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Homes for Sale Near Winter Park High in Orlando - 64 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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  • 4485 TRAPP LN, ORLANDO, FL 32814

    $1,129,00067 Days on yellowkey   MLS ID: O6378114

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

    For Sale O6378114 - 4485 TRAPP LN, ORLANDO, FL 32814 37 photos

    Bed: 3   Bath: 2.5   Gar: 3
    Liv Area Sq Ft: 2386
       Built: 2003
    Monthly Fee: $82
       Tax: $15,154 (2025)
    Community: Baldwin Park
    Single Family


    Estimated Monthly Payment: $7,531 (change assumption)
    Mortgage ($6,186) + Fees ($82) + Taxes in 2025 ($1,263)


    Taxes:$15,154

    Elementary School: Baldwin Park Elementary

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 3506 PELICAN LN, ORLANDO, FL 32803

    $429,99968 Days on yellowkey   MLS ID: O6375875

    0 Days Off yellowkey (back on 3/30/2026)

    For Sale O6375875 - 3506 PELICAN LN, ORLANDO, FL 32803 35 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1463
       Built: 1955   Tax: $3,320 (2024)
    Community: Audubon Park Card Heights Sec
    Single Family


    Estimated Monthly Payment: $2,633 (change assumption)
    Mortgage ($2,356) + Taxes in 2024 ($277)


    Taxes:$3,320

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Audubon Park K-8


  • 1954 MEETING PL, ORLANDO, FL 32814

    $890,000Listed 04/05/2026 5:13PM   MLS ID: O6394286

    For Sale O6394286 - 1954 MEETING PL, ORLANDO, FL 32814 40 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2410
       Built: 2005
    Monthly Fee: $523
       Tax: $8,022 (2025)
    Community: Baldwin Park
    Townhouse


    Estimated Monthly Payment: $6,068 (change assumption)
    Mortgage ($4,877) + Fees ($523) + Taxes in 2025 ($668)


    Taxes:$8,022

    Elementary School: Baldwin Park Elementary

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 5460 PENWAY DR, ORLANDO, FL 32814

    $1,085,00043 Days on yellowkey   MLS ID: O6373241

    For Sale O6373241 - 5460 PENWAY DR, ORLANDO, FL 32814 43 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2590
       Built: 2006
    Monthly Fee: $102
       Tax: $15,411 (2025)
    Community: Baldwin Park
    Single Family


    Estimated Monthly Payment: $7,331 (change assumption)
    Mortgage ($5,945) + Fees ($102) + Taxes in 2025 ($1,284)


    Taxes:$15,411

    Elementary School: Baldwin Park Elementary

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 1864 PROSPECT AVE, ORLANDO, FL 32814

    $649,00039 Days on yellowkey   MLS ID: O6383275

    For Sale O6383275 - 1864 PROSPECT AVE, ORLANDO, FL 32814 100 photos

    Bed: 3   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2434
       Built: 2009
    Monthly Fee: $592
       Tax: $11,810 (2024)
    Community: Baldwin Park
    Townhouse


    Estimated Monthly Payment: $5,132 (change assumption)
    Mortgage ($3,556) + Fees ($592) + Taxes in 2024 ($984)


    Taxes:$11,810

    Elementary School: Baldwin Park Elementary

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Glenridge Middle


  • 4550 LOWER PARK RD, ORLANDO, FL 32814

    $725,00014 Days on yellowkey   MLS ID: O6389072

    For Sale O6389072 - 4550 LOWER PARK RD, ORLANDO, FL 32814 40 photos

    Bed: 3   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2258
       Built: 2014
    Monthly Fee: $592
       Tax: $6,875 (2024)
    Community: Baldwin Park Un #3 Rep 3
    Townhouse


    Estimated Monthly Payment: $5,137 (change assumption)
    Mortgage ($3,973) + Fees ($592) + Taxes in 2024 ($573)


    Taxes:$6,875

    Elementary School: Baldwin Park Elementary

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Glenridge Middle


  • 4333 ROUSH AVE, ORLANDO, FL 32803

    $517,37042 Days on yellowkey   MLS ID: TB8479380

    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: $3,168 (change assumption)
    Mortgage ($2,835) + 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


  • 901 LAKE BALDWIN LN, ORLANDO, FL 32803

    $632,81674 Days on yellowkey   MLS ID: TB8467804

    For Sale TB8467804 - 901 LAKE BALDWIN LN, ORLANDO, FL 32803 35 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1932
       Built: 2025
    Monthly Fee: $290
       Tax: $517 (2024)
    Community: Baldwin Crossing
    Townhouse


    Estimated Monthly Payment: $3,800 (change assumption)
    Mortgage ($3,467) + Fees ($290) + Taxes in 2024 ($43)


    Taxes:$517

    Elementary School: Baldwin Park Elementary

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Glenridge Middle


  • 5416 PENWAY DR, ORLANDO, FL 32814

    $995,000150 Days on yellowkey   MLS ID: O6357821

    For Sale O6357821 - 5416 PENWAY DR, ORLANDO, FL 32814 78 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2518
       Built: 2006
    Monthly Fee: $93
       Tax: $7,918 (2024)
    Community: Baldwin Park Poa
    Single Family


    Estimated Monthly Payment: $6,205 (change assumption)
    Mortgage ($5,452) + Fees ($93) + Taxes in 2024 ($660)


    Taxes:$7,918

    Elementary School: Baldwin Park Elementary

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Glenridge Middle


  • 2415 LAURA PL, ORLANDO, FL 32803

    $1,600,00031 Days on yellowkey   MLS ID: O6386133

    REDUCED by $80,000 (4.8%) on 04/03/2026

    For Sale O6386133 - 2415 LAURA PL, ORLANDO, FL 32803 37 photos

    Bed: 5   Bath: 5.5   Gar: 2
    Liv Area Sq Ft: 3500
       Built: 2026   Tax: $5,502 (2025)
    Community: Colonial Acres
    Single Family


    Estimated Monthly Payment: $9,225 (change assumption)
    Mortgage ($8,767) + Taxes in 2025 ($459)


    Taxes:$5,502

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 3709 MOCKINGBIRD LN, ORLANDO, FL 32803

    $595,00032 Days on yellowkey   MLS ID: O6387642

    For Sale O6387642 - 3709 MOCKINGBIRD LN, ORLANDO, FL 32803 33 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1675
       Built: 1954   Tax: $6,647 (2025)
    Community: Audubon Park Tanager Sec
    Single Family


    Estimated Monthly Payment: $3,814 (change assumption)
    Mortgage ($3,260) + Taxes in 2025 ($554)


    Taxes:$6,647

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 4571 VIRGINIA DR, ORLANDO, FL 32814

    $690,000149 Days on yellowkey   MLS ID: O6357766

    For Sale O6357766 - 4571 VIRGINIA DR, ORLANDO, FL 32814 68 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 2284
       Built: 2005
    Monthly Fee: $574
       Tax: $12,397 (2024)
    Community: Baldwin Park
    Townhouse


    Estimated Monthly Payment: $5,388 (change assumption)
    Mortgage ($3,781) + Fees ($574) + Taxes in 2024 ($1,033)


    Taxes:$12,397

    Elementary School: Baldwin Park Elementary

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Glenridge Middle


  • 4201 PARK LAKE ST, ORLANDO, FL 32803

    $475,00048 Days on yellowkey   MLS ID: S5143905

    REDUCED by $14,900 (3.0%) on 04/04/2026

    For Sale S5143905 - 4201 PARK LAKE ST, ORLANDO, FL 32803 42 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1601
       Built: 1958   Tax: $4,914 (2024)
    Community: Tinker Heights
    Single Family


    Estimated Monthly Payment: $3,012 (change assumption)
    Mortgage ($2,603) + Taxes in 2024 ($410)


    Taxes:$4,914

    Elementary School: Baldwin Park Elementary

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Glenridge Middle


  • 1353 CHATFIELD PL, ORLANDO, FL 32814

    $610,00024 Days on yellowkey   MLS ID: O6389946

    For Sale O6389946 - 1353 CHATFIELD PL, ORLANDO, FL 32814 30 photos

    Bed: 3   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 1994
       Built: 2004
    Monthly Fee: $93
       Tax: $9,917 (2025)
    Community: Baldwin Park 115
    Townhouse


    Estimated Monthly Payment: $4,262 (change assumption)
    Mortgage ($3,342) + Fees ($93) + Taxes in 2025 ($826)


    Taxes:$9,917

    Elementary School: Baldwin Park Elementary

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 3504 FINCH ST, ORLANDO, FL 32803

    $799,00080 Days on yellowkey   MLS ID: O6371554

    For Sale O6371554 - 3504 FINCH ST, ORLANDO, FL 32803 34 photos

    Bed: 3   Bath: 1.5   Gar: 2
    Liv Area Sq Ft: 1332
       Built: 1955   Tax: $5,038 (2024)
    Community: Audubon Park
    Single Family


    Estimated Monthly Payment: $4,798 (change assumption)
    Mortgage ($4,378) + Taxes in 2024 ($420)


    Taxes:$5,038

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Audubon Park K-8


  • 3838 HAWS LN, ORLANDO, FL 32814

    $1,200,000194 Days on yellowkey   MLS ID: O6344126

    For Sale O6344126 - 3838 HAWS LN, ORLANDO, FL 32814 65 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2731
       Built: 2005
    Monthly Fee: $92
       Tax: $16,584 (2024)
    Community: Baldwin Park
    Single Family


    Estimated Monthly Payment: $8,049 (change assumption)
    Mortgage ($6,575) + Fees ($92) + Taxes in 2024 ($1,382)


    Taxes:$16,584

    Elementary School: Baldwin Park Elementary

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Glenridge Middle


  • 2001 GALE ST, ORLANDO, FL 32803

    $698,9003 Days on yellowkey   MLS ID: O6396150

    For Sale O6396150 - 2001 GALE ST, ORLANDO, FL 32803 43 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1682
       Built: 1954   Tax: $6,632 (2025)
    Community: North Hampton Park
    Single Family


    Estimated Monthly Payment: $4,382 (change assumption)
    Mortgage ($3,829) + Taxes in 2025 ($553)


    Taxes:$6,632

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 9528 LAKE DOUGLAS PL, ORLANDO, FL 32817

    $525,00040 Days on yellowkey   MLS ID: O6385746

    1 Days Off yellowkey (back on 4/3/2026)

    For Sale O6385746 - 9528 LAKE DOUGLAS PL, ORLANDO, FL 32817 59 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2190
       Built: 1985   Tax: $2,191 (2024)
    Community: Arbor Ridge West
    Single Family


    Estimated Monthly Payment: $3,059 (change assumption)
    Mortgage ($2,877) + Taxes in 2024 ($183)


    Taxes:$2,191

    Elementary School: Arbor Ridge Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Arbor Ridge Middle


  • 2613 JAMIE CIR, ORLANDO, FL 32803

    $400,0005 Days on yellowkey   MLS ID: O6395373

    For Sale O6395373 - 2613 JAMIE CIR, ORLANDO, FL 32803 7 photos

    Bed: 2   Bath: 1.0
    Liv Area Sq Ft: 840
       Built: 1954   Tax: $1,312 (2025)
    Community: Colonial Acres
    Single Family


    Estimated Monthly Payment: $2,301 (change assumption)
    Mortgage ($2,192) + Taxes in 2025 ($109)


    Taxes:$1,312

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 5314 OLD CHENEY HWY, ORLANDO, FL 32807

    $289,00067 Days on yellowkey   MLS ID: O6375898

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

    For Sale O6375898 - 5314 OLD CHENEY HWY, ORLANDO, FL 32807 35 photos

    Bed: 2   Bath: 1.0   Gar: 1
    Liv Area Sq Ft: 830
       Built: 1951   Tax: $2,132 (2024)
    Community: Lake Barton Park
    Single Family


    Estimated Monthly Payment: $1,761 (change assumption)
    Mortgage ($1,584) + Taxes in 2024 ($178)


    Taxes:$2,132

    Elementary School: Baldwin Park Elementary

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Glenridge 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.