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Homes for Sale Near Winter Park High in Orlando - 71 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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  • 5314 OLD CHENEY HWY, ORLANDO, FL 32807

    $289,00070 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


  • 2260 GRENWICH AVE #2260, ORLANDO, FL 32817

    $215,00013 Days on yellowkey   MLS ID: O6392730

    For Sale O6392730 - 2260 GRENWICH AVE #2260, ORLANDO, FL 32817 47 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 874
       Built: 1991   Tax: $2,591 (2025)
    Community: Colonial Landings Ph 05
    Condo


    Estimated Monthly Payment: $1,394 (change assumption)
    Mortgage ($1,178) + Taxes in 2025 ($216)


    Taxes:$2,591

    Elementary School: Cheney Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Union Park Middle


  • 4416 TWINVIEW LN, ORLANDO, FL 32814

    $1,695,00052 Days on yellowkey   MLS ID: O6382016

    For Sale O6382016 - 4416 TWINVIEW LN, ORLANDO, FL 32814 70 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 4026
       Built: 2003
    Monthly Fee: $93
       Tax: $19,932 (2025)
    Community: Baldwin Park Ut 01 50 121
    Single Family


    Estimated Monthly Payment: $11,041 (change assumption)
    Mortgage ($9,287) + Fees ($93) + Taxes in 2025 ($1,661)


    Taxes:$19,932

    Elementary School: Baldwin Park Elementary

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 3884 LOWER PARK RD, ORLANDO, FL 32814

    $2,090,00016 Days on yellowkey   MLS ID: O6393290

    For Sale O6393290 - 3884 LOWER PARK RD, ORLANDO, FL 32814 53 photos

    Bed: 6   Bath: 5.5   Gar: 3
    Liv Area Sq Ft: 4315
       Built: 2004
    Monthly Fee: $93
       Tax: $17,622 (2025)
    Community: Baldwin Park
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $13,013 (change assumption)
    Mortgage ($11,452) + Fees ($93) + Taxes in 2025 ($1,469)


    Taxes:$17,622

    Elementary School: Baldwin Park Elementary

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 1800 PALM LN, ORLANDO, FL 32803

    $364,900109 Days on yellowkey   MLS ID: O6368846

    0 Days Off yellowkey (back on 4/8/2026)

    For Sale O6368846 - 1800 PALM LN, ORLANDO, FL 32803 36 photos

    Bed: 3   Bath: 1.0
    Liv Area Sq Ft: 1153
       Built: 1955   Tax: $5,299 (2025)
    Community: Lake Sue Park
    Single Family


    Estimated Monthly Payment: $2,441 (change assumption)
    Mortgage ($1,999) + Taxes in 2025 ($442)


    Taxes:$5,299

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 2142 LAKEMONT AVE, ORLANDO, FL 32814

    $799,000168 Days on yellowkey   MLS ID: O6354684

    1 Days Off yellowkey (back on 4/8/2026)

    For Sale O6354684 - 2142 LAKEMONT AVE, ORLANDO, FL 32814 75 photos

    Bed: 3   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2179
       Built: 2015
    Monthly Fee: $605
       Tax: $8,582 (2024)
    Community: City Homes
    Townhouse


    Estimated Monthly Payment: $5,698 (change assumption)
    Mortgage ($4,378) + Fees ($605) + Taxes in 2024 ($715)


    Taxes:$8,582

    Elementary School: Baldwin Park Elementary

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Glenridge Middle


  • 5218 DEXTER ST, ORLANDO, FL 32807

    $450,00020 Days on yellowkey   MLS ID: O6392244

    For Sale O6392244 - 5218 DEXTER ST, ORLANDO, FL 32807 31 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1391
       Built: 1959   Tax: $5,256 (2025)
    Community: Lake Barton Park
    Single Family


    Estimated Monthly Payment: $2,904 (change assumption)
    Mortgage ($2,466) + Taxes in 2025 ($438)


    Taxes:$5,256

    Elementary School: Baldwin Park Elementary

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 1302 MOSELLE AVE, ORLANDO, FL 32807

    $495,00013 Days on yellowkey   MLS ID: O6393827

    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: $2,768 (change assumption)
    Mortgage ($2,712) + Taxes in 2025 ($56)


    Taxes:$671

    Elementary School: Baldwin Park Elementary

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 3709 MOCKINGBIRD LN, ORLANDO, FL 32803

    $595,00035 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


  • 9717 LAKE DOUGLAS PL, ORLANDO, FL 32817

    $599,99914 Days on yellowkey   MLS ID: O6391068

    For Sale O6391068 - 9717 LAKE DOUGLAS PL, ORLANDO, FL 32817 49 photos

    Bed: 6   Bath: 6.0   Gar: 2
    Liv Area Sq Ft: 2855
       Built: 1987   Tax: $4,727 (2025)
    Community: Arbor Club
    Single Family


    Estimated Monthly Payment: $3,682 (change assumption)
    Mortgage ($3,288) + Taxes in 2025 ($394)


    Taxes:$4,727

    Elementary School: Arbor Ridge Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Union Park Middle


  • 2639 BETTY ST, ORLANDO, FL 32803

    $470,00021 Days on yellowkey   MLS ID: O6391321

    0 Days Off yellowkey (back on 4/7/2026)

    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


  • 2503 JAMIE CIR, ORLANDO, FL 32803

    $560,00062 Days on yellowkey   MLS ID: O6380344

    For Sale O6380344 - 2503 JAMIE CIR, ORLANDO, FL 32803 25 photos

    Bed: 4   Bath: 2.5
    Liv Area Sq Ft: 1449
       Built: 1954   Tax: $6,700 (2024)
    Community: Colonial Acres
    Single Family


    Estimated Monthly Payment: $3,627 (change assumption)
    Mortgage ($3,068) + Taxes in 2024 ($558)


    Taxes:$6,700

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Audubon Park K-8


  • 5441 BALDWIN PARK ST, ORLANDO, FL 32814

    $574,00020 Days on yellowkey   MLS ID: O6391146

    For Sale O6391146 - 5441 BALDWIN PARK ST, ORLANDO, FL 32814 60 photos

    Bed: 3   Bath: 2.5   Gar: 1
    Liv Area Sq Ft: 1640
       Built: 2007
    Monthly Fee: $534
       Tax: $6,059 (2025)
    Community: Baldwin Park
    Spa: No

    Townhouse


    Estimated Monthly Payment: $4,184 (change assumption)
    Mortgage ($3,145) + Fees ($534) + Taxes in 2025 ($505)


    Taxes:$6,059

    Elementary School: Baldwin Park Elementary

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 2001 GALE ST, ORLANDO, FL 32803

    $698,9006 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
    Spa: No

    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


  • 1954 MEETING PL, ORLANDO, FL 32814

    $890,0004 Days on yellowkey   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


  • 2613 JAMIE CIR, ORLANDO, FL 32803

    $400,0008 Days on yellowkey   MLS ID: O6395373

    2 Days Off yellowkey (back on 4/7/2026)

    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


  • 3504 FINCH ST, ORLANDO, FL 32803

    $799,00083 Days on yellowkey   MLS ID: O6371554

    2 Days Off yellowkey (back on 4/7/2026)

    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


  • 2721 E MARKS ST, ORLANDO, FL 32803

    $677,50083 Days on yellowkey   MLS ID: O6374453

    For Sale O6374453 - 2721 E MARKS ST, ORLANDO, FL 32803 21 photos

    Bed: 3   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1569
       Built: 1955   Tax: $9,249 (2025)
    Community: Primrose Terrace
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,483 (change assumption)
    Mortgage ($3,712) + Taxes in 2025 ($771)


    Taxes:$9,249

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 5460 PENWAY DR, ORLANDO, FL 32814

    $1,085,00046 Days on yellowkey   MLS ID: O6373241

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

    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


  • 8101 DOMINGUIN ST, ORLANDO, FL 32817

    $289,000418 Days on yellowkey   MLS ID: S5120808

    For Sale S5120808 - 8101 DOMINGUIN ST, ORLANDO, FL 32817 22 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1200
       Built: 1960   Tax: $3,558 (2024)
    Community: Sun Haven First Add
    Single Family


    Estimated Monthly Payment: $1,880 (change assumption)
    Mortgage ($1,584) + Taxes in 2024 ($297)


    Taxes:$3,558

    Elementary School: Cheney Elem

    High School: Winter Park High

    Tax Year: 2024

    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.