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Homes for Sale Near Osceola High School in Kissimmee - 66 homes

Osceola High School is an High School in Osceola County. Find homes for sale close to Osceola High School. Our REALTORS® can assist you in your search for Osceola High School, Kissimmee nearby homes.

Location: Kissimmee

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  • 2902 PERSHING ST, KISSIMMEE, FL 34741

    $167,000Listed 04/14/2026 12:32PM   MLS ID: S5147272

    For Sale S5147272 - 2902 PERSHING ST, KISSIMMEE, FL 34741 6 photos

    Bed: 3   Bath: 1.0   Gar: 1
    Liv Area Sq Ft: 882
       Built: 1958   Tax: $2,476 (2025)
    Community: Gilbert Park
    Single Family


    Estimated Monthly Payment: $1,121 (change assumption)
    Mortgage ($915) + Taxes in 2025 ($206)


    Taxes:$2,476

    Elementary School: Pleasant Hill Elem

    High School: Osceola High School

    Tax Year: 2025

    Middle School: Kissimmee Middle


  • 2979 WHITE CEDAR CIR, KISSIMMEE, FL 34741

    $410,0004 Days on yellowkey   MLS ID: O6397695

    For Sale O6397695 - 2979 WHITE CEDAR CIR, KISSIMMEE, FL 34741 38 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1942
       Built: 2004
    Monthly Fee: $80
       Tax: $4,235 (2025)
    Community: Windsor Point Ph 2
    Single Family


    Estimated Monthly Payment: $2,679 (change assumption)
    Mortgage ($2,247) + Fees ($80) + Taxes in 2025 ($353)


    Taxes:$4,235

    Elementary School: Floral Ridge Elementary

    High School: Osceola High School

    Tax Year: 2025

    Middle School: Kissimmee Middle


  • 2365 RAPOLLO DR, KISSIMMEE, FL 34741

    $514,90020 Days on yellowkey   MLS ID: O6379468

    REDUCED by $15,000 (2.8%) on 04/14/2026

    For Sale O6379468 - 2365 RAPOLLO DR, KISSIMMEE, FL 34741 46 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2391
       Built: 2018
    Monthly Fee: $167
       Tax: $8,804 (2025)
    Community: Tapestry Ph 4
    Single Family


    Estimated Monthly Payment: $3,722 (change assumption)
    Mortgage ($2,821) + Fees ($167) + Taxes in 2025 ($734)


    Taxes:$8,804

    Elementary School: Floral Ridge Elementary

    High School: Osceola High School

    Tax Year: 2025

    Middle School: Kissimmee Middle


  • 2879 OCONNELL DR, KISSIMMEE, FL 34741

    $435,00032 Days on yellowkey   MLS ID: O6390445

    For Sale O6390445 - 2879 OCONNELL DR, KISSIMMEE, FL 34741 34 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2245
       Built: 2005
    Monthly Fee: $100
       Tax: $2,760 (2025)
    Community: Cypress Reserve
    Single Family


    Estimated Monthly Payment: $2,714 (change assumption)
    Mortgage ($2,384) + Fees ($100) + Taxes in 2025 ($230)


    Taxes:$2,760

    Elementary School: Floral Ridge Elementary

    High School: Osceola High School

    Tax Year: 2025

    Middle School: Kissimmee Middle


  • 1870 KING EDWARD DR, KISSIMMEE, FL 34744

    $599,90050 Days on yellowkey   MLS ID: O6384598

    1 Days Off yellowkey (back on 3/8/2026)

    For Sale O6384598 - 1870 KING EDWARD DR, KISSIMMEE, FL 34744 38 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2760
       Built: 1988   Tax: $3,177 (2025)
    Community: Kings Point
    Single Family


    Estimated Monthly Payment: $3,552 (change assumption)
    Mortgage ($3,287) + Taxes in 2025 ($265)


    Taxes:$3,177

    Elementary School: Partin Settlement Elem

    High School: Osceola High School

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 2513 HIGHLAND AVE, KISSIMMEE, FL 34741

    $300,0004 Days on yellowkey   MLS ID: O6397907

    For Sale O6397907 - 2513 HIGHLAND AVE, KISSIMMEE, FL 34741 45 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1450
       Built: 1959   Tax: $3,615 (2025)
    Community: Kissimmee Highlands 1St Add
    Single Family


    Estimated Monthly Payment: $1,945 (change assumption)
    Mortgage ($1,644) + Taxes in 2025 ($301)


    Taxes:$3,615

    Elementary School: Highlands Elem

    High School: Osceola High School

    Tax Year: 2025

    Middle School: Denn John Middle


  • 1714 CHERYL LN, KISSIMMEE, FL 34744

    $749,00011 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)


  • 3051 GREYSTONE LOOP #106, KISSIMMEE, FL 34741

    $255,90091 Days on yellowkey   MLS ID: O6372010

    For Sale O6372010 - 3051 GREYSTONE LOOP #106, KISSIMMEE, FL 34741 39 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1433
       Built: 2006   Tax: $4,222 (2025)
    Community: Flora Ridge Condo Ph 2 Bldg 5
    Condo


    Estimated Monthly Payment: $1,754 (change assumption)
    Mortgage ($1,402) + Taxes in 2025 ($352)


    Taxes:$4,222

    Elementary School: Floral Ridge Elementary

    High School: Osceola High School

    Tax Year: 2025

    Middle School: Kissimmee Middle


  • 405 FOUNTAINHEAD CIR #246, KISSIMMEE, FL 34741

    $200,00021 Days on yellowkey   MLS ID: O6393382

    For Sale O6393382 - 405 FOUNTAINHEAD CIR #246, KISSIMMEE, FL 34741 23 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1246
       Built: 1988
    Monthly Fee: $437
       Tax: $2,760 (2024)
    Community: Bella Vista Condo
    Condo


    Estimated Monthly Payment: $1,763 (change assumption)
    Mortgage ($1,096) + Fees ($437) + Taxes in 2024 ($230)


    Taxes:$2,760

    Elementary School: Central Avenue Elem

    High School: Osceola High School

    Tax Year: 2024

    Middle School: Denn John Middle


  • 409 FOUNTAINHEAD CIR #236, KISSIMMEE, FL 34741

    $165,000124 Days on yellowkey   MLS ID: O6366787

    For Sale O6366787 - 409 FOUNTAINHEAD CIR #236, KISSIMMEE, FL 34741 23 photos

    Bed: 2   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 932
       Built: 1988
    Monthly Fee: $324
       Tax: $2,127 (2024)
    Community: Bella Vista Condo
    Condo


    Estimated Monthly Payment: $1,405 (change assumption)
    Mortgage ($904) + Fees ($324) + Taxes in 2024 ($177)


    Taxes:$2,127

    Elementary School: Central Avenue Elem

    High School: Osceola High School

    Tax Year: 2024

    Middle School: Denn John Middle


  • 658 HUDSON ST, KISSIMMEE, FL 34741

    $279,000187 Days on yellowkey   MLS ID: S5136343

    For Sale S5136343 - 658 HUDSON ST, KISSIMMEE, FL 34741 2 photos

    Bed: 3   Bath: 1.0
    Liv Area Sq Ft: 1176
       Built: 1948   Tax: $1,231 (2024)
    Community: Eureka
    Single Family


    Estimated Monthly Payment: $1,631 (change assumption)
    Mortgage ($1,529) + Taxes in 2024 ($103)


    Taxes:$1,231

    Elementary School: Kissimmee Elem

    High School: Osceola High School

    Tax Year: 2024

    Middle School: Kissimmee Middle


  • 1947 ESTANCIA CIR #8C, KISSIMMEE, FL 34741

    $275,00068 Days on yellowkey   MLS ID: O6379378

    For Sale O6379378 - 1947 ESTANCIA CIR #8C, KISSIMMEE, FL 34741 18 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1705
       Built: 2006
    Monthly Fee: $305
       Tax: $3,036 (2025)
    Community: Villas At Estancia
    Condo


    Estimated Monthly Payment: $2,065 (change assumption)
    Mortgage ($1,507) + Fees ($305) + Taxes in 2025 ($253)


    Taxes:$3,036

    Elementary School: Thacker Avenue Elem (K 5)

    High School: Osceola High School

    Tax Year: 2025

    Middle School: Denn John Middle


  • 3246 RIVER BRANCH CIR #0, KISSIMMEE, FL 34741

    $319,99981 Days on yellowkey   MLS ID: R4910599

    INCREASED by $99 (0.0%) on 04/13/2026

    For Sale R4910599 - 3246 RIVER BRANCH CIR #0, KISSIMMEE, FL 34741 31 photos

    Bed: 2   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1542
       Built: 2000
    Monthly Fee: $342
       Tax: $1,877 (2025)
    Community: Sterling Park At Stonefield
    Townhouse


    Estimated Monthly Payment: $2,252 (change assumption)
    Mortgage ($1,753) + Fees ($342) + Taxes in 2025 ($156)


    Taxes:$1,877

    Elementary School: Central Avenue Elem

    High School: Osceola High School

    Tax Year: 2025

    Middle School: Kissimmee Middle


  • 1030 VAQUERO LN, KISSIMMEE, FL 34741

    $365,00059 Days on yellowkey   MLS ID: S5143900

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

    For Sale S5143900 - 1030 VAQUERO LN, KISSIMMEE, FL 34741 43 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1720
       Built: 2004
    Monthly Fee: $83
       Tax: $1,672 (2025)
    Community: Estancia
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,222 (change assumption)
    Mortgage ($2,000) + Fees ($83) + Taxes in 2025 ($139)


    Taxes:$1,672

    Elementary School: Thacker Avenue Elem (K 5)

    High School: Osceola High School

    Tax Year: 2025

    Middle School: Denn John Middle


  • 877 HACIENDA CIR, KISSIMMEE, FL 34741

    $365,0002 Days on yellowkey   MLS ID: S5147690

    For Sale S5147690 - 877 HACIENDA CIR, KISSIMMEE, FL 34741 6 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1955
       Built: 2005
    Monthly Fee: $76
       Tax: $5,410 (2025)
    Community: Estancia
    Single Family


    Estimated Monthly Payment: $2,527 (change assumption)
    Mortgage ($2,000) + Fees ($76) + Taxes in 2025 ($451)


    Taxes:$5,410

    Elementary School: Thacker Avenue Elem (K 5)

    High School: Osceola High School

    Tax Year: 2025

    Middle School: Denn John Middle


  • 2123 ST MARTEEN CT, KISSIMMEE, FL 34741

    $205,00038 Days on yellowkey   MLS ID: O6387879

    For Sale O6387879 - 2123 ST MARTEEN CT, KISSIMMEE, FL 34741 15 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 991
       Built: 1989
    Monthly Fee: $278
       Tax: $312 (2025)
    Community: Caribbean Villas Condo Ph A-F
    Villa


    Estimated Monthly Payment: $1,427 (change assumption)
    Mortgage ($1,123) + Fees ($278) + Taxes in 2025 ($26)


    Taxes:$312

    Elementary School: Kissimmee Elem

    High School: Osceola High School

    Tax Year: 2025

    Middle School: Narcoossee Middle


  • 1135 CHEROKEE DR, KISSIMMEE, FL 34744

    $375,99043 Days on yellowkey   MLS ID: S5144943

    For Sale S5144943 - 1135 CHEROKEE DR, KISSIMMEE, FL 34744 12 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1358
       Built: 1964   Tax: $1,014 (2025)
    Community: Osceola Acres
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,145 (change assumption)
    Mortgage ($2,060) + Taxes in 2025 ($85)


    Taxes:$1,014

    Elementary School: Mill Creek Elem (K 5)

    High School: Osceola High School

    Tax Year: 2025

    Middle School: Denn John Middle


  • 7 WESTCHESTER DR, KISSIMMEE, FL 34744

    $439,000331 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)


  • 1495 SKYLINE DR, KISSIMMEE, FL 34744

    $524,90039 Days on yellowkey   MLS ID: S5145209

    For Sale S5145209 - 1495 SKYLINE DR, KISSIMMEE, FL 34744 50 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2094
       Built: 1973
    Monthly Fee: $16
       Tax: $5,404 (2025)
    Community: Harbour Oaks Unit 1
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,342 (change assumption)
    Mortgage ($2,876) + Fees ($16) + Taxes in 2025 ($450)


    Taxes:$5,404

    Elementary School: Partin Settlement Elem

    High School: Osceola High School

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 2260 SAN VITAL DR #108, KISSIMMEE, FL 34741

    $240,00021 Days on yellowkey   MLS ID: O6393472

    1 Days Off yellowkey (back on 4/8/2026)

    For Sale O6393472 - 2260 SAN VITAL DR #108, KISSIMMEE, FL 34741 24 photos

    Bed: 4   Bath: 3.0
    Liv Area Sq Ft: 1470
       Built: 2006
    Monthly Fee: $517
       Tax: $3,014 (2025)
    Community: Venetian Bay Village Condo Ph 3
    Condo


    Estimated Monthly Payment: $2,083 (change assumption)
    Mortgage ($1,315) + Fees ($517) + Taxes in 2025 ($251)


    Taxes:$3,014

    Elementary School: Kissimmee Elem

    High School: Osceola High School

    Tax Year: 2025

    Middle School: Kissimmee Middle




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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.