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Homes for Sale Near Winter Park High in Orlando - 109 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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  • 5362 CHATAS LN, ORLANDO, FL 32814

    $749,000Listed 06/13/2026 12:05PM   MLS ID: O6415259

    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


  • 4033 IBIS DR, ORLANDO, FL 32803

    $525,00010 Days on yellowkey   MLS ID: O6413734

    For Sale O6413734 - 4033 IBIS DR, ORLANDO, FL 32803 29 photos

    Bed: 3   Bath: 1.0   Gar: 1
    Liv Area Sq Ft: 1190
       Built: 1956   Tax: $7,091 (2025)
    Community: Audubon Park Card Heights Sec
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,468 (change assumption)
    Mortgage ($2,877) + Taxes in 2025 ($591)


    Taxes:$7,091

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 4392 WARDELL PL #201, ORLANDO, FL 32814

    $615,0004 Days on yellowkey   MLS ID: O6411195

    For Sale O6411195 - 4392 WARDELL PL #201, ORLANDO, FL 32814 34 photos

    Bed: 3   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1434
       Built: 2006
    Monthly Fee: $838
       Tax: $4,311 (2025)
    Community: Baldwin Park #5
    Condo


    Estimated Monthly Payment: $4,567 (change assumption)
    Mortgage ($3,370) + Fees ($838) + Taxes in 2025 ($359)


    Taxes:$4,311

    Elementary School: Baldwin Park Elementary

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 1777 FIREHOUSE LN #26104, ORLANDO, FL 32814

    $735,00011 Days on yellowkey   MLS ID: O6411996

    For Sale O6411996 - 1777 FIREHOUSE LN #26104, ORLANDO, FL 32814 50 photos

    Bed: 3   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1737
       Built: 2010
    Monthly Fee: $93
       Tax: $5,136 (2025)
    Community: Baldwin Park 07
    Spa: No

    Condo


    Estimated Monthly Payment: $4,548 (change assumption)
    Mortgage ($4,027) + Fees ($93) + Taxes in 2025 ($428)


    Taxes:$5,136

    Elementary School: Baldwin Park Elementary

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 4743 LAKE SHARP DR, ORLANDO, FL 32817

    $450,00017 Days on yellowkey   MLS ID: O6411081

    For Sale O6411081 - 4743 LAKE SHARP DR, ORLANDO, FL 32817 35 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1879
       Built: 1991
    Monthly Fee: $6
       Tax: $1,692 (2025)
    Community: Watermill Sec 07
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,613 (change assumption)
    Mortgage ($2,466) + Fees ($6) + Taxes in 2025 ($141)


    Taxes:$1,692

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 1408 VILLA MARIE DR, ORLANDO, FL 32807

    $339,00033 Days on yellowkey   MLS ID: O6407157

    For Sale O6407157 - 1408 VILLA MARIE DR, ORLANDO, FL 32807 41 photos

    Bed: 3   Bath: 1.0   Gar: 1
    Liv Area Sq Ft: 1152
       Built: 1959   Tax: $2,320 (2025)
    Community: Corrine Terrace
    Single Family


    Estimated Monthly Payment: $2,051 (change assumption)
    Mortgage ($1,857) + Taxes in 2025 ($193)


    Taxes:$2,320

    Elementary School: Baldwin Park Elementary

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 771 LAKE BALDWIN LN, ORLANDO, FL 32803

    $599,00031 Days on yellowkey   MLS ID: O6407201

    REDUCED by $20,000 (3.2%) on 06/03/2026

    For Sale O6407201 - 771 LAKE BALDWIN LN, ORLANDO, FL 32803 36 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2001
       Built: 2020
    Monthly Fee: $80
       Tax: $8,054 (2025)
    Community: Lake Baldwin 5
    Townhouse


    Estimated Monthly Payment: $4,033 (change assumption)
    Mortgage ($3,282) + Fees ($80) + Taxes in 2025 ($671)


    Taxes:$8,054

    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

    $269,90091 Days on yellowkey   MLS ID: O6390840

    REDUCED by $5,000 (1.8%) on 06/11/2026

    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: $2,124 (change assumption)
    Mortgage ($1,479) + 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


  • 9509 HANDLEY CT, ORLANDO, FL 32817

    $399,0001 Day 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


  • 4301 UPPER UNION RD, ORLANDO, FL 32814

    $1,549,0002 Days on yellowkey   MLS ID: O6415559

    For Sale O6415559 - 4301 UPPER UNION RD, ORLANDO, FL 32814 51 photos

    Bed: 4   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 3107
       Built: 2004
    Monthly Fee: $102
       Tax: $16,475 (2025)
    Community: Baldwin Park
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $9,962 (change assumption)
    Mortgage ($8,487) + Fees ($102) + Taxes in 2025 ($1,373)


    Taxes:$16,475

    Elementary School: Baldwin Park Elementary

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 3861 BENTFORD CT, ORLANDO, FL 32817

    $399,90093 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 21 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


  • 2501 LONG MEADOW WAY, ORLANDO, FL 32817

    $299,0002 Days on yellowkey   MLS ID: O6415787

    For Sale O6415787 - 2501 LONG MEADOW WAY, ORLANDO, FL 32817 20 photos

    Bed: 3   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1079
       Built: 1986
    Monthly Fee: $13
       Tax: $4,044 (2025)
    Community: Carmel Park
    Spa: No

    Half Duplex


    Estimated Monthly Payment: $1,988 (change assumption)
    Mortgage ($1,638) + Fees ($13) + Taxes in 2025 ($337)


    Taxes:$4,044

    Elementary School: Arbor Ridge Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 1310 COLETTA DR, ORLANDO, FL 32807

    $314,99989 Days on yellowkey   MLS ID: O6386157

    REDUCED by $5,000 (1.6%) on 06/12/2026

    For Sale O6386157 - 1310 COLETTA DR, ORLANDO, FL 32807 34 photos

    Bed: 3   Bath: 1.5
    Liv Area Sq Ft: 1513
       Built: 1952   Tax: $5,177 (2025)
    Community: J J Kates Sub
    Single Family


    Estimated Monthly Payment: $2,157 (change assumption)
    Mortgage ($1,726) + Taxes in 2025 ($431)


    Taxes:$5,177

    Elementary School: Baldwin Park Elementary

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 4357 ROUSH AVE, ORLANDO, FL 32803

    $633,20236 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

    $517,50036 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


  • 2620 CAVANAUGH DR, ORLANDO, FL 32817

    $600,000173 Days on yellowkey   MLS ID: O6369315

    REDUCED by $25,000 (4.0%) on 06/12/2026

    For Sale O6369315 - 2620 CAVANAUGH DR, ORLANDO, FL 32817 2 photos

    Bed: 5   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2560
       Built: 2025
    Monthly Fee: $130
       Tax: $887 (2025)
    Community: Harrell Oaks
    Single Family


    Estimated Monthly Payment: $3,492 (change assumption)
    Mortgage ($3,288) + Fees ($130) + Taxes in 2025 ($74)


    Taxes:$887

    Elementary School: Cheney Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 4495 TWINVIEW LN, ORLANDO, FL 32814

    $875,0008 Days on yellowkey   MLS ID: O6412567

    For Sale O6412567 - 4495 TWINVIEW LN, ORLANDO, FL 32814 40 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2667
       Built: 2004
    Monthly Fee: $523
       Tax: $9,154 (2025)
    Community: Baldwin Park Unit 1
    Townhouse


    Estimated Monthly Payment: $6,080 (change assumption)
    Mortgage ($4,794) + Fees ($523) + Taxes in 2025 ($763)


    Taxes:$9,154

    Elementary School: Baldwin Park Elementary

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 5437 LEHIGH AVE, ORLANDO, FL 32807

    $385,0003 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


  • 918 SHOREVIEW DR, ORLANDO, FL 32807

    $309,00083 Days on yellowkey   MLS ID: O6392300

    0 Days Off yellowkey (back on 6/11/2026)

    REDUCED by $10,000 (3.1%) on 05/28/2026

    For Sale O6392300 - 918 SHOREVIEW DR, ORLANDO, FL 32807 40 photos

    Bed: 3   Bath: 1.0
    Liv Area Sq Ft: 1286
       Built: 1925   Tax: $4,837 (2025)
    Community: Lake Barton Park
    Single Family


    Estimated Monthly Payment: $2,096 (change assumption)
    Mortgage ($1,693) + Taxes in 2025 ($403)


    Taxes:$4,837

    Elementary School: Baldwin Park Elementary

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 1563 COMMON WAY RD, ORLANDO, FL 32814

    $599,990156 Days on yellowkey   MLS ID: O6371726

    REDUCED by $9,010 (1.5%) on 06/11/2026

    For Sale O6371726 - 1563 COMMON WAY RD, ORLANDO, FL 32814 43 photos

    Bed: 3   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 1871
       Built: 2005
    Monthly Fee: $620
       Tax: $10,738 (2024)
    Community: Baldwin Park
    Townhouse


    Estimated Monthly Payment: $4,802 (change assumption)
    Mortgage ($3,288) + Fees ($620) + Taxes in 2024 ($895)


    Taxes:$10,738

    Elementary School: Baldwin Park Elementary

    High School: Winter Park High

    Tax Year: 2024

    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.