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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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  • 2103 GALE ST, ORLANDO, FL 32803

    $1,639,00027 Days on yellowkey   MLS ID: O6417061

    For Sale O6417061 - 2103 GALE ST, ORLANDO, FL 32803 51 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3497
       Built: 2026   Tax: $6,406 (2025)
    Community: North Hampton Park
    Single Family


    Estimated Monthly Payment: $9,514 (change assumption)
    Mortgage ($8,981) + Taxes in 2025 ($534)


    Taxes:$6,406

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 4747 JETTY ST, ORLANDO, FL 32817

    $594,9007 Days on yellowkey   MLS ID: O6424535

    For Sale O6424535 - 4747 JETTY ST, ORLANDO, FL 32817 43 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2948
       Built: 2002
    Monthly Fee: $53
       Tax: $8,813 (2025)
    Community: Georgia Cove 44/1
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,047 (change assumption)
    Mortgage ($3,260) + Fees ($53) + Taxes in 2025 ($734)


    Taxes:$8,813

    Elementary School: Arbor Ridge Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 4495 TWINVIEW LN, ORLANDO, FL 32814

    $825,00047 Days on yellowkey   MLS ID: O6412567

    REDUCED by $50,000 (5.7%) on 07/09/2026

    For Sale O6412567 - 4495 TWINVIEW LN, ORLANDO, FL 32814 40 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2667
       Built: 2004
    Monthly Fee: $523
       Tax: $9,154 (2025)
    Community: Baldwin Park Unit 1
    Townhouse


    Estimated Monthly Payment: $5,806 (change assumption)
    Mortgage ($4,520) + Fees ($523) + Taxes in 2025 ($763)


    Taxes:$9,154

    Elementary School: Baldwin Park Elementary

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 2315 UPPER PARK RD #302, ORLANDO, FL 32814

    $599,90092 Days on yellowkey   MLS ID: O6399861

    REDUCED by $10,100 (1.7%) on 06/06/2026

    For Sale O6399861 - 2315 UPPER PARK RD #302, ORLANDO, FL 32814 35 photos

    Bed: 3   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1307
       Built: 2006   Tax: $8,191 (2025)
    Community: Baldwin Park #4 Condo
    Condo


    Estimated Monthly Payment: $3,970 (change assumption)
    Mortgage ($3,287) + Taxes in 2025 ($683)


    Taxes:$8,191

    Elementary School: Baldwin Park Elementary

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 1131 FERN AVE, ORLANDO, FL 32814

    $1,750,000302 Days on yellowkey   MLS ID: O6346976

    For Sale O6346976 - 1131 FERN AVE, ORLANDO, FL 32814 62 photos

    Bed: 4   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 3461
       Built: 2004
    Monthly Fee: $102
       Tax: $13,827 (2025)
    Community: Baldwin Park Unit 1
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $10,843 (change assumption)
    Mortgage ($9,589) + Fees ($102) + Taxes in 2025 ($1,152)


    Taxes:$13,827

    Elementary School: Baldwin Park Elementary

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 9550 BRIMTON DR, ORLANDO, FL 32817

    $370,0008 Days on yellowkey   MLS ID: O6424800

    0 Days Off yellowkey (back on 7/19/2026)

    For Sale O6424800 - 9550 BRIMTON DR, ORLANDO, FL 32817 36 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1224
       Built: 1983   Tax: $4,819 (2025)
    Community: Arbor Ridge West
    Single Family


    Estimated Monthly Payment: $2,429 (change assumption)
    Mortgage ($2,027) + Taxes in 2025 ($402)


    Taxes:$4,819

    Elementary School: Arbor Ridge Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Union Park Middle


  • 1909 JASPER DR, ORLANDO, FL 32807

    $310,00036 Days on yellowkey   MLS ID: O6417479

    0 Days Off yellowkey (back on 7/17/2026)

    REDUCED by $10,000 (3.1%) on 07/14/2026

    For Sale O6417479 - 1909 JASPER DR, ORLANDO, FL 32807 28 photos

    Bed: 3   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1488
       Built: 1945   Tax: $4,725 (2025)
    Community: Tiffany Terrace
    Single Family


    Estimated Monthly Payment: $2,092 (change assumption)
    Mortgage ($1,699) + Taxes in 2025 ($394)


    Taxes:$4,725

    Elementary School: Cheney Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 2655 LAKE SHORE DR, ORLANDO, FL 32803

    $2,525,00024 Days on yellowkey   MLS ID: O6419043

    REDUCED by $170,000 (6.3%) on 07/11/2026

    For Sale O6419043 - 2655 LAKE SHORE DR, ORLANDO, FL 32803 25 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 4094
       Built: 1958   Tax: $12,042 (2025)
    Community: Rose Isle Sec 03
    Spa: No

    Single Family


    Estimated Monthly Payment: $14,839 (change assumption)
    Mortgage ($13,835) + Taxes in 2025 ($1,004)


    Taxes:$12,042

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 4392 WARDELL PL #201, ORLANDO, FL 32814

    $598,00043 Days on yellowkey   MLS ID: O6411195

    REDUCED by $17,000 (2.8%) on 07/12/2026

    For Sale O6411195 - 4392 WARDELL PL #201, ORLANDO, FL 32814 34 photos

    Bed: 3   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1434
       Built: 2006
    Monthly Fee: $838
       Tax: $4,311 (2025)
    Community: Baldwin Park #5
    Condo


    Estimated Monthly Payment: $4,474 (change assumption)
    Mortgage ($3,277) + Fees ($838) + Taxes in 2025 ($359)


    Taxes:$4,311

    Elementary School: Baldwin Park Elementary

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 2522 LESTON CT, ORLANDO, FL 32817

    $369,00041 Days on yellowkey   MLS ID: O6416038

    3 Days Off yellowkey (back on 7/6/2026)

    For Sale O6416038 - 2522 LESTON CT, ORLANDO, FL 32817 23 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1500
       Built: 1986   Tax: $5,607 (2025)
    Community: Arbor Ridge West
    Single Family


    Estimated Monthly Payment: $2,489 (change assumption)
    Mortgage ($2,022) + Taxes in 2025 ($467)


    Taxes:$5,607

    Elementary School: Cheney Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Union Park Middle


  • 4401 PARK LAKE ST, ORLANDO, FL 32803

    $1,180,0006 Days on yellowkey   MLS ID: O6425452

    For Sale O6425452 - 4401 PARK LAKE ST, ORLANDO, FL 32803 68 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3329
       Built: 2023   Tax: $15,749 (2025)
    Community: Tinker Heights
    Single Family


    Estimated Monthly Payment: $7,778 (change assumption)
    Mortgage ($6,466) + Taxes in 2025 ($1,312)


    Taxes:$15,749

    Elementary School: Baldwin Park Elementary

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 5656 ROYAL PINE BLVD #27, ORLANDO, FL 32807

    $185,000154 Days on yellowkey   MLS ID: O6384013

    REDUCED by $10,000 (5.1%) on 06/17/2026

    For Sale O6384013 - 5656 ROYAL PINE BLVD #27, ORLANDO, FL 32807 26 photos

    Bed: 3   Bath: 1.5
    Liv Area Sq Ft: 1133
       Built: 1978
    Monthly Fee: $264
       Tax: $2,052 (2024)
    Community: Semoran Club Condo
    Condo


    Estimated Monthly Payment: $1,449 (change assumption)
    Mortgage ($1,014) + Fees ($264) + Taxes in 2024 ($171)


    Taxes:$2,052

    Elementary School: Baldwin Park Elementary

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Glenridge Middle


  • 4201 PARK LAKE ST, ORLANDO, FL 32803

    $390,00090 Days on yellowkey   MLS ID: O6402149

    REDUCED by $19,999 (4.9%) on 07/17/2026

    For Sale O6402149 - 4201 PARK LAKE ST, ORLANDO, FL 32803 21 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1601
       Built: 1958   Tax: $5,467 (2025)
    Community: Tinker Heights
    Single Family


    Estimated Monthly Payment: $2,593 (change assumption)
    Mortgage ($2,137) + Taxes in 2025 ($456)


    Taxes:$5,467

    Elementary School: Baldwin Park Elementary

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 8422 MARGARITA DR, ORLANDO, FL 32817

    $455,0007 Days on yellowkey   MLS ID: O6425526

    For Sale O6425526 - 8422 MARGARITA DR, ORLANDO, FL 32817 17 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1845
       Built: 1984   Tax: $6,571 (2025)
    Community: Orange Ridge
    Single Family


    Estimated Monthly Payment: $3,041 (change assumption)
    Mortgage ($2,493) + Taxes in 2025 ($548)


    Taxes:$6,571

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 5437 LEHIGH AVE, ORLANDO, FL 32807

    $374,50042 Days on yellowkey   MLS ID: O6413840

    3 Days Off yellowkey (back on 7/16/2026)

    REDUCED by $10,500 (2.7%) on 07/02/2026

    For Sale O6413840 - 5437 LEHIGH AVE, ORLANDO, FL 32807 38 photos

    Bed: 3   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1097
       Built: 1998   Tax: $5,116 (2025)
    Community: Lake Barton Park
    Single Family


    Estimated Monthly Payment: $2,478 (change assumption)
    Mortgage ($2,052) + Taxes in 2025 ($426)


    Taxes:$5,116

    Elementary School: Baldwin Park Elementary

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 2713 YUCCA ST, ORLANDO, FL 32807

    $450,00062 Days on yellowkey   MLS ID: O6409204

    REDUCED by $25,000 (5.3%) on 06/27/2026

    For Sale O6409204 - 2713 YUCCA ST, ORLANDO, FL 32807 54 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1709
       Built: 1968   Tax: $5,666 (2025)
    Community: Evergreen Terrace
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,938 (change assumption)
    Mortgage ($2,466) + Taxes in 2025 ($472)


    Taxes:$5,666

    Elementary School: Cheney Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 4333 ROUSH AVE, ORLANDO, FL 32803

    $499,900150 Days on yellowkey   MLS ID: TB8479380

    2 Days Off yellowkey (back on 7/16/2026)

    REDUCED by $17,470 (3.4%) on 05/26/2026

    For Sale TB8479380 - 4333 ROUSH AVE, ORLANDO, FL 32803 36 photos

    Bed: 2   Bath: 2.5   Gar: 1
    Liv Area Sq Ft: 1390
       Built: 2026
    Monthly Fee: $290
       Tax: $517 (2025)
    Community: Baldwin Crossing
    Townhouse


    Estimated Monthly Payment: $3,072 (change assumption)
    Mortgage ($2,739) + 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


  • 2425 LAKE SUE DR, ORLANDO, FL 32803

    $950,0008 Days on yellowkey   MLS ID: O6425047

    For Sale O6425047 - 2425 LAKE SUE DR, ORLANDO, FL 32803 43 photos

    Bed: 3   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2586
       Built: 1959   Tax: $9,055 (2025)
    Community: Beeman Park
    Single Family


    Estimated Monthly Payment: $5,960 (change assumption)
    Mortgage ($5,205) + Taxes in 2025 ($755)


    Taxes:$9,055

    Elementary School: Baldwin Park Elementary

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 3021 PLAZA TERRACE DR, ORLANDO, FL 32803

    $649,00039 Days on yellowkey   MLS ID: O6415562

    For Sale O6415562 - 3021 PLAZA TERRACE DR, ORLANDO, FL 32803 31 photos

    Bed: 3   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1752
       Built: 1967   Tax: $10,530 (2025)
    Community: Plaza Terrace
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $4,434 (change assumption)
    Mortgage ($3,556) + Taxes in 2025 ($878)


    Taxes:$10,530

    Elementary School: Baldwin Park Elementary

    High School: Winter Park High

    Tax Year: 2025

    Middle School: None


  • 2806 MOSS GROVE BLVD, ORLANDO, FL 32807

    $349,99049 Days on yellowkey   MLS ID: S5151206

    0 Days Off yellowkey (back on 6/11/2026)

    For Sale S5151206 - 2806 MOSS GROVE BLVD, ORLANDO, FL 32807 20 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1272
       Built: 1975   Tax: $1,398 (2025)
    Community: Hanging Moss Estates
    Single Family


    Estimated Monthly Payment: $2,034 (change assumption)
    Mortgage ($1,918) + Taxes in 2025 ($117)


    Taxes:$1,398

    Elementary School: Cheney Elem

    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.