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Homes For Sale in Kissimmee 34744 - 299 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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  • 2661 AMES HAVEN RD, KISSIMMEE, FL 34744

    $439,00053 Days on yellowkey   MLS ID: S5145125

    REDUCED by $6,000 (1.3%) on 03/31/2026

    For Sale S5145125 - 2661 AMES HAVEN RD, KISSIMMEE, FL 34744 51 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1666
       Built: 1984   Tax: $4,502 (2025)
    Community: Emerald Lake Colony Unit 1
    Single Family


    Estimated Monthly Payment: $2,781 (change assumption)
    Mortgage ($2,405) + Taxes in 2025 ($375)


    Taxes:$4,502

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1714 CHERYL LN, KISSIMMEE, FL 34744

    $749,00023 Days on yellowkey   MLS ID: O6395426

    For Sale O6395426 - 1714 CHERYL LN, KISSIMMEE, FL 34744 33 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)


  • 1433 RIVERBOAT DR, KISSIMMEE, FL 34744

    $380,000192 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)


  • 2604 BLOWING BREEZE AVE, KISSIMMEE, FL 34744

    $507,000160 Days on yellowkey   MLS ID: O6360718

    2 Days Off yellowkey (back on 4/15/2026)

    For Sale O6360718 - 2604 BLOWING BREEZE AVE, KISSIMMEE, FL 34744 64 photos

    Bed: 5   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2590
       Built: 2022
    Monthly Fee: $10
       Tax: $8,552 (2024)
    Community: Tohoqua Ph 4A
    Single Family


    Estimated Monthly Payment: $3,501 (change assumption)
    Mortgage ($2,778) + Fees ($10) + Taxes in 2024 ($713)


    Taxes:$8,552

    Elementary School: Neptune Elementary

    High School: Gateway High School (9 12)

    Tax Year: 2024

    Middle School: Neptune Middle (6-8)


  • 1488 SOPHIE WAY, KISSIMMEE, FL 34744

    $399,00014 Days on yellowkey   MLS ID: S5147658

    1 Days Off yellowkey (back on 4/15/2026)

    For Sale S5147658 - 1488 SOPHIE WAY, KISSIMMEE, FL 34744 49 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1552
       Built: 1993
    Monthly Fee: $33
       Tax: $713 (2025)
    Community: Westminster Gardens Ph 1
    Single Family


    Estimated Monthly Payment: $2,279 (change assumption)
    Mortgage ($2,186) + Fees ($33) + Taxes in 2025 ($59)


    Taxes:$713

    Elementary School: Partin Settlement Elem

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 2374 ROSS ST, KISSIMMEE, FL 34744

    $167,000428 Days on yellowkey   MLS ID: O6275526

    0 Days Off yellowkey (back on 2/22/2025)

    For Sale O6275526 - 2374 ROSS ST, KISSIMMEE, FL 34744 1 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1382
       Built: 1920   Tax: $1,430 (2023)
    Community: Gilchrist 2Nd Add
    Single Family


    Estimated Monthly Payment: $1,034 (change assumption)
    Mortgage ($915) + Taxes in 2023 ($119)


    Taxes:$1,430

    Elementary School: None

    High School: None

    Tax Year: 2023

    Middle School: None


  • 1906 DAMON AVE, KISSIMMEE, FL 34744

    $199,000236 Days on yellowkey   MLS ID: O6337678

    0 Days Off yellowkey (back on 9/10/2025)

    For Sale O6337678 - 1906 DAMON AVE, KISSIMMEE, FL 34744 8 photos

    Bed: 4   Bath: 2.0
    Liv Area Sq Ft: 1224
       Built: 1972   Tax: $1,376 (2024)
    Community: Kissimmee Heights
    Single Family


    Estimated Monthly Payment: $1,205 (change assumption)
    Mortgage ($1,090) + Taxes in 2024 ($115)


    Taxes:$1,376

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 3824 BLUE DASHER DR, KISSIMMEE, FL 34744

    $499,990328 Days on yellowkey   MLS ID: O6314514

    For Sale O6314514 - 3824 BLUE DASHER DR, KISSIMMEE, FL 34744 48 photos

    Bed: 5   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 3783
       Built: 2004
    Monthly Fee: $106
       Tax: $6,729 (2024)
    Community: Springlake Village Ph 03
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $3,406 (change assumption)
    Mortgage ($2,740) + Fees ($106) + Taxes in 2024 ($561)


    Taxes:$6,729

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 1764 STAMEN DR, KISSIMMEE, FL 34744

    $447,99039 Days on yellowkey   MLS ID: O6391946

    REDUCED by $2,010 (0.4%) on 04/14/2026

    For Sale O6391946 - 1764 STAMEN DR, KISSIMMEE, FL 34744 20 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1985
       Built: 2023
    Monthly Fee: $160
       Tax: $4,505 (2025)
    Community: Pennyroyal
    Single Family


    Estimated Monthly Payment: $2,990 (change assumption)
    Mortgage ($2,455) + Fees ($160) + Taxes in 2025 ($375)


    Taxes:$4,505

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2540 BLOWING BREEZE AVE, KISSIMMEE, FL 34744

    $370,000108 Days on yellowkey   MLS ID: S5141277

    For Sale S5141277 - 2540 BLOWING BREEZE AVE, KISSIMMEE, FL 34744 29 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1700
       Built: 2021
    Monthly Fee: $154
       Tax: $6,407 (2025)
    Community: Tohoqua Ph 1B
    Townhouse


    Estimated Monthly Payment: $2,715 (change assumption)
    Mortgage ($2,027) + Fees ($154) + Taxes in 2025 ($534)


    Taxes:$6,407

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1590 BARBERRY DR, KISSIMMEE, FL 34744

    $459,900248 Days on yellowkey   MLS ID: S5133065

    REDUCED by $30,000 (6.1%) on 04/14/2026

    For Sale S5133065 - 1590 BARBERRY DR, KISSIMMEE, FL 34744 48 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2142
       Built: 2023
    Monthly Fee: $15
       Tax: $8,284 (2024)
    Community: Kindred Ph 2C & 2D
    Single Family


    Estimated Monthly Payment: $3,225 (change assumption)
    Mortgage ($2,520) + Fees ($15) + Taxes in 2024 ($690)


    Taxes:$8,284

    Elementary School: None

    High School: Gateway High School (9 12)

    Tax Year: 2024

    Middle School: None


  • 1540 GRANDVIEW BLVD, KISSIMMEE, FL 34744

    $949,90072 Days on yellowkey   MLS ID: S5143565

    REDUCED by $50,000 (5.0%) on 04/14/2026

    For Sale S5143565 - 1540 GRANDVIEW BLVD, KISSIMMEE, FL 34744 56 photos

    Bed: 4   Bath: 4.5   Gar: 3
    Liv Area Sq Ft: 5207
       Built: 1981   Tax: $7,032 (2025)
    Community: Regal Oak Shores Unit 1
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $5,791 (change assumption)
    Mortgage ($5,205) + Taxes in 2025 ($586)


    Taxes:$7,032

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2518 BOWMER DR, KISSIMMEE, FL 34744

    $359,900628 Days on yellowkey   MLS ID: S5109889

    For Sale S5109889 - 2518 BOWMER DR, KISSIMMEE, FL 34744 21 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1523
       Built: 1982   Tax: $1,246 (2025)
    Community: Mill Run Unit 3
    Single Family


    Estimated Monthly Payment: $2,076 (change assumption)
    Mortgage ($1,972) + Taxes in 2025 ($104)


    Taxes:$1,246

    Elementary School: Mill Creek Elem (K 5)

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Denn John Middle


  • 2728 PORTCHESTER CT, KISSIMMEE, FL 34744

    $399,900347 Days on yellowkey   MLS ID: S5126915

    For Sale S5126915 - 2728 PORTCHESTER CT, KISSIMMEE, FL 34744 14 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 1960
       Built: 2005
    Monthly Fee: $7
       Tax: $6,060 (2024)
    Community: Somerset
    Single Family


    Estimated Monthly Payment: $2,703 (change assumption)
    Mortgage ($2,191) + Fees ($7) + Taxes in 2024 ($505)


    Taxes:$6,060

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 1705 BRIDGETS CT, KISSIMMEE, FL 34744

    $565,00048 Days on yellowkey   MLS ID: S5145159

    REDUCED by $10,000 (1.7%) on 04/14/2026

    For Sale S5145159 - 1705 BRIDGETS CT, KISSIMMEE, FL 34744 57 photos

    Bed: 4   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 2994
       Built: 2004
    Monthly Fee: $190
       Tax: $5,502 (2025)
    Community: M3 At Kissimmee Bay
    Single Family


    Estimated Monthly Payment: $3,744 (change assumption)
    Mortgage ($3,096) + Fees ($190) + Taxes in 2025 ($459)


    Taxes:$5,502

    Elementary School: Partin Settlement Elem

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 1737 KATO WAY, KISSIMMEE, FL 34744

    $355,00025 Days on yellowkey   MLS ID: TB8492414

    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: $2,449 (change assumption)
    Mortgage ($1,945) + 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


  • 2061 WALNUT CREEK DR, KISSIMMEE, FL 34744

    $458,99019 Days on yellowkey   MLS ID: O6396945

    2 Days Off yellowkey (back on 4/14/2026)

    For Sale O6396945 - 2061 WALNUT CREEK DR, KISSIMMEE, FL 34744 50 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: $2,833 (change assumption)
    Mortgage ($2,515) + Fees ($11) + Taxes in 2025 ($307)


    Taxes:$3,684

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1563 CROSS PRAIRIE PKWY, KISSIMMEE, FL 34744

    $360,00013 Days on yellowkey   MLS ID: S5147463

    SHORT SALE S5147463 - 1563 CROSS PRAIRIE PKWY, KISSIMMEE, FL 34744 54 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1802
       Built: 2023
    Monthly Fee: $10
       Tax: $7,403 (2025)
    Community: Tohoqua Ph 3
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,599 (change assumption)
    Mortgage ($1,973) + Fees ($10) + Taxes in 2025 ($617)


    Taxes:$7,403

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2538 CROWN RIDGE CIR, KISSIMMEE, FL 34744

    $365,000175 Days on yellowkey   MLS ID: O6357310

    REDUCED by $5,900 (1.6%) on 04/14/2026

    For Sale O6357310 - 2538 CROWN RIDGE CIR, KISSIMMEE, FL 34744 15 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1766
       Built: 2001
    Monthly Fee: $14
       Tax: $2,928 (2024)
    Community: Remington Prcl H Ph 1
    Single Family


    Estimated Monthly Payment: $2,258 (change assumption)
    Mortgage ($2,000) + Fees ($14) + Taxes in 2024 ($244)


    Taxes:$2,928

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 2619 PEACE OF MIND AVE, KISSIMMEE, FL 34744

    $483,00079 Days on yellowkey   MLS ID: O6380357

    REDUCED by $6,000 (1.2%) on 04/13/2026

    For Sale O6380357 - 2619 PEACE OF MIND AVE, KISSIMMEE, FL 34744 57 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2109
       Built: 2025
    Monthly Fee: $10
       Tax: $3,729 (2025)
    Community: Tohoqua 50S
    Single Family


    Estimated Monthly Payment: $2,967 (change assumption)
    Mortgage ($2,647) + Fees ($10) + Taxes in 2025 ($311)


    Taxes:$3,729

    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.