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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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  • 1807 GOOD NEIGHBOR LOOP, KISSIMMEE, FL 34744

    $440,000103 Days on yellowkey   MLS ID: O6395467

    1 Days Off yellowkey (back on 7/10/2026)

    For Sale O6395467 - 1807 GOOD NEIGHBOR LOOP, KISSIMMEE, FL 34744 32 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


  • 1980 SUMMER CT, KISSIMMEE, FL 34744

    $525,000111 Days on yellowkey   MLS ID: O6392643

    REDUCED by $4,000 (0.8%) on 06/10/2026

    For Sale O6392643 - 1980 SUMMER CT, KISSIMMEE, FL 34744 38 photos

    Bed: 3   Bath: 3.0   Gar: 4
    Liv Area Sq Ft: 2687
       Built: 2005   Tax: $6,583 (2025)
    Community: Meadow Spgs
    Single Family


    Estimated Monthly Payment: $3,425 (change assumption)
    Mortgage ($2,877) + Taxes in 2025 ($549)


    Taxes:$6,583

    Elementary School: Partin Settlement Elem

    High School: Osceola High School

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 2789 WOODLAND CREEK LOOP, KISSIMMEE, FL 34744

    $525,00056 Days on yellowkey   MLS ID: O6409086

    REDUCED by $25,000 (4.5%) on 07/10/2026

    For Sale O6409086 - 2789 WOODLAND CREEK LOOP, KISSIMMEE, FL 34744 25 photos

    Bed: 4   Bath: 2.5   Gar: 3
    Liv Area Sq Ft: 2419
       Built: 2004
    Monthly Fee: $41
       Tax: $2,204 (2025)
    Community: Woodland Creek
    Single Family


    Estimated Monthly Payment: $3,101 (change assumption)
    Mortgage ($2,877) + Fees ($41) + Taxes in 2025 ($184)


    Taxes:$2,204

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1833 SPRING SHOWER CIR, KISSIMMEE, FL 34744

    $320,0005 Days on yellowkey   MLS ID: O6422244

    For Sale O6422244 - 1833 SPRING SHOWER CIR, KISSIMMEE, FL 34744 48 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1559
       Built: 2022
    Monthly Fee: $220
       Tax: $1,146 (2025)
    Community: Tohoqua Ph 5A
    Villa


    Estimated Monthly Payment: $2,069 (change assumption)
    Mortgage ($1,753) + Fees ($220) + Taxes in 2025 ($96)


    Taxes:$1,146

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2890 FRONTIER DR, KISSIMMEE, FL 34744

    $1,375,00015 Days on yellowkey   MLS ID: O6420732

    For Sale O6420732 - 2890 FRONTIER DR, KISSIMMEE, FL 34744 62 photos

    Bed: 3   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 2250
       Built: 1998   Tax: $8,809 (2025)
    Community: Pine Oaks
    Single Family


    Estimated Monthly Payment: $8,268 (change assumption)
    Mortgage ($7,534) + Taxes in 2025 ($734)


    Taxes:$8,809

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 4316 SILVER CREEK ST, KISSIMMEE, FL 34744

    $479,0005 Days on yellowkey   MLS ID: L4963348

    For Sale L4963348 - 4316 SILVER CREEK ST, KISSIMMEE, FL 34744 45 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2022
       Built: 2020
    Monthly Fee: $123
       Tax: $4,225 (2025)
    Community: Creekside At Boggy Creek Ph 2
    Single Family


    Estimated Monthly Payment: $3,100 (change assumption)
    Mortgage ($2,625) + Fees ($123) + Taxes in 2025 ($352)


    Taxes:$4,225

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1740 SAINT TROPEZ CT, KISSIMMEE, FL 34744

    $320,00055 Days on yellowkey   MLS ID: O6409575

    REDUCED by $15,000 (4.5%) on 06/29/2026

    For Sale O6409575 - 1740 SAINT TROPEZ CT, KISSIMMEE, FL 34744 32 photos

    Bed: 3   Bath: 2.5   Gar: 1
    Liv Area Sq Ft: 2104
       Built: 1991
    Monthly Fee: $180
       Tax: $2,753 (2025)
    Community: Monaco Villas Ph 2
    Townhouse


    Estimated Monthly Payment: $2,163 (change assumption)
    Mortgage ($1,753) + Fees ($180) + Taxes in 2025 ($229)


    Taxes:$2,753

    Elementary School: Partin Settlement Elem

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 4735 CHELSEA CT, KISSIMMEE, FL 34744

    $699,000421 Days on yellowkey   MLS ID: O6309757

    REDUCED by $50,900 (6.8%) on 07/10/2026

    For Sale O6309757 - 4735 CHELSEA CT, KISSIMMEE, FL 34744 48 photos

    Bed: 4   Bath: 3.0   Gar: 6
    Liv Area Sq Ft: 1936
       Built: 2005
    Monthly Fee: $10
       Tax: $631 (2024)
    Community: Rustic Acres Unit 1
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $3,893 (change assumption)
    Mortgage ($3,830) + Fees ($10) + Taxes in 2024 ($53)


    Taxes:$631

    Elementary School: East Lake Elem

    High School: Tohopekaliga High School

    Tax Year: 2024

    Middle School: Narcoossee Middle


  • 1805 MICHIGAN AVE #D, KISSIMMEE, FL 34744

    $129,90043 Days on yellowkey   MLS ID: S5150908

    REDUCED by $9,100 (6.5%) on 06/03/2026

    For Sale S5150908 - 1805 MICHIGAN AVE #D, KISSIMMEE, FL 34744 9 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1118
       Built: 1973
    Monthly Fee: $345
       Tax: $2,118 (2025)
    Community: Essex Park Villas Condo
    Condo


    Estimated Monthly Payment: $1,233 (change assumption)
    Mortgage ($712) + Fees ($345) + Taxes in 2025 ($176)


    Taxes:$2,118

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1956 EGRET MEADOWS AVE, KISSIMMEE, FL 34744

    $379,99054 Days on yellowkey   MLS ID: O6409425

    4 Days Off yellowkey (back on 6/16/2026)

    REDUCED by $15,000 (3.8%) on 06/01/2026

    For Sale O6409425 - 1956 EGRET MEADOWS AVE, KISSIMMEE, FL 34744 21 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1516
       Built: 2020
    Monthly Fee: $11
       Tax: $6,661 (2025)
    Community: Kindred Ph 2A
    Single Family


    Estimated Monthly Payment: $2,648 (change assumption)
    Mortgage ($2,082) + Fees ($11) + Taxes in 2025 ($555)


    Taxes:$6,661

    Elementary School: Neptune Elementary

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 2406 KAM CT, KISSIMMEE, FL 34744

    $300,0005 Days on yellowkey   MLS ID: O6422076

    For Sale O6422076 - 2406 KAM CT, KISSIMMEE, FL 34744 30 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1148
       Built: 2000
    Monthly Fee: $213
       Tax: $2,878 (2025)
    Community: Jade East Unit 2
    Townhouse


    Estimated Monthly Payment: $2,097 (change assumption)
    Mortgage ($1,644) + Fees ($213) + Taxes in 2025 ($240)


    Taxes:$2,878

    Elementary School: Partin Settlement Elem

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 3127 CONRAD CT, KISSIMMEE, FL 34744

    $579,70010 Days on yellowkey   MLS ID: S5152828

    For Sale S5152828 - 3127 CONRAD CT, KISSIMMEE, FL 34744 36 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2302
       Built: 2005
    Monthly Fee: $53
       Tax: $5,935 (2025)
    Community: Fells Cove Unit 2 Ph 1
    Single Family


    Estimated Monthly Payment: $3,724 (change assumption)
    Mortgage ($3,176) + Fees ($53) + Taxes in 2025 ($495)


    Taxes:$5,935

    Elementary School: East Lake Elementary-OS

    High School: Tohopekaliga High School

    Tax Year: 2025

    Middle School: Narcoossee Middle


  • KISSIMMEE, FL 34744

    $499,9005 Days on yellowkey   MLS ID: S5152516

    For Sale S5152516 - KISSIMMEE, FL 34744 20 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2272
       Built: 2023
    Monthly Fee: $129
       Tax: $6,118 (2025)
    Community: Pennyroyal
    Single Family


    Estimated Monthly Payment: $3,378 (change assumption)
    Mortgage ($2,739) + Fees ($129) + Taxes in 2025 ($510)


    Taxes:$6,118

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 4027 LONGWORTH LOOP, KISSIMMEE, FL 34744

    $344,9005 Days on yellowkey   MLS ID: TB8522361

    For Sale TB8522361 - 4027 LONGWORTH LOOP, KISSIMMEE, FL 34744 15 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1484
       Built: 2007
    Monthly Fee: $83
       Tax: $801 (2025)
    Community: Turnberry Reserve Unit 2
    Single Family


    Estimated Monthly Payment: $2,040 (change assumption)
    Mortgage ($1,890) + Fees ($83) + Taxes in 2025 ($67)


    Taxes:$801

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2663 GOLD DUST CIR, KISSIMMEE, FL 34744

    $419,9007 Days on yellowkey   MLS ID: S5153091

    For Sale S5153091 - 2663 GOLD DUST CIR, KISSIMMEE, FL 34744 62 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2085
       Built: 2000
    Monthly Fee: $34
       Tax: $5,587 (2025)
    Community: Fortune Lakes
    Single Family


    Estimated Monthly Payment: $2,800 (change assumption)
    Mortgage ($2,301) + Fees ($34) + Taxes in 2025 ($466)


    Taxes:$5,587

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1034 CHALCEDONY ST, KISSIMMEE, FL 34744

    $274,90025 Days on yellowkey   MLS ID: S5152151

    REDUCED by $5,000 (1.8%) on 07/09/2026

    For Sale S5152151 - 1034 CHALCEDONY ST, KISSIMMEE, FL 34744 22 photos

    Bed: 2   Bath: 2.5   Gar: 1
    Liv Area Sq Ft: 1386
       Built: 2009
    Monthly Fee: $170
       Tax: $3,670 (2025)
    Community: Amber Pointe Unit 2
    Townhouse


    Estimated Monthly Payment: $1,982 (change assumption)
    Mortgage ($1,506) + Fees ($170) + Taxes in 2025 ($306)


    Taxes:$3,670

    Elementary School: Partin Settlement Elem

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Denn John Middle


  • 1850 CHAUCER WAY, KISSIMMEE, FL 34744

    $398,95035 Days on yellowkey   MLS ID: S5151405

    REDUCED by $6,050 (1.5%) on 07/09/2026

    For Sale S5151405 - 1850 CHAUCER WAY, KISSIMMEE, FL 34744 19 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1828
       Built: 1988
    Monthly Fee: $13
       Tax: $5,352 (2025)
    Community: Brighton Place
    Single Family


    Estimated Monthly Payment: $2,645 (change assumption)
    Mortgage ($2,186) + Fees ($13) + Taxes in 2025 ($446)


    Taxes:$5,352

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2356 ROYALE OAKS BLVD, KISSIMMEE, FL 34744

    $409,90034 Days on yellowkey   MLS ID: S5151604

    REDUCED by $5,100 (1.2%) on 07/09/2026

    For Sale S5151604 - 2356 ROYALE OAKS BLVD, KISSIMMEE, FL 34744 30 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2079
       Built: 1989   Tax: $4,158 (2025)
    Community: Royale Oaks Ph 1
    Single Family


    Estimated Monthly Payment: $2,592 (change assumption)
    Mortgage ($2,246) + Taxes in 2025 ($347)


    Taxes:$4,158

    Elementary School: Mill Creek Elem (K 5)

    High School: Osceola High School

    Tax Year: 2025

    Middle School: Denn John Middle


  • 4737 CHELSEA CT, KISSIMMEE, FL 34744

    $480,00018 Days on yellowkey   MLS ID: O6420303

    0 Days Off yellowkey (back on 7/9/2026)

    INCREASED by $5,000 (1.1%) on 07/08/2026

    For Sale O6420303 - 4737 CHELSEA CT, KISSIMMEE, FL 34744 50 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2198
       Built: 1986
    Monthly Fee: $10
       Tax: $2,532 (2025)
    Community: Rustic Acres Unit 1
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,851 (change assumption)
    Mortgage ($2,630) + Fees ($10) + Taxes in 2025 ($211)


    Taxes:$2,532

    Elementary School: East Lake Elem

    High School: Tohopekaliga High School

    Tax Year: 2025

    Middle School: Narcoossee Middle


  • 14 GLENDALE DR, KISSIMMEE, FL 34744

    $485,000123 Days on yellowkey   MLS ID: S5145799

    REDUCED by $10,000 (2.0%) on 07/09/2026

    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: $3,129 (change assumption)
    Mortgage ($2,657) + Taxes in 2025 ($472)


    Taxes:$5,664

    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.