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Homes for Sale Near Osceola High School in Kissimmee - 84 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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  • 2477 TOSCOLONA DR, KISSIMMEE, FL 34741

    $294,000124 Days on yellowkey   MLS ID: O6367342

    REDUCED by $5,000 (1.7%) on 04/15/2026

    For Sale O6367342 - 2477 TOSCOLONA DR, KISSIMMEE, FL 34741 36 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1528
       Built: 2019
    Monthly Fee: $304
       Tax: $5,407 (2024)
    Community: Tapestry Ph 4
    Townhouse


    Estimated Monthly Payment: $2,366 (change assumption)
    Mortgage ($1,611) + Fees ($304) + Taxes in 2024 ($451)


    Taxes:$5,407

    Elementary School: Floral Ridge Elementary

    High School: Osceola High School

    Tax Year: 2024

    Middle School: Kissimmee Middle


  • 2300 PAINTER LN, KISSIMMEE, FL 34741

    $395,00064 Days on yellowkey   MLS ID: O6382119

    For Sale O6382119 - 2300 PAINTER LN, KISSIMMEE, FL 34741 1 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1820
       Built: 2016
    Monthly Fee: $304
       Tax: $5,420 (2025)
    Community: Cypress Reserve Villas
    Townhouse


    Estimated Monthly Payment: $2,920 (change assumption)
    Mortgage ($2,164) + Fees ($304) + Taxes in 2025 ($452)


    Taxes:$5,420

    Elementary School: Floral Ridge Elementary

    High School: Osceola High School

    Tax Year: 2025

    Middle School: Kissimmee Middle


  • 1495 SKYLINE DR, KISSIMMEE, FL 34744

    $499,90043 Days on yellowkey   MLS ID: S5145209

    REDUCED by $25,000 (4.8%) on 04/15/2026

    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: $3,205 (change assumption)
    Mortgage ($2,739) + 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)


  • 1714 CHERYL LN, KISSIMMEE, FL 34744

    $749,00015 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)


  • 2973 LANGDON LN N, KISSIMMEE, FL 34741

    $329,900138 Days on yellowkey   MLS ID: P4937057

    0 Days Off yellowkey (back on 3/18/2026)

    For Sale P4937057 - 2973 LANGDON LN N, KISSIMMEE, FL 34741 41 photos

    Bed: 3   Bath: 2.5   Gar: 1
    Liv Area Sq Ft: 2013
       Built: 2005
    Monthly Fee: $233
       Tax: $4,888 (2024)
    Community: Townhomes Of Flora Ridge
    Townhouse


    Estimated Monthly Payment: $2,448 (change assumption)
    Mortgage ($1,808) + Fees ($233) + Taxes in 2024 ($407)


    Taxes:$4,888

    Elementary School: Floral Ridge Elementary

    High School: Osceola High School

    Tax Year: 2024

    Middle School: Kissimmee Middle


  • 2827 NEWCOMBE LN, KISSIMMEE, FL 34741

    $279,900193 Days on yellowkey   MLS ID: O6350162

    3 Days Off yellowkey (back on 3/23/2026)

    For Sale O6350162 - 2827 NEWCOMBE LN, KISSIMMEE, FL 34741 21 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1475
       Built: 2025   Tax: $1,871 (2024)
    Community: Tropical Park Unit 4
    Manufactured Home


    Estimated Monthly Payment: $1,690 (change assumption)
    Mortgage ($1,534) + Taxes in 2024 ($156)


    Taxes:$1,871

    Elementary School: Highlands Elem

    High School: Osceola High School

    Tax Year: 2024

    Middle School: Denn John Middle


  • 2805 CARTER GROVE LN, KISSIMMEE, FL 34741

    $670,000192 Days on yellowkey   MLS ID: O6350502

    For Sale O6350502 - 2805 CARTER GROVE LN, KISSIMMEE, FL 34741 50 photos

    Bed: 5   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 3233
       Built: 2014
    Monthly Fee: $97
       Tax: $7,985 (2024)
    Community: Preserve At Tapestry Ph 1
    Single Family


    Estimated Monthly Payment: $4,434 (change assumption)
    Mortgage ($3,671) + Fees ($97) + Taxes in 2024 ($665)


    Taxes:$7,985

    Elementary School: Floral Ridge Elementary

    High School: Osceola High School

    Tax Year: 2024

    Middle School: Kissimmee Middle


  • 4177 FLYING FORTRESS AVE, KISSIMMEE, FL 34741

    $190,000119 Days on yellowkey   MLS ID: S5140466

    4 Days Off yellowkey (back on 4/14/2026)

    For Sale S5140466 - 4177 FLYING FORTRESS AVE, KISSIMMEE, FL 34741 36 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 930
       Built: 1984
    Monthly Fee: $50
       Tax: $149 (2024)
    Community: Waterway Village
    Townhouse


    Estimated Monthly Payment: $1,104 (change assumption)
    Mortgage ($1,041) + Fees ($50) + Taxes in 2024 ($12)


    Taxes:$149

    Elementary School: Kissimmee Elem

    High School: Osceola High School

    Tax Year: 2024

    Middle School: Kissimmee Middle


  • 3249 FALCON POINT DR, KISSIMMEE, FL 34741

    $445,00079 Days on yellowkey   MLS ID: O6376917

    REDUCED by $13,000 (2.8%) on 04/14/2026

    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
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,068 (change assumption)
    Mortgage ($2,438) + 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


  • 3331 WHITESTONE CIR #201, KISSIMMEE, FL 34741

    $240,000183 Days on yellowkey   MLS ID: O6353322

    0 Days Off yellowkey (back on 4/14/2026)

    For Sale O6353322 - 3331 WHITESTONE CIR #201, KISSIMMEE, FL 34741 37 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1495
       Built: 2006
    Monthly Fee: $389
       Tax: $3,843 (2024)
    Community: Flora Ridge Condo Ph 7 Bldg 12
    Condo


    Estimated Monthly Payment: $2,024 (change assumption)
    Mortgage ($1,315) + Fees ($389) + Taxes in 2024 ($320)


    Taxes:$3,843

    Elementary School: Floral Ridge Elementary

    High School: Osceola High School

    Tax Year: 2024

    Middle School: Kissimmee Middle


  • 2979 WHITE CEDAR CIR, KISSIMMEE, FL 34741

    $410,0008 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

    $514,90024 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

    $435,00036 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

    $599,90054 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

    $300,0008 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


  • 3051 GREYSTONE LOOP #106, KISSIMMEE, FL 34741

    $255,90095 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


  • 658 HUDSON ST, KISSIMMEE, FL 34741

    $279,000191 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


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

    $319,99985 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

    $365,00063 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

    $365,0006 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




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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.