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Homes for Sale Near Winter Park High in Orlando - 106 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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  • 1567 LAKE BALDWIN LN, ORLANDO, FL 32814

    $1,399,00038 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

    $385,0004 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

    $399,90094 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

    $399,0003 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


  • 1777 FIREHOUSE LN #26104, ORLANDO, FL 32814

    $674,90012 Days on yellowkey   MLS ID: O6411996

    REDUCED by $60,100 (8.2%) on 06/15/2026

    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: $4,219 (change assumption)
    Mortgage ($3,698) + 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


  • 9915 KONA ISLE CT, ORLANDO, FL 32817

    $449,90024 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

    $455,90014 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


  • 9517 DARIEN AVE #9517, ORLANDO, FL 32817

    $190,000178 Days on yellowkey   MLS ID: O6368148

    REDUCED by $2,000 (1.0%) on 06/04/2026

    For Sale O6368148 - 9517 DARIEN AVE #9517, ORLANDO, FL 32817 26 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 992
       Built: 1987   Tax: $2,298 (2024)
    Community: Colonial Landings Ph 04
    Condo


    Estimated Monthly Payment: $1,233 (change assumption)
    Mortgage ($1,041) + Taxes in 2024 ($192)


    Taxes:$2,298

    Elementary School: Cheney Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Union Park Middle


  • 5362 CHATAS LN, ORLANDO, FL 32814

    $749,0002 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

    $355,00084 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

    $1,895,00083 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


  • 1408 VILLA MARIE DR, ORLANDO, FL 32807

    $339,00034 Days on yellowkey   MLS ID: O6407157

    0 Days Off yellowkey (back on 6/14/2026)

    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


  • 4512 BRIDGEWATER DR, ORLANDO, FL 32817

    $890,000191 Days on yellowkey   MLS ID: O6365659

    REDUCED by $5,000 (0.6%) on 06/14/2026

    For Sale O6365659 - 4512 BRIDGEWATER DR, ORLANDO, FL 32817 46 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2091
       Built: 1983   Tax: $7,214 (2025)
    Community: Watermill Sec 01
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $5,478 (change assumption)
    Mortgage ($4,877) + Taxes in 2025 ($601)


    Taxes:$7,214

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 4392 WARDELL PL #201, ORLANDO, FL 32814

    $615,0005 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


  • 771 LAKE BALDWIN LN, ORLANDO, FL 32803

    $599,00032 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


  • 4495 TWINVIEW LN, ORLANDO, FL 32814

    $875,0009 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


  • 9717 LAKE DOUGLAS PL, ORLANDO, FL 32817

    $679,00081 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


  • 4301 UPPER UNION RD, ORLANDO, FL 32814

    $1,549,0003 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


  • 4033 IBIS DR, ORLANDO, FL 32803

    $525,00011 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


  • 4743 LAKE SHARP DR, ORLANDO, FL 32817

    $450,00018 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




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.