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Homes for Sale Near Winter Park High in Winter Park - 212 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, Winter Park nearby homes.

Location: Winter Park

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  • 914 ENCLAVE PL, WINTER PARK, FL 32792

    $1,895,000117 Days on yellowkey   MLS ID: O6391825

    For Sale O6391825 - 914 ENCLAVE PL, WINTER PARK, FL 32792 3 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3617
       Built: 2026
    Monthly Fee: $372
       Tax: $10,000 (2025)
    Community: The Enclave Winter Park
    Single Family


    Estimated Monthly Payment: $11,589 (change assumption)
    Mortgage ($10,383) + Fees ($372) + Taxes in 2025 ($833)


    Taxes:$10,000

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 1751 GLENCOE RD, WINTER PARK, FL 32789

    $3,390,000253 Days on yellowkey   MLS ID: O6339739

    REDUCED by $100,000 (2.9%) on 06/06/2026

    For Sale O6339739 - 1751 GLENCOE RD, WINTER PARK, FL 32789 45 photos

    Bed: 5   Bath: 6.0   Gar: 2
    Liv Area Sq Ft: 4520
       Built: 2025   Tax: $12,895 (2024)
    Community: Forest Hills
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $19,649 (change assumption)
    Mortgage ($18,575) + Taxes in 2024 ($1,075)


    Taxes:$12,895

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Audubon Park K-8


  • 275 N RANGER BLVD, WINTER PARK, FL 32792

    $775,00035 Days on yellowkey   MLS ID: O6415904

    For Sale O6415904 - 275 N RANGER BLVD, WINTER PARK, FL 32792 32 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 1950
       Built: 1965   Tax: $6,817 (2025)
    Community: Winter Park Pines Merrie Oaks
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,815 (change assumption)
    Mortgage ($4,246) + Taxes in 2025 ($568)


    Taxes:$6,817

    Elementary School: Aloma Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 1037 N VIRGINIA AVE, WINTER PARK, FL 32789

    $649,00020 Days on yellowkey   MLS ID: O6419694

    For Sale O6419694 - 1037 N VIRGINIA AVE, WINTER PARK, FL 32789 35 photos

    Bed: 3   Bath: 1.0   Gar: 1
    Liv Area Sq Ft: 1101
       Built: 1960   Tax: $7,186 (2024)
    Community: Tantum Add
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,155 (change assumption)
    Mortgage ($3,556) + Taxes in 2024 ($599)


    Taxes:$7,186

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Maitland Middle


  • 770 W WEBSTER AVE, WINTER PARK, FL 32789

    $725,000377 Days on yellowkey   MLS ID: O6323574

    1 Days Off yellowkey (back on 4/11/2026)

    For Sale O6323574 - 770 W WEBSTER AVE, WINTER PARK, FL 32789 34 photos

    Bed: 4   Bath: 2.0
    Liv Area Sq Ft: 1008
       Built: 1967   Tax: $4,856 (2024)
    Community: Capens Add
    Single Family


    Estimated Monthly Payment: $4,377 (change assumption)
    Mortgage ($3,973) + Taxes in 2024 ($405)


    Taxes:$4,856

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Maitland Middle


  • 1180 VIA LUGANO, WINTER PARK, FL 32789

    $4,900,00016 Days on yellowkey   MLS ID: O6413198

    For Sale O6413198 - 1180 VIA LUGANO, WINTER PARK, FL 32789 67 photos

    Bed: 5   Bath: 5.5   Gar: 3
    Liv Area Sq Ft: 4961
       Built: 2006   Tax: $43,400 (2025)
    Community: Woodmere Terrace Rep
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $30,465 (change assumption)
    Mortgage ($26,849) + Taxes in 2025 ($3,617)


    Taxes:$43,400

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 303 SCOTTSDALE SQ #303, WINTER PARK, FL 32792

    $80,0005 Days on yellowkey   MLS ID: O6424296

    For Sale O6424296 - 303 SCOTTSDALE SQ #303, WINTER PARK, FL 32792 3 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1020
       Built: 1974   Tax: $1,392 (2025)
    Community: Winter Park Woods Condo
    Condo


    Estimated Monthly Payment: $554 (change assumption)
    Mortgage ($438) + Taxes in 2025 ($116)


    Taxes:$1,392

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 2010 SUMMERFIELD RD, WINTER PARK, FL 32792

    $594,5005 Days on yellowkey   MLS ID: O6420140

    For Sale O6420140 - 2010 SUMMERFIELD RD, WINTER PARK, FL 32792 40 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1889
       Built: 1957   Tax: $7,917 (2025)
    Community: Kenilworth Shores Sec 07
    Single Family


    Estimated Monthly Payment: $3,917 (change assumption)
    Mortgage ($3,257) + Taxes in 2025 ($660)


    Taxes:$7,917

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 3019 ANTIQUE OAKS CIR #124, WINTER PARK, FL 32792

    $142,500327 Days on yellowkey   MLS ID: O6337083

    REDUCED by $2,000 (1.4%) on 07/10/2026

    For Sale O6337083 - 3019 ANTIQUE OAKS CIR #124, WINTER PARK, FL 32792 26 photos

    Bed: 1   Bath: 1.0
    Liv Area Sq Ft: 749
       Built: 1984
    Monthly Fee: $300
       Tax: $2,050 (2024)
    Community: Parkview Village
    Spa: No

    Condo


    Estimated Monthly Payment: $1,252 (change assumption)
    Mortgage ($781) + Fees ($300) + Taxes in 2024 ($171)


    Taxes:$2,050

    Elementary School: Aloma Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Glenridge Middle


  • 1946 STRATHAVEN RD, WINTER PARK, FL 32792

    $625,00049 Days on yellowkey   MLS ID: O6411329

    REDUCED by $25,000 (3.8%) on 07/10/2026

    For Sale O6411329 - 1946 STRATHAVEN RD, WINTER PARK, FL 32792 37 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2102
       Built: 1960   Tax: $8,540 (2025)
    Community: Kenilworth Shores Sec 07
    Single Family


    Estimated Monthly Payment: $4,136 (change assumption)
    Mortgage ($3,425) + Taxes in 2025 ($712)


    Taxes:$8,540

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 106 S INTERLACHEN AVE #118, WINTER PARK, FL 32789

    $1,295,000159 Days on yellowkey   MLS ID: O6380506

    3 Days Off yellowkey (back on 7/10/2026)

    REDUCED by $65,000 (4.8%) on 06/08/2026

    For Sale O6380506 - 106 S INTERLACHEN AVE #118, WINTER PARK, FL 32789 55 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1834
       Built: 1971   Tax: $9,767 (2025)
    Community: Cloisters Condo
    Condo


    Estimated Monthly Payment: $7,910 (change assumption)
    Mortgage ($7,096) + Taxes in 2025 ($814)


    Taxes:$9,767

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 3381 CEDAR SPRINGS PL #151, WINTER PARK, FL 32792

    $179,90020 Days on yellowkey   MLS ID: O6419959

    For Sale O6419959 - 3381 CEDAR SPRINGS PL #151, WINTER PARK, FL 32792 32 photos

    Bed: 2   Bath: 2.5
    Liv Area Sq Ft: 1031
       Built: 1984   Tax: $197 (2025)
    Community: Hidden. Oaks
    Spa: No

    Condo


    Estimated Monthly Payment: $1,002 (change assumption)
    Mortgage ($986) + Taxes in 2025 ($16)


    Taxes:$197

    Elementary School: Aloma Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 2700 CADY WAY, WINTER PARK, FL 32792

    $649,000288 Days on yellowkey   MLS ID: O6347690

    4 Days Off yellowkey (back on 7/10/2026)

    For Sale O6347690 - 2700 CADY WAY, WINTER PARK, FL 32792 49 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1876
       Built: 1965   Tax: $8,335 (2024)
    Community: Winter Park Pines Unit 4
    Single Family


    Estimated Monthly Payment: $4,251 (change assumption)
    Mortgage ($3,556) + Taxes in 2024 ($695)


    Taxes:$8,335

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Glenridge Middle


  • 981 ARAGON AVE, WINTER PARK, FL 32789

    $535,00019 Days on yellowkey   MLS ID: O6420093

    For Sale O6420093 - 981 ARAGON AVE, WINTER PARK, FL 32789 7 photos

    Bed: 2   Bath: 1.0   Gar: 1
    Liv Area Sq Ft: 857
       Built: 1956   Tax: $6,248 (2025)
    Community: Seville Park
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $3,452 (change assumption)
    Mortgage ($2,931) + Taxes in 2025 ($521)


    Taxes:$6,248

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 1138 S PENNSYLVANIA AVE, WINTER PARK, FL 32789

    $1,050,00019 Days on yellowkey   MLS ID: O6420090

    For Sale O6420090 - 1138 S PENNSYLVANIA AVE, WINTER PARK, FL 32789 35 photos

    Bed: 3   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2434
       Built: 2005
    Monthly Fee: $500
       Tax: $10,213 (2025)
    Community: Virginia Heights Rep
    Townhouse


    Estimated Monthly Payment: $7,104 (change assumption)
    Mortgage ($5,753) + Fees ($500) + Taxes in 2025 ($851)


    Taxes:$10,213

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 7471 CANFORD CT #19, WINTER PARK, FL 32792

    $199,000279 Days on yellowkey   MLS ID: G5103114

    For Sale G5103114 - 7471 CANFORD CT #19, WINTER PARK, FL 32792 15 photos

    Bed: 2   Bath: 1.5
    Liv Area Sq Ft: 1393
       Built: 1974   Tax: $2,750 (2024)
    Community: Whisperwood Condo
    Condo


    Estimated Monthly Payment: $1,320 (change assumption)
    Mortgage ($1,090) + Taxes in 2024 ($229)


    Taxes:$2,750

    Elementary School: Cheney Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Glenridge Middle


  • 311 E MORSE BLVD #7-19, WINTER PARK, FL 32789

    $284,900198 Days on yellowkey   MLS ID: O6368912

    REDUCED by $5,000 (1.7%) on 05/21/2026

    For Sale O6368912 - 311 E MORSE BLVD #7-19, WINTER PARK, FL 32789 27 photos

    Bed: 1   Bath: 1.0
    Liv Area Sq Ft: 482
       Built: 1960
    Monthly Fee: $870
       Tax: $3,161 (2024)
    Community: Whispering Waters
    Condo


    Estimated Monthly Payment: $2,694 (change assumption)
    Mortgage ($1,561) + Fees ($870) + Taxes in 2024 ($263)


    Taxes:$3,161

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Audubon Park K-8


  • 1830 EDWIN BLVD, WINTER PARK, FL 32789

    $625,00090 Days on yellowkey   MLS ID: O6400055

    0 Days Off yellowkey (back on 7/9/2026)

    REDUCED by $14,900 (2.3%) on 06/15/2026

    For Sale O6400055 - 1830 EDWIN BLVD, WINTER PARK, FL 32789 48 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1287
       Built: 1957   Tax: $3,955 (2025)
    Community: Campo Bello
    Single Family


    Estimated Monthly Payment: $3,754 (change assumption)
    Mortgage ($3,425) + Taxes in 2025 ($330)


    Taxes:$3,955

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 758 WARRENTON RD, WINTER PARK, FL 32792

    $318,985105 Days on yellowkey   MLS ID: O6395298

    For Sale O6395298 - 758 WARRENTON RD, WINTER PARK, FL 32792 52 photos

    Bed: 3   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1196
       Built: 1988
    Monthly Fee: $86
       Tax: $3,689 (2025)
    Community: Winter Park Pines Patio Homes
    Half Duplex


    Estimated Monthly Payment: $2,141 (change assumption)
    Mortgage ($1,748) + Fees ($86) + Taxes in 2025 ($307)


    Taxes:$3,689

    Elementary School: Aloma Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 609 S PHELPS AVE, WINTER PARK, FL 32789

    $2,829,000121 Days on yellowkey   MLS ID: O6388598

    For Sale O6388598 - 609 S PHELPS AVE, WINTER PARK, FL 32789 20 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 4018
       Built: 2026   Tax: $8,522 (2024)
    Community: Kenilworth Shores Sec 06
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $16,211 (change assumption)
    Mortgage ($15,501) + Taxes in 2024 ($710)


    Taxes:$8,522

    Elementary School: Brookshire 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, Winter Park . You can use our website to view Multiple Listing Service (MLS) data on Winter Park 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.