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Homes For Sale in Kissimmee 34744 - 354 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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  • 1135 CHEROKEE DR, KISSIMMEE, FL 34744

    $360,00011 Days on yellowkey   MLS ID: S5152754

    REDUCED by $5,000 (1.4%) on 07/08/2026

    For Sale S5152754 - 1135 CHEROKEE DR, KISSIMMEE, FL 34744 16 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: $2,057 (change assumption)
    Mortgage ($1,973) + Taxes in 2025 ($85)


    Taxes:$1,014

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 162 HARWOOD CIR, KISSIMMEE, FL 34744

    $449,00040 Days on yellowkey   MLS ID: O6412762

    REDUCED by $14,500 (3.1%) on 07/08/2026

    FORECLOSURE O6412762 - 162 HARWOOD CIR, KISSIMMEE, FL 34744 35 photos

    Bed: 4   Bath: 2.5   Gar: 3
    Liv Area Sq Ft: 2516
       Built: 1998
    Monthly Fee: $14
       Tax: $6,859 (2025)
    Community: Remington Ph 1 Tr D
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,046 (change assumption)
    Mortgage ($2,460) + Fees ($14) + Taxes in 2025 ($572)


    Taxes:$6,859

    Elementary School: Partin Settlement Elem

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 1647 WINDSOR OAK CT, KISSIMMEE, FL 34744

    $245,000285 Days on yellowkey   MLS ID: S5134784

    For Sale S5134784 - 1647 WINDSOR OAK CT, KISSIMMEE, FL 34744 24 photos

    Bed: 3   Bath: 2.5
    Liv Area Sq Ft: 1380
       Built: 1999
    Monthly Fee: $185
       Tax: $2,492 (2024)
    Community: Windsor Oaks
    Townhouse


    Estimated Monthly Payment: $1,735 (change assumption)
    Mortgage ($1,342) + Fees ($185) + Taxes in 2024 ($208)


    Taxes:$2,492

    Elementary School: Mill Creek Elem (K 5)

    High School: Gateway High School (9 12)

    Tax Year: 2024

    Middle School: Denn John Middle


  • 4408 BREEZE ISLE LN, KISSIMMEE, FL 34744

    $650,000106 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 47 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


  • 1076 UNIVERSAL REST PL, KISSIMMEE, FL 34744

    $230,0009 Days on yellowkey   MLS ID: S5152671

    For Sale S5152671 - 1076 UNIVERSAL REST PL, KISSIMMEE, FL 34744 24 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1603
       Built: 1994
    Monthly Fee: $202
       Tax: $1,332 (2025)
    Community: Eric Estates
    Townhouse


    Estimated Monthly Payment: $1,573 (change assumption)
    Mortgage ($1,260) + Fees ($202) + Taxes in 2025 ($111)


    Taxes:$1,332

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1002 BELVOIR DR, KISSIMMEE, FL 34744

    $515,00023 Days on yellowkey   MLS ID: O6417742

    REDUCED by $10,000 (1.9%) on 07/08/2026

    For Sale O6417742 - 1002 BELVOIR DR, KISSIMMEE, FL 34744 87 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3460
       Built: 2005
    Monthly Fee: $13
       Tax: $7,923 (2025)
    Community: Somerset
    Single Family


    Estimated Monthly Payment: $3,495 (change assumption)
    Mortgage ($2,822) + Fees ($13) + Taxes in 2025 ($660)


    Taxes:$7,923

    Elementary School: Partin Settlement Elem

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Parkway Middle


  • 1810 N BRACK ST, KISSIMMEE, FL 34744

    $250,0005 Days on yellowkey   MLS ID: O6422750

    For Sale O6422750 - 1810 N BRACK ST, KISSIMMEE, FL 34744 28 photos

    Bed: 2   Bath: 1.0
    Liv Area Sq Ft: 816
       Built: 1962   Tax: $1,589 (2024)
    Community: Robert Bass Add
    Single Family


    Estimated Monthly Payment: $1,502 (change assumption)
    Mortgage ($1,370) + Taxes in 2024 ($132)


    Taxes:$1,589

    Elementary School: Central Avenue Elem

    High School: Osceola High School

    Tax Year: 2024

    Middle School: Denn John Middle


  • 2754 CALLAWAY LN, KISSIMMEE, FL 34744

    $420,000173 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


  • 2213 LANGE ST, KISSIMMEE, FL 34744

    $419,90015 Days on yellowkey   MLS ID: O6419441

    For Sale O6419441 - 2213 LANGE ST, KISSIMMEE, FL 34744 26 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1737
       Built: 1999
    Monthly Fee: $23
       Tax: $1,781 (2025)
    Community: Woods At Kings Crest The Ph 3
    Single Family


    Estimated Monthly Payment: $2,472 (change assumption)
    Mortgage ($2,301) + Fees ($23) + Taxes in 2025 ($148)


    Taxes:$1,781

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 170 CLUB VILLAS LN, KISSIMMEE, FL 34744

    $289,0005 Days on yellowkey   MLS ID: S5152939

    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: $2,246 (change assumption)
    Mortgage ($1,584) + 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)


  • 2305 JESSICA LN, KISSIMMEE, FL 34744

    $464,00058 Days on yellowkey   MLS ID: O6407917

    REDUCED by $1,000 (0.2%) on 07/08/2026

    For Sale O6407917 - 2305 JESSICA LN, KISSIMMEE, FL 34744 46 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1820
       Built: 2000
    Monthly Fee: $14
       Tax: $4,461 (2025)
    Community: Woods At Kings Crest The Ph 4
    Single Family


    Estimated Monthly Payment: $2,928 (change assumption)
    Mortgage ($2,542) + Fees ($14) + Taxes in 2025 ($372)


    Taxes:$4,461

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1701 BULL HILL RD, KISSIMMEE, FL 34744

    $579,99075 Days on yellowkey   MLS ID: S5148728

    For Sale S5148728 - 1701 BULL HILL RD, KISSIMMEE, FL 34744 24 photos

    Bed: 4   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 2852
       Built: 2024
    Monthly Fee: $16
       Tax: $7,143 (2025)
    Community: Kindred Ph 3B 3C & 3D
    Single Family


    Estimated Monthly Payment: $3,789 (change assumption)
    Mortgage ($3,178) + Fees ($16) + Taxes in 2025 ($595)


    Taxes:$7,143

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 3210 QUEEN ALEXANDRIA DR, KISSIMMEE, FL 34744

    $369,900120 Days on yellowkey   MLS ID: O6389027

    1 Days Off yellowkey (back on 7/8/2026)

    REDUCED by $12,100 (3.2%) on 06/01/2026

    For Sale O6389027 - 3210 QUEEN ALEXANDRIA DR, KISSIMMEE, FL 34744 26 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1541
       Built: 2011
    Monthly Fee: $136
       Tax: $4,861 (2025)
    Community: Raintree At Springlake Village Ph 2
    Single Family


    Estimated Monthly Payment: $2,568 (change assumption)
    Mortgage ($2,027) + Fees ($136) + Taxes in 2025 ($405)


    Taxes:$4,861

    Elementary School: East Lake Elem

    High School: Tohopekaliga High School

    Tax Year: 2025

    Middle School: Narcoossee Middle


  • 2823 SAIL BREEZE WAY, KISSIMMEE, FL 34744

    $474,999375 Days on yellowkey   MLS ID: S5130069

    1 Days Off yellowkey (back on 7/8/2026)

    REDUCED by $14,001 (2.9%) on 05/26/2026

    For Sale S5130069 - 2823 SAIL BREEZE WAY, KISSIMMEE, FL 34744 50 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2251
       Built: 2012
    Monthly Fee: $112
       Tax: $4,907 (2024)
    Community: North Point Ph 1A
    Single Family


    Estimated Monthly Payment: $3,124 (change assumption)
    Mortgage ($2,603) + Fees ($112) + Taxes in 2024 ($409)


    Taxes:$4,907

    Elementary School: East Lake Elem

    High School: Tohopekaliga High School

    Tax Year: 2024

    Middle School: Narcoossee Middle


  • 1508 JENNI LEE CT, KISSIMMEE, FL 34744

    $444,90056 Days on yellowkey   MLS ID: TB8508177

    REDUCED by $15,000 (3.3%) on 07/08/2026

    For Sale TB8508177 - 1508 JENNI LEE CT, KISSIMMEE, FL 34744 15 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2077
       Built: 1996
    Monthly Fee: $21
       Tax: $1,877 (2025)
    Community: Woods At Kings Crest The Ph 1
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,615 (change assumption)
    Mortgage ($2,438) + Fees ($21) + Taxes in 2025 ($156)


    Taxes:$1,877

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2601 GOLD DUST CIR, KISSIMMEE, FL 34744

    $479,000107 Days on yellowkey   MLS ID: S5146084

    REDUCED by $5,999 (1.2%) on 07/08/2026

    For Sale S5146084 - 2601 GOLD DUST CIR, KISSIMMEE, FL 34744 23 photos

    Bed: 4   Bath: 3.5   Gar: 18
    Liv Area Sq Ft: 2691
       Built: 2001
    Monthly Fee: $47
       Tax: $4,131 (2025)
    Community: Fortune Lakes
    Single Family


    Estimated Monthly Payment: $3,016 (change assumption)
    Mortgage ($2,625) + Fees ($47) + Taxes in 2025 ($344)


    Taxes:$4,131

    Elementary School: Partin Settlement Elem

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 1371 FAIR OAKS AVE, KISSIMMEE, FL 34744

    $370,00040 Days on yellowkey   MLS ID: S5150771

    0 Days Off yellowkey (back on 6/7/2026)

    For Sale S5150771 - 1371 FAIR OAKS AVE, KISSIMMEE, FL 34744 29 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1771
       Built: 1967   Tax: $1,767 (2025)
    Community: Cadillac Homes
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,175 (change assumption)
    Mortgage ($2,027) + Taxes in 2025 ($147)


    Taxes:$1,767

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2716 WORTHAM LN, KISSIMMEE, FL 34744

    $410,000134 Days on yellowkey   MLS ID: O6385986

    REDUCED by $5,000 (1.2%) on 07/08/2026

    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: $2,790 (change assumption)
    Mortgage ($2,247) + 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)


  • 604 CHADBURY WAY, KISSIMMEE, FL 34744

    $439,00012 Days on yellowkey   MLS ID: O6420445

    For Sale O6420445 - 604 CHADBURY WAY, KISSIMMEE, FL 34744 39 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 1719
       Built: 2005
    Monthly Fee: $78
       Tax: $5,214 (2025)
    Community: Remington Prcl M1
    Single Family


    Estimated Monthly Payment: $2,918 (change assumption)
    Mortgage ($2,405) + Fees ($78) + Taxes in 2025 ($434)


    Taxes:$5,214

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 4421 JIM BRANCH RD, KISSIMMEE, FL 34744

    $849,9004 Days on yellowkey   MLS ID: S5153225

    For Sale S5153225 - 4421 JIM BRANCH RD, KISSIMMEE, FL 34744 46 photos

    Bed: 3   Bath: 2.0   Gar: 3
    Liv Area Sq Ft: 2000
       Built: 2020   Tax: $5,348 (2025)
    Community: N/A
    Single Family


    Estimated Monthly Payment: $5,103 (change assumption)
    Mortgage ($4,657) + Taxes in 2025 ($446)


    Taxes:$5,348

    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.