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Homes for Sale Near Osceola High School in Kissimmee - 38 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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  • 1135 CHEROKEE DR, KISSIMMEE, FL 34744

    $375,99031 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
    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


  • 2424 VARENNA LOOP, KISSIMMEE, FL 34741

    $675,00053 Days on yellowkey   MLS ID: O6380818

    For Sale O6380818 - 2424 VARENNA LOOP, KISSIMMEE, FL 34741 42 photos

    Bed: 3   Bath: 2.5   Gar: 3
    Liv Area Sq Ft: 2351
       Built: 2020
    Monthly Fee: $208
       Tax: $7,544 (2024)
    Community: Tapestry Ph 5
    Single Family


    Estimated Monthly Payment: $4,535 (change assumption)
    Mortgage ($3,699) + Fees ($208) + Taxes in 2024 ($629)


    Taxes:$7,544

    Elementary School: Floral Ridge Elementary

    High School: Osceola High School

    Tax Year: 2024

    Middle School: Kissimmee Middle


  • 3154 STONEHURST CIR, KISSIMMEE, FL 34741

    $405,00024 Days on yellowkey   MLS ID: S5143536

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

    For Sale S5143536 - 3154 STONEHURST CIR, KISSIMMEE, FL 34741 28 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1650
       Built: 2002
    Monthly Fee: $223
       Tax: $6,272 (2025)
    Community: Stonehurst At Stonefield
    Single Family


    Estimated Monthly Payment: $2,965 (change assumption)
    Mortgage ($2,219) + Fees ($223) + Taxes in 2025 ($523)


    Taxes:$6,272

    Elementary School: Floral Ridge Elementary

    High School: Osceola High School

    Tax Year: 2025

    Middle School: Kissimmee Middle


  • 2365 RAPOLLO DR, KISSIMMEE, FL 34741

    $529,9008 Days on yellowkey   MLS ID: O6379468

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

    Bed: 4   Bath: 2.5   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: $3,804 (change assumption)
    Mortgage ($2,903) + 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


  • 2213 GRAND CAYMAN CT #1135, KISSIMMEE, FL 34741

    $210,000Listed 04/01/2026 6:54PM   MLS ID: O6395435

    For Sale O6395435 - 2213 GRAND CAYMAN CT #1135, KISSIMMEE, FL 34741 33 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1026
       Built: 1999
    Monthly Fee: $375
       Tax: $3,113 (2025)
    Community: Villas Del Sol At Kissimmee Condo
    Condo


    Estimated Monthly Payment: $1,785 (change assumption)
    Mortgage ($1,151) + Fees ($375) + Taxes in 2025 ($259)


    Taxes:$3,113

    Elementary School: Kissimmee Elem

    High School: Osceola High School

    Tax Year: 2025

    Middle School: Kissimmee Middle


  • 2591 SWOOP CIR, KISSIMMEE, FL 34741

    $649,98046 Days on yellowkey   MLS ID: O6382854

    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
    Single Family


    Estimated Monthly Payment: $4,507 (change assumption)
    Mortgage ($3,561) + 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


  • 627 WOODLAND CREEK BLVD, KISSIMMEE, FL 34744

    $469,90014 Days on yellowkey   MLS ID: O6392189

    For Sale O6392189 - 627 WOODLAND CREEK BLVD, KISSIMMEE, FL 34744 47 photos

    Bed: 4   Bath: 2.5   Gar: 3
    Liv Area Sq Ft: 2846
       Built: 2005
    Monthly Fee: $41
       Tax: $3,538 (2025)
    Community: Woodland Creek
    Single Family


    Estimated Monthly Payment: $2,911 (change assumption)
    Mortgage ($2,575) + Fees ($41) + Taxes in 2025 ($295)


    Taxes:$3,538

    Elementary School: Mill Creek Elem (K 5)

    High School: Osceola High School

    Tax Year: 2025

    Middle School: Denn John Middle


  • 2908 LANGDON LN S, KISSIMMEE, FL 34741

    $304,00029 Days on yellowkey   MLS ID: O6381377

    For Sale O6381377 - 2908 LANGDON LN S, KISSIMMEE, FL 34741 31 photos

    Bed: 3   Bath: 2.5   Gar: 1
    Liv Area Sq Ft: 1749
       Built: 2006
    Monthly Fee: $240
       Tax: $5,064 (2025)
    Community: Townhomes Of Flora Ridge Ph 2
    Townhouse


    Estimated Monthly Payment: $2,328 (change assumption)
    Mortgage ($1,666) + Fees ($240) + Taxes in 2025 ($422)


    Taxes:$5,064

    Elementary School: Floral Ridge Elementary

    High School: Osceola High School

    Tax Year: 2025

    Middle School: Kissimmee Middle


  • 1115 PROSPERITY AVE, KISSIMMEE, FL 34744

    $499,00013 Days on yellowkey   MLS ID: S5146235

    For Sale S5146235 - 1115 PROSPERITY AVE, KISSIMMEE, FL 34744 32 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2085
       Built: 2003
    Monthly Fee: $90
       Tax: $2,454 (2025)
    Community: Fortune Lakes
    Single Family


    Estimated Monthly Payment: $3,029 (change assumption)
    Mortgage ($2,734) + Fees ($90) + Taxes in 2025 ($205)


    Taxes:$2,454

    Elementary School: Mill Creek Elem (K 5)

    High School: Osceola High School

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 903 N FORREST AVE, KISSIMMEE, FL 34741

    $250,000122 Days on yellowkey   MLS ID: S5139279

    3 Days Off yellowkey (back on 2/9/2026)

    For Sale S5139279 - 903 N FORREST AVE, KISSIMMEE, FL 34741 33 photos

    Bed: 2   Bath: 1.0
    Liv Area Sq Ft: 1104
       Built: 1952   Tax: $622 (2025)
    Community: Magnolia Park
    Single Family


    Estimated Monthly Payment: $1,422 (change assumption)
    Mortgage ($1,370) + Taxes in 2025 ($52)


    Taxes:$622

    Elementary School: Thacker Avenue Elem (K 5)

    High School: Osceola High School

    Tax Year: 2025

    Middle School: Kissimmee Middle


  • 279 MAGICAL WAY, KISSIMMEE, FL 34744

    $399,800217 Days on yellowkey   MLS ID: S5133398

    For Sale S5133398 - 279 MAGICAL WAY, KISSIMMEE, FL 34744 51 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 1797
       Built: 2007
    Monthly Fee: $63
       Tax: $5,000 (2025)
    Community: Magic Landings Ph 2
    Single Family


    Estimated Monthly Payment: $2,670 (change assumption)
    Mortgage ($2,191) + Fees ($63) + Taxes in 2025 ($417)


    Taxes:$5,000

    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

    $439,000319 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)


  • 3249 FALCON POINT DR, KISSIMMEE, FL 34741

    $458,00063 Days on yellowkey   MLS ID: O6376917

    For Sale O6376917 - 3249 FALCON POINT DR, KISSIMMEE, FL 34741 54 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2059
       Built: 1999
    Monthly Fee: $58
       Tax: $6,864 (2025)
    Community: Herons Landing Ph 03
    Single Family


    Estimated Monthly Payment: $3,140 (change assumption)
    Mortgage ($2,510) + Fees ($58) + Taxes in 2025 ($572)


    Taxes:$6,864

    Elementary School: Central Avenue Elem

    High School: Osceola High School

    Tax Year: 2025

    Middle School: Kissimmee Middle


  • 1212 SHAWNEE DR, KISSIMMEE, FL 34744

    $400,000180 Days on yellowkey   MLS ID: S5135868

    For Sale S5135868 - 1212 SHAWNEE DR, KISSIMMEE, FL 34744 29 photos

    Bed: 4   Bath: 2.0
    Liv Area Sq Ft: 1848
       Built: 1964   Tax: $2,097 (2024)
    Community: Osceola Acres
    Single Family


    Estimated Monthly Payment: $2,367 (change assumption)
    Mortgage ($2,192) + Taxes in 2024 ($175)


    Taxes:$2,097

    Elementary School: Mill Creek Elem (K 5)

    High School: Osceola High School

    Tax Year: 2024

    Middle School: Denn John Middle


  • 302 E DRURY AVE, KISSIMMEE, FL 34744

    $399,000188 Days on yellowkey   MLS ID: S5135477

    For Sale S5135477 - 302 E DRURY AVE, KISSIMMEE, FL 34744 67 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1528
       Built: 1950   Tax: $540 (2024)
    Community: Cape Breeze
    Single Family


    Estimated Monthly Payment: $2,231 (change assumption)
    Mortgage ($2,186) + Taxes in 2024 ($45)


    Taxes:$540

    Elementary School: Central Avenue Elem

    High School: Osceola High School

    Tax Year: 2024

    Middle School: Denn John Middle


  • 2598 TRIELLE AVE, KISSIMMEE, FL 34741

    $490,000120 Days on yellowkey   MLS ID: S5139043

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

    For Sale S5139043 - 2598 TRIELLE AVE, KISSIMMEE, FL 34741 37 photos

    Bed: 4   Bath: 3.0
    Liv Area Sq Ft: 2282
       Built: 2021
    Monthly Fee: $208
       Tax: $6,776 (2025)
    Community: Tapestry Ph 5
    Single Family


    Estimated Monthly Payment: $3,457 (change assumption)
    Mortgage ($2,685) + Fees ($208) + Taxes in 2025 ($565)


    Taxes:$6,776

    Elementary School: Floral Ridge Elementary

    High School: Osceola High School

    Tax Year: 2025

    Middle School: Kissimmee Middle


  • 3000 LAUREL PARK #305, KISSIMMEE, FL 34741

    $250,00035 Days on yellowkey   MLS ID: O6385722

    For Sale O6385722 - 3000 LAUREL PARK #305, KISSIMMEE, FL 34741 69 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1433
       Built: 2006   Tax: $4,276 (2025)
    Community: Flora Ridge Condominiums
    Condo


    Estimated Monthly Payment: $1,726 (change assumption)
    Mortgage ($1,370) + Taxes in 2025 ($356)


    Taxes:$4,276

    Elementary School: Floral Ridge Elementary

    High School: Osceola High School

    Tax Year: 2025

    Middle School: Kissimmee Middle


  • 2621 PALISADE BLVD, KISSIMMEE, FL 34741

    $465,000123 Days on yellowkey   MLS ID: O6363542

    For Sale O6363542 - 2621 PALISADE BLVD, KISSIMMEE, FL 34741 41 photos

    Bed: 3   Bath: 2.5
    Liv Area Sq Ft: 2120
       Built: 2017
    Monthly Fee: $170
       Tax: $4,588 (2024)
    Community: Tapestry Ph 2
    Single Family


    Estimated Monthly Payment: $3,100 (change assumption)
    Mortgage ($2,548) + Fees ($170) + Taxes in 2024 ($382)


    Taxes:$4,588

    Elementary School: Floral Ridge Elementary

    High School: Osceola High School

    Tax Year: 2024

    Middle School: Kissimmee Middle


  • 2615 CECILE ST, KISSIMMEE, FL 34741

    $369,00076 Days on yellowkey   MLS ID: S5141774

    For Sale S5141774 - 2615 CECILE ST, KISSIMMEE, FL 34741 30 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1532
       Built: 1972   Tax: $3,048 (2025)
    Community: Orange Gardens Sec 4
    Single Family


    Estimated Monthly Payment: $2,276 (change assumption)
    Mortgage ($2,022) + Taxes in 2025 ($254)


    Taxes:$3,048

    Elementary School: Thacker Avenue Elem (K 5)

    High School: Osceola High School

    Tax Year: 2025

    Middle School: Kissimmee Middle


  • 3463 FOREST RIDGE LN, KISSIMMEE, FL 34741

    $629,90069 Days on yellowkey   MLS ID: O6376287

    REDUCED by $20,000 (3.1%) on 03/31/2026

    For Sale O6376287 - 3463 FOREST RIDGE LN, KISSIMMEE, FL 34741 58 photos

    Bed: 4   Bath: 3.5
    Liv Area Sq Ft: 3807
       Built: 2003
    Monthly Fee: $80
       Tax: $8,939 (2025)
    Community: Crestwood Ph 2
    Single Family


    Estimated Monthly Payment: $4,276 (change assumption)
    Mortgage ($3,451) + Fees ($80) + Taxes in 2025 ($745)


    Taxes:$8,939

    Elementary School: Floral Ridge Elementary

    High School: Osceola High School

    Tax Year: 2025

    Middle School: Kissimmee Middle


12


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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.