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Homes for Sale Near Winter Park High in Orlando - 108 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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  • 9717 LAKE DOUGLAS PL, ORLANDO, FL 32817

    $635,000119 Days on yellowkey   MLS ID: O6391068

    REDUCED by $44,000 (6.5%) on 07/01/2026

    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: $3,873 (change assumption)
    Mortgage ($3,479) + 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


  • 1426 KINGSTON AVE, ORLANDO, FL 32807

    $349,90036 Days on yellowkey   MLS ID: O6417700

    5 Days Off yellowkey (back on 7/1/2026)

    For Sale O6417700 - 1426 KINGSTON AVE, ORLANDO, FL 32807 32 photos

    Bed: 3   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1658
       Built: 1974   Tax: $1,260 (2025)
    Community: Leawood
    Single Family


    Estimated Monthly Payment: $2,022 (change assumption)
    Mortgage ($1,917) + Taxes in 2025 ($105)


    Taxes:$1,260

    Elementary School: Baldwin Park Elementary

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 2936 MOORCROFT CT, ORLANDO, FL 32817

    $485,00048 Days on yellowkey   MLS ID: O6413385

    For Sale O6413385 - 2936 MOORCROFT CT, ORLANDO, FL 32817 20 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1670
       Built: 1994   Tax: $2,294 (2025)
    Community: Arbor Pointe
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $2,849 (change assumption)
    Mortgage ($2,657) + Taxes in 2025 ($191)


    Taxes:$2,294

    Elementary School: Arbor Ridge Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 2959 UPPER PARK RD, ORLANDO, FL 32814

    $589,00049 Days on yellowkey   MLS ID: O6412043

    3 Days Off yellowkey (back on 6/29/2026)

    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


  • 2506 WOODSIDE AVE, ORLANDO, FL 32803

    $1,149,00050 Days on yellowkey   MLS ID: O6413252

    For Sale O6413252 - 2506 WOODSIDE AVE, ORLANDO, FL 32803 41 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


  • 3861 BENTFORD CT, ORLANDO, FL 32817

    $399,900132 Days on yellowkey   MLS ID: O6388156

    0 Days Off yellowkey (back on 6/27/2026)

    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


  • 2312 MONTANA ST, ORLANDO, FL 32803

    $1,425,00085 Days on yellowkey   MLS ID: TB8502758

    3 Days Off yellowkey (back on 6/26/2026)

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

    For Sale TB8502758 - 2312 MONTANA ST, ORLANDO, FL 32803 4 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


  • 2721 E MARKS ST, ORLANDO, FL 32803

    $675,000188 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


  • 5362 CHATAS LN, ORLANDO, FL 32814

    $749,00040 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


  • 1777 FIREHOUSE LN #26104, ORLANDO, FL 32814

    $674,90050 Days on yellowkey   MLS ID: O6411996

    0 Days Off yellowkey (back on 6/19/2026)

    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


  • 2501 COLE RD, ORLANDO, FL 32803

    $1,875,00079 Days on yellowkey   MLS ID: O6403103

    For Sale O6403103 - 2501 COLE RD, ORLANDO, FL 32803 13 photos

    Bed: 5   Bath: 5.5   Gar: 2
    Liv Area Sq Ft: 3750
       Built: 2026   Tax: $846 (2025)
    Community: Phillips Rep 01 Lakewood
    Single Family


    Estimated Monthly Payment: $10,344 (change assumption)
    Mortgage ($10,274) + Taxes in 2025 ($71)


    Taxes:$846

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 8013 RHEA CIR, ORLANDO, FL 32807

    $320,000190 Days on yellowkey   MLS ID: O6373437

    0 Days Off yellowkey (back on 6/18/2026)

    REDUCED by $10,000 (3.0%) on 05/16/2026

    For Sale O6373437 - 8013 RHEA CIR, ORLANDO, FL 32807 31 photos

    Bed: 3   Bath: 1.0
    Liv Area Sq Ft: 1025
       Built: 1970   Tax: $3,535 (2025)
    Community: Ivanhoe Estates
    Single Family


    Estimated Monthly Payment: $2,048 (change assumption)
    Mortgage ($1,753) + Taxes in 2025 ($295)


    Taxes:$3,535

    Elementary School: Cheney Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 4301 UPPER UNION RD, ORLANDO, FL 32814

    $1,549,00041 Days on yellowkey   MLS ID: O6415559

    1 Days Off yellowkey (back on 6/17/2026)

    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


  • 1353 CHATFIELD PL, ORLANDO, FL 32814

    $569,000132 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


  • 1567 LAKE BALDWIN LN, ORLANDO, FL 32814

    $1,399,00076 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


  • 8825 BUTTERNUT BLVD, ORLANDO, FL 32817

    $455,90052 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


  • 3884 LOWER PARK RD, ORLANDO, FL 32814

    $1,895,000121 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


  • 2726 & 2740 N DEAN RD, ORLANDO, FL 32817

    $2,600,0001192 Days on yellowkey   MLS ID: O6104701

    12 Days Off yellowkey (back on 8/2/2023)

    For Sale O6104701 - 2726 & 2740 N DEAN RD, ORLANDO, FL 32817 9 photos

    Bed: 6   Bath: 4.0
    Liv Area Sq Ft: 4304
       Built: 1947   Tax: $2,320 (2022)
    Community: Orlando
    Single Family


    Estimated Monthly Payment: $14,440 (change assumption)
    Mortgage ($14,246) + Taxes in 2022 ($193)


    Taxes:$2,320

    Elementary School: Arbor Ridge Elem

    High School: Winter Park High

    Tax Year: 2022

    Middle School: Union Park Middle


  • 2733 MIDDLE ST, ORLANDO, FL 32807

    $395,000118 Days on yellowkey   MLS ID: O6394410

    REDUCED by $5,000 (1.3%) on 05/26/2026

    For Sale O6394410 - 2733 MIDDLE ST, ORLANDO, FL 32807 23 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1204
       Built: 1975   Tax: $5,667 (2025)
    Community: Hanging Moss Estates
    Single Family


    Estimated Monthly Payment: $2,637 (change assumption)
    Mortgage ($2,164) + Taxes in 2025 ($472)


    Taxes:$5,667

    Elementary School: Cheney Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 4036 BIBB LN, ORLANDO, FL 32817

    $440,000167 Days on yellowkey   MLS ID: O6379247

    REDUCED by $10,000 (2.2%) on 05/26/2026

    For Sale O6379247 - 4036 BIBB LN, ORLANDO, FL 32817 32 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1645
       Built: 1980   Tax: $3,374 (2024)
    Community: Harbor East
    Single Family


    Estimated Monthly Payment: $2,692 (change assumption)
    Mortgage ($2,411) + Taxes in 2024 ($281)


    Taxes:$3,374

    Elementary School: Aloma Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Glenridge Middle




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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.