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Homes For Sale in Kissimmee 34744 - 299 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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  • 4436 AZURE ISLE WAY, KISSIMMEE, FL 34744

    $499,00078 Days on yellowkey   MLS ID: O6379702

    For Sale O6379702 - 4436 AZURE ISLE WAY, KISSIMMEE, FL 34744 35 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2251
       Built: 2013
    Monthly Fee: $108
       Tax: $3,771 (2025)
    Community: North Point Ph 1B
    Single Family


    Estimated Monthly Payment: $3,156 (change assumption)
    Mortgage ($2,734) + Fees ($108) + Taxes in 2025 ($314)


    Taxes:$3,771

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2705 WILLOW GLEN CIR, KISSIMMEE, FL 34744

    $390,00087 Days on yellowkey   MLS ID: G5107373

    0 Days Off yellowkey (back on 4/8/2026)

    For Sale G5107373 - 2705 WILLOW GLEN CIR, KISSIMMEE, FL 34744 14 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 1679
       Built: 2001
    Monthly Fee: $19
       Tax: $6,110 (2025)
    Community: Gleneagles
    Single Family


    Estimated Monthly Payment: $2,665 (change assumption)
    Mortgage ($2,137) + Fees ($19) + Taxes in 2025 ($509)


    Taxes:$6,110

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 305 POINCIANA CIR, KISSIMMEE, FL 34744

    $360,00088 Days on yellowkey   MLS ID: S5142338

    0 Days Off yellowkey (back on 1/26/2026)

    For Sale S5142338 - 305 POINCIANA CIR, KISSIMMEE, FL 34744 1 photos

    Bed: 4   Bath: 2.0
    Liv Area Sq Ft: 1361
       Built: 1955   Tax: $521 (2025)
    Community: Dellwood Park
    Single Family


    Estimated Monthly Payment: $2,016 (change assumption)
    Mortgage ($1,973) + Taxes in 2025 ($43)


    Taxes:$521

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2670 REAGAN LN, KISSIMMEE, FL 34744

    $370,00057 Days on yellowkey   MLS ID: O6385604

    For Sale O6385604 - 2670 REAGAN LN, KISSIMMEE, FL 34744 65 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1294
       Built: 1981   Tax: $1,125 (2025)
    Community: Gehrett Gardens
    Single Family


    Estimated Monthly Payment: $2,121 (change assumption)
    Mortgage ($2,027) + Taxes in 2025 ($94)


    Taxes:$1,125

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2921 PUERTA DEL SOL BLVD, KISSIMMEE, FL 34744

    $257,800400 Days on yellowkey   MLS ID: S5123068

    REDUCED by $9,199 (3.4%) on 04/08/2026

    For Sale S5123068 - 2921 PUERTA DEL SOL BLVD, KISSIMMEE, FL 34744 34 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1274
       Built: 2014
    Monthly Fee: $362
       Tax: $5,527 (2024)
    Community: Villa Sol
    Townhouse


    Estimated Monthly Payment: $2,235 (change assumption)
    Mortgage ($1,413) + Fees ($362) + Taxes in 2024 ($461)


    Taxes:$5,527

    Elementary School: East Lake Elem

    High School: Tohopekaliga High School

    Tax Year: 2024

    Middle School: Neptune Middle (6-8)


  • 1917 HOWARD MESA DR, KISSIMMEE, FL 34744

    $414,99017 Days on yellowkey   MLS ID: O6397006

    For Sale O6397006 - 1917 HOWARD MESA DR, KISSIMMEE, FL 34744 34 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1614
       Built: 2025
    Monthly Fee: $11
       Tax: $3,684 (2025)
    Community: Kindred Ph 3B 3C & 3D
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,592 (change assumption)
    Mortgage ($2,274) + Fees ($11) + Taxes in 2025 ($307)


    Taxes:$3,684

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2864 RUNNING BROOK CIR, KISSIMMEE, FL 34744

    $380,00017 Days on yellowkey   MLS ID: S5146976

    For Sale S5146976 - 2864 RUNNING BROOK CIR, KISSIMMEE, FL 34744 45 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1607
       Built: 2012
    Monthly Fee: $167
       Tax: $2,952 (2025)
    Community: North Shore Vlg Ph 2
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,495 (change assumption)
    Mortgage ($2,082) + Fees ($167) + Taxes in 2025 ($246)


    Taxes:$2,952

    Elementary School: East Lake Elementary-OS

    High School: Tohopekaliga High School

    Tax Year: 2025

    Middle School: Narcoossee Middle


  • 1740 KING GEORGE DR, KISSIMMEE, FL 34744

    $364,90070 Days on yellowkey   MLS ID: S5143831

    4 Days Off yellowkey (back on 4/7/2026)

    For Sale S5143831 - 1740 KING GEORGE DR, KISSIMMEE, FL 34744 22 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1574
       Built: 1984   Tax: $1,737 (2025)
    Community: Kings Point
    Single Family


    Estimated Monthly Payment: $2,144 (change assumption)
    Mortgage ($1,999) + Taxes in 2025 ($145)


    Taxes:$1,737

    Elementary School: Partin Settlement Elem

    High School: Osceola High School

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 815 BAY ST, KISSIMMEE, FL 34744

    $289,90049 Days on yellowkey   MLS ID: S5145265

    For Sale S5145265 - 815 BAY ST, KISSIMMEE, FL 34744 39 photos

    Bed: 2   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1458
       Built: 1951   Tax: $4,764 (2025)
    Community: Robert Bass Add
    Single Family


    Estimated Monthly Payment: $1,985 (change assumption)
    Mortgage ($1,588) + Taxes in 2025 ($397)


    Taxes:$4,764

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2406 KAM CT, KISSIMMEE, FL 34744

    $298,900184 Days on yellowkey   MLS ID: S5137174

    For Sale S5137174 - 2406 KAM CT, KISSIMMEE, FL 34744 31 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1148
       Built: 2000
    Monthly Fee: $193
       Tax: $3,214 (2024)
    Community: Jade East Unit 2
    Townhouse


    Estimated Monthly Payment: $2,099 (change assumption)
    Mortgage ($1,638) + Fees ($193) + Taxes in 2024 ($268)


    Taxes:$3,214

    Elementary School: Partin Settlement Elem

    High School: Gateway High School (9 12)

    Tax Year: 2024

    Middle School: Neptune Middle (6-8)


  • 1326 SWEETWOOD BLVD, KISSIMMEE, FL 34744

    $435,00018 Days on yellowkey   MLS ID: S5147282

    For Sale S5147282 - 1326 SWEETWOOD BLVD, KISSIMMEE, FL 34744 20 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1571
       Built: 1978   Tax: $5,280 (2025)
    Community: Sweetwood Estates
    Single Family


    Estimated Monthly Payment: $2,824 (change assumption)
    Mortgage ($2,384) + Taxes in 2025 ($440)


    Taxes:$5,280

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 422 JANICE KAY PL, KISSIMMEE, FL 34744

    $479,000239 Days on yellowkey   MLS ID: S5133405

    REDUCED by $10,000 (2.0%) on 04/06/2026

    For Sale S5133405 - 422 JANICE KAY PL, KISSIMMEE, FL 34744 19 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 3424
       Built: 2004
    Monthly Fee: $13
       Tax: $7,517 (2024)
    Community: Eagles Landing
    Single Family


    Estimated Monthly Payment: $3,264 (change assumption)
    Mortgage ($2,625) + Fees ($13) + Taxes in 2024 ($626)


    Taxes:$7,517

    Elementary School: Partin Settlement Elem

    High School: Gateway High School (9 12)

    Tax Year: 2024

    Middle School: Neptune Middle (6-8)


  • 1237 MARYGON ST, KISSIMMEE, FL 34744

    $324,90086 Days on yellowkey   MLS ID: S5142677

    For Sale S5142677 - 1237 MARYGON ST, KISSIMMEE, FL 34744 37 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1176
       Built: 1968   Tax: $2,001 (2025)
    Community: Johnston Park Rep
    Spa: No

    Single Family


    Estimated Monthly Payment: $1,947 (change assumption)
    Mortgage ($1,780) + Taxes in 2025 ($167)


    Taxes:$2,001

    Elementary School: Mill Creek Elem (K 5)

    High School: Osceola High School

    Tax Year: 2025

    Middle School: Denn John Middle


  • 109 THORNBURY DR, KISSIMMEE, FL 34744

    $360,00021 Days on yellowkey   MLS ID: O6395896

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

    Bed: 3   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: $2,493 (change assumption)
    Mortgage ($1,973) + Fees ($14) + Taxes in 2025 ($506)


    Taxes:$6,074

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 3120 BOGGY TERRACE DR, KISSIMMEE, FL 34744

    $345,00084 Days on yellowkey   MLS ID: L4958919

    3 Days Off yellowkey (back on 4/6/2026)

    For Sale L4958919 - 3120 BOGGY TERRACE DR, KISSIMMEE, FL 34744 45 photos

    Bed: 1   Bath: 1.0   Gar: 2
    Liv Area Sq Ft: 360
       Built: 1965   Tax: $3,010 (2025)
    Community: Acreage & Unrec
    Modular Home


    Estimated Monthly Payment: $2,141 (change assumption)
    Mortgage ($1,890) + Taxes in 2025 ($251)


    Taxes:$3,010

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2629 BALMORAL CT, KISSIMMEE, FL 34744

    $399,000191 Days on yellowkey   MLS ID: O6352456

    3 Days Off yellowkey (back on 4/6/2026)

    For Sale O6352456 - 2629 BALMORAL CT, KISSIMMEE, FL 34744 20 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2300
       Built: 2002
    Monthly Fee: $14
       Tax: $7,183 (2024)
    Community: Remington Prcl G Ph 01
    Single Family


    Estimated Monthly Payment: $2,799 (change assumption)
    Mortgage ($2,186) + Fees ($14) + Taxes in 2024 ($599)


    Taxes:$7,183

    Elementary School: Partin Settlement Elem

    High School: Gateway High School (9 12)

    Tax Year: 2024

    Middle School: Neptune Middle (6-8)


  • 2405 SW HASSONITE ST, KISSIMMEE, FL 34744

    $279,90057 Days on yellowkey   MLS ID: O6377194

    3 Days Off yellowkey (back on 4/6/2026)

    REDUCED by $5,000 (1.8%) on 04/02/2026

    For Sale O6377194 - 2405 SW HASSONITE ST, KISSIMMEE, FL 34744 17 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1684
       Built: 2006
    Monthly Fee: $170
       Tax: $4,235 (2025)
    Community: Amber Pointe
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,057 (change assumption)
    Mortgage ($1,534) + Fees ($170) + Taxes in 2025 ($353)


    Taxes:$4,235

    Elementary School: Partin Settlement Elem

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Denn John Middle


  • 417 BENITA ST, KISSIMMEE, FL 34744

    $284,000436 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


  • 1831 BRIGHT SKY DR, KISSIMMEE, FL 34744

    $467,201143 Days on yellowkey   MLS ID: O6364329

    1 Days Off yellowkey (back on 4/2/2026)

    REDUCED by $30,000 (6.0%) on 03/31/2026

    For Sale O6364329 - 1831 BRIGHT SKY DR, KISSIMMEE, FL 34744 29 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2139
       Built: 2025
    Monthly Fee: $10

    Community: Tohoqua 50S
    Single Family


    Estimated Monthly Payment: $2,570 (change assumption)
    Mortgage ($2,560) + Fees ($10) + Taxes in 2024 ($0)


    Taxes:$0

    Elementary School: Neptune Elementary

    High School: Gateway High School (9 12)

    Tax Year: 2024

    Middle School: Neptune Middle (6-8)


  • 2512 BLOWING BREEZE AVE, KISSIMMEE, FL 34744

    $340,00058 Days on yellowkey   MLS ID: S5144271

    REDUCED by $10,000 (2.9%) on 04/05/2026

    For Sale S5144271 - 2512 BLOWING BREEZE AVE, KISSIMMEE, FL 34744 40 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1528
       Built: 2021
    Monthly Fee: $154
       Tax: $5,017 (2025)
    Community: Tohoqua Ph 1B
    Townhouse


    Estimated Monthly Payment: $2,435 (change assumption)
    Mortgage ($1,863) + Fees ($154) + Taxes in 2025 ($418)


    Taxes:$5,017

    Elementary School: None

    High School: None

    Tax Year: 2025

    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.