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Homes For Sale in Kissimmee 34744 - 240 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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  • 1807 GOOD NEIGHBOR LOOP, KISSIMMEE, FL 34744

    $440,000Listed 04/02/2026 11:07AM   MLS ID: O6395467

    For Sale O6395467 - 1807 GOOD NEIGHBOR LOOP, KISSIMMEE, FL 34744 33 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2151
       Built: 2022
    Monthly Fee: $30
       Tax: $1,907 (2025)
    Community: Tohoqua Ph 2
    Single Family


    Estimated Monthly Payment: $2,600 (change assumption)
    Mortgage ($2,411) + Fees ($30) + Taxes in 2025 ($159)


    Taxes:$1,907

    Elementary School: None

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: None


  • 1135 CHEROKEE DR, KISSIMMEE, FL 34744

    $375,99031 Days on yellowkey   MLS ID: S5144943

    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
    Single Family


    Estimated Monthly Payment: $2,145 (change assumption)
    Mortgage ($2,060) + 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


  • 1989 SPRING SHOWER CIR, KISSIMMEE, FL 34744

    $415,00077 Days on yellowkey   MLS ID: O6371277

    REDUCED by $5,000 (1.2%) on 04/02/2026

    For Sale O6371277 - 1989 SPRING SHOWER CIR, KISSIMMEE, FL 34744 63 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2087
       Built: 2023
    Monthly Fee: $136
       Tax: $7,473 (2025)
    Community: Tohoqua Reserve
    Single Family


    Estimated Monthly Payment: $3,033 (change assumption)
    Mortgage ($2,274) + Fees ($136) + Taxes in 2025 ($623)


    Taxes:$7,473

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2678 FOREST VIEW LN, KISSIMMEE, FL 34744

    $348,99014 Days on yellowkey   MLS ID: O6391606

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

    For Sale O6391606 - 2678 FOREST VIEW LN, KISSIMMEE, FL 34744 30 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1194
       Built: 1990   Tax: $1,689 (2025)
    Community: Oak Run Unit 7
    Single Family


    Estimated Monthly Payment: $2,053 (change assumption)
    Mortgage ($1,912) + Taxes in 2025 ($141)


    Taxes:$1,689

    Elementary School: Mill Creek Elem (K 5)

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Denn John Middle


  • 1502 BITTEROOT ST, KISSIMMEE, FL 34744

    $450,00083 Days on yellowkey   MLS ID: O6372306

    For Sale O6372306 - 1502 BITTEROOT ST, KISSIMMEE, FL 34744 29 photos

    Bed: 5   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2674
       Built: 2024
    Monthly Fee: $11
       Tax: $8,691 (2025)
    Community: Kindred Ph 3B 3C & 3D
    Single Family


    Estimated Monthly Payment: $3,201 (change assumption)
    Mortgage ($2,466) + Fees ($11) + Taxes in 2025 ($724)


    Taxes:$8,691

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 14 GLENDALE DR, KISSIMMEE, FL 34744

    $534,90020 Days on yellowkey   MLS ID: S5145799

    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: $3,403 (change assumption)
    Mortgage ($2,931) + Taxes in 2025 ($472)


    Taxes:$5,664

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1608 BARBERRY DR, KISSIMMEE, FL 34744

    $559,00064 Days on yellowkey   MLS ID: S5142703

    For Sale S5142703 - 1608 BARBERRY DR, KISSIMMEE, FL 34744 86 photos

    Bed: 4   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 2851
       Built: 2023
    Monthly Fee: $11
       Tax: $9,049 (2025)
    Community: Kindred Ph 2C & 2D
    Single Family


    Estimated Monthly Payment: $3,828 (change assumption)
    Mortgage ($3,063) + Fees ($11) + Taxes in 2025 ($754)


    Taxes:$9,049

    Elementary School: Neptune Elementary

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Harmony Middle


  • 1595 SHADY OAK DR, KISSIMMEE, FL 34744

    $457,00035 Days on yellowkey   MLS ID: S5144261

    For Sale S5144261 - 1595 SHADY OAK DR, KISSIMMEE, FL 34744 39 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2116
       Built: 1981   Tax: $4,757 (2025)
    Community: Regal Oak Shores Unit 6
    Single Family


    Estimated Monthly Payment: $2,900 (change assumption)
    Mortgage ($2,504) + Taxes in 2025 ($396)


    Taxes:$4,757

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1831 BRIGHT SKY DR, KISSIMMEE, FL 34744

    $467,201121 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)


  • 2400 VOLUNTEER AVE, KISSIMMEE, FL 34744

    $455,701121 Days on yellowkey   MLS ID: O6364319

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

    REDUCED by $27,000 (5.6%) on 03/31/2026

    For Sale O6364319 - 2400 VOLUNTEER AVE, 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: $2,507 (change assumption)
    Mortgage ($2,497) + 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)


  • 4424 SILVER CREEK ST, KISSIMMEE, FL 34744

    $494,90069 Days on yellowkey   MLS ID: L4958851

    For Sale L4958851 - 4424 SILVER CREEK ST, KISSIMMEE, FL 34744 28 photos

    Bed: 5   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2370
       Built: 2019
    Monthly Fee: $123
       Tax: $6,332 (2025)
    Community: Creekside At Boggy Creek Ph 1
    Single Family


    Estimated Monthly Payment: $3,362 (change assumption)
    Mortgage ($2,712) + Fees ($123) + Taxes in 2025 ($528)


    Taxes:$6,332

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2753 BURROWS AVE, KISSIMMEE, FL 34744

    $174,990106 Days on yellowkey   MLS ID: S5140396

    4 Days Off yellowkey (back on 3/23/2026)

    For Sale S5140396 - 2753 BURROWS AVE, KISSIMMEE, FL 34744 8 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1086
       Built: 1984   Tax: $2,004 (2024)
    Community: Lee Bel Park
    Manufactured Home


    Estimated Monthly Payment: $1,126 (change assumption)
    Mortgage ($959) + Taxes in 2024 ($167)


    Taxes:$2,004

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 1673 BARBERRY DR, KISSIMMEE, FL 34744

    $460,000Listed 04/01/2026 11:13PM   MLS ID: S5147034

    For Sale S5147034 - 1673 BARBERRY DR, KISSIMMEE, FL 34744 34 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1846
       Built: 2023
    Monthly Fee: $11
       Tax: $6,214 (2025)
    Community: Kindred Ph 2C & 2D
    Single Family


    Estimated Monthly Payment: $3,049 (change assumption)
    Mortgage ($2,520) + Fees ($11) + Taxes in 2025 ($518)


    Taxes:$6,214

    Elementary School: Island Village Elementary School

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 1757 QUAIL RIDGE LOOP, KISSIMMEE, FL 34744

    $344,9993 Days on yellowkey   MLS ID: O6391222

    For Sale O6391222 - 1757 QUAIL RIDGE LOOP, KISSIMMEE, FL 34744 20 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1109
       Built: 1992   Tax: $4,829 (2025)
    Community: Quail Hollow Ph 1
    Single Family


    Estimated Monthly Payment: $2,293 (change assumption)
    Mortgage ($1,890) + Taxes in 2025 ($402)


    Taxes:$4,829

    Elementary School: Mill Creek Elem (K 5)

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Denn John Middle


  • 1737 KATO WAY, KISSIMMEE, FL 34744

    $355,0001 Day on yellowkey   MLS ID: TB8492414

    For Sale TB8492414 - 1737 KATO WAY, KISSIMMEE, FL 34744 33 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1935
       Built: 2018
    Monthly Fee: $168
       Tax: $4,031 (2025)
    Community: Heritage Run
    Townhouse


    Estimated Monthly Payment: $2,449 (change assumption)
    Mortgage ($1,945) + Fees ($168) + Taxes in 2025 ($336)


    Taxes:$4,031

    Elementary School: Mill Creek Elem (K 5)

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Denn John Middle


  • 3136 QUEEN ALEXANDRIA DR, KISSIMMEE, FL 34744

    $399,00017 Days on yellowkey   MLS ID: O6390824

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

    For Sale O6390824 - 3136 QUEEN ALEXANDRIA DR, KISSIMMEE, FL 34744 47 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1860
       Built: 2010
    Monthly Fee: $136
       Tax: $3,327 (2025)
    Community: Raintree At Springlake Village Ph 2
    Single Family


    Estimated Monthly Payment: $2,599 (change assumption)
    Mortgage ($2,186) + Fees ($136) + Taxes in 2025 ($277)


    Taxes:$3,327

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2335 WOODSIDE WAY, KISSIMMEE, FL 34744

    $359,9006 Days on yellowkey   MLS ID: S5146629

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

    For Sale S5146629 - 2335 WOODSIDE WAY, KISSIMMEE, FL 34744 34 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1712
       Built: 1974   Tax: $3,278 (2025)
    Community: Heather Oaks
    Single Family


    Estimated Monthly Payment: $2,245 (change assumption)
    Mortgage ($1,972) + Taxes in 2025 ($273)


    Taxes:$3,278

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 214 FARRINGTON LN, KISSIMMEE, FL 34744

    $585,000185 Days on yellowkey   MLS ID: S5135561

    For Sale S5135561 - 214 FARRINGTON LN, KISSIMMEE, FL 34744 54 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 3332
       Built: 1999   Tax: $4,069 (2024)
    Community: Remington Ph 1 Tr E
    Single Family


    Estimated Monthly Payment: $3,544 (change assumption)
    Mortgage ($3,205) + Taxes in 2024 ($339)


    Taxes:$4,069

    Elementary School: Partin Settlement Elem

    High School: Gateway High School (9 12)

    Tax Year: 2024

    Middle School: Neptune Middle (6-8)


  • 1872 TOHOQUA BLVD, KISSIMMEE, FL 34744

    $359,90028 Days on yellowkey   MLS ID: S5145177

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

    For Sale S5145177 - 1872 TOHOQUA BLVD, KISSIMMEE, FL 34744 22 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1600
       Built: 2023
    Monthly Fee: $126
       Tax: $5,504 (2025)
    Community: Tohoqua Ph 6
    Townhouse


    Estimated Monthly Payment: $2,557 (change assumption)
    Mortgage ($1,972) + Fees ($126) + Taxes in 2025 ($459)


    Taxes:$5,504

    Elementary School: Neptune Elementary

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 2806 VIA LARGO CT, KISSIMMEE, FL 34744

    $499,000178 Days on yellowkey   MLS ID: O6349411

    For Sale O6349411 - 2806 VIA LARGO CT, KISSIMMEE, FL 34744 43 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 3088
       Built: 2008
    Monthly Fee: $163
       Tax: $8,855 (2024)
    Community: Villa Sol Village 2
    Single Family


    Estimated Monthly Payment: $3,635 (change assumption)
    Mortgage ($2,734) + Fees ($163) + Taxes in 2024 ($738)


    Taxes:$8,855

    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.