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Homes for Sale Near Winter Park High in Orlando - 113 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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  • 4392 WARDELL PL #201, ORLANDO, FL 32814

    $615,000Listed 06/10/2026 4:32PM   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

    $599,00028 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


  • 4743 LAKE SHARP DR, ORLANDO, FL 32817

    $450,00014 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


  • 803 HASKELL AVE, ORLANDO, FL 32807

    $369,99935 Days on yellowkey   MLS ID: TB8505733

    REDUCED by $5,001 (1.3%) on 06/10/2026

    For Sale TB8505733 - 803 HASKELL AVE, ORLANDO, FL 32807 18 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1197
       Built: 1957   Tax: $2,461 (2025)
    Community: Lake Barton Park
    Single Family


    Estimated Monthly Payment: $2,232 (change assumption)
    Mortgage ($2,027) + Taxes in 2025 ($205)


    Taxes:$2,461

    Elementary School: Baldwin Park Elementary

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 1408 VILLA MARIE DR, ORLANDO, FL 32807

    $339,00030 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


  • 5416 PENWAY DR, ORLANDO, FL 32814

    $939,000216 Days on yellowkey   MLS ID: O6357821

    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


  • 4495 TWINVIEW LN, ORLANDO, FL 32814

    $875,0005 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


  • 2409 GARBELIA AVE, ORLANDO, FL 32817

    $340,000199 Days on yellowkey   MLS ID: O6362011

    0 Days Off yellowkey (back on 4/30/2026)

    For Sale O6362011 - 2409 GARBELIA AVE, ORLANDO, FL 32817 83 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1010
       Built: 1970   Tax: $2,597 (2024)
    Community: Harrell Heights Rep
    Single Family


    Estimated Monthly Payment: $2,079 (change assumption)
    Mortgage ($1,863) + Taxes in 2024 ($216)


    Taxes:$2,597

    Elementary School: Cheney Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Union Park Middle


  • 224 CAPE SABLE DR, ORLANDO, FL 32825

    $459,0003 Days on yellowkey   MLS ID: O6414734

    For Sale O6414734 - 224 CAPE SABLE DR, ORLANDO, FL 32825 21 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1832
       Built: 2004
    Monthly Fee: $100
       Tax: $6,143 (2025)
    Community: Woodland Lakes
    Single Family


    Estimated Monthly Payment: $3,127 (change assumption)
    Mortgage ($2,515) + Fees ($100) + Taxes in 2025 ($512)


    Taxes:$6,143

    Elementary School: Cypress Springs Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Legacy Middle


  • 1777 FIREHOUSE LN #26104, ORLANDO, FL 32814

    $735,0008 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


  • 8825 BUTTERNUT BLVD, ORLANDO, FL 32817

    $455,90010 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


  • 918 SHOREVIEW DR, ORLANDO, FL 32807

    $309,00080 Days on yellowkey   MLS ID: O6392300

    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


  • 1604 COLE RD, ORLANDO, FL 32803

    $1,399,0004 Days on yellowkey   MLS ID: TB8516648

    For Sale TB8516648 - 1604 COLE RD, ORLANDO, FL 32803 4 photos

    Bed: 5   Bath: 4.0   Gar: 3
    Liv Area Sq Ft: 3465
       Built: 2026   Tax: $3,458 (2025)
    Community: Phillips Rep 01 Lakewood
    Single Family


    Estimated Monthly Payment: $7,954 (change assumption)
    Mortgage ($7,666) + Taxes in 2025 ($288)


    Taxes:$3,458

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 4029 TAMARISK WAY, ORLANDO, FL 32817

    $475,00022 Days on yellowkey   MLS ID: O6409365

    0 Days Off yellowkey (back on 5/22/2026)

    For Sale O6409365 - 4029 TAMARISK WAY, ORLANDO, FL 32817 49 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1992
       Built: 1979
    Monthly Fee: $67
       Tax: $2,650 (2025)
    Community: Woodside Village
    Single Family


    Estimated Monthly Payment: $2,891 (change assumption)
    Mortgage ($2,603) + Fees ($67) + Taxes in 2025 ($221)


    Taxes:$2,650

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 2506 WOODSIDE AVE, ORLANDO, FL 32803

    $1,149,0008 Days on yellowkey   MLS ID: O6413252

    For Sale O6413252 - 2506 WOODSIDE AVE, ORLANDO, FL 32803 21 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2642
       Built: 2017   Tax: $14,777 (2025)
    Community: Beeman Park
    Single Family


    Estimated Monthly Payment: $7,527 (change assumption)
    Mortgage ($6,296) + Taxes in 2025 ($1,231)


    Taxes:$14,777

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 1554 CHATFIELD PL, ORLANDO, FL 32814

    $715,0007 Days on yellowkey   MLS ID: O6413905

    For Sale O6413905 - 1554 CHATFIELD PL, ORLANDO, FL 32814 41 photos

    Bed: 3   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 1887
       Built: 2005
    Monthly Fee: $494
       Tax: $9,472 (2025)
    Community: Baldwin Park Unit 3
    Townhouse


    Estimated Monthly Payment: $5,201 (change assumption)
    Mortgage ($3,918) + Fees ($494) + Taxes in 2025 ($789)


    Taxes:$9,472

    Elementary School: Baldwin Park Elementary

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 4033 IBIS DR, ORLANDO, FL 32803

    $525,0007 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


  • 9717 LAKE DOUGLAS PL, ORLANDO, FL 32817

    $679,00077 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


  • 3861 BENTFORD CT, ORLANDO, FL 32817

    $399,90090 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


  • 2312 MONTANA ST, ORLANDO, FL 32803

    $1,425,00043 Days on yellowkey   MLS ID: TB8502758

    INCREASED by $46,000 (3.3%) on 06/07/2026

    For Sale TB8502758 - 2312 MONTANA ST, ORLANDO, FL 32803 2 photos

    Bed: 5   Bath: 4.0   Gar: 3
    Liv Area Sq Ft: 3465
       Built: 2026   Tax: $1,643 (2025)
    Community: Phillips Rep 01 Lakewood
    Spa: No

    Single Family


    Estimated Monthly Payment: $7,945 (change assumption)
    Mortgage ($7,808) + Taxes in 2025 ($137)


    Taxes:$1,643

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8




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.