMEE, FL 34744 28 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1965
       Built: 2023
    Monthly Fee: $160
       Tax: $5,861 (2025)
    Community: Pennyroyal
    Single Family


    Estimated Monthly Payment: $3,363 (change assumption)
    Mortgage ($2,715) + Fees ($160) + Taxes in 2025 ($488)


    Taxes:$5,861

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1213 CHEROKEE DR, KISSIMMEE, FL 34744

    $325,00019 Days on yellowkey   MLS ID: K4903584

    For Sale K4903584 - 1213 CHEROKEE DR, KISSIMMEE, FL 34744 5 photos

    Bed: 3   Bath: 1.0
    Liv Area Sq Ft: 1715
       Built: 1965   Tax: $4,057 (2025)
    Community: Osceola Acres
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,119 (change assumption)
    Mortgage ($1,781) + Taxes in 2025 ($338)


    Taxes:$4,057

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2122 SOUTHBURY DR, KISSIMMEE, FL 34744

    $386,49021 Days on yellowkey   MLS ID: O6418725

    For Sale O6418725 - 2122 SOUTHBURY DR, KISSIMMEE, FL 34744 27 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1770
       Built: 2026
    Monthly Fee: $126
       Tax: $1,920 (2025)
    Community: Tohoqua
    Spa: No

    Townhouse


    Estimated Monthly Payment: $2,404 (change assumption)
    Mortgage ($2,118) + Fees ($126) + Taxes in 2025 ($160)


    Taxes:$1,920

    Elementary School: Neptune Elementary

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 1502 JADEWOOD WAY, KISSIMMEE, FL 34744

    $350,000691 Days on yellowkey   MLS ID: O6233314

    0 Days Off yellowkey (back on 6/18/2026)

    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


  • 1620 MARINA LAKE DR, KISSIMMEE, FL 34744

    $790,00052 Days on yellowkey   MLS ID: S5150329

    For Sale S5150329 - 1620 MARINA LAKE DR, KISSIMMEE, FL 34744 95 photos

    Bed: 5   Bath: 4.0   Gar: 3
    Liv Area Sq Ft: 3643
       Built: 2000
    Monthly Fee: $75
       Tax: $5,686 (2025)
    Community: Ashley Cove Unit 1
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $4,877 (change assumption)
    Mortgage ($4,329) + Fees ($75) + Taxes in 2025 ($474)


    Taxes:$5,686

    Elementary School: Partin Settlement Elem

    High School: None

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 2705 PRESTWICK LN, KISSIMMEE, FL 34744

    $410,000137 Days on yellowkey   MLS ID: O6384546

    For Sale O6384546 - 2705 PRESTWICK LN, KISSIMMEE, FL 34744 43 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 1719
       Built: 2005
    Monthly Fee: $73
       Tax: $6,174 (2025)
    Community: Remington Prcl M1
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,834 (change assumption)
    Mortgage ($2,247) + Fees ($73) + Taxes in 2025 ($515)


    Taxes:$6,174

    Elementary School: Partin Settlement Elem

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 3215 STRATTON CIR, KISSIMMEE, FL 34744

    $450,00050 Days on yellowkey   MLS ID: S5150428

    REDUCED by $10,000 (2.2%) on 06/21/2026

    For Sale S5150428 - 3215 STRATTON CIR, KISSIMMEE, FL 34744 24 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2432
       Built: 2018
    Monthly Fee: $80
       Tax: $4,244 (2025)
    Community: South Pointe
    Single Family


    Estimated Monthly Payment: $2,899 (change assumption)
    Mortgage ($2,466) + Fees ($80) + Taxes in 2025 ($354)


    Taxes:$4,244

    Elementary School: East Lake Elementary-OS

    High School: Tohopekaliga High School

    Tax Year: 2025

    Middle School: Narcoossee Middle


  • 1541 AMHERST LN, KISSIMMEE, FL 34744

    $400,000264 Days on yellowkey   MLS ID: O6354005

    REDUCED by $5,000 (1.2%) on 06/16/2026

    For Sale O6354005 - 1541 AMHERST LN, KISSIMMEE, FL 34744 26 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2002
       Built: 1989   Tax: $1,317 (2024)
    Community: Oak Hollow Ph 4
    Single Family


    Estimated Monthly Payment: $2,302 (change assumption)
    Mortgage ($2,192) + Taxes in 2024 ($110)


    Taxes:$1,317

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 1692 TOHOQUA BLVD, KISSIMMEE, FL 34744

    $369,99057 Days on yellowkey   MLS ID: O6408176

    REDUCED by $5,000 (1.3%) on 06/21/2026

    For Sale O6408176 - 1692 TOHOQUA BLVD, KISSIMMEE, FL 34744 29 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1780
       Built: 2022
    Monthly Fee: $137
       Tax: $6,593 (2025)
    Community: Tohoqua Ph 6
    Townhouse


    Estimated Monthly Payment: $2,714 (change assumption)
    Mortgage ($2,027) + Fees ($137) + Taxes in 2025 ($549)


    Taxes:$6,593

    Elementary School: Canoe Creek K-8

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Canoe Creek K-8


  • 1743 GOOD NEIGHBOR LOOP, KISSIMMEE, FL 34744

    $449,00068 Days on yellowkey   MLS ID: O6403890

    REDUCED by $20,000 (4.3%) on 06/21/2026

    For Sale O6403890 - 1743 GOOD NEIGHBOR LOOP, KISSIMMEE, FL 34744 17 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2133
       Built: 2022
    Monthly Fee: $7
       Tax: $8,696 (2025)
    Community: Tohoqua Ph 2
    Single Family


    Estimated Monthly Payment: $3,192 (change assumption)
    Mortgage ($2,460) + Fees ($7) + Taxes in 2025 ($725)


    Taxes:$8,696

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2685 ROBIN AVE, KISSIMMEE, FL 34744

    $346,00029 Days on yellowkey   MLS ID: S5151844

    0 Days Off yellowkey (back on 6/20/2026)

    For Sale S5151844 - 2685 ROBIN AVE, KISSIMMEE, FL 34744 26 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1661
       Built: 1974   Tax: $1,560 (2025)
    Community: Emerald Lake Colony Unit 1
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,026 (change assumption)
    Mortgage ($1,896) + Taxes in 2025 ($130)


    Taxes:$1,560

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2345 SOUTHBURY, KISSIMMEE, FL 34744

    $369,00029 Days on yellowkey   MLS ID: S5151680

    For Sale S5151680 - 2345 SOUTHBURY, KISSIMMEE, FL 34744 22 photos

    Bed: 3   Bath: 2.5   Gar: 4
    Liv Area Sq Ft: 1553
       Built: 2025
    Monthly Fee: $127
       Tax: $2,000 (2025)
    Community: Tohoqua Phase 1
    Townhouse


    Estimated Monthly Payment: $2,316 (change assumption)
    Mortgage ($2,022) + Fees ($127) + Taxes in 2025 ($167)


    Taxes:$2,000

    Elementary School: Neptune Elementary

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 2619 PEACE OF MIND AVE, KISSIMMEE, FL 34744

    $479,000155 Days on yellowkey   MLS ID: O6380357

    REDUCED by $4,000 (0.8%) on 05/28/2026

    For Sale O6380357 - 2619 PEACE OF MIND AVE, KISSIMMEE, FL 34744 57 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2109
       Built: 2025
    Monthly Fee: $10
       Tax: $3,729 (2025)
    Community: Tohoqua 50S
    Single Family


    Estimated Monthly Payment: $2,945 (change assumption)
    Mortgage ($2,625) + Fees ($10) + Taxes in 2025 ($311)


    Taxes:$3,729

    Elementary School: Neptune Elementary

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 1631 BITTEROOT ST, KISSIMMEE, FL 34744

    $364,99085 Days on yellowkey   MLS ID: S5147958

    REDUCED by $5,000 (1.4%) on 06/01/2026

    For Sale S5147958 - 1631 BITTEROOT ST, KISSIMMEE, FL 34744 57 photos

    Bed: 3   Bath: 2.5   Gar: 1
    Liv Area Sq Ft: 1814
       Built: 2024
    Monthly Fee: $11
       Tax: $5,432 (2025)
    Community: Kindred
    Townhouse


    Estimated Monthly Payment: $2,464 (change assumption)
    Mortgage ($2,000) + Fees ($11) + Taxes in 2025 ($453)


    Taxes:$5,432

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1959 SUMMER SERENITY DR, KISSIMMEE, FL 34744

    $390,00022 Days on yellowkey   MLS ID: S5151902

    For Sale S5151902 - 1959 SUMMER SERENITY DR, KISSIMMEE, FL 34744 34 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2072
       Built: 2023
    Monthly Fee: $7
       Tax: $6,594 (2025)
    Community: Tohoqua Ph 4B
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,693 (change assumption)
    Mortgage ($2,137) + Fees ($7) + Taxes in 2025 ($550)


    Taxes:$6,594

    Elementary School: Neptune Elementary

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 2370 VALLEY AVE, KISSIMMEE, FL 34744

    $290,00022 Days on yellowkey   MLS ID: S5152035

    For Sale S5152035 - 2370 VALLEY AVE, KISSIMMEE, FL 34744 22 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1596
       Built: 1973   Tax: $534 (2025)
    Community: Town & Country Estates Unit 1
    Single Family


    Estimated Monthly Payment: $1,633 (change assumption)
    Mortgage ($1,589) + Taxes in 2025 ($44)


    Taxes:$534

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1034 CHALCEDONY ST, KISSIMMEE, FL 34744

    $279,90022 Days on yellowkey   MLS ID: S5152151

    For Sale S5152151 - 1034 CHALCEDONY ST, KISSIMMEE, FL 34744 22 photos

    Bed: 2   Bath: 2.5   Gar: 1
    Liv Area Sq Ft: 1386
       Built: 2009
    Monthly Fee: $170
       Tax: $3,670 (2025)
    Community: Amber Pointe Unit 2
    Townhouse


    Estimated Monthly Payment: $2,009 (change assumption)
    Mortgage ($1,534) + Fees ($170) + Taxes in 2025 ($306)


    Taxes:$3,670

    Elementary School: Partin Settlement Elem

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Denn John 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.