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Homes For Sale in Kissimmee 34744 - 347 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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  • 1673 BARBERRY DR, KISSIMMEE, FL 34744

    $449,90056 Days on yellowkey   MLS ID: S5147034

    REDUCED by $10,100 (2.2%) on 05/26/2026

    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: $2,994 (change assumption)
    Mortgage ($2,465) + 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)


  • 1425 RIVIERA DR, KISSIMMEE, FL 34744

    $944,90083 Days on yellowkey   MLS ID: O6386384

    For Sale O6386384 - 1425 RIVIERA DR, KISSIMMEE, FL 34744 82 photos

    Bed: 6   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 4654
       Built: 2002
    Monthly Fee: $183
       Tax: $7,220 (2025)
    Community: Regal Bay
    Single Family


    Estimated Monthly Payment: $5,962 (change assumption)
    Mortgage ($5,177) + Fees ($183) + Taxes in 2025 ($602)


    Taxes:$7,220

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1578 CONTENTMENT LOOP, KISSIMMEE, FL 34744

    $511,0008 Days on yellowkey   MLS ID: S5150200

    For Sale S5150200 - 1578 CONTENTMENT LOOP, KISSIMMEE, FL 34744 16 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2113
       Built: 2023
    Monthly Fee: $7
       Tax: $6,094 (2025)
    Community: Tohoqua Ph 3
    Single Family


    Estimated Monthly Payment: $3,315 (change assumption)
    Mortgage ($2,800) + Fees ($7) + Taxes in 2025 ($508)


    Taxes:$6,094

    Elementary School: Island Village Elementary School

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Narcoossee Middle


  • 1724 CROSS PRAIRIE PKWY, KISSIMMEE, FL 34744

    $389,900121 Days on yellowkey   MLS ID: O6376465

    0 Days Off yellowkey (back on 3/22/2026)

    For Sale O6376465 - 1724 CROSS PRAIRIE PKWY, KISSIMMEE, FL 34744 24 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2044
       Built: 2022
    Monthly Fee: $10
       Tax: $6,652 (2025)
    Community: Tohoqua Ph 2
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,701 (change assumption)
    Mortgage ($2,136) + Fees ($10) + Taxes in 2025 ($554)


    Taxes:$6,652

    Elementary School: None

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: None


  • 1777 WALNUT CREEK DR, KISSIMMEE, FL 34744

    $439,90065 Days on yellowkey   MLS ID: O6390965

    REDUCED by $5,000 (1.1%) on 05/26/2026

    For Sale O6390965 - 1777 WALNUT CREEK DR, KISSIMMEE, FL 34744 74 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2339
       Built: 2023
    Monthly Fee: $11
       Tax: $3,358 (2025)
    Community: Kindred Ph 3A
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,701 (change assumption)
    Mortgage ($2,410) + Fees ($11) + Taxes in 2025 ($280)


    Taxes:$3,358

    Elementary School: None

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 1763 RANGER HIGHLANDS RD, KISSIMMEE, FL 34744

    $559,500136 Days on yellowkey   MLS ID: O6372301

    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


  • 1812 HOWARD MESA DR, KISSIMMEE, FL 34744

    $464,99023 Days on yellowkey   MLS ID: O6404680

    4 Days Off yellowkey (back on 5/26/2026)

    INCREASED by $2,000 (0.4%) on 05/12/2026

    For Sale O6404680 - 1812 HOWARD MESA DR, KISSIMMEE, FL 34744 51 photos

    Bed: 5   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2447
       Built: 2025
    Monthly Fee: $11
       Tax: $3,684 (2025)
    Community: Kindred Ph 3B 3C & 3D
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,866 (change assumption)
    Mortgage ($2,548) + Fees ($11) + Taxes in 2025 ($307)


    Taxes:$3,684

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 918 BRACK ST, KISSIMMEE, FL 34744

    $230,0005 Days on yellowkey   MLS ID: S5150267

    1 Days Off yellowkey (back on 5/26/2026)

    For Sale S5150267 - 918 BRACK ST, KISSIMMEE, FL 34744 16 photos

    Bed: 2   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1008
       Built: 1981   Tax: $380 (2025)
    Community: R Bass
    Single Family


    Estimated Monthly Payment: $1,292 (change assumption)
    Mortgage ($1,260) + Taxes in 2025 ($32)


    Taxes:$380

    Elementary School: Central Avenue Elem

    High School: Osceola High School

    Tax Year: 2025

    Middle School: Denn John Middle


  • 1631 BITTEROOT ST, KISSIMMEE, FL 34744

    $369,99040 Days on yellowkey   MLS ID: S5147958

    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: $2,491 (change assumption)
    Mortgage ($2,027) + Fees ($11) + Taxes in 2025 ($453)


    Taxes:$5,432

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 636 ADRIANE PARK CIR, KISSIMMEE, FL 34744

    $474,9002 Days on yellowkey   MLS ID: S5150339

    For Sale S5150339 - 636 ADRIANE PARK CIR, KISSIMMEE, FL 34744 49 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2444
       Built: 1992
    Monthly Fee: $37
       Tax: $3,345 (2025)
    Community: Adriane Park
    Single Family


    Estimated Monthly Payment: $2,918 (change assumption)
    Mortgage ($2,602) + Fees ($37) + Taxes in 2025 ($279)


    Taxes:$3,345

    Elementary School: Partin Settlement Elem

    High School: Osceola High School

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 1723 FLOURISH AVE, KISSIMMEE, FL 34744

    $385,0002 Days on yellowkey   MLS ID: O6410022

    For Sale O6410022 - 1723 FLOURISH AVE, KISSIMMEE, FL 34744 19 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1617
       Built: 2021
    Monthly Fee: $10
       Tax: $5,566 (2025)
    Community: Tohoqua Ph 1
    Single Family


    Estimated Monthly Payment: $2,583 (change assumption)
    Mortgage ($2,110) + Fees ($10) + Taxes in 2025 ($464)


    Taxes:$5,566

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1783 SMARTS RULE ST, KISSIMMEE, FL 34744

    $525,0002 Days on yellowkey   MLS ID: S5150485

    For Sale S5150485 - 1783 SMARTS RULE ST, KISSIMMEE, FL 34744 38 photos

    Bed: 5   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2500
       Built: 2022
    Monthly Fee: $10
       Tax: $9,191 (2025)
    Community: Tohoqua Ph 1B
    Single Family


    Estimated Monthly Payment: $3,653 (change assumption)
    Mortgage ($2,877) + Fees ($10) + Taxes in 2025 ($766)


    Taxes:$9,191

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2668 WILLOW GLEN CIR, KISSIMMEE, FL 34744

    $395,0002 Days on yellowkey   MLS ID: S5150227

    For Sale S5150227 - 2668 WILLOW GLEN CIR, KISSIMMEE, FL 34744 29 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1676
       Built: 2003
    Monthly Fee: $23
       Tax: $6,164 (2025)
    Community: Gleneagles
    Single Family


    Estimated Monthly Payment: $2,701 (change assumption)
    Mortgage ($2,164) + Fees ($23) + Taxes in 2025 ($514)


    Taxes:$6,164

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1489 TWIN VALLEY TER, KISSIMMEE, FL 34744

    $539,90063 Days on yellowkey   MLS ID: O6390966

    REDUCED by $5,000 (0.9%) on 05/23/2026

    For Sale O6390966 - 1489 TWIN VALLEY TER, KISSIMMEE, FL 34744 78 photos

    Bed: 5   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2674
       Built: 2017
    Monthly Fee: $11
       Tax: $7,067 (2025)
    Community: Kindred Ph 1A & 1B
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,558 (change assumption)
    Mortgage ($2,958) + Fees ($11) + Taxes in 2025 ($589)


    Taxes:$7,067

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 3044 CAMINO REAL DR S, KISSIMMEE, FL 34744

    $489,00020 Days on yellowkey   MLS ID: O6406104

    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: $3,298 (change assumption)
    Mortgage ($2,679) + 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


  • 1740 NEPTUNE RD, KISSIMMEE, FL 34744

    $435,000112 Days on yellowkey   MLS ID: O6379685

    For Sale O6379685 - 1740 NEPTUNE RD, KISSIMMEE, FL 34744 49 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 2013
       Built: 1966   Tax: $1,925 (2025)
    Community: Neptune Shores 1
    Single Family


    Estimated Monthly Payment: $2,544 (change assumption)
    Mortgage ($2,384) + Taxes in 2025 ($160)


    Taxes:$1,925

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 237 STRATHMORE CIR, KISSIMMEE, FL 34744

    $435,00023 Days on yellowkey   MLS ID: O6403214

    For Sale O6403214 - 237 STRATHMORE CIR, KISSIMMEE, FL 34744 55 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2278
       Built: 1999
    Monthly Fee: $18
       Tax: $4,632 (2025)
    Community: Remington Ph 1 Tr B
    Single Family


    Estimated Monthly Payment: $2,787 (change assumption)
    Mortgage ($2,384) + Fees ($18) + Taxes in 2025 ($386)


    Taxes:$4,632

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1426 AXEL GRAESON AVE, KISSIMMEE, FL 34744

    $597,0009 Days on yellowkey   MLS ID: S5150202

    For Sale S5150202 - 1426 AXEL GRAESON AVE, KISSIMMEE, FL 34744 27 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2070
       Built: 2024
    Monthly Fee: $80
       Tax: $4,873 (2025)
    Community: Seasons At Big Sky Ph 1
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,757 (change assumption)
    Mortgage ($3,271) + Fees ($80) + Taxes in 2025 ($406)


    Taxes:$4,873

    Elementary School: Partin Settlement Elem

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 2754 CALLAWAY LN, KISSIMMEE, FL 34744

    $420,000128 Days on yellowkey   MLS ID: S5141838

    0 Days Off yellowkey (back on 5/7/2026)

    For Sale S5141838 - 2754 CALLAWAY LN, KISSIMMEE, FL 34744 50 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2513
       Built: 2004
    Monthly Fee: $78
       Tax: $6,917 (2025)
    Community: Remington Prcl M1
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,956 (change assumption)
    Mortgage ($2,301) + Fees ($78) + Taxes in 2025 ($576)


    Taxes:$6,917

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 3570 SOUTHERN CROSS LOOP, KISSIMMEE, FL 34744

    $400,000293 Days on yellowkey   MLS ID: O6333789

    INCREASED by $1,000 (0.3%) on 04/08/2026

    For Sale O6333789 - 3570 SOUTHERN CROSS LOOP, KISSIMMEE, FL 34744 36 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1554
       Built: 2018
    Monthly Fee: $118
       Tax: $3,192 (2024)
    Community: East Lake Preserve
    Single Family


    Estimated Monthly Payment: $2,576 (change assumption)
    Mortgage ($2,192) + Fees ($118) + Taxes in 2024 ($266)


    Taxes:$3,192

    Elementary School: East Lake Elementary-OS

    High School: Tohopekaliga High School

    Tax Year: 2024

    Middle School: Narcoossee 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.