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Homes For Sale in Kissimmee 34744 - 295 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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  • 4306 BISCAYNE COVE CT, KISSIMMEE, FL 34744

    $700,000105 Days on yellowkey   MLS ID: O6370990

    REDUCED by $25,000 (3.4%) on 04/21/2026

    For Sale O6370990 - 4306 BISCAYNE COVE CT, KISSIMMEE, FL 34744 48 photos

    Bed: 5   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 3828
       Built: 2015
    Monthly Fee: $108
       Tax: $5,600 (2025)
    Community: North Point Ph 2B-2C
    Single Family


    Estimated Monthly Payment: $4,410 (change assumption)
    Mortgage ($3,836) + Fees ($108) + Taxes in 2025 ($467)


    Taxes:$5,600

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2220 EMPEROR DR, KISSIMMEE, FL 34744

    $624,900Listed 04/21/2026 4:58PM   MLS ID: S5148275

    For Sale S5148275 - 2220 EMPEROR DR, KISSIMMEE, FL 34744 36 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2502
       Built: 1991   Tax: $3,970 (2025)
    Community: Cane Brake Ph 2
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,755 (change assumption)
    Mortgage ($3,424) + Taxes in 2025 ($331)


    Taxes:$3,970

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1805 MICHIGAN AVE #D, KISSIMMEE, FL 34744

    $139,000Listed 04/21/2026 8:50PM   MLS ID: S5148360

    For Sale S5148360 - 1805 MICHIGAN AVE #D, KISSIMMEE, FL 34744 9 photos

    Bed: 2   Bath: 0.0
    Liv Area Sq Ft: 1118
       Built: 1973
    Monthly Fee: $345
       Tax: $2,118 (2025)
    Community: Essex Park Villas Condo
    Apartment


    Estimated Monthly Payment: $1,283 (change assumption)
    Mortgage ($762) + Fees ($345) + Taxes in 2025 ($176)


    Taxes:$2,118

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1211 LEHIGH ST, KISSIMMEE, FL 34744

    $369,90015 Days on yellowkey   MLS ID: S5147242

    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: $2,452 (change assumption)
    Mortgage ($2,027) + 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


  • 1489 TWIN VALLEY TER, KISSIMMEE, FL 34744

    $549,90027 Days on yellowkey   MLS ID: O6390966

    REDUCED by $10,100 (1.8%) on 04/18/2026

    For Sale O6390966 - 1489 TWIN VALLEY TER, KISSIMMEE, FL 34744 77 photos

    Bed: 5   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2674
       Built: 2017
    Monthly Fee: $11
       Tax: $7,067 (2025)
    Community: Kindred Ph 1A & 1B
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,613 (change assumption)
    Mortgage ($3,013) + Fees ($11) + Taxes in 2025 ($589)


    Taxes:$7,067

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1724 RANGER HIGHLANDS RD, KISSIMMEE, FL 34744

    $367,000276 Days on yellowkey   MLS ID: TB8408985

    REDUCED by $1,000 (0.3%) on 04/02/2026

    For Sale TB8408985 - 1724 RANGER HIGHLANDS RD, KISSIMMEE, FL 34744 53 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1910
       Built: 2018
    Monthly Fee: $11
       Tax: $5,835 (2024)
    Community: Kindred Ph 1D
    Single Family


    Estimated Monthly Payment: $2,508 (change assumption)
    Mortgage ($2,011) + Fees ($11) + Taxes in 2024 ($486)


    Taxes:$5,835

    Elementary School: Neptune Elementary

    High School: Gateway High School (9 12)

    Tax Year: 2024

    Middle School: Neptune Middle (6-8)


  • 2601 GOLD DUST CIR, KISSIMMEE, FL 34744

    $495,00026 Days on yellowkey   MLS ID: S5146084

    REDUCED by $15,000 (2.9%) on 04/08/2026

    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: $3,104 (change assumption)
    Mortgage ($2,712) + 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)


  • 1608 BARBERRY DR, KISSIMMEE, FL 34744

    $559,00083 Days on yellowkey   MLS ID: S5142703

    2 Days Off yellowkey (back on 4/10/2026)

    For Sale S5142703 - 1608 BARBERRY DR, KISSIMMEE, FL 34744 86 photos

    Bed: 4   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 2851
       Built: 2023
    Monthly Fee: $11
       Tax: $9,049 (2025)
    Community: Kindred Ph 2C & 2D
    Single Family


    Estimated Monthly Payment: $3,828 (change assumption)
    Mortgage ($3,063) + Fees ($11) + Taxes in 2025 ($754)


    Taxes:$9,049

    Elementary School: Neptune Elementary

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Harmony Middle


  • 1776 FULFILLMENT DR, KISSIMMEE, FL 34744

    $395,000Listed 04/21/2026 1:29PM   MLS ID: S5148323

    For Sale S5148323 - 1776 FULFILLMENT DR, KISSIMMEE, FL 34744 24 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1620
       Built: 2020
    Monthly Fee: $55
       Tax: $5,091 (2025)
    Community: Tohoqua Ph 1
    Townhouse


    Estimated Monthly Payment: $2,644 (change assumption)
    Mortgage ($2,164) + Fees ($55) + Taxes in 2025 ($424)


    Taxes:$5,091

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1632 REGAL COVE CT, KISSIMMEE, FL 34744

    $1,099,700223 Days on yellowkey   MLS ID: S5134100

    REDUCED by $50 (0.0%) on 04/21/2026

    For Sale S5134100 - 1632 REGAL COVE CT, KISSIMMEE, FL 34744 76 photos

    Bed: 6   Bath: 5.5   Gar: 3
    Liv Area Sq Ft: 4621
       Built: 1993
    Monthly Fee: $100
       Tax: $10,804 (2024)
    Community: Regal Cove
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $7,026 (change assumption)
    Mortgage ($6,026) + Fees ($100) + Taxes in 2024 ($900)


    Taxes:$10,804

    Elementary School: Partin Settlement Elem

    High School: Osceola High School

    Tax Year: 2024

    Middle School: Neptune Middle (6-8)


  • 1604 REGAL COVE CT, KISSIMMEE, FL 34744

    $1,385,77739 Days on yellowkey   MLS ID: S5145793

    0 Days Off yellowkey (back on 4/21/2026)

    For Sale S5145793 - 1604 REGAL COVE CT, KISSIMMEE, FL 34744 57 photos

    Bed: 5   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 3664
       Built: 2000
    Monthly Fee: $133
       Tax: $6,996 (2025)
    Community: Regal Cove
    Spa: No

    Single Family


    Estimated Monthly Payment: $8,309 (change assumption)
    Mortgage ($7,593) + Fees ($133) + Taxes in 2025 ($583)


    Taxes:$6,996

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2602 BIRCHWOOD AVE, KISSIMMEE, FL 34744

    $435,00060 Days on yellowkey   MLS ID: O6383961

    REDUCED by $32,000 (6.9%) on 04/21/2026

    For Sale O6383961 - 2602 BIRCHWOOD AVE, KISSIMMEE, FL 34744 34 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1393
       Built: 1989   Tax: $5,428 (2025)
    Community: Oak Hollow Ph 4
    Single Family


    Estimated Monthly Payment: $2,836 (change assumption)
    Mortgage ($2,384) + Taxes in 2025 ($452)


    Taxes:$5,428

    Elementary School: Mill Creek Elem (K 5)

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Denn John Middle


  • 1760 SAINT TROPEZ CT, KISSIMMEE, FL 34744

    $305,00061 Days on yellowkey   MLS ID: O6383696

    REDUCED by $25,000 (7.6%) on 04/21/2026

    For Sale O6383696 - 1760 SAINT TROPEZ CT, KISSIMMEE, FL 34744 35 photos

    Bed: 3   Bath: 2.5   Gar: 1
    Liv Area Sq Ft: 2104
       Built: 1992
    Monthly Fee: $398
       Tax: $4,610 (2025)
    Community: Monaco Villas Ph 5 & 14
    Spa: No

    Townhouse


    Estimated Monthly Payment: $2,453 (change assumption)
    Mortgage ($1,671) + Fees ($398) + Taxes in 2025 ($384)


    Taxes:$4,610

    Elementary School: Partin Settlement Elem

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 1724 CROSS PRAIRIE PKWY, KISSIMMEE, FL 34744

    $389,90085 Days on yellowkey   MLS ID: O6376465

    0 Days Off yellowkey (back on 3/22/2026)

    For Sale O6376465 - 1724 CROSS PRAIRIE PKWY, KISSIMMEE, FL 34744 24 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2044
       Built: 2022
    Monthly Fee: $10
       Tax: $6,652 (2025)
    Community: Tohoqua Ph 2
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,701 (change assumption)
    Mortgage ($2,136) + Fees ($10) + Taxes in 2025 ($554)


    Taxes:$6,652

    Elementary School: None

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: None


  • 1911 SPRING SHOWER CIR, KISSIMMEE, FL 34744

    $368,00077 Days on yellowkey   MLS ID: O6378988

    REDUCED by $2,000 (0.5%) on 04/21/2026

    For Sale O6378988 - 1911 SPRING SHOWER CIR, KISSIMMEE, FL 34744 52 photos

    Bed: 2   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1579
       Built: 2024
    Monthly Fee: $220
       Tax: $6,234 (2025)
    Community: Tohoqua Reserve
    Spa: No

    Villa


    Estimated Monthly Payment: $2,756 (change assumption)
    Mortgage ($2,016) + Fees ($220) + Taxes in 2025 ($520)


    Taxes:$6,234

    Elementary School: Neptune Elementary

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 4408 BREEZE ISLE LN, KISSIMMEE, FL 34744

    $675,00025 Days on yellowkey   MLS ID: O6393234

    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: $4,216 (change assumption)
    Mortgage ($3,699) + Fees ($111) + Taxes in 2025 ($407)


    Taxes:$4,883

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2605 PLAY HARD ALY, KISSIMMEE, FL 34744

    $375,00064 Days on yellowkey   MLS ID: S5143916

    For Sale S5143916 - 2605 PLAY HARD ALY, KISSIMMEE, FL 34744 40 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1603
       Built: 2019
    Monthly Fee: $154
       Tax: $4,220 (2025)
    Community: Tohoqua Ph 1
    Townhouse


    Estimated Monthly Payment: $2,560 (change assumption)
    Mortgage ($2,055) + Fees ($154) + Taxes in 2025 ($352)


    Taxes:$4,220

    Elementary School: Neptune Elementary

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 2506 VOLUNTEER AVE, KISSIMMEE, FL 34744

    $520,00011 Days on yellowkey   MLS ID: O6398097

    For Sale O6398097 - 2506 VOLUNTEER AVE, KISSIMMEE, FL 34744 45 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3199
       Built: 2019
    Monthly Fee: $7
       Tax: $9,289 (2025)
    Community: Tohoqua Ph 1
    Single Family


    Estimated Monthly Payment: $3,630 (change assumption)
    Mortgage ($2,849) + Fees ($7) + Taxes in 2025 ($774)


    Taxes:$9,289

    Elementary School: Neptune Elementary

    High School: Gateway High School (9 12)

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 2661 ELLEN AVE, KISSIMMEE, FL 34744

    $450,0005 Days on yellowkey   MLS ID: O6399716

    For Sale O6399716 - 2661 ELLEN AVE, KISSIMMEE, FL 34744 25 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1864
       Built: 1972   Tax: $5,005 (2025)
    Community: Emerald Lake Colony Unit 3
    Single Family


    Estimated Monthly Payment: $2,883 (change assumption)
    Mortgage ($2,466) + Taxes in 2025 ($417)


    Taxes:$5,005

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1407 WATER LILLY LN, KISSIMMEE, FL 34744

    $980,000359 Days on yellowkey   MLS ID: S5125695

    For Sale S5125695 - 1407 WATER LILLY LN, KISSIMMEE, FL 34744 68 photos

    Bed: 5   Bath: 4.5   Gar: 3
    Liv Area Sq Ft: 3845
       Built: 2004
    Monthly Fee: $195
       Tax: $10,992 (2024)
    Community: Kissimmee Bay
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $6,481 (change assumption)
    Mortgage ($5,370) + Fees ($195) + Taxes in 2024 ($916)


    Taxes:$10,992

    Elementary School: None

    High School: None

    Tax Year: 2024

    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.