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Homes for Sale Near Winter Park High in Orlando - 54 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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  • 4333 ROUSH AVE, ORLANDO, FL 32803

    $517,37038 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


  • 1511 HARSTON AVE, ORLANDO, FL 32814

    $2,090,000123 Days on yellowkey   MLS ID: O6363907

    0 Days Off yellowkey (back on 1/31/2026)

    For Sale O6363907 - 1511 HARSTON AVE, ORLANDO, FL 32814 83 photos

    Bed: 5   Bath: 5.5   Gar: 3
    Liv Area Sq Ft: 4823
       Built: 2006
    Monthly Fee: $93
       Tax: $29,213 (2025)
    Community: Baldwin Park Unit 9A
    Single Family


    Estimated Monthly Payment: $13,979 (change assumption)
    Mortgage ($11,452) + Fees ($93) + Taxes in 2025 ($2,434)


    Taxes:$29,213

    Elementary School: Baldwin Park Elementary

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 5460 PENWAY DR, ORLANDO, FL 32814

    $1,085,00039 Days on yellowkey   MLS ID: O6373241

    For Sale O6373241 - 5460 PENWAY DR, ORLANDO, FL 32814 42 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


  • 7920 DUNSTABLE CIR, ORLANDO, FL 32817

    $518,00077 Days on yellowkey   MLS ID: TB8464605

    For Sale TB8464605 - 7920 DUNSTABLE CIR, ORLANDO, FL 32817 24 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1988
       Built: 1984
    Monthly Fee: $7
       Tax: $2,993 (2025)
    Community: Aloma Estates
    Single Family


    Estimated Monthly Payment: $3,095 (change assumption)
    Mortgage ($2,838) + Fees ($7) + Taxes in 2025 ($249)


    Taxes:$2,993

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 2613 JAMIE CIR, ORLANDO, FL 32803

    $400,0001 Day on yellowkey   MLS ID: O6395373

    For Sale O6395373 - 2613 JAMIE CIR, ORLANDO, FL 32803 5 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


  • 1735 FOSS AVE, ORLANDO, FL 32814

    $3,295,000Listed 04/01/2026 3:33PM   MLS ID: O6394768

    For Sale O6394768 - 1735 FOSS AVE, ORLANDO, FL 32814 43 photos

    Bed: 5   Bath: 5.5   Gar: 2
    Liv Area Sq Ft: 5358
       Built: 2014
    Monthly Fee: $200
       Tax: $26,052 (2025)
    Community: Baldwin Park
    Single Family


    Estimated Monthly Payment: $20,425 (change assumption)
    Mortgage ($18,054) + Fees ($200) + Taxes in 2025 ($2,171)


    Taxes:$26,052

    Elementary School: Baldwin Park Elementary

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 8407 ROANNE DR, ORLANDO, FL 32817

    $398,5003 Days on yellowkey   MLS ID: O6394593

    For Sale O6394593 - 8407 ROANNE DR, ORLANDO, FL 32817 33 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1498
       Built: 1978   Tax: $5,198 (2025)
    Community: Glenwood Park Sub
    Single Family


    Estimated Monthly Payment: $2,617 (change assumption)
    Mortgage ($2,184) + Taxes in 2025 ($433)


    Taxes:$5,198

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 901 LAKE BALDWIN LN, ORLANDO, FL 32803

    $632,81670 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


  • 3504 FINCH ST, ORLANDO, FL 32803

    $799,00076 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


  • 972 BALDWIN COVE WAY, ORLANDO, FL 32803

    $610,00034 Days on yellowkey   MLS ID: O6385329

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

    For Sale O6385329 - 972 BALDWIN COVE WAY, ORLANDO, FL 32803 28 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2040
       Built: 2014
    Monthly Fee: $142
       Tax: $6,537 (2025)
    Community: Baldwin Cove
    Single Family


    Estimated Monthly Payment: $4,029 (change assumption)
    Mortgage ($3,342) + Fees ($142) + Taxes in 2025 ($545)


    Taxes:$6,537

    Elementary School: Baldwin Park Elementary

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 2035 LAKE SUE DR, ORLANDO, FL 32803

    $1,195,00037 Days on yellowkey   MLS ID: O6380179

    For Sale O6380179 - 2035 LAKE SUE DR, ORLANDO, FL 32803 45 photos

    Bed: 5   Bath: 3.5   Gar: 1
    Liv Area Sq Ft: 3490
       Built: 1938   Tax: $11,880 (2025)
    Community: Beeman Park
    Single Family


    Estimated Monthly Payment: $7,538 (change assumption)
    Mortgage ($6,548) + Taxes in 2025 ($990)


    Taxes:$11,880

    Elementary School: None

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 4408 LIPTON CT, ORLANDO, FL 32817

    $410,0008 Days on yellowkey   MLS ID: O6393729

    1 Days Off yellowkey (back on 3/31/2026)

    For Sale O6393729 - 4408 LIPTON CT, ORLANDO, FL 32817 34 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1715
       Built: 1988
    Monthly Fee: $8
       Tax: $6,174 (2025)
    Community: Watermill Sec 04
    Single Family


    Estimated Monthly Payment: $2,769 (change assumption)
    Mortgage ($2,247) + Fees ($8) + Taxes in 2025 ($515)


    Taxes:$6,174

    Elementary School: Arbor Ridge Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 4571 VIRGINIA DR, ORLANDO, FL 32814

    $690,000145 Days on yellowkey   MLS ID: O6357766

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

    Bed: 4   Bath: 4.0
    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


  • 9730 LINGWOOD TRL, ORLANDO, FL 32817

    $359,0003 Days on yellowkey   MLS ID: NS1087435

    For Sale NS1087435 - 9730 LINGWOOD TRL, ORLANDO, FL 32817 31 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1318
       Built: 1989   Tax: $1,532 (2025)
    Community: Arbor Ridge North Unit 3
    Single Family


    Estimated Monthly Payment: $2,095 (change assumption)
    Mortgage ($1,967) + Taxes in 2025 ($128)


    Taxes:$1,532

    Elementary School: Arbor Ridge Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Union Park Middle


  • 1206 COLETTA DR, ORLANDO, FL 32807

    $299,000154 Days on yellowkey   MLS ID: O6356330

    For Sale O6356330 - 1206 COLETTA DR, ORLANDO, FL 32807 20 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1520
       Built: 1979   Tax: $4,457 (2025)
    Community: J J Kates Sub
    Single Family


    Estimated Monthly Payment: $2,010 (change assumption)
    Mortgage ($1,638) + Taxes in 2025 ($371)


    Taxes:$4,457

    Elementary School: Baldwin Park Elementary

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 9717 LAKE DOUGLAS PL, ORLANDO, FL 32817

    $599,9997 Days on yellowkey   MLS ID: O6391068

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

    Bed: 6   Bath: 6.0
    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


  • 5441 BALDWIN PARK ST, ORLANDO, FL 32814

    $574,00013 Days on yellowkey   MLS ID: O6391146

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

    Bed: 3   Bath: 2.5
    Liv Area Sq Ft: 1640
       Built: 2007
    Monthly Fee: $534
       Tax: $6,059 (2025)
    Community: Baldwin Park
    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


  • 2414 ILLINOIS ST, ORLANDO, FL 32803

    $465,000182 Days on yellowkey   MLS ID: NS1086116

    For Sale NS1086116 - 2414 ILLINOIS ST, ORLANDO, FL 32803 33 photos

    Bed: 2   Bath: 1.0
    Liv Area Sq Ft: 1094
       Built: 1953   Tax: $7,656 (2024)
    Community: Colonial Acres
    Single Family


    Estimated Monthly Payment: $3,186 (change assumption)
    Mortgage ($2,548) + Taxes in 2024 ($638)


    Taxes:$7,656

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Audubon Park K-8


  • 8213 LOST LAKE DR, ORLANDO, FL 32817

    $459,00055 Days on yellowkey   MLS ID: O6376481

    3 Days Off yellowkey (back on 3/10/2026)

    For Sale O6376481 - 8213 LOST LAKE DR, ORLANDO, FL 32817 37 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1792
       Built: 1981
    Monthly Fee: $17
       Tax: $2,291 (2024)
    Community: Lost Lake Village
    Single Family


    Estimated Monthly Payment: $2,723 (change assumption)
    Mortgage ($2,515) + Fees ($17) + Taxes in 2024 ($191)


    Taxes:$2,291

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Maitland Middle


  • 1902 MERRITT PARK DR, ORLANDO, FL 32803

    $685,0003 Days on yellowkey   MLS ID: O6394769

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

    For Sale O6394769 - 1902 MERRITT PARK DR, ORLANDO, FL 32803 1 photos

    Bed: 4   Bath: 2.0
    Liv Area Sq Ft: 2000
       Built: 1958   Tax: $10,273 (2025)
    Community: Merritt Park
    Single Family


    Estimated Monthly Payment: $4,609 (change assumption)
    Mortgage ($3,753) + Taxes in 2025 ($856)


    Taxes:$10,273

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


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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.