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Homes For Sale in Kissimmee 34744 - 341 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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  • 1503 OAK RESERVE DR, KISSIMMEE, FL 34744

    $440,000102 Days on yellowkey   MLS ID: S5144250

    REDUCED by $5,000 (1.1%) on 04/22/2026

    For Sale S5144250 - 1503 OAK RESERVE DR, KISSIMMEE, FL 34744 34 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1846
       Built: 2022   Tax: $7,738 (2025)
    Community: Kindred Ph 2C & 2D
    Single Family


    Estimated Monthly Payment: $3,056 (change assumption)
    Mortgage ($2,411) + Taxes in 2025 ($645)


    Taxes:$7,738

    Elementary School: Neptune Elementary

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: St. Cloud Middle (6-8)


  • 1767 SMARTS RULE ST, KISSIMMEE, FL 34744

    $509,90022 Days on yellowkey   MLS ID: S5149626

    For Sale S5149626 - 1767 SMARTS RULE ST, KISSIMMEE, FL 34744 38 photos

    Bed: 5   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2764
       Built: 2022
    Monthly Fee: $1
       Tax: $7,949 (2024)
    Community: Tohoqua Ph 1B
    Single Family


    Estimated Monthly Payment: $3,457 (change assumption)
    Mortgage ($2,794) + Fees ($1) + Taxes in 2024 ($662)


    Taxes:$7,949

    Elementary School: Neptune Elementary

    High School: Gateway High School (9 12)

    Tax Year: 2024

    Middle School: Neptune Middle (6-8)


  • 710 E JACKSON ST, KISSIMMEE, FL 34744

    $320,00017 Days on yellowkey   MLS ID: S5149877

    For Sale S5149877 - 710 E JACKSON ST, KISSIMMEE, FL 34744 31 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1338
       Built: 1957   Tax: $2,295 (2025)
    Community: Michigan Terrace
    Single Family


    Estimated Monthly Payment: $1,945 (change assumption)
    Mortgage ($1,753) + Taxes in 2025 ($191)


    Taxes:$2,295

    Elementary School: Kissimmee Elem

    High School: Osceola High School

    Tax Year: 2025

    Middle School: Denn John Middle


  • KISSIMMEE, FL 34744

    $327,00080 Days on yellowkey   MLS ID: O6388756

    2 Days Off yellowkey (back on 5/24/2026)

    REDUCED by $22,000 (6.3%) on 04/22/2026

    For Sale O6388756 - KISSIMMEE, FL 34744 1 photos

    Bed: 4   Bath: 2.0
    Liv Area Sq Ft: 1792
       Built: 1982   Tax: $3,556 (2025)
    Community: Kissimmee Heights
    Single Family


    Estimated Monthly Payment: $2,088 (change assumption)
    Mortgage ($1,792) + Taxes in 2025 ($296)


    Taxes:$3,556

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1211 LEHIGH ST, KISSIMMEE, FL 34744

    $364,90056 Days on yellowkey   MLS ID: S5147242

    REDUCED by $5,000 (1.4%) on 05/07/2026

    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: $2,425 (change assumption)
    Mortgage ($1,999) + 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


  • 1433 RIVERBOAT DR, KISSIMMEE, FL 34744

    $380,000228 Days on yellowkey   MLS ID: G5103345

    INCREASED by $5,000 (1.3%) on 04/15/2026

    For Sale G5103345 - 1433 RIVERBOAT DR, KISSIMMEE, FL 34744 44 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1846
       Built: 2021
    Monthly Fee: $11
       Tax: $7,119 (2024)
    Community: Kindred Ph 1
    Single Family


    Estimated Monthly Payment: $2,686 (change assumption)
    Mortgage ($2,082) + Fees ($11) + Taxes in 2024 ($593)


    Taxes:$7,119

    Elementary School: Neptune Elementary

    High School: Gateway High School (9 12)

    Tax Year: 2024

    Middle School: Neptune Middle (6-8)


  • 155 THORNBURY DR, KISSIMMEE, FL 34744

    $375,00018 Days on yellowkey   MLS ID: L4961841

    1 Days Off yellowkey (back on 5/17/2026)

    For Sale L4961841 - 155 THORNBURY DR, KISSIMMEE, FL 34744 43 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1642
       Built: 2002
    Monthly Fee: $14
       Tax: $6,077 (2025)
    Community: Remington Prcl H Ph 2
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $2,575 (change assumption)
    Mortgage ($2,055) + Fees ($14) + Taxes in 2025 ($506)


    Taxes:$6,077

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1541 AMHERST LN, KISSIMMEE, FL 34744

    $405,000224 Days on yellowkey   MLS ID: O6354005

    REDUCED by $25,000 (5.8%) on 05/21/2026

    For Sale O6354005 - 1541 AMHERST LN, KISSIMMEE, FL 34744 26 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2002
       Built: 1989   Tax: $1,317 (2024)
    Community: Oak Hollow Ph 4
    Single Family


    Estimated Monthly Payment: $2,329 (change assumption)
    Mortgage ($2,219) + Taxes in 2024 ($110)


    Taxes:$1,317

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 4405 BISCAYNE BREEZE WAY, KISSIMMEE, FL 34744

    $475,00051 Days on yellowkey   MLS ID: O6398072

    REDUCED by $10,000 (2.1%) on 04/28/2026

    For Sale O6398072 - 4405 BISCAYNE BREEZE WAY, KISSIMMEE, FL 34744 24 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2601
       Built: 2011
    Monthly Fee: $111
       Tax: $4,260 (2025)
    Community: North Point Ph 1A
    Single Family


    Estimated Monthly Payment: $3,069 (change assumption)
    Mortgage ($2,603) + Fees ($111) + Taxes in 2025 ($355)


    Taxes:$4,260

    Elementary School: East Lake Elem

    High School: Tohopekaliga High School

    Tax Year: 2025

    Middle School: Narcoossee Middle


  • 3001 MANDOLIN DR, KISSIMMEE, FL 34744

    $449,777184 Days on yellowkey   MLS ID: S5139386

    REDUCED by $10,123 (2.2%) on 05/24/2026

    For Sale S5139386 - 3001 MANDOLIN DR, KISSIMMEE, FL 34744 67 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2392
       Built: 2005
    Monthly Fee: $83
       Tax: $5,737 (2024)
    Community: Turnberry Reserve Unit 1
    Single Family


    Estimated Monthly Payment: $3,026 (change assumption)
    Mortgage ($2,464) + Fees ($83) + Taxes in 2024 ($478)


    Taxes:$5,737

    Elementary School: East Lake Elem

    High School: Tohopekaliga High School

    Tax Year: 2024

    Middle School: Narcoossee Middle


  • 216 MAGICAL WAY, KISSIMMEE, FL 34744

    $359,00045 Days on yellowkey   MLS ID: O6396457

    3 Days Off yellowkey (back on 5/24/2026)

    For Sale O6396457 - 216 MAGICAL WAY, KISSIMMEE, FL 34744 33 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 1832
       Built: 2005
    Monthly Fee: $127
       Tax: $4,782 (2025)
    Community: Magic Landings
    Single Family


    Estimated Monthly Payment: $2,493 (change assumption)
    Mortgage ($1,967) + Fees ($127) + Taxes in 2025 ($399)


    Taxes:$4,782

    Elementary School: Mill Creek Elem (K 5)

    High School: Osceola High School

    Tax Year: 2025

    Middle School: Denn John Middle


  • 2705 PRESTWICK LN, KISSIMMEE, FL 34744

    $410,00097 Days on yellowkey   MLS ID: O6384546

    For Sale O6384546 - 2705 PRESTWICK LN, KISSIMMEE, FL 34744 43 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 1719
       Built: 2005
    Monthly Fee: $73
       Tax: $6,174 (2025)
    Community: Remington Prcl M1
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,834 (change assumption)
    Mortgage ($2,247) + Fees ($73) + Taxes in 2025 ($515)


    Taxes:$6,174

    Elementary School: Partin Settlement Elem

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 1956 EGRET MEADOWS AVE, KISSIMMEE, FL 34744

    $394,99011 Days on yellowkey   MLS ID: O6409425

    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: $2,730 (change assumption)
    Mortgage ($2,164) + 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)


  • 1550 REGAL OAK DR, KISSIMMEE, FL 34744

    $480,00017 Days on yellowkey   MLS ID: S5150034

    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: $2,916 (change assumption)
    Mortgage ($2,630) + Taxes in 2025 ($286)


    Taxes:$3,426

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1737 KATO WAY, KISSIMMEE, FL 34744

    $345,00061 Days on yellowkey   MLS ID: TB8492414

    REDUCED by $10,000 (2.8%) on 05/19/2026

    For Sale TB8492414 - 1737 KATO WAY, KISSIMMEE, FL 34744 33 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1935
       Built: 2018
    Monthly Fee: $168
       Tax: $4,031 (2025)
    Community: Heritage Run
    Townhouse


    Estimated Monthly Payment: $2,394 (change assumption)
    Mortgage ($1,890) + Fees ($168) + Taxes in 2025 ($336)


    Taxes:$4,031

    Elementary School: Mill Creek Elem (K 5)

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Denn John Middle


  • 1892 BRIGHT SKY DR, KISSIMMEE, FL 34744

    $468,000109 Days on yellowkey   MLS ID: S5143785

    For Sale S5143785 - 1892 BRIGHT SKY DR, KISSIMMEE, FL 34744 12 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2522
       Built: 2025
    Monthly Fee: $7
       Tax: $2,686 (2025)
    Community: Tohoqua Ph 7
    Single Family


    Estimated Monthly Payment: $2,795 (change assumption)
    Mortgage ($2,564) + Fees ($7) + Taxes in 2025 ($224)


    Taxes:$2,686

    Elementary School: Neptune Elementary

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 1666 MARINA LAKE DR, KISSIMMEE, FL 34744

    $899,99032 Days on yellowkey   MLS ID: O6401678

    REDUCED by $75,010 (7.7%) on 05/21/2026

    For Sale O6401678 - 1666 MARINA LAKE DR, KISSIMMEE, FL 34744 48 photos

    Bed: 5   Bath: 4.0   Gar: 3
    Liv Area Sq Ft: 3721
       Built: 2000
    Monthly Fee: $75
       Tax: $9,365 (2025)
    Community: Ashley Cove Unit 2
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $5,787 (change assumption)
    Mortgage ($4,931) + Fees ($75) + Taxes in 2025 ($780)


    Taxes:$9,365

    Elementary School: Partin Settlement Elem

    High School: Osceola High School

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 1828 PARTIN TERRACE RD, KISSIMMEE, FL 34744

    $414,900117 Days on yellowkey   MLS ID: S5143083

    For Sale S5143083 - 1828 PARTIN TERRACE RD, KISSIMMEE, FL 34744 47 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1846
       Built: 2017
    Monthly Fee: $10
       Tax: $8,257 (2025)
    Community: Kindred Ph 1C
    Single Family


    Estimated Monthly Payment: $2,971 (change assumption)
    Mortgage ($2,273) + Fees ($10) + Taxes in 2025 ($688)


    Taxes:$8,257

    Elementary School: Neptune Elementary

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 1595 SHADY OAK DR, KISSIMMEE, FL 34744

    $450,00095 Days on yellowkey   MLS ID: S5144261

    REDUCED by $7,000 (1.5%) on 04/30/2026

    For Sale S5144261 - 1595 SHADY OAK DR, KISSIMMEE, FL 34744 39 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2116
       Built: 1981   Tax: $4,757 (2025)
    Community: Regal Oak Shores Unit 6
    Single Family


    Estimated Monthly Payment: $2,862 (change assumption)
    Mortgage ($2,466) + Taxes in 2025 ($396)


    Taxes:$4,757

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 3215 STRATTON CIR, KISSIMMEE, FL 34744

    $460,00010 Days on yellowkey   MLS ID: S5150428

    For Sale S5150428 - 3215 STRATTON CIR, KISSIMMEE, FL 34744 23 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2432
       Built: 2018
    Monthly Fee: $80
       Tax: $4,244 (2025)
    Community: South Pointe
    Single Family


    Estimated Monthly Payment: $2,954 (change assumption)
    Mortgage ($2,520) + Fees ($80) + Taxes in 2025 ($354)


    Taxes:$4,244

    Elementary School: East Lake Elementary-OS

    High School: Tohopekaliga High School

    Tax Year: 2025

    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.