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Homes for Sale Near Winter Park High in Orlando - 105 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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  • 1353 CHATFIELD PL, ORLANDO, FL 32814

    $569,00097 Days on yellowkey   MLS ID: O6389946

    REDUCED by $26,000 (4.4%) on 06/16/2026

    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: $4,037 (change assumption)
    Mortgage ($3,118) + 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


  • 9889 LAKE GEORGIA DR, ORLANDO, FL 32817

    $2,790,00015 Days on yellowkey   MLS ID: O6412657

    For Sale O6412657 - 9889 LAKE GEORGIA DR, ORLANDO, FL 32817 82 photos

    Bed: 5   Bath: 6.5   Gar: 3
    Liv Area Sq Ft: 5638
       Built: 2022   Tax: $22,108 (2025)
    Community: Lake Georgia Shores
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $17,130 (change assumption)
    Mortgage ($15,287) + Taxes in 2025 ($1,842)


    Taxes:$22,108

    Elementary School: Arbor Ridge Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 9717 LAKE DOUGLAS PL, ORLANDO, FL 32817

    $679,00084 Days on yellowkey   MLS ID: O6391068

    REDUCED by $70,000 (9.3%) on 05/29/2026

    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: $4,114 (change assumption)
    Mortgage ($3,720) + 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


  • 2959 UPPER PARK RD, ORLANDO, FL 32814

    $589,00014 Days on yellowkey   MLS ID: O6412043

    For Sale O6412043 - 2959 UPPER PARK RD, ORLANDO, FL 32814 63 photos

    Bed: 2   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1897
       Built: 2005
    Monthly Fee: $534
       Tax: $9,857 (2025)
    Community: Baldwin Park
    Townhouse


    Estimated Monthly Payment: $4,583 (change assumption)
    Mortgage ($3,227) + Fees ($534) + Taxes in 2025 ($821)


    Taxes:$9,857

    Elementary School: Baldwin Park Elementary

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 9405 HOLBROOK DR, ORLANDO, FL 32817

    $380,000525 Days on yellowkey   MLS ID: O6270005

    For Sale O6270005 - 9405 HOLBROOK DR, ORLANDO, FL 32817 14 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1828
       Built: 1986   Tax: $6,453 (2024)
    Community: Watermill Sec 02
    Single Family


    Estimated Monthly Payment: $2,620 (change assumption)
    Mortgage ($2,082) + Taxes in 2024 ($538)


    Taxes:$6,453

    Elementary School: Arbor Ridge Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Maitland Middle


  • 4365 ROUSH AVE, ORLANDO, FL 32803

    $516,57040 Days on yellowkey   MLS ID: TB8505940

    For Sale TB8505940 - 4365 ROUSH AVE, ORLANDO, FL 32803 22 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: $3,163 (change assumption)
    Mortgage ($2,830) + 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


  • 4345 ROUSH AVE, ORLANDO, FL 32803

    $517,37043 Days on yellowkey   MLS ID: TB8505792

    For Sale TB8505792 - 4345 ROUSH AVE, ORLANDO, FL 32803 20 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: $3,167 (change assumption)
    Mortgage ($2,835) + 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


  • 4357 ROUSH AVE, ORLANDO, FL 32803

    $633,20240 Days on yellowkey   MLS ID: TB8507003

    For Sale TB8507003 - 4357 ROUSH AVE, ORLANDO, FL 32803 32 photos

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


    Estimated Monthly Payment: $3,803 (change assumption)
    Mortgage ($3,470) + 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


  • 4353 ROUSH AVE, ORLANDO, FL 32803

    $517,50040 Days on yellowkey   MLS ID: TB8507013

    For Sale TB8507013 - 4353 ROUSH AVE, ORLANDO, FL 32803 34 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


  • 5416 PENWAY DR, ORLANDO, FL 32814

    $939,000223 Days on yellowkey   MLS ID: O6357821

    0 Days Off yellowkey (back on 6/15/2026)

    REDUCED by $10,999 (1.2%) on 06/09/2026

    For Sale O6357821 - 5416 PENWAY DR, ORLANDO, FL 32814 79 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: $5,898 (change assumption)
    Mortgage ($5,145) + 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


  • 2721 E MARKS ST, ORLANDO, FL 32803

    $675,000153 Days on yellowkey   MLS ID: O6374453

    REDUCED by $2,500 (0.4%) on 04/29/2026

    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: $4,469 (change assumption)
    Mortgage ($3,699) + 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


  • 1567 LAKE BALDWIN LN, ORLANDO, FL 32814

    $1,399,00041 Days on yellowkey   MLS ID: O6406178

    3 Days Off yellowkey (back on 6/15/2026)

    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


  • 5437 LEHIGH AVE, ORLANDO, FL 32807

    $385,0007 Days on yellowkey   MLS ID: O6413840

    For Sale O6413840 - 5437 LEHIGH AVE, ORLANDO, FL 32807 38 photos

    Bed: 3   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1097
       Built: 1998   Tax: $5,116 (2025)
    Community: Lake Barton Park
    Single Family


    Estimated Monthly Payment: $2,536 (change assumption)
    Mortgage ($2,110) + Taxes in 2025 ($426)


    Taxes:$5,116

    Elementary School: Baldwin Park Elementary

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 3861 BENTFORD CT, ORLANDO, FL 32817

    $399,90097 Days on yellowkey   MLS ID: O6388156

    REDUCED by $10,100 (2.5%) on 04/17/2026

    For Sale O6388156 - 3861 BENTFORD CT, ORLANDO, FL 32817 25 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1571
       Built: 1990
    Monthly Fee: $28
       Tax: $5,492 (2024)
    Community: Bradford Cove Ph 01
    Single Family


    Estimated Monthly Payment: $2,677 (change assumption)
    Mortgage ($2,191) + Fees ($28) + Taxes in 2024 ($458)


    Taxes:$5,492

    Elementary School: Aloma Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Glenridge Middle


  • 9509 HANDLEY CT, ORLANDO, FL 32817

    $399,0006 Days on yellowkey   MLS ID: O6416400

    For Sale O6416400 - 9509 HANDLEY CT, ORLANDO, FL 32817 25 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1142
       Built: 1987   Tax: $5,163 (2025)
    Community: Arbor Ridge North
    Single Family


    Estimated Monthly Payment: $2,617 (change assumption)
    Mortgage ($2,186) + Taxes in 2025 ($430)


    Taxes:$5,163

    Elementary School: Arbor Ridge Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Arbor Ridge Middle


  • 9915 KONA ISLE CT, ORLANDO, FL 32817

    $449,90027 Days on yellowkey   MLS ID: O6409497

    0 Days Off yellowkey (back on 6/15/2026)

    For Sale O6409497 - 9915 KONA ISLE CT, ORLANDO, FL 32817 28 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1965
       Built: 1998
    Monthly Fee: $35
       Tax: $2,442 (2025)
    Community: Deans Reserve
    Single Family


    Estimated Monthly Payment: $2,704 (change assumption)
    Mortgage ($2,465) + Fees ($35) + Taxes in 2025 ($204)


    Taxes:$2,442

    Elementary School: Arbor Ridge Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 8825 BUTTERNUT BLVD, ORLANDO, FL 32817

    $455,90017 Days on yellowkey   MLS ID: O6404329

    0 Days Off yellowkey (back on 6/8/2026)

    For Sale O6404329 - 8825 BUTTERNUT BLVD, ORLANDO, FL 32817 50 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1722
       Built: 1979
    Monthly Fee: $67
       Tax: $2,346 (2025)
    Community: Woodside Village
    Single Family


    Estimated Monthly Payment: $2,761 (change assumption)
    Mortgage ($2,498) + Fees ($67) + Taxes in 2025 ($196)


    Taxes:$2,346

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 5362 CHATAS LN, ORLANDO, FL 32814

    $749,0005 Days on yellowkey   MLS ID: O6415259

    0 Days Off yellowkey (back on 6/15/2026)

    For Sale O6415259 - 5362 CHATAS LN, ORLANDO, FL 32814 27 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1509
       Built: 2006
    Monthly Fee: $102
       Tax: $8,052 (2025)
    Community: Baldwin Park Un 09A
    Single Family


    Estimated Monthly Payment: $4,877 (change assumption)
    Mortgage ($4,104) + Fees ($102) + Taxes in 2025 ($671)


    Taxes:$8,052

    Elementary School: Baldwin Park Elementary

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 2620 WOODS EDGE CIR, ORLANDO, FL 32817

    $355,00087 Days on yellowkey   MLS ID: O6391878

    For Sale O6391878 - 2620 WOODS EDGE CIR, ORLANDO, FL 32817 26 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1498
       Built: 1997
    Monthly Fee: $9
       Tax: $4,195 (2025)
    Community: Econ River Estates
    Single Family


    Estimated Monthly Payment: $2,304 (change assumption)
    Mortgage ($1,945) + Fees ($9) + Taxes in 2025 ($350)


    Taxes:$4,195

    Elementary School: Arbor Ridge Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Union Park Middle


  • 3884 LOWER PARK RD, ORLANDO, FL 32814

    $1,895,00086 Days on yellowkey   MLS ID: O6393290

    3 Days Off yellowkey (back on 6/15/2026)

    REDUCED by $195,000 (9.3%) on 05/28/2026

    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: $11,945 (change assumption)
    Mortgage ($10,383) + 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




Why Bother Searching Elsewhere for Homes For Sale and Real Estate nearby Winter Park High?

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.