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Homes for Sale Near Osceola High School in Kissimmee - 144 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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  • 4960 WINDERMERE AVE, KISSIMMEE, FL 34746

    $445,000135 Days on yellowkey   MLS ID: O6379770

    4 Days Off yellowkey (back on 6/1/2026)

    For Sale O6379770 - 4960 WINDERMERE AVE, KISSIMMEE, FL 34746 31 photos

    Bed: 4   Bath: 3.0
    Liv Area Sq Ft: 1914
       Built: 2018
    Monthly Fee: $286
       Tax: $7,794 (2025)
    Community: Storey Lake
    Townhouse


    Estimated Monthly Payment: $3,374 (change assumption)
    Mortgage ($2,438) + Fees ($286) + Taxes in 2025 ($649)


    Taxes:$7,794

    Elementary School: Floral Ridge Elementary

    High School: Osceola High School

    Tax Year: 2025

    Middle School: Kissimmee Middle


  • 2591 SWOOP CIR, KISSIMMEE, FL 34741

    $639,990126 Days on yellowkey   MLS ID: O6382854

    2 Days Off yellowkey (back on 5/31/2026)

    REDUCED by $9,990 (1.5%) on 05/03/2026

    For Sale O6382854 - 2591 SWOOP CIR, KISSIMMEE, FL 34741 59 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2368
       Built: 2010
    Monthly Fee: $215
       Tax: $8,767 (2024)
    Community: Avilla
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $4,452 (change assumption)
    Mortgage ($3,507) + Fees ($215) + Taxes in 2024 ($731)


    Taxes:$8,767

    Elementary School: Floral Ridge Elementary

    High School: Osceola High School

    Tax Year: 2024

    Middle School: Kissimmee Middle


  • 3400 MT VERNON WAY, KISSIMMEE, FL 34741

    $435,000396 Days on yellowkey   MLS ID: S5127303

    3 Days Off yellowkey (back on 5/31/2026)

    For Sale S5127303 - 3400 MT VERNON WAY, KISSIMMEE, FL 34741 38 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1964
       Built: 2014
    Monthly Fee: $90
       Tax: $4,426 (2024)
    Community: Preserve At Tapestry Ph 1
    Single Family


    Estimated Monthly Payment: $2,842 (change assumption)
    Mortgage ($2,384) + Fees ($90) + Taxes in 2024 ($369)


    Taxes:$4,426

    Elementary School: Floral Ridge Elementary

    High School: Osceola High School

    Tax Year: 2024

    Middle School: Kissimmee Middle


  • 2683 AMATI DR, KISSIMMEE, FL 34741

    $674,90022 Days on yellowkey   MLS ID: O6410751

    For Sale O6410751 - 2683 AMATI DR, KISSIMMEE, FL 34741 35 photos

    Bed: 5   Bath: 4.0   Gar: 3
    Liv Area Sq Ft: 3105
       Built: 2016
    Monthly Fee: $173
       Tax: $8,359 (2024)
    Community: Tapestry
    Single Family


    Estimated Monthly Payment: $4,568 (change assumption)
    Mortgage ($3,698) + Fees ($173) + Taxes in 2024 ($697)


    Taxes:$8,359

    Elementary School: Floral Ridge Elementary

    High School: Osceola High School

    Tax Year: 2024

    Middle School: Kissimmee Middle


  • 6 VIOLA ST, KISSIMMEE, FL 34741

    $300,00033 Days on yellowkey   MLS ID: O6409235

    REDUCED by $40,000 (11.8%) on 05/25/2026

    For Sale O6409235 - 6 VIOLA ST, KISSIMMEE, FL 34741 29 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1495
       Built: 1971   Tax: $3,899 (2025)
    Community: W Rush
    Single Family


    Estimated Monthly Payment: $1,969 (change assumption)
    Mortgage ($1,644) + Taxes in 2025 ($325)


    Taxes:$3,899

    Elementary School: Thacker Avenue Elem (K 5)

    High School: Osceola High School

    Tax Year: 2025

    Middle School: Kissimmee Middle


  • 445 FOUNTAINHEAD CIR #257, KISSIMMEE, FL 34741

    $169,70045 Days on yellowkey   MLS ID: S5149211

    For Sale S5149211 - 445 FOUNTAINHEAD CIR #257, KISSIMMEE, FL 34741 23 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 932
       Built: 1988   Tax: $1,174 (2025)
    Community: Bella Vista A Condo
    Spa: No

    Condo


    Estimated Monthly Payment: $1,028 (change assumption)
    Mortgage ($930) + Taxes in 2025 ($98)


    Taxes:$1,174

    Elementary School: Central Avenue Elem

    High School: Osceola High School

    Tax Year: 2025

    Middle School: Denn John Middle


  • 2208 SAN VITTORINO CIR #107, KISSIMMEE, FL 34741

    $280,000266 Days on yellowkey   MLS ID: O6347920

    For Sale O6347920 - 2208 SAN VITTORINO CIR #107, KISSIMMEE, FL 34741 41 photos

    Bed: 4   Bath: 3.0
    Liv Area Sq Ft: 1470
       Built: 2004
    Monthly Fee: $496
       Tax: $3,726 (2024)
    Community: Venetian Bay Village Condo Ph 2
    Townhouse


    Estimated Monthly Payment: $2,341 (change assumption)
    Mortgage ($1,534) + Fees ($496) + Taxes in 2024 ($311)


    Taxes:$3,726

    Elementary School: Kissimmee Elem

    High School: Osceola High School

    Tax Year: 2024

    Middle School: Kissimmee Middle


  • 2219 CARIBBEAN DR S #27, KISSIMMEE, FL 34741

    $160,00055 Days on yellowkey   MLS ID: S5148755

    REDUCED by $15,000 (8.6%) on 05/29/2026

    For Sale S5148755 - 2219 CARIBBEAN DR S #27, KISSIMMEE, FL 34741 8 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 991
       Built: 1984   Tax: $2,501 (2025)
    Community: Caribbean Villas Condo Phs A-F
    Condo


    Estimated Monthly Payment: $1,085 (change assumption)
    Mortgage ($877) + Taxes in 2025 ($208)


    Taxes:$2,501

    Elementary School: None

    High School: Osceola High School

    Tax Year: 2025

    Middle School: Kissimmee Middle


  • 1601 COLUMBIA ARMS CIR #201, KISSIMMEE, FL 34741

    $195,00039 Days on yellowkey   MLS ID: O6407642

    REDUCED by $5,000 (2.5%) on 05/29/2026

    For Sale O6407642 - 1601 COLUMBIA ARMS CIR #201, KISSIMMEE, FL 34741 19 photos

    Bed: 2   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1098
       Built: 1994
    Monthly Fee: $378
       Tax: $755 (2025)
    Community: Columbia Arms Condo
    Condo


    Estimated Monthly Payment: $1,509 (change assumption)
    Mortgage ($1,068) + Fees ($378) + Taxes in 2025 ($63)


    Taxes:$755

    Elementary School: Central Avenue Elem

    High School: Osceola High School

    Tax Year: 2025

    Middle School: Denn John Middle


  • 2921 CELLO LN, KISSIMMEE, FL 34741

    $335,00024 Days on yellowkey   MLS ID: O6411611

    For Sale O6411611 - 2921 CELLO LN, KISSIMMEE, FL 34741 21 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1528
       Built: 2016
    Monthly Fee: $289
       Tax: $7,015 (2025)
    Community: Tapestry
    Townhouse


    Estimated Monthly Payment: $2,709 (change assumption)
    Mortgage ($1,836) + Fees ($289) + Taxes in 2025 ($585)


    Taxes:$7,015

    Elementary School: Floral Ridge Elementary

    High School: Osceola High School

    Tax Year: 2025

    Middle School: Kissimmee Middle


  • 2456 TEMPLE GROVE LANE, KISSIMMEE, FL 34741

    $298,90025 Days on yellowkey   MLS ID: S5150646

    For Sale S5150646 - 2456 TEMPLE GROVE LANE, KISSIMMEE, FL 34741 35 photos

    Bed: 3   Bath: 2.5   Gar: 3
    Liv Area Sq Ft: 1384
       Built: 2006
    Monthly Fee: $147
       Tax: $2,765 (2025)
    Community: Donegan Twnhms
    Townhouse


    Estimated Monthly Payment: $2,015 (change assumption)
    Mortgage ($1,638) + Fees ($147) + Taxes in 2025 ($230)


    Taxes:$2,765

    Elementary School: Highlands Elem

    High School: Osceola High School

    Tax Year: 2025

    Middle School: Kissimmee Middle


  • 2573 FOLIO WAY, KISSIMMEE, FL 34741

    $349,00025 Days on yellowkey   MLS ID: O6401958

    For Sale O6401958 - 2573 FOLIO WAY, KISSIMMEE, FL 34741 81 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1603
       Built: 2017
    Monthly Fee: $289
       Tax: $5,767 (2025)
    Community: Tapestry
    Townhouse


    Estimated Monthly Payment: $2,682 (change assumption)
    Mortgage ($1,912) + Fees ($289) + Taxes in 2025 ($481)


    Taxes:$5,767

    Elementary School: Kissimmee Elem

    High School: Osceola High School

    Tax Year: 2025

    Middle School: Kissimmee Middle


  • 2331 PEPPERCORN ST, KISSIMMEE, FL 34741

    $419,90030 Days on yellowkey   MLS ID: L4962084

    2 Days Off yellowkey (back on 5/27/2026)

    For Sale L4962084 - 2331 PEPPERCORN ST, KISSIMMEE, FL 34741 51 photos

    Bed: 3   Bath: 2.0   Gar: 3
    Liv Area Sq Ft: 1769
       Built: 1987
    Monthly Fee: $25
       Tax: $1,475 (2025)
    Community: Shadow Bay Unit 4
    Single Family


    Estimated Monthly Payment: $2,449 (change assumption)
    Mortgage ($2,301) + Fees ($25) + Taxes in 2025 ($123)


    Taxes:$1,475

    Elementary School: Kissimmee Elem

    High School: Osceola High School

    Tax Year: 2025

    Middle School: Kissimmee Middle


  • 750 PARK LN, KISSIMMEE, FL 34741

    $269,00093 Days on yellowkey   MLS ID: S5146239

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

    REDUCED by $6,000 (2.2%) on 05/12/2026

    For Sale S5146239 - 750 PARK LN, KISSIMMEE, FL 34741 4 photos

    Bed: 2   Bath: 1.0
    Liv Area Sq Ft: 1064
       Built: 1967   Tax: $837 (2025)
    Community: Tropical Park Unit 1
    Single Family


    Estimated Monthly Payment: $1,544 (change assumption)
    Mortgage ($1,474) + Taxes in 2025 ($70)


    Taxes:$837

    Elementary School: Highlands Elem

    High School: Osceola High School

    Tax Year: 2025

    Middle School: Denn John Middle


  • 918 BRACK ST, KISSIMMEE, FL 34744

    $230,00030 Days on yellowkey   MLS ID: S5150267

    1 Days Off yellowkey (back on 5/26/2026)

    For Sale S5150267 - 918 BRACK ST, KISSIMMEE, FL 34744 16 photos

    Bed: 2   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1008
       Built: 1981   Tax: $380 (2025)
    Community: R Bass
    Single Family


    Estimated Monthly Payment: $1,292 (change assumption)
    Mortgage ($1,260) + Taxes in 2025 ($32)


    Taxes:$380

    Elementary School: Central Avenue Elem

    High School: Osceola High School

    Tax Year: 2025

    Middle School: Denn John Middle


  • 9021 FLAMINGO KEY WAY, KISSIMMEE, FL 34747

    $510,000314 Days on yellowkey   MLS ID: O6334076

    For Sale O6334076 - 9021 FLAMINGO KEY WAY, KISSIMMEE, FL 34747 41 photos

    Bed: 4   Bath: 3.5   Gar: 1
    Liv Area Sq Ft: 2478
       Built: 2019
    Monthly Fee: $719
       Tax: $6,243 (2024)
    Community: Solara Resort
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $4,034 (change assumption)
    Mortgage ($2,794) + Fees ($719) + Taxes in 2024 ($520)


    Taxes:$6,243

    Elementary School: Westside K-8

    High School: Osceola High School

    Tax Year: 2024

    Middle School: West Side


  • 2208 ANTIGUA PL #938, KISSIMMEE, FL 34741

    $189,90041 Days on yellowkey   MLS ID: O6405626

    For Sale O6405626 - 2208 ANTIGUA PL #938, KISSIMMEE, FL 34741 28 photos

    Bed: 2   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1026
       Built: 1999   Tax: $3,339 (2025)
    Community: Villas Del Sol At Kissimmee Condo
    Condo


    Estimated Monthly Payment: $1,319 (change assumption)
    Mortgage ($1,041) + Taxes in 2025 ($278)


    Taxes:$3,339

    Elementary School: Kissimmee Elem

    High School: Osceola High School

    Tax Year: 2025

    Middle School: Kissimmee Middle


  • 2216 GRAND CAYMAN CT #1435, KISSIMMEE, FL 34741

    $194,90045 Days on yellowkey   MLS ID: O6405612

    For Sale O6405612 - 2216 GRAND CAYMAN CT #1435, KISSIMMEE, FL 34741 29 photos

    Bed: 2   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1026
       Built: 1999   Tax: $3,339 (2025)
    Community: Villas Del Sol At Kissimmee Condo
    Condo


    Estimated Monthly Payment: $1,346 (change assumption)
    Mortgage ($1,068) + Taxes in 2025 ($278)


    Taxes:$3,339

    Elementary School: Kissimmee Elem

    High School: Osceola High School

    Tax Year: 2025

    Middle School: Kissimmee Middle


  • 2210 GRAND CAYMAN CT #1736, KISSIMMEE, FL 34741

    $194,90057 Days on yellowkey   MLS ID: O6402276

    0 Days Off yellowkey (back on 5/25/2026)

    For Sale O6402276 - 2210 GRAND CAYMAN CT #1736, KISSIMMEE, FL 34741 23 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1026
       Built: 1999   Tax: $3,339 (2025)
    Community: Villas Del Sol At Kissimmee Condo
    Condo


    Estimated Monthly Payment: $1,346 (change assumption)
    Mortgage ($1,068) + Taxes in 2025 ($278)


    Taxes:$3,339

    Elementary School: Kissimmee Elem

    High School: Osceola High School

    Tax Year: 2025

    Middle School: Kissimmee Middle


  • 2202 KEY WEST CT #633, KISSIMMEE, FL 34741

    $174,900436 Days on yellowkey   MLS ID: O6298878

    For Sale O6298878 - 2202 KEY WEST CT #633, KISSIMMEE, FL 34741 33 photos

    Bed: 2   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1026
       Built: 1999
    Monthly Fee: $348
       Tax: $3,201 (2024)
    Community: Villas Del Sol At Kissimmee Condo
    Condo


    Estimated Monthly Payment: $1,573 (change assumption)
    Mortgage ($958) + Fees ($348) + Taxes in 2024 ($267)


    Taxes:$3,201

    Elementary School: Kissimmee Elem

    High School: Osceola High School

    Tax Year: 2024

    Middle School: Kissimmee Middle




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Home, townhome, condo, villa, and other listing sales data closeby Osceola High School is continuously updated on yellowkeyrealty.com. yellowkeyrealty.com offers one of the most exhaustive, current, and relevant set of data you can find on homes for sale nearby Osceola High School, Kissimmee . You can use our website to view Multiple Listing Service (MLS) data on Kissimmee homes near Osceola High School. 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 listings that are close to Osceola High School.



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.