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Homes for Sale Near Osceola High School in Kissimmee - 153 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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  • 107 E CYPRESS ST, KISSIMMEE, FL 34744

    $169,90014 Days on yellowkey   MLS ID: S5149938

    For Sale S5149938 - 107 E CYPRESS ST, KISSIMMEE, FL 34744 19 photos

    Bed: 2   Bath: 1.0
    Liv Area Sq Ft: 576
       Built: 1966   Tax: $2,111 (2025)
    Community: Robert Bass Add
    Single Family


    Estimated Monthly Payment: $1,107 (change assumption)
    Mortgage ($931) + Taxes in 2025 ($176)


    Taxes:$2,111

    Elementary School: Central Avenue Elem

    High School: Osceola High School

    Tax Year: 2025

    Middle School: Denn John Middle


  • 1714 CHERYL LN, KISSIMMEE, FL 34744

    $699,90055 Days on yellowkey   MLS ID: O6395426

    REDUCED by $49,100 (6.6%) on 05/14/2026

    For Sale O6395426 - 1714 CHERYL LN, KISSIMMEE, FL 34744 31 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: $4,132 (change assumption)
    Mortgage ($3,835) + 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)


  • 2139 BALBOA WAY, KISSIMMEE, FL 34741

    $258,90078 Days on yellowkey   MLS ID: S5144054

    For Sale S5144054 - 2139 BALBOA WAY, KISSIMMEE, FL 34741 20 photos

    Bed: 2   Bath: 2.5   Gar: 1
    Liv Area Sq Ft: 1418
       Built: 1986
    Monthly Fee: $164
       Tax: $683 (2025)
    Community: Royale Bermuda Twnhs
    Townhouse


    Estimated Monthly Payment: $1,640 (change assumption)
    Mortgage ($1,419) + Fees ($164) + Taxes in 2025 ($57)


    Taxes:$683

    Elementary School: Central Avenue Elem

    High School: Osceola High School

    Tax Year: 2025

    Middle School: Denn John Middle


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

    $200,00015 Days on yellowkey   MLS ID: O6407642

    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: $1,537 (change assumption)
    Mortgage ($1,096) + 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


  • 406 S LATONIA ST, KISSIMMEE, FL 34741

    $345,00084 Days on yellowkey   MLS ID: O6387083

    REDUCED by $5,000 (1.4%) on 04/20/2026

    For Sale O6387083 - 406 S LATONIA ST, KISSIMMEE, FL 34741 26 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1592
       Built: 1995   Tax: $5,317 (2025)
    Community: Rosewood Unit 2
    Single Family


    Estimated Monthly Payment: $2,333 (change assumption)
    Mortgage ($1,890) + Taxes in 2025 ($443)


    Taxes:$5,317

    Elementary School: Thacker Avenue Elem (K 5)

    High School: Osceola High School

    Tax Year: 2025

    Middle School: Kissimmee Middle


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

    $175,00031 Days on yellowkey   MLS ID: S5148755

    REDUCED by $25,000 (12.5%) on 05/13/2026

    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: $1,167 (change assumption)
    Mortgage ($959) + Taxes in 2025 ($208)


    Taxes:$2,501

    Elementary School: None

    High School: Osceola High School

    Tax Year: 2025

    Middle School: Kissimmee Middle


  • 501 SUMNER ST, KISSIMMEE, FL 34741

    $789,00023 Days on yellowkey   MLS ID: S5149281

    REDUCED by $10,000 (1.3%) on 05/12/2026

    For Sale S5149281 - 501 SUMNER ST, KISSIMMEE, FL 34741 1 photos

    Bed: 5   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 3518
       Built: 1926   Tax: $5,741 (2025)
    Community: Oneal & Osborns Add
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,802 (change assumption)
    Mortgage ($4,323) + Taxes in 2025 ($478)


    Taxes:$5,741

    Elementary School: Central Avenue Elem

    High School: Osceola High School

    Tax Year: 2025

    Middle School: Denn John Middle


  • 902 N THACKER AVE, KISSIMMEE, FL 34741

    $329,99070 Days on yellowkey   MLS ID: O6392187

    For Sale O6392187 - 902 N THACKER AVE, KISSIMMEE, FL 34741 36 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1300
       Built: 1956   Tax: $4,636 (2025)
    Community: Orange Gardens
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,194 (change assumption)
    Mortgage ($1,808) + Taxes in 2025 ($386)


    Taxes:$4,636

    Elementary School: Thacker Avenue Elem (K 5)

    High School: Osceola High School

    Tax Year: 2025

    Middle School: Kissimmee Middle


  • 3005 SLOUGH CREEK DR, KISSIMMEE, FL 34744

    $530,00074 Days on yellowkey   MLS ID: O6388753

    REDUCED by $5,000 (0.9%) on 05/12/2026

    For Sale O6388753 - 3005 SLOUGH CREEK DR, KISSIMMEE, FL 34744 43 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2790
       Built: 2022
    Monthly Fee: $129
       Tax: $6,220 (2024)
    Community: Creekside At Boggy Creek Ph 3
    Single Family


    Estimated Monthly Payment: $3,551 (change assumption)
    Mortgage ($2,904) + Fees ($129) + Taxes in 2024 ($518)


    Taxes:$6,220

    Elementary School: East Lake Elem

    High School: Osceola High School

    Tax Year: 2024

    Middle School: Narcoossee Middle


  • 1905 MAGICAL LN, KISSIMMEE, FL 34744

    $390,00027 Days on yellowkey   MLS ID: O6403327

    1 Days Off yellowkey (back on 5/12/2026)

    For Sale O6403327 - 1905 MAGICAL LN, KISSIMMEE, FL 34744 34 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 1790
       Built: 2005
    Monthly Fee: $63
       Tax: $4,388 (2025)
    Community: Magic Landings Ph 2
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $2,566 (change assumption)
    Mortgage ($2,137) + Fees ($63) + Taxes in 2025 ($366)


    Taxes:$4,388

    Elementary School: Mill Creek Elem (K 5)

    High School: Osceola High School

    Tax Year: 2025

    Middle School: Denn John Middle


  • 3831 NAUTICAL WAY #203, KISSIMMEE, FL 34741

    $167,99090 Days on yellowkey   MLS ID: O6385814

    For Sale O6385814 - 3831 NAUTICAL WAY #203, KISSIMMEE, FL 34741 33 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 910
       Built: 1989
    Monthly Fee: $435
       Tax: $2,318 (2025)
    Community: Arbors Of Sendera
    Condo


    Estimated Monthly Payment: $1,549 (change assumption)
    Mortgage ($920) + Fees ($435) + Taxes in 2025 ($193)


    Taxes:$2,318

    Elementary School: Kissimmee Elem

    High School: Osceola High School

    Tax Year: 2025

    Middle School: Kissimmee Middle


  • 3814 BAY CLUB CIR #204, KISSIMMEE, FL 34741

    $169,99088 Days on yellowkey   MLS ID: O6386706

    For Sale O6386706 - 3814 BAY CLUB CIR #204, KISSIMMEE, FL 34741 25 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 910
       Built: 1988
    Monthly Fee: $435
       Tax: $2,286 (2025)
    Community: Arbors Of Sendera
    Condo


    Estimated Monthly Payment: $1,557 (change assumption)
    Mortgage ($931) + Fees ($435) + Taxes in 2025 ($191)


    Taxes:$2,286

    Elementary School: Kissimmee Elem

    High School: Osceola High School

    Tax Year: 2025

    Middle School: Kissimmee Middle


  • 4004 SANTA MARIA DR #101, KISSIMMEE, FL 34741

    $279,900321 Days on yellowkey   MLS ID: S5130668

    REDUCED by $14,000 (4.8%) on 05/12/2026

    For Sale S5130668 - 4004 SANTA MARIA DR #101, KISSIMMEE, FL 34741 42 photos

    Bed: 4   Bath: 3.0
    Liv Area Sq Ft: 1470
       Built: 2005
    Monthly Fee: $500
       Tax: $3,772 (2024)
    Community: Venetian Bay Village Condo Ph 3
    Condo


    Estimated Monthly Payment: $2,348 (change assumption)
    Mortgage ($1,534) + Fees ($500) + Taxes in 2024 ($314)


    Taxes:$3,772

    Elementary School: Kissimmee Elem

    High School: Osceola High School

    Tax Year: 2024

    Middle School: Kissimmee Middle


  • 1081 SALSONA AVE, KISSIMMEE, FL 34744

    $415,00024 Days on yellowkey   MLS ID: S5149132

    5 Days Off yellowkey (back on 5/11/2026)

    For Sale S5149132 - 1081 SALSONA AVE, KISSIMMEE, FL 34744 34 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2090
       Built: 1979   Tax: $2,071 (2025)
    Community: Neptune Shores
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,447 (change assumption)
    Mortgage ($2,274) + Taxes in 2025 ($173)


    Taxes:$2,071

    Elementary School: Partin Settlement Elem

    High School: Osceola High School

    Tax Year: 2025

    Middle School: Neptune Middle (6-8)


  • 2542 NOUVEAU WAY, KISSIMMEE, FL 34741

    $529,000112 Days on yellowkey   MLS ID: O6379913

    For Sale O6379913 - 2542 NOUVEAU WAY, KISSIMMEE, FL 34741 34 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2132
       Built: 2018
    Monthly Fee: $397
       Tax: $8,184 (2025)
    Community: Tapestry Ph 2
    Single Family


    Estimated Monthly Payment: $3,978 (change assumption)
    Mortgage ($2,899) + Fees ($397) + Taxes in 2025 ($682)


    Taxes:$8,184

    Elementary School: Floral Ridge Elementary

    High School: Osceola High School

    Tax Year: 2025

    Middle School: Kissimmee Middle


  • 3000 LAUREL PARK LN #302, KISSIMMEE, FL 34741

    $230,000105 Days on yellowkey   MLS ID: S5143800

    REDUCED by $5,000 (2.1%) on 05/09/2026

    For Sale S5143800 - 3000 LAUREL PARK LN #302, KISSIMMEE, FL 34741 28 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1634
       Built: 2006   Tax: $4,529 (2025)
    Community: Flora Ridge Condo Ph 5 Bldg 2
    Condo


    Estimated Monthly Payment: $1,638 (change assumption)
    Mortgage ($1,260) + Taxes in 2025 ($377)


    Taxes:$4,529

    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

    $189,00057 Days on yellowkey   MLS ID: O6395435

    1 Days Off yellowkey (back on 5/8/2026)

    REDUCED by $21,000 (10.0%) on 04/28/2026

    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: $1,670 (change assumption)
    Mortgage ($1,036) + 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


  • 1792 BULL HILL RD, KISSIMMEE, FL 34744

    $417,990341 Days on yellowkey   MLS ID: O6318608

    For Sale O6318608 - 1792 BULL HILL RD, KISSIMMEE, FL 34744 32 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1614
       Built: 2024
    Monthly Fee: $11
       Tax: $3,776 (2024)
    Community: Kindred Ph 3B 3C & 3D
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,616 (change assumption)
    Mortgage ($2,290) + Fees ($11) + Taxes in 2024 ($315)


    Taxes:$3,776

    Elementary School: Neptune Elementary

    High School: Osceola High School

    Tax Year: 2024

    Middle School: Neptune Middle (6-8)


  • 7 S THACKER AVE, KISSIMMEE, FL 34741

    $250,00028 Days on yellowkey   MLS ID: S5148939

    1 Days Off yellowkey (back on 5/7/2026)

    For Sale S5148939 - 7 S THACKER AVE, KISSIMMEE, FL 34741 21 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1354
       Built: 1960   Tax: $732 (2025)
    Community: Florida Land & Improv Co Add
    Single Family


    Estimated Monthly Payment: $1,431 (change assumption)
    Mortgage ($1,370) + Taxes in 2025 ($61)


    Taxes:$732

    Elementary School: Thacker Avenue Elem (K 5)

    High School: Osceola High School

    Tax Year: 2025

    Middle School: Kissimmee Middle


  • 1622 COLUMBIA ARMS CIR #268, KISSIMMEE, FL 34741

    $139,00072 Days on yellowkey   MLS ID: S5146000

    REDUCED by $13,000 (8.6%) on 04/18/2026

    For Sale S5146000 - 1622 COLUMBIA ARMS CIR #268, KISSIMMEE, FL 34741 14 photos

    Bed: 1   Bath: 1.0
    Liv Area Sq Ft: 834
       Built: 1994   Tax: $2,314 (2025)
    Community: Columbia Arms Condo
    Spa: Yes

    Condo


    Estimated Monthly Payment: $954 (change assumption)
    Mortgage ($762) + Taxes in 2025 ($193)


    Taxes:$2,314

    Elementary School: Central Avenue Elem

    High School: Osceola High School

    Tax Year: 2025

    Middle School: Denn John 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.