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Homes For Sale in Kissimmee 34744 - 244 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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  • 1714 CHERYL LN, KISSIMMEE, FL 34744

    $749,000Listed 04/03/2026 5:12PM   MLS ID: O6395426

    For Sale O6395426 - 1714 CHERYL LN, KISSIMMEE, FL 34744 0 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3609
       Built: 1989   Tax: $3,559 (2025)
    Community: Regal Oak Shores Unit 8
    Single Family


    Estimated Monthly Payment: $4,401 (change assumption)
    Mortgage ($4,104) + Taxes in 2025 ($297)


    Taxes:$3,559

    Elementary School: Partin Settlement Elem

    High School: Osceola High School

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 1872 RUSTIC FALLS DR, KISSIMMEE, FL 34744

    $565,000Listed 04/03/2026 10:57AM   MLS ID: O6396038

    For Sale O6396038 - 1872 RUSTIC FALLS DR, KISSIMMEE, FL 34744 28 photos

    Bed: 8   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2824
       Built: 2020
    Monthly Fee: $125
       Tax: $8,846 (2025)
    Community: Kindred Ph 1Fa
    Single Family


    Estimated Monthly Payment: $3,958 (change assumption)
    Mortgage ($3,096) + Fees ($125) + Taxes in 2025 ($737)


    Taxes:$8,846

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1831 BRIGHT SKY DR, KISSIMMEE, FL 34744

    $467,201122 Days on yellowkey   MLS ID: O6364329

    1 Days Off yellowkey (back on 4/2/2026)

    REDUCED by $30,000 (6.0%) on 03/31/2026

    For Sale O6364329 - 1831 BRIGHT SKY DR, KISSIMMEE, FL 34744 29 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2139
       Built: 2025
    Monthly Fee: $10

    Community: Tohoqua 50S
    Single Family


    Estimated Monthly Payment: $2,570 (change assumption)
    Mortgage ($2,560) + Fees ($10) + Taxes in 2024 ($0)


    Taxes:$0

    Elementary School: Neptune Elementary

    High School: Gateway High School (9 12)

    Tax Year: 2024

    Middle School: Neptune Middle (6-8)


  • 109 THORNBURY DR, KISSIMMEE, FL 34744

    $360,000Listed 04/03/2026 11:48AM   MLS ID: O6395896

    For Sale O6395896 - 109 THORNBURY DR, KISSIMMEE, FL 34744 21 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1622
       Built: 2003
    Monthly Fee: $14
       Tax: $6,074 (2025)
    Community: Remington Prcl H Ph 1
    Single Family


    Estimated Monthly Payment: $2,493 (change assumption)
    Mortgage ($1,973) + Fees ($14) + Taxes in 2025 ($506)


    Taxes:$6,074

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1980 SUMMER CT, KISSIMMEE, FL 34744

    $549,0009 Days on yellowkey   MLS ID: O6392643

    For Sale O6392643 - 1980 SUMMER CT, KISSIMMEE, FL 34744 40 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: $3,557 (change assumption)
    Mortgage ($3,008) + 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)


  • 1941 PARTIN TERRACE RD, KISSIMMEE, FL 34744

    $520,00035 Days on yellowkey   MLS ID: O6386096

    REDUCED by $9,000 (1.7%) on 04/03/2026

    For Sale O6386096 - 1941 PARTIN TERRACE RD, KISSIMMEE, FL 34744 35 photos

    Bed: 4   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 2787
       Built: 2019
    Monthly Fee: $11
       Tax: $3,624 (2025)
    Community: Kindred 100 Rep
    Single Family


    Estimated Monthly Payment: $3,162 (change assumption)
    Mortgage ($2,849) + Fees ($11) + Taxes in 2025 ($302)


    Taxes:$3,624

    Elementary School: Neptune Elementary

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 7 WESTCHESTER DR, KISSIMMEE, FL 34744

    $439,000320 Days on yellowkey   MLS ID: O6309992

    REDUCED by $5,500 (1.2%) on 04/01/2026

    For Sale O6309992 - 7 WESTCHESTER DR, KISSIMMEE, FL 34744 45 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1786
       Built: 1962   Tax: $1,988 (2024)
    Community: Fairlawn Manor
    Single Family


    Estimated Monthly Payment: $2,571 (change assumption)
    Mortgage ($2,405) + Taxes in 2024 ($166)


    Taxes:$1,988

    Elementary School: Partin Settlement Elem

    High School: Osceola High School

    Tax Year: 2024

    Middle School: Neptune Middle (6-8)


  • 2394 OLD DIXIE HWY, KISSIMMEE, FL 34744

    $289,99922 Days on yellowkey   MLS ID: O6366826

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

    For Sale O6366826 - 2394 OLD DIXIE HWY, KISSIMMEE, FL 34744 3 photos

    Bed: 4   Bath: 3.0
    Liv Area Sq Ft: 1567
       Built: 1958   Tax: $3,253 (2024)
    Community: Colonial Estates
    Single Family


    Estimated Monthly Payment: $1,860 (change assumption)
    Mortgage ($1,589) + Taxes in 2024 ($271)


    Taxes:$3,253

    Elementary School: Central Avenue Elem

    High School: Osceola High School

    Tax Year: 2024

    Middle School: Denn John Middle


  • 1839 GOOD NEIGHBOR LOOP, KISSIMMEE, FL 34744

    $475,000259 Days on yellowkey   MLS ID: O6328214

    For Sale O6328214 - 1839 GOOD NEIGHBOR LOOP, KISSIMMEE, FL 34744 44 photos

    Bed: 4   Bath: 4.0
    Liv Area Sq Ft: 2717
       Built: 2021
    Monthly Fee: $10
       Tax: $9,250 (2024)
    Community: Tohoqua Ph 2
    Single Family


    Estimated Monthly Payment: $3,384 (change assumption)
    Mortgage ($2,603) + Fees ($10) + Taxes in 2024 ($771)


    Taxes:$9,250

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 1436 MASSA ST, KISSIMMEE, FL 34744

    $339,000207 Days on yellowkey   MLS ID: O6342301

    1 Days Off yellowkey (back on 4/3/2026)

    For Sale O6342301 - 1436 MASSA ST, KISSIMMEE, FL 34744 28 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1192
       Built: 1983   Tax: $2,380 (2024)
    Community: Mill Run, Lot 4
    Single Family


    Estimated Monthly Payment: $2,056 (change assumption)
    Mortgage ($1,857) + Taxes in 2024 ($198)


    Taxes:$2,380

    Elementary School: Mill Creek Elem (K 5)

    High School: Gateway High School (9 12)

    Tax Year: 2024

    Middle School: Denn John Middle


  • 1807 GOOD NEIGHBOR LOOP, KISSIMMEE, FL 34744

    $440,0001 Day on yellowkey   MLS ID: O6395467

    For Sale O6395467 - 1807 GOOD NEIGHBOR LOOP, KISSIMMEE, FL 34744 33 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


  • 1528 ERIN BREEZE LN, KISSIMMEE, FL 34744

    $390,000Listed 04/03/2026 8:59AM   MLS ID: S5147056

    For Sale S5147056 - 1528 ERIN BREEZE LN, KISSIMMEE, FL 34744 24 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1509
       Built: 2024
    Monthly Fee: $280
       Tax: $4,867 (2025)
    Community: Seasons At Big Sky Ph 1
    Townhouse


    Estimated Monthly Payment: $2,823 (change assumption)
    Mortgage ($2,137) + Fees ($280) + Taxes in 2025 ($406)


    Taxes:$4,867

    Elementary School: Partin Settlement Elem

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 1395 EMERALD DR, KISSIMMEE, FL 34744

    $398,900150 Days on yellowkey   MLS ID: O6357655

    3 Days Off yellowkey (back on 4/3/2026)

    For Sale O6357655 - 1395 EMERALD DR, KISSIMMEE, FL 34744 79 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1760
       Built: 1991   Tax: $3,100 (2024)
    Community: Emerald Lake Colony Unit 2
    Single Family


    Estimated Monthly Payment: $2,444 (change assumption)
    Mortgage ($2,186) + Taxes in 2024 ($258)


    Taxes:$3,100

    Elementary School: Neptune Elementary

    High School: Gateway High School (9 12)

    Tax Year: 2024

    Middle School: Neptune Middle (6-8)


  • 1774 GOOD NEIGHBOR LOOP, KISSIMMEE, FL 34744

    $445,00035 Days on yellowkey   MLS ID: O6385521

    REDUCED by $4,999 (1.1%) on 04/03/2026

    For Sale O6385521 - 1774 GOOD NEIGHBOR LOOP, KISSIMMEE, FL 34744 31 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2068
       Built: 2022
    Monthly Fee: $7
       Tax: $7,509 (2025)
    Community: Tohoqua Ph 2
    Single Family


    Estimated Monthly Payment: $3,071 (change assumption)
    Mortgage ($2,438) + Fees ($7) + Taxes in 2025 ($626)


    Taxes:$7,509

    Elementary School: Neptune Elementary

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 1438 LONDRA LN, KISSIMMEE, FL 34744

    $425,000189 Days on yellowkey   MLS ID: S5135117

    For Sale S5135117 - 1438 LONDRA LN, KISSIMMEE, FL 34744 30 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1896
       Built: 1992   Tax: $5,501 (2024)
    Community: Mill Run Park Unit 2
    Single Family


    Estimated Monthly Payment: $2,787 (change assumption)
    Mortgage ($2,329) + Taxes in 2024 ($458)


    Taxes:$5,501

    Elementary School: Mill Creek Elem (K 5)

    High School: Gateway High School (9 12)

    Tax Year: 2024

    Middle School: Denn John Middle


  • 1842 W VIRGINIA DR, KISSIMMEE, FL 34744

    $519,900168 Days on yellowkey   MLS ID: O6352827

    REDUCED by $20,000 (3.7%) on 04/03/2026

    For Sale O6352827 - 1842 W VIRGINIA DR, KISSIMMEE, FL 34744 33 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2336
       Built: 1996   Tax: $5,724 (2024)
    Community: Neptune Shores Unit 7 Ph 2
    Single Family


    Estimated Monthly Payment: $3,326 (change assumption)
    Mortgage ($2,849) + Taxes in 2024 ($477)


    Taxes:$5,724

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 1340 SAWDUST TRL, KISSIMMEE, FL 34744

    $239,90076 Days on yellowkey   MLS ID: G5106887

    For Sale G5106887 - 1340 SAWDUST TRL, KISSIMMEE, FL 34744 24 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 924
       Built: 1996   Tax: $2,377 (2025)
    Community: Marydia
    Manufactured Home


    Estimated Monthly Payment: $1,513 (change assumption)
    Mortgage ($1,314) + Taxes in 2025 ($198)


    Taxes:$2,377

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2961 BIG SKY BLVD, KISSIMMEE, FL 34744

    $390,9901 Day on yellowkey   MLS ID: S5147103

    For Sale S5147103 - 2961 BIG SKY BLVD, KISSIMMEE, FL 34744 22 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1860
       Built: 1986   Tax: $5,305 (2025)
    Community: Big Sky Unit 1
    Single Family


    Estimated Monthly Payment: $2,584 (change assumption)
    Mortgage ($2,142) + Taxes in 2025 ($442)


    Taxes:$5,305

    Elementary School: Partin Settlement Elem

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 1673 BARBERRY DR, KISSIMMEE, FL 34744

    $460,0001 Day on yellowkey   MLS ID: S5147034

    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: $3,049 (change assumption)
    Mortgage ($2,520) + 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)


  • 1595 SHADY OAK DR, KISSIMMEE, FL 34744

    $457,00036 Days on yellowkey   MLS ID: S5144261

    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: $2,900 (change assumption)
    Mortgage ($2,504) + Taxes in 2025 ($396)


    Taxes:$4,757

    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.