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Homes For Sale in Kissimmee 34744 - 355 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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  • 1880 SPRING SHOWER CIR, KISSIMMEE, FL 34744

    $349,990152 Days on yellowkey   MLS ID: S5141218

    For Sale S5141218 - 1880 SPRING SHOWER CIR, KISSIMMEE, FL 34744 43 photos

    Bed: 2   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1559
       Built: 2024
    Monthly Fee: $220
       Tax: $1,141 (2025)
    Community: Tohoqua Ph 5B
    Single Family


    Estimated Monthly Payment: $2,233 (change assumption)
    Mortgage ($1,918) + Fees ($220) + Taxes in 2025 ($95)


    Taxes:$1,141

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2665 MILL RUN BLVD, KISSIMMEE, FL 34744

    $314,50039 Days on yellowkey   MLS ID: O6404497

    REDUCED by $13,000 (4.0%) on 06/09/2026

    FORECLOSURE O6404497 - 2665 MILL RUN BLVD, KISSIMMEE, FL 34744 11 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1282
       Built: 1986   Tax: $1,712 (2025)
    Community: Mill Run Un 5
    Single Family


    Estimated Monthly Payment: $1,866 (change assumption)
    Mortgage ($1,723) + Taxes in 2025 ($143)


    Taxes:$1,712

    Elementary School: Mill Creek Elem (K 5)

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Denn John Middle


  • 1838 TOHOQUA BLVD, KISSIMMEE, FL 34744

    $309,90065 Days on yellowkey   MLS ID: S5147475

    REDUCED by $11,090 (3.5%) on 05/14/2026

    For Sale S5147475 - 1838 TOHOQUA BLVD, KISSIMMEE, FL 34744 43 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1600
       Built: 2023
    Monthly Fee: $139
       Tax: $6,276 (2025)
    Community: Tohoqua Ph 6
    Townhouse


    Estimated Monthly Payment: $2,360 (change assumption)
    Mortgage ($1,698) + Fees ($139) + Taxes in 2025 ($523)


    Taxes:$6,276

    Elementary School: Neptune Elementary

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 2728 PORTCHESTER CT, KISSIMMEE, FL 34744

    $394,900395 Days on yellowkey   MLS ID: S5126915

    REDUCED by $5,000 (1.3%) on 06/09/2026

    For Sale S5126915 - 2728 PORTCHESTER CT, KISSIMMEE, FL 34744 16 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 1960
       Built: 2005
    Monthly Fee: $7
       Tax: $6,060 (2024)
    Community: Somerset
    Single Family


    Estimated Monthly Payment: $2,676 (change assumption)
    Mortgage ($2,164) + Fees ($7) + Taxes in 2024 ($505)


    Taxes:$6,060

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 2513 CROWN RIDGE CIR, KISSIMMEE, FL 34744

    $379,90036 Days on yellowkey   MLS ID: S5149544

    For Sale S5149544 - 2513 CROWN RIDGE CIR, KISSIMMEE, FL 34744 68 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1766
       Built: 2001
    Monthly Fee: $14
       Tax: $3,026 (2025)
    Community: Remington
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,348 (change assumption)
    Mortgage ($2,082) + Fees ($14) + Taxes in 2025 ($252)


    Taxes:$3,026

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1550 REGAL OAK DR, KISSIMMEE, FL 34744

    $470,00029 Days on yellowkey   MLS ID: S5150034

    REDUCED by $10,000 (2.1%) on 06/09/2026

    For Sale S5150034 - 1550 REGAL OAK DR, KISSIMMEE, FL 34744 44 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2312
       Built: 1983   Tax: $3,426 (2025)
    Community: Regal Oak Shores Unit 4
    Single Family


    Estimated Monthly Payment: $2,861 (change assumption)
    Mortgage ($2,575) + Taxes in 2025 ($286)


    Taxes:$3,426

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2705 WILLOW GLEN CIR, KISSIMMEE, FL 34744

    $434,9999 Days on yellowkey   MLS ID: G5113160

    For Sale G5113160 - 2705 WILLOW GLEN CIR, KISSIMMEE, FL 34744 33 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 1679
       Built: 2001
    Monthly Fee: $23
       Tax: $6,110 (2025)
    Community: Gleneagles
    Single Family


    Estimated Monthly Payment: $2,916 (change assumption)
    Mortgage ($2,383) + Fees ($23) + Taxes in 2025 ($509)


    Taxes:$6,110

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 7 WESTCHESTER DR, KISSIMMEE, FL 34744

    $434,000391 Days on yellowkey   MLS ID: O6309992

    1 Days Off yellowkey (back on 4/20/2026)

    REDUCED by $5,000 (1.1%) on 04/16/2026

    For Sale O6309992 - 7 WESTCHESTER DR, KISSIMMEE, FL 34744 45 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1786
       Built: 1962   Tax: $1,988 (2024)
    Community: Fairlawn Manor
    Single Family


    Estimated Monthly Payment: $2,544 (change assumption)
    Mortgage ($2,378) + Taxes in 2024 ($166)


    Taxes:$1,988

    Elementary School: Partin Settlement Elem

    High School: Osceola High School

    Tax Year: 2024

    Middle School: Neptune Middle (6-8)


  • 1211 LEHIGH ST, KISSIMMEE, FL 34744

    $359,00068 Days on yellowkey   MLS ID: S5147242

    REDUCED by $5,900 (1.6%) on 06/09/2026

    For Sale S5147242 - 1211 LEHIGH ST, KISSIMMEE, FL 34744 22 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1685
       Built: 1960   Tax: $5,105 (2025)
    Community: Johnston Park Rep
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,392 (change assumption)
    Mortgage ($1,967) + Taxes in 2025 ($425)


    Taxes:$5,105

    Elementary School: Mill Creek Elem (K 5)

    High School: Osceola High School

    Tax Year: 2025

    Middle School: Parkway Middle


  • 2716 WORTHAM LN, KISSIMMEE, FL 34744

    $415,000106 Days on yellowkey   MLS ID: O6385986

    0 Days Off yellowkey (back on 6/8/2026)

    REDUCED by $2,500 (0.6%) on 05/27/2026

    For Sale O6385986 - 2716 WORTHAM LN, KISSIMMEE, FL 34744 29 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2341
       Built: 1998
    Monthly Fee: $13
       Tax: $6,364 (2025)
    Community: Remington Ph 1 Tr E
    Single Family


    Estimated Monthly Payment: $2,817 (change assumption)
    Mortgage ($2,274) + Fees ($13) + Taxes in 2025 ($530)


    Taxes:$6,364

    Elementary School: Partin Settlement Elem

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 202 WOODSON CT, KISSIMMEE, FL 34744

    $623,0005 Days on yellowkey   MLS ID: O6414003

    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: $3,879 (change assumption)
    Mortgage ($3,414) + 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)


  • 1819 WILD RYE WAY, KISSIMMEE, FL 34744

    $379,0005 Days on yellowkey   MLS ID: S5151456

    SHORT SALE S5151456 - 1819 WILD RYE WAY, KISSIMMEE, FL 34744 1 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1504
       Built: 2022
    Monthly Fee: $11
       Tax: $6,436 (2025)
    Community: Kindred Ph 3B 3C & 3D
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,624 (change assumption)
    Mortgage ($2,077) + Fees ($11) + Taxes in 2025 ($536)


    Taxes:$6,436

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1660 CROSS PRAIRIE PKWY, KISSIMMEE, FL 34744

    $445,00010 Days on yellowkey   MLS ID: R4911380

    REDUCED by $5,000 (1.1%) on 06/09/2026

    For Sale R4911380 - 1660 CROSS PRAIRIE PKWY, KISSIMMEE, FL 34744 30 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1802
       Built: 2022
    Monthly Fee: $20
       Tax: $6,147 (2025)
    Community: Tohoqua Ph 2
    Single Family


    Estimated Monthly Payment: $2,971 (change assumption)
    Mortgage ($2,438) + Fees ($20) + Taxes in 2025 ($512)


    Taxes:$6,147

    Elementary School: Neptune Elementary

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 1686 CONTENTMENT LOOP, KISSIMMEE, FL 34744

    $369,990249 Days on yellowkey   MLS ID: S5136114

    For Sale S5136114 - 1686 CONTENTMENT LOOP, KISSIMMEE, FL 34744 30 photos

    Bed: 3   Bath: 2.5
    Liv Area Sq Ft: 1755
       Built: 2024
    Monthly Fee: $137
       Tax: $1,351 (2024)
    Community: Tohoqua Ph 3
    Townhouse


    Estimated Monthly Payment: $2,277 (change assumption)
    Mortgage ($2,027) + Fees ($137) + Taxes in 2024 ($113)


    Taxes:$1,351

    Elementary School: Neptune Elementary

    High School: Gateway High School (9 12)

    Tax Year: 2024

    Middle School: Neptune Middle (6-8)


  • 2955 RED OAK DR, KISSIMMEE, FL 34744

    $375,00044 Days on yellowkey   MLS ID: O6401588

    0 Days Off yellowkey (back on 6/8/2026)

    For Sale O6401588 - 2955 RED OAK DR, KISSIMMEE, FL 34744 33 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1365
       Built: 1996   Tax: $1,310 (2025)
    Community: Westwood Forest
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,164 (change assumption)
    Mortgage ($2,055) + Taxes in 2025 ($109)


    Taxes:$1,310

    Elementary School: Mill Creek Elem (K 5)

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Denn John Middle


  • 1384 E LAKE SHORE BLVD, KISSIMMEE, FL 34744

    $939,900485 Days on yellowkey   MLS ID: O6278826

    3 Days Off yellowkey (back on 6/8/2026)

    REDUCED by $15,100 (1.6%) on 04/23/2026

    For Sale O6278826 - 1384 E LAKE SHORE BLVD, KISSIMMEE, FL 34744 30 photos

    Bed: 4   Bath: 4.0   Gar: 3
    Liv Area Sq Ft: 3606
       Built: 2008   Tax: $4,881 (2023)
    Community: East Lake Shores
    Single Family


    Estimated Monthly Payment: $5,557 (change assumption)
    Mortgage ($5,150) + Taxes in 2023 ($407)


    Taxes:$4,881

    Elementary School: Partin Settlement Elem

    High School: Gateway High School (9 12)

    Tax Year: 2023

    Middle School: Neptune Middle (6-8)


  • 1763 RANGER HIGHLANDS RD, KISSIMMEE, FL 34744

    $559,500153 Days on yellowkey   MLS ID: O6372301

    4 Days Off yellowkey (back on 6/8/2026)

    REDUCED by $5,400 (1.0%) on 05/26/2026

    For Sale O6372301 - 1763 RANGER HIGHLANDS RD, KISSIMMEE, FL 34744 41 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2851
       Built: 2018
    Monthly Fee: $11
       Tax: $8,343 (2025)
    Community: Kindred Ph 1D
    Single Family


    Estimated Monthly Payment: $3,772 (change assumption)
    Mortgage ($3,066) + Fees ($11) + Taxes in 2025 ($695)


    Taxes:$8,343

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1670 TAYLOR RIDGE LOOP, KISSIMMEE, FL 34744

    $633,500255 Days on yellowkey   MLS ID: S5135712

    REDUCED by $3,500 (0.5%) on 05/31/2026

    For Sale S5135712 - 1670 TAYLOR RIDGE LOOP, KISSIMMEE, FL 34744 36 photos

    Bed: 4   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 2359
       Built: 2004
    Monthly Fee: $150
       Tax: $4,749 (2025)
    Community: Taylor Ridge
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $4,017 (change assumption)
    Mortgage ($3,471) + Fees ($150) + Taxes in 2025 ($396)


    Taxes:$4,749

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2627 CLEAR NIGHT AVENUE, KISSIMMEE, FL 34744

    $646,11015 Days on yellowkey   MLS ID: O6412075

    INCREASED by $19,000 (3.0%) on 06/08/2026

    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: $3,693 (change assumption)
    Mortgage ($3,540) + 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)


  • 2275 SOUTHBURY DR, KISSIMMEE, FL 34744

    $346,790103 Days on yellowkey   MLS ID: O6386802

    REDUCED by $2,000 (0.6%) on 06/08/2026

    For Sale O6386802 - 2275 SOUTHBURY DR, KISSIMMEE, FL 34744 24 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1553
       Built: 2026
    Monthly Fee: $130
       Tax: $1,610 (2025)
    Community: Tohoqua
    Spa: No

    Townhouse


    Estimated Monthly Payment: $2,164 (change assumption)
    Mortgage ($1,900) + Fees ($130) + Taxes in 2025 ($134)


    Taxes:$1,610

    Elementary School: Neptune Elementary

    High School: Gateway High School (9 12)

    Tax Year: 2025

    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.