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Homes for Sale Near Winter Park High in Orlando - 58 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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  • 2483 BECKY SUE DR, ORLANDO, FL 32807

    $359,000Listed 04/02/2026 6:43PM   MLS ID: V4947557

    For Sale V4947557 - 2483 BECKY SUE DR, ORLANDO, FL 32807 36 photos

    Bed: 4   Bath: 2.0
    Liv Area Sq Ft: 1709
       Built: 1971   Tax: $5,021 (2025)
    Community: Ivanhoe Estates
    Single Family


    Estimated Monthly Payment: $2,386 (change assumption)
    Mortgage ($1,967) + Taxes in 2025 ($418)


    Taxes:$5,021

    Elementary School: Cheney Elem

    High School: Winter Park High

    Tax Year: 2025

    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


  • 5416 PENWAY DR, ORLANDO, FL 32814

    $995,000146 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


  • 1407 MOSELLE AVE, ORLANDO, FL 32807

    $319,00031 Days on yellowkey   MLS ID: S5144920

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

    For Sale S5144920 - 1407 MOSELLE AVE, ORLANDO, FL 32807 15 photos

    Bed: 3   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1473
       Built: 1959   Tax: $2,800 (2025)
    Community: Corrine Terrace
    Single Family


    Estimated Monthly Payment: $1,981 (change assumption)
    Mortgage ($1,748) + Taxes in 2025 ($233)


    Taxes:$2,800

    Elementary School: Baldwin Park Elementary

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 2613 JAMIE CIR, ORLANDO, FL 32803

    $400,0001 Day on yellowkey   MLS ID: O6395373

    For Sale O6395373 - 2613 JAMIE CIR, ORLANDO, FL 32803 6 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


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

    $279,90018 Days on yellowkey   MLS ID: O6390840

    REDUCED by $5,100 (1.8%) on 04/02/2026

    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: $2,179 (change assumption)
    Mortgage ($1,534) + 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


  • 1206 COLETTA DR, ORLANDO, FL 32807

    $299,000154 Days on yellowkey   MLS ID: O6356330

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

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

    Bed: 3   Bath: 2.0   Gar: 1
    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


  • 1864 PROSPECT AVE, ORLANDO, FL 32814

    $649,00035 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


  • 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


  • 9730 LINGWOOD TRL, ORLANDO, FL 32817

    $359,0003 Days on yellowkey   MLS ID: NS1087435

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

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

    Bed: 3   Bath: 2.0   Gar: 2
    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


  • 1735 FOSS AVE, ORLANDO, FL 32814

    $3,295,0001 Day on yellowkey   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


  • 1550 LAKE BALDWIN LN #A, B, C, ORLANDO, FL 32814

    $1,228,000104 Days on yellowkey   MLS ID: O6368240

    4 Days Off yellowkey (back on 2/23/2026)

    For Sale O6368240 - 1550 LAKE BALDWIN LN #A, B, C, ORLANDO, FL 32814 56 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 3150
       Built: 2006
    Monthly Fee: $1,058
       Tax: $13,687 (2025)
    Community: Baldwin Park Unit 3 Rep 1
    Townhouse


    Estimated Monthly Payment: $8,927 (change assumption)
    Mortgage ($6,729) + Fees ($1,058) + Taxes in 2025 ($1,141)


    Taxes:$13,687

    Elementary School: Baldwin Park Elementary

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 1550 LAKE BALDWIN LN, ORLANDO, FL 32814

    $1,228,000105 Days on yellowkey   MLS ID: O6368227

    4 Days Off yellowkey (back on 2/23/2026)

    For Sale O6368227 - 1550 LAKE BALDWIN LN, ORLANDO, FL 32814 57 photos

    Bed: 7   Bath: 0.0   Gar: 2
    Liv Area Sq Ft: 3150
       Built: 2006
    Monthly Fee: $1,058
       Tax: $13,687 (2025)
    Community: Baldwin Park Unit 3 Rep 1
    Apartment


    Estimated Monthly Payment: $8,927 (change assumption)
    Mortgage ($6,729) + Fees ($1,058) + Taxes in 2025 ($1,141)


    Taxes:$13,687

    Elementary School: Baldwin Park Elementary

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 5218 DEXTER ST, ORLANDO, FL 32807

    $450,00013 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


  • 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


  • 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


  • 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


  • 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


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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.