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Homes For Sale in Kissimmee 34744 - 376 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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  • 170 CLUB VILLAS LN, KISSIMMEE, FL 34744

    $280,0008 Days on yellowkey   MLS ID: S5152939

    REDUCED by $9,000 (3.1%) on 07/14/2026

    For Sale S5152939 - 170 CLUB VILLAS LN, KISSIMMEE, FL 34744 51 photos

    Bed: 2   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1417
       Built: 1998
    Monthly Fee: $312
       Tax: $4,209 (2025)
    Community: Remington Ph 1 Tr A
    Spa: No

    Townhouse


    Estimated Monthly Payment: $2,197 (change assumption)
    Mortgage ($1,534) + Fees ($312) + Taxes in 2025 ($351)


    Taxes:$4,209

    Elementary School: Partin Settlement Elem

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 1527 BEECHMONT DR, KISSIMMEE, FL 34744

    $480,990Listed 07/14/2026 11:26AM   MLS ID: O6424972

    For Sale O6424972 - 1527 BEECHMONT DR, KISSIMMEE, FL 34744 51 photos

    Bed: 5   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2077
       Built: 2025
    Monthly Fee: $11
       Tax: $3,094 (2025)
    Community: Kindred Ph 2A
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,904 (change assumption)
    Mortgage ($2,635) + Fees ($11) + Taxes in 2025 ($258)


    Taxes:$3,094

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 4408 BREEZE ISLE LN, KISSIMMEE, FL 34744

    $650,000109 Days on yellowkey   MLS ID: O6393234

    REDUCED by $25,000 (3.7%) on 05/11/2026

    For Sale O6393234 - 4408 BREEZE ISLE LN, KISSIMMEE, FL 34744 51 photos

    Bed: 5   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 3267
       Built: 2014
    Monthly Fee: $111
       Tax: $4,883 (2025)
    Community: North Point Ph Ic
    Single Family


    Estimated Monthly Payment: $4,079 (change assumption)
    Mortgage ($3,562) + Fees ($111) + Taxes in 2025 ($407)


    Taxes:$4,883

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1350 ROCKY RD, KISSIMMEE, FL 34744

    $320,000Listed 07/14/2026 10:49AM   MLS ID: O6422670

    For Sale O6422670 - 1350 ROCKY RD, KISSIMMEE, FL 34744 14 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1108
       Built: 1983   Tax: $4,613 (2025)
    Community: Pebble Creek
    Single Family


    Estimated Monthly Payment: $2,138 (change assumption)
    Mortgage ($1,753) + Taxes in 2025 ($384)


    Taxes:$4,613

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 131 WESTMORELAND CIR, KISSIMMEE, FL 34744

    $399,99967 Days on yellowkey   MLS ID: O6406202

    REDUCED by $15,001 (3.6%) on 07/14/2026

    For Sale O6406202 - 131 WESTMORELAND CIR, KISSIMMEE, FL 34744 63 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2285
       Built: 1997
    Monthly Fee: $14
       Tax: $6,651 (2025)
    Community: Remington Ph 1 Tr F
    Single Family


    Estimated Monthly Payment: $2,760 (change assumption)
    Mortgage ($2,192) + Fees ($14) + Taxes in 2025 ($554)


    Taxes:$6,651

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1852 HOWARD MESA DR, KISSIMMEE, FL 34744

    $460,99033 Days on yellowkey   MLS ID: O6416113

    2 Days Off yellowkey (back on 7/14/2026)

    REDUCED by $10,000 (2.1%) on 07/02/2026

    For Sale O6416113 - 1852 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: $2,844 (change assumption)
    Mortgage ($2,526) + Fees ($11) + Taxes in 2025 ($307)


    Taxes:$3,684

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 177 CLUB VILLAS LN, KISSIMMEE, FL 34744

    $265,00081 Days on yellowkey   MLS ID: S5148569

    0 Days Off yellowkey (back on 6/15/2026)

    REDUCED by $10,000 (3.6%) on 05/14/2026

    For Sale S5148569 - 177 CLUB VILLAS LN, KISSIMMEE, FL 34744 20 photos

    Bed: 2   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1397
       Built: 1998
    Monthly Fee: $315
       Tax: $5,028 (2025)
    Community: Remington Ph 1 Tr A
    Spa: No

    Townhouse


    Estimated Monthly Payment: $2,186 (change assumption)
    Mortgage ($1,452) + Fees ($315) + Taxes in 2025 ($419)


    Taxes:$5,028

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2675 HILLIARD CT, KISSIMMEE, FL 34744

    $575,00039 Days on yellowkey   MLS ID: S5151356

    3 Days Off yellowkey (back on 6/12/2026)

    For Sale S5151356 - 2675 HILLIARD CT, KISSIMMEE, FL 34744 30 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2614
       Built: 1999   Tax: $3,961 (2025)
    Community: Hilliard Place
    Single Family


    Estimated Monthly Payment: $3,481 (change assumption)
    Mortgage ($3,151) + Taxes in 2025 ($330)


    Taxes:$3,961

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1913 BLISSFUL DR, KISSIMMEE, FL 34744

    $469,9006 Days on yellowkey   MLS ID: O6423291

    For Sale O6423291 - 1913 BLISSFUL DR, KISSIMMEE, FL 34744 50 photos

    Bed: 5   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2113
       Built: 2025
    Monthly Fee: $7
       Tax: $3,844 (2025)
    Community: Tohoqua Ph 7
    Single Family


    Estimated Monthly Payment: $2,902 (change assumption)
    Mortgage ($2,575) + Fees ($7) + Taxes in 2025 ($320)


    Taxes:$3,844

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 518 TOHOPEKALIGA AVE, KISSIMMEE, FL 34744

    $440,0001 Day on yellowkey   MLS ID: S5153656

    For Sale S5153656 - 518 TOHOPEKALIGA AVE, KISSIMMEE, FL 34744 33 photos

    Bed: 4   Bath: 2.0
    Liv Area Sq Ft: 1952
       Built: 1957   Tax: $5,333 (2025)
    Community: Neptune Rep
    Single Family


    Estimated Monthly Payment: $2,855 (change assumption)
    Mortgage ($2,411) + Taxes in 2025 ($444)


    Taxes:$5,333

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2726 SUMMER RETREAT LN, KISSIMMEE, FL 34744

    $349,9001 Day on yellowkey   MLS ID: TB8528728

    For Sale TB8528728 - 2726 SUMMER RETREAT LN, KISSIMMEE, FL 34744 41 photos

    Bed: 2   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1559
       Built: 2023
    Monthly Fee: $220
       Tax: $5,075 (2025)
    Community: Tohoqua Ph 5B
    Villa


    Estimated Monthly Payment: $2,560 (change assumption)
    Mortgage ($1,917) + Fees ($220) + Taxes in 2025 ($423)


    Taxes:$5,075

    Elementary School: Neptune Elementary

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 2026 WALNUT CREEK DR, KISSIMMEE, FL 34744

    $389,9901 Day on yellowkey   MLS ID: O6424608

    For Sale O6424608 - 2026 WALNUT CREEK DR, KISSIMMEE, FL 34744 67 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: $2,455 (change assumption)
    Mortgage ($2,137) + Fees ($11) + Taxes in 2025 ($307)


    Taxes:$3,684

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2704 KENDALL AVE, KISSIMMEE, FL 34744

    $349,9001 Day on yellowkey   MLS ID: S5153613

    For Sale S5153613 - 2704 KENDALL AVE, KISSIMMEE, FL 34744 17 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1156
       Built: 1990   Tax: $2,687 (2025)
    Community: Oak Run Unit 6
    Single Family


    Estimated Monthly Payment: $2,141 (change assumption)
    Mortgage ($1,917) + Taxes in 2025 ($224)


    Taxes:$2,687

    Elementary School: Mill Creek Elem (K 5)

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Denn John Middle


  • 1762 BROCKRIDGE RD, KISSIMMEE, FL 34744

    $374,9901 Day on yellowkey   MLS ID: S5153601

    For Sale S5153601 - 1762 BROCKRIDGE RD, KISSIMMEE, FL 34744 16 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1676
       Built: 2018
    Monthly Fee: $11
       Tax: $6,917 (2025)
    Community: Kindred Ph 1D
    Single Family


    Estimated Monthly Payment: $2,642 (change assumption)
    Mortgage ($2,055) + Fees ($11) + Taxes in 2025 ($576)


    Taxes:$6,917

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1967 RANKIN ST, KISSIMMEE, FL 34744

    $510,00096 Days on yellowkey   MLS ID: O6397893

    For Sale O6397893 - 1967 RANKIN ST, KISSIMMEE, FL 34744 44 photos

    Bed: 4   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 2142
       Built: 2023
    Monthly Fee: $11

    Community: Kindred
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $2,805 (change assumption)
    Mortgage ($2,794) + Fees ($11) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1491 AUGUST GRAY DR, KISSIMMEE, FL 34744

    $419,90096 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)


  • 2045 RANKIN ST, KISSIMMEE, FL 34744

    $524,900199 Days on yellowkey   MLS ID: O6369099

    For Sale O6369099 - 2045 RANKIN ST, KISSIMMEE, FL 34744 38 photos

    Bed: 4   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 2142
       Built: 2023
    Monthly Fee: $11
       Tax: $8,511 (2024)
    Community: Kindred Ph 3A
    Single Family


    Estimated Monthly Payment: $3,596 (change assumption)
    Mortgage ($2,876) + Fees ($11) + Taxes in 2024 ($709)


    Taxes:$8,511

    Elementary School: None

    High School: Gateway High School (9 12)

    Tax Year: 2024

    Middle School: None


  • 1792 BULL HILL RD, KISSIMMEE, FL 34744

    $417,990388 Days on yellowkey   MLS ID: O6318608

    For Sale O6318608 - 1792 BULL HILL RD, KISSIMMEE, FL 34744 32 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1614
       Built: 2024
    Monthly Fee: $11
       Tax: $3,776 (2024)
    Community: Kindred Ph 3B 3C & 3D
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,616 (change assumption)
    Mortgage ($2,290) + Fees ($11) + Taxes in 2024 ($315)


    Taxes:$3,776

    Elementary School: Neptune Elementary

    High School: Osceola High School

    Tax Year: 2024

    Middle School: Neptune Middle (6-8)


  • 2713 BARNSLEY LN, KISSIMMEE, FL 34744

    $405,00034 Days on yellowkey   MLS ID: S5151648

    REDUCED by $10,000 (2.4%) on 07/13/2026

    For Sale S5151648 - 2713 BARNSLEY LN, KISSIMMEE, FL 34744 37 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 1993
       Built: 1998
    Monthly Fee: $14
       Tax: $6,501 (2025)
    Community: Remington Ph 1 Tr F
    Single Family


    Estimated Monthly Payment: $2,775 (change assumption)
    Mortgage ($2,219) + Fees ($14) + Taxes in 2025 ($542)


    Taxes:$6,501

    Elementary School: Partin Settlement Elem

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 2604 SERENITY GARDEN DRIVE, KISSIMMEE, FL 34744

    $488,12047 Days on yellowkey   MLS ID: O6411675

    REDUCED by $10,000 (2.0%) on 07/13/2026

    For Sale O6411675 - 2604 SERENITY GARDEN DRIVE, KISSIMMEE, FL 34744 25 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1850
       Built: 2025
    Monthly Fee: $20
       Tax: $1,329 (2025)
    Community: Tohoqua
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,805 (change assumption)
    Mortgage ($2,675) + Fees ($20) + 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)




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.