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Homes for Sale Near Winter Park High in Orlando - 108 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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  • 4036 BIBB LN, ORLANDO, FL 32817

    $440,000116 Days on yellowkey   MLS ID: O6379247

    REDUCED by $10,000 (2.2%) on 05/26/2026

    For Sale O6379247 - 4036 BIBB LN, ORLANDO, FL 32817 32 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1645
       Built: 1980   Tax: $3,374 (2024)
    Community: Harbor East
    Single Family


    Estimated Monthly Payment: $2,692 (change assumption)
    Mortgage ($2,411) + Taxes in 2024 ($281)


    Taxes:$3,374

    Elementary School: Aloma Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Glenridge Middle


  • 2639 BETTY ST, ORLANDO, FL 32803

    $470,00075 Days on yellowkey   MLS ID: O6391321

    For Sale O6391321 - 2639 BETTY ST, ORLANDO, FL 32803 21 photos

    Bed: 3   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1263
       Built: 1953   Tax: $6,785 (2025)
    Community: Colonial Acres
    Single Family


    Estimated Monthly Payment: $3,141 (change assumption)
    Mortgage ($2,575) + Taxes in 2025 ($565)


    Taxes:$6,785

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 4353 ROUSH AVE, ORLANDO, FL 32803

    $517,50024 Days on yellowkey   MLS ID: TB8507013

    For Sale TB8507013 - 4353 ROUSH AVE, ORLANDO, FL 32803 36 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 ($2,836) + 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


  • 1353 CHATFIELD PL, ORLANDO, FL 32814

    $595,00081 Days on yellowkey   MLS ID: O6389946

    REDUCED by $15,000 (2.5%) on 04/17/2026

    For Sale O6389946 - 1353 CHATFIELD PL, ORLANDO, FL 32814 33 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: $4,180 (change assumption)
    Mortgage ($3,260) + 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


  • 1567 LAKE BALDWIN LN, ORLANDO, FL 32814

    $1,399,00024 Days on yellowkey   MLS ID: O6406181

    For Sale O6406181 - 1567 LAKE BALDWIN LN, ORLANDO, FL 32814 59 photos

    Bed: 0   Bath: 0.0   Gar: 2
    Liv Area Sq Ft: 3129
       Built: 2006
    Monthly Fee: $900
       Tax: $15,030 (2025)
    Community: Baldwin Parka
    Apartment


    Estimated Monthly Payment: $9,818 (change assumption)
    Mortgage ($7,666) + Fees ($900) + Taxes in 2025 ($1,252)


    Taxes:$15,030

    Elementary School: Baldwin Park Elementary

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 1567 LAKE BALDWIN LN, ORLANDO, FL 32814

    $1,399,00025 Days on yellowkey   MLS ID: O6406178

    For Sale O6406178 - 1567 LAKE BALDWIN LN, ORLANDO, FL 32814 59 photos

    Bed: 6   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3129
       Built: 2006
    Monthly Fee: $900
       Tax: $15,030 (2025)
    Community: Baldwin Parka
    Townhouse


    Estimated Monthly Payment: $9,818 (change assumption)
    Mortgage ($7,666) + Fees ($900) + Taxes in 2025 ($1,252)


    Taxes:$15,030

    Elementary School: Baldwin Park Elementary

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 3004 PLAZA TERRACE DR #3004, ORLANDO, FL 32803

    $274,90079 Days on yellowkey   MLS ID: O6390840

    REDUCED by $5,000 (1.8%) on 05/22/2026

    For Sale O6390840 - 3004 PLAZA TERRACE DR #3004, ORLANDO, FL 32803 30 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 890
       Built: 1972
    Monthly Fee: $289
       Tax: $4,271 (2025)
    Community: Audubon Place City Condo
    Condo


    Estimated Monthly Payment: $2,151 (change assumption)
    Mortgage ($1,506) + Fees ($289) + Taxes in 2025 ($356)


    Taxes:$4,271

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 8874 ASPEN AVE, ORLANDO, FL 32817

    $429,00019 Days on yellowkey   MLS ID: O6407158

    0 Days Off yellowkey (back on 5/23/2026)

    For Sale O6407158 - 8874 ASPEN AVE, ORLANDO, FL 32817 43 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1602
       Built: 1979
    Monthly Fee: $67
       Tax: $1,968 (2025)
    Community: Woodside Village
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,582 (change assumption)
    Mortgage ($2,351) + Fees ($67) + Taxes in 2025 ($164)


    Taxes:$1,968

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 4602 JETTY ST, ORLANDO, FL 32817

    $625,00018 Days on yellowkey   MLS ID: O6406721

    1 Days Off yellowkey (back on 5/23/2026)

    For Sale O6406721 - 4602 JETTY ST, ORLANDO, FL 32817 32 photos

    Bed: 4   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 2682
       Built: 2001
    Monthly Fee: $53
       Tax: $643 (2025)
    Community: Georgia Cove 44/1
    Single Family


    Estimated Monthly Payment: $3,531 (change assumption)
    Mortgage ($3,425) + Fees ($53) + Taxes in 2025 ($54)


    Taxes:$643

    Elementary School: Arbor Ridge Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 2713 YUCCA ST, ORLANDO, FL 32807

    $475,00011 Days on yellowkey   MLS ID: O6409204

    For Sale O6409204 - 2713 YUCCA ST, ORLANDO, FL 32807 28 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: $3,075 (change assumption)
    Mortgage ($2,603) + Taxes in 2025 ($472)


    Taxes:$5,666

    Elementary School: Cheney Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 711 HIGH ST, ORLANDO, FL 32803

    $285,00018 Days on yellowkey   MLS ID: O6406516

    0 Days Off yellowkey (back on 5/22/2026)

    For Sale O6406516 - 711 HIGH ST, ORLANDO, FL 32803 26 photos

    Bed: 2   Bath: 1.0
    Liv Area Sq Ft: 874
       Built: 1956   Tax: $3,619 (2025)
    Community: Lake Barton Shores
    Single Family


    Estimated Monthly Payment: $1,863 (change assumption)
    Mortgage ($1,562) + Taxes in 2025 ($302)


    Taxes:$3,619

    Elementary School: Baldwin Park Elementary

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 4029 TAMARISK WAY, ORLANDO, FL 32817

    $475,00013 Days on yellowkey   MLS ID: O6409365

    0 Days Off yellowkey (back on 5/22/2026)

    For Sale O6409365 - 4029 TAMARISK WAY, ORLANDO, FL 32817 49 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1992
       Built: 1979
    Monthly Fee: $67
       Tax: $2,650 (2025)
    Community: Woodside Village
    Single Family


    Estimated Monthly Payment: $2,891 (change assumption)
    Mortgage ($2,603) + Fees ($67) + Taxes in 2025 ($221)


    Taxes:$2,650

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 3709 MOCKINGBIRD LN, ORLANDO, FL 32803

    $575,00089 Days on yellowkey   MLS ID: O6387642

    0 Days Off yellowkey (back on 5/22/2026)

    REDUCED by $20,000 (3.4%) on 05/05/2026

    For Sale O6387642 - 3709 MOCKINGBIRD LN, ORLANDO, FL 32803 35 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: $3,705 (change assumption)
    Mortgage ($3,151) + 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


  • 3715 WREN LANE, ORLANDO, FL 32803

    $699,00018 Days on yellowkey   MLS ID: O6404996

    0 Days Off yellowkey (back on 5/22/2026)

    For Sale O6404996 - 3715 WREN LANE, ORLANDO, FL 32803 36 photos

    Bed: 3   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1425
       Built: 1956   Tax: $6,730 (2025)
    Community: Audubon Park Tanager Sec
    Single Family


    Estimated Monthly Payment: $4,391 (change assumption)
    Mortgage ($3,830) + Taxes in 2025 ($561)


    Taxes:$6,730

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 9504 CANNON DR, ORLANDO, FL 32817

    $420,00045 Days on yellowkey   MLS ID: O6400350

    0 Days Off yellowkey (back on 5/13/2026)

    For Sale O6400350 - 9504 CANNON DR, ORLANDO, FL 32817 27 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1521
       Built: 1985   Tax: $3,518 (2025)
    Community: Watermill Sec 03
    Single Family


    Estimated Monthly Payment: $2,594 (change assumption)
    Mortgage ($2,301) + Taxes in 2025 ($293)


    Taxes:$3,518

    Elementary School: Arbor Ridge Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 2268 OSPREY AVE, ORLANDO, FL 32814

    $789,00069 Days on yellowkey   MLS ID: O6393457

    0 Days Off yellowkey (back on 5/21/2026)

    For Sale O6393457 - 2268 OSPREY AVE, ORLANDO, FL 32814 65 photos

    Bed: 2   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2019
       Built: 2005
    Monthly Fee: $490
       Tax: $6,986 (2025)
    Community: Baldwin Park
    Townhouse


    Estimated Monthly Payment: $5,395 (change assumption)
    Mortgage ($4,323) + Fees ($490) + Taxes in 2025 ($582)


    Taxes:$6,986

    Elementary School: Baldwin Park Elementary

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 2326 VIVADA ST, ORLANDO, FL 32803

    $1,365,000103 Days on yellowkey   MLS ID: TB8478263

    4 Days Off yellowkey (back on 5/21/2026)

    For Sale TB8478263 - 2326 VIVADA ST, ORLANDO, FL 32803 22 photos

    Bed: 4   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3497
       Built: 2026   Tax: $5,937 (2025)
    Community: Colonialtown North
    Single Family


    Estimated Monthly Payment: $7,974 (change assumption)
    Mortgage ($7,479) + Taxes in 2025 ($495)


    Taxes:$5,937

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 4201 PARK LAKE ST, ORLANDO, FL 32803

    $409,99939 Days on yellowkey   MLS ID: O6402149

    REDUCED by $50,001 (10.9%) on 05/21/2026

    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: $2,702 (change assumption)
    Mortgage ($2,247) + Taxes in 2025 ($456)


    Taxes:$5,467

    Elementary School: Baldwin Park Elementary

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 925 HANLEY ALY, ORLANDO, FL 32814

    $1,100,00046 Days on yellowkey   MLS ID: O6398590

    1 Days Off yellowkey (back on 5/20/2026)

    For Sale O6398590 - 925 HANLEY ALY, ORLANDO, FL 32814 59 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2160
       Built: 2003
    Monthly Fee: $102
       Tax: $10,144 (2025)
    Community: Baldwin Park Ut 01 50 121
    Single Family


    Estimated Monthly Payment: $6,975 (change assumption)
    Mortgage ($6,027) + Fees ($102) + Taxes in 2025 ($845)


    Taxes:$10,144

    Elementary School: Baldwin Park Elementary

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 1302 MOSELLE AVE, ORLANDO, FL 32807

    $485,00067 Days on yellowkey   MLS ID: O6393827

    4 Days Off yellowkey (back on 5/19/2026)

    REDUCED by $10,000 (2.0%) on 05/01/2026

    For Sale O6393827 - 1302 MOSELLE AVE, ORLANDO, FL 32807 29 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1768
       Built: 2026   Tax: $671 (2025)
    Community: J J Kates Sub
    Single Family


    Estimated Monthly Payment: $2,713 (change assumption)
    Mortgage ($2,657) + Taxes in 2025 ($56)


    Taxes:$671

    Elementary School: Baldwin Park Elementary

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle




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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.