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Homes for Sale Near Winter Park High in Orlando - 111 homes

Winter Park High is an High School in Orange County. Find homes for sale close to Winter Park High. Our REALTORS® can assist you in your search for Winter Park High, Orlando nearby homes.

Location: Orlando

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  • 1822 JASPER DR, ORLANDO, FL 32807

    $334,9009 Days on yellowkey   MLS ID: O6424897

    For Sale O6424897 - 1822 JASPER DR, ORLANDO, FL 32807 15 photos

    Bed: 3   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1196
       Built: 1976   Tax: $4,803 (2025)
    Community: Tiffany Terrace
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,235 (change assumption)
    Mortgage ($1,835) + Taxes in 2025 ($400)


    Taxes:$4,803

    Elementary School: Cheney Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 1563 COMMON WAY RD, ORLANDO, FL 32814

    $599,990195 Days on yellowkey   MLS ID: O6371726

    REDUCED by $9,010 (1.5%) on 06/11/2026

    For Sale O6371726 - 1563 COMMON WAY RD, ORLANDO, FL 32814 43 photos

    Bed: 3   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 1963
       Built: 2005
    Monthly Fee: $494
       Tax: $10,738 (2024)
    Community: Baldwin Park
    Townhouse


    Estimated Monthly Payment: $4,676 (change assumption)
    Mortgage ($3,288) + Fees ($494) + Taxes in 2024 ($895)


    Taxes:$10,738

    Elementary School: Baldwin Park Elementary

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Glenridge Middle


  • 4353 ROUSH AVE, ORLANDO, FL 32803

    $517,48575 Days on yellowkey   MLS ID: TB8507013

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

    REDUCED by $15 (0.0%) on 06/24/2026

    For Sale TB8507013 - 4353 ROUSH AVE, ORLANDO, FL 32803 34 photos

    Bed: 2   Bath: 2.5   Gar: 1
    Liv Area Sq Ft: 1390
       Built: 2025
    Monthly Fee: $289
       Tax: $517 (2025)
    Community: Baldwin Crossing
    Townhouse


    Estimated Monthly Payment: $3,168 (change assumption)
    Mortgage ($2,835) + Fees ($289) + Taxes in 2025 ($43)


    Taxes:$517

    Elementary School: Baldwin Park Elementary

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 4345 ROUSH AVE, ORLANDO, FL 32803

    $517,35578 Days on yellowkey   MLS ID: TB8505792

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

    REDUCED by $15 (0.0%) on 06/24/2026

    For Sale TB8505792 - 4345 ROUSH AVE, ORLANDO, FL 32803 20 photos

    Bed: 2   Bath: 2.5   Gar: 1
    Liv Area Sq Ft: 1390
       Built: 2025
    Monthly Fee: $289
       Tax: $517 (2025)
    Community: Baldwin Crossing
    Townhouse


    Estimated Monthly Payment: $3,167 (change assumption)
    Mortgage ($2,835) + Fees ($289) + Taxes in 2025 ($43)


    Taxes:$517

    Elementary School: Baldwin Park Elementary

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 4357 ROUSH AVE, ORLANDO, FL 32803

    $633,20275 Days on yellowkey   MLS ID: TB8507003

    4 Days Off yellowkey (back on 6/30/2026)

    For Sale TB8507003 - 4357 ROUSH AVE, ORLANDO, FL 32803 32 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1932
       Built: 2025
    Monthly Fee: $290
       Tax: $517 (2025)
    Community: Baldwin Crossing
    Townhouse


    Estimated Monthly Payment: $3,803 (change assumption)
    Mortgage ($3,470) + Fees ($290) + Taxes in 2025 ($43)


    Taxes:$517

    Elementary School: Baldwin Park Elementary

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 4341 ROUSH AVE, ORLANDO, FL 32803

    $632,43075 Days on yellowkey   MLS ID: TB8506998

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

    For Sale TB8506998 - 4341 ROUSH AVE, ORLANDO, FL 32803 36 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1932
       Built: 2025
    Monthly Fee: $290
       Tax: $517 (2025)
    Community: Baldwin Crossing
    Townhouse


    Estimated Monthly Payment: $3,798 (change assumption)
    Mortgage ($3,465) + Fees ($290) + Taxes in 2025 ($43)


    Taxes:$517

    Elementary School: Baldwin Park Elementary

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 9502 DARIEN AVE #9502, ORLANDO, FL 32817

    $200,000374 Days on yellowkey   MLS ID: O6326912

    0 Days Off yellowkey (back on 7/13/2026)

    For Sale O6326912 - 9502 DARIEN AVE #9502, ORLANDO, FL 32817 34 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 992
       Built: 1987   Tax: $2,555 (2024)
    Community: Colonial Landings Ph 04
    Condo


    Estimated Monthly Payment: $1,309 (change assumption)
    Mortgage ($1,096) + Taxes in 2024 ($213)


    Taxes:$2,555

    Elementary School: Cheney Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Union Park Middle


  • 4740 ANSON LN, ORLANDO, FL 32814

    $715,00013 Days on yellowkey   MLS ID: O6423583

    0 Days Off yellowkey (back on 7/13/2026)

    For Sale O6423583 - 4740 ANSON LN, ORLANDO, FL 32814 39 photos

    Bed: 3   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2094
       Built: 2003
    Monthly Fee: $494
       Tax: $10,055 (2025)
    Community: Baldwin Park
    Townhouse


    Estimated Monthly Payment: $5,250 (change assumption)
    Mortgage ($3,918) + Fees ($494) + Taxes in 2025 ($838)


    Taxes:$10,055

    Elementary School: Baldwin Park Elementary

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 995 JUEL ST, ORLANDO, FL 32814

    $660,000250 Days on yellowkey   MLS ID: O6360876

    For Sale O6360876 - 995 JUEL ST, ORLANDO, FL 32814 45 photos

    Bed: 2   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2070
       Built: 2003
    Monthly Fee: $606
       Tax: $6,882 (2024)
    Community: Baldwin Park
    Townhouse


    Estimated Monthly Payment: $4,796 (change assumption)
    Mortgage ($3,616) + Fees ($606) + Taxes in 2024 ($573)


    Taxes:$6,882

    Elementary School: Baldwin Park Elementary

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Glenridge Middle


  • 8061 CRUSHED PEPPER AVE, ORLANDO, FL 32817

    $768,00013 Days on yellowkey   MLS ID: O6424119

    0 Days Off yellowkey (back on 7/13/2026)

    For Sale O6424119 - 8061 CRUSHED PEPPER AVE, ORLANDO, FL 32817 63 photos

    Bed: 5   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 3075
       Built: 2007
    Monthly Fee: $83
       Tax: $5,811 (2025)
    Community: Enclave/Lk Jean
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $4,775 (change assumption)
    Mortgage ($4,208) + Fees ($83) + Taxes in 2025 ($484)


    Taxes:$5,811

    Elementary School: Aloma Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 2680 CAVANAUGH DR, ORLANDO, FL 32817

    $648,990208 Days on yellowkey   MLS ID: O6369656

    For Sale O6369656 - 2680 CAVANAUGH DR, ORLANDO, FL 32817 15 photos

    Bed: 5   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 3198
       Built: 2026
    Monthly Fee: $130
       Tax: $887 (2025)
    Community: Harrell Oaks
    Single Family


    Estimated Monthly Payment: $3,760 (change assumption)
    Mortgage ($3,556) + Fees ($130) + Taxes in 2025 ($74)


    Taxes:$887

    Elementary School: Cheney Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 1420 LAKE BALDWIN LN, ORLANDO, FL 32814

    $1,149,00028 Days on yellowkey   MLS ID: O6419759

    REDUCED by $50,000 (4.2%) on 07/12/2026

    For Sale O6419759 - 1420 LAKE BALDWIN LN, ORLANDO, FL 32814 47 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 3150
       Built: 2007
    Monthly Fee: $102
       Tax: $14,105 (2025)
    Community: Baldwin Park Unit 3 - Replat 1 58/76 Lot 559
    Townhouse


    Estimated Monthly Payment: $7,573 (change assumption)
    Mortgage ($6,296) + Fees ($102) + Taxes in 2025 ($1,175)


    Taxes:$14,105

    Elementary School: Baldwin Park Elementary

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 1659 COMMON WAY RD, ORLANDO, FL 32814

    $605,00030 Days on yellowkey   MLS ID: O6417414

    For Sale O6417414 - 1659 COMMON WAY RD, ORLANDO, FL 32814 31 photos

    Bed: 3   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 1950
       Built: 2005
    Monthly Fee: $102
       Tax: $10,269 (2025)
    Community: Baldwin Park
    Townhouse


    Estimated Monthly Payment: $4,273 (change assumption)
    Mortgage ($3,315) + Fees ($102) + Taxes in 2025 ($856)


    Taxes:$10,269

    Elementary School: Baldwin Park Elementary

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 8531 PORT SAID ST, ORLANDO, FL 32817

    $435,00023 Days on yellowkey   MLS ID: TB8524745

    For Sale TB8524745 - 8531 PORT SAID ST, ORLANDO, FL 32817 30 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1484
       Built: 1981   Tax: $2,215 (2025)
    Community: Harbor East
    Single Family


    Estimated Monthly Payment: $2,568 (change assumption)
    Mortgage ($2,384) + Taxes in 2025 ($185)


    Taxes:$2,215

    Elementary School: None

    High School: Winter Park High

    Tax Year: 2025

    Middle School: None


  • 3701 VIRGINIA DR, ORLANDO, FL 32803

    $699,99037 Days on yellowkey   MLS ID: O6417195

    REDUCED by $25,010 (3.4%) on 07/11/2026

    For Sale O6417195 - 3701 VIRGINIA DR, ORLANDO, FL 32803 58 photos

    Bed: 4   Bath: 0.0
    Liv Area Sq Ft: 2044
       Built: 1954   Tax: $7,924 (2025)
    Community: Audubon Park Tanager Sec
    Apartment


    Estimated Monthly Payment: $4,496 (change assumption)
    Mortgage ($3,835) + Taxes in 2025 ($660)


    Taxes:$7,924

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: None


  • 3701 VIRGINIA DR, ORLANDO, FL 32803

    $699,99037 Days on yellowkey   MLS ID: O6416950

    REDUCED by $25,010 (3.4%) on 07/11/2026

    For Sale O6416950 - 3701 VIRGINIA DR, ORLANDO, FL 32803 58 photos

    Bed: 4   Bath: 3.0
    Liv Area Sq Ft: 2044
       Built: 1954   Tax: $7,924 (2025)
    Community: Audubon Park Tanager Sec
    Single Family


    Estimated Monthly Payment: $4,496 (change assumption)
    Mortgage ($3,835) + Taxes in 2025 ($660)


    Taxes:$7,924

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: None


  • 7923 THURMOND CT, ORLANDO, FL 32817

    $465,00099 Days on yellowkey   MLS ID: O6399360

    REDUCED by $10,000 (2.1%) on 06/01/2026

    For Sale O6399360 - 7923 THURMOND CT, ORLANDO, FL 32817 63 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1820
       Built: 1984
    Monthly Fee: $7
       Tax: $2,979 (2025)
    Community: Aloma Estates
    Single Family


    Estimated Monthly Payment: $2,803 (change assumption)
    Mortgage ($2,548) + Fees ($7) + Taxes in 2025 ($248)


    Taxes:$2,979

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 2843 UPPER PARK RD, ORLANDO, FL 32814

    $660,00032 Days on yellowkey   MLS ID: O6418525

    For Sale O6418525 - 2843 UPPER PARK RD, ORLANDO, FL 32814 50 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1818
       Built: 2005
    Monthly Fee: $490
       Tax: $4,936 (2025)
    Community: Baldwin Park 6
    Townhouse


    Estimated Monthly Payment: $4,518 (change assumption)
    Mortgage ($3,616) + Fees ($490) + Taxes in 2025 ($411)


    Taxes:$4,936

    Elementary School: Baldwin Park Elementary

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 980 BURNS ST, ORLANDO, FL 32803

    $729,90023 Days on yellowkey   MLS ID: O6421001

    For Sale O6421001 - 980 BURNS ST, ORLANDO, FL 32803 54 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2446
       Built: 2020   Tax: $9,574 (2025)
    Community: Jamajo
    Single Family


    Estimated Monthly Payment: $4,797 (change assumption)
    Mortgage ($3,999) + Taxes in 2025 ($798)


    Taxes:$9,574

    Elementary School: Baldwin Park Elementary

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 2293 OSPREY AVE, ORLANDO, FL 32814

    $1,195,00031 Days on yellowkey   MLS ID: S5152219

    REDUCED by $63,000 (5.0%) on 07/11/2026

    For Sale S5152219 - 2293 OSPREY AVE, ORLANDO, FL 32814 45 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3159
       Built: 2005
    Monthly Fee: $523
       Tax: $10,414 (2025)
    Community: Baldwin Park
    Townhouse


    Estimated Monthly Payment: $7,939 (change assumption)
    Mortgage ($6,548) + Fees ($523) + Taxes in 2025 ($868)


    Taxes:$10,414

    Elementary School: Baldwin Park Elementary

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle




Why Bother Searching Elsewhere for Homes For Sale and Real Estate nearby Winter Park High?

Home, townhome, condo, villa, and other listing sales data closeby Winter Park High 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 Winter Park High, Orlando . You can use our website to view Multiple Listing Service (MLS) data on Orlando homes near Winter Park High. 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 Winter Park High.



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.