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Homes for Sale Near Winter Park High in Winter Park - 128 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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  • 1210 FAIRWAY DR, WINTER PARK, FL 32792

    $549,000Listed 04/13/2026 11:42AM   MLS ID: O6398533

    For Sale O6398533 - 1210 FAIRWAY DR, WINTER PARK, FL 32792 38 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1737
       Built: 1979   Tax: $7,265 (2025)
    Community: Golfside Sec 3
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,614 (change assumption)
    Mortgage ($3,008) + Taxes in 2025 ($605)


    Taxes:$7,265

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 240 N PHELPS AVE, WINTER PARK, FL 32789

    $2,279,00035 Days on yellowkey   MLS ID: O6389035

    For Sale O6389035 - 240 N PHELPS AVE, WINTER PARK, FL 32789 68 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 2889
       Built: 2026   Tax: $6,605 (2025)
    Community: Sylvan Heights
    Spa: No

    Single Family


    Estimated Monthly Payment: $13,038 (change assumption)
    Mortgage ($12,487) + Taxes in 2025 ($550)


    Taxes:$6,605

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 543 E LAKE SUE AVE, WINTER PARK, FL 32789

    $1,875,0004 Days on yellowkey   MLS ID: O6397480

    1 Days Off yellowkey (back on 4/13/2026)

    For Sale O6397480 - 543 E LAKE SUE AVE, WINTER PARK, FL 32789 47 photos

    Bed: 4   Bath: 4.5   Gar: 3
    Liv Area Sq Ft: 3657
       Built: 1986   Tax: $14,126 (2025)
    Community: Lake Virginia Pt Rep
    Spa: No

    Single Family


    Estimated Monthly Payment: $11,451 (change assumption)
    Mortgage ($10,274) + Taxes in 2025 ($1,177)


    Taxes:$14,126

    Elementary School: None

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


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

    $299,900105 Days on yellowkey   MLS ID: O6368912

    For Sale O6368912 - 311 E MORSE BLVD #7-19, WINTER PARK, FL 32789 34 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: $2,777 (change assumption)
    Mortgage ($1,643) + 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


  • 3054 BLUEBROOK DR, WINTER PARK, FL 32792

    $427,500Listed 04/12/2026 11:09PM   MLS ID: O6398450

    For Sale O6398450 - 3054 BLUEBROOK DR, WINTER PARK, FL 32792 27 photos

    Bed: 3   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1939
       Built: 1973   Tax: $6,422 (2025)
    Community: Laurel Spgs
    Single Family


    Estimated Monthly Payment: $2,878 (change assumption)
    Mortgage ($2,342) + Taxes in 2025 ($535)


    Taxes:$6,422

    Elementary School: Aloma Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 2919 BOWER RD, WINTER PARK, FL 32792

    $779,00025 Days on yellowkey   MLS ID: O6391025

    3 Days Off yellowkey (back on 4/13/2026)

    For Sale O6391025 - 2919 BOWER RD, WINTER PARK, FL 32792 38 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2325
       Built: 1971   Tax: $9,857 (2025)
    Community: Winter Park Pines
    Single Family


    Estimated Monthly Payment: $5,090 (change assumption)
    Mortgage ($4,268) + Taxes in 2025 ($821)


    Taxes:$9,857

    Elementary School: None

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 647 RANDY LN, WINTER PARK, FL 32789

    $1,795,00035 Days on yellowkey   MLS ID: O6387217

    For Sale O6387217 - 647 RANDY LN, WINTER PARK, FL 32789 64 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2851
       Built: 1957   Tax: $5,627 (2025)
    Community: Timberlane
    Single Family


    Estimated Monthly Payment: $10,304 (change assumption)
    Mortgage ($9,835) + Taxes in 2025 ($469)


    Taxes:$5,627

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 850 JUANITA RAEL, WINTER PARK, FL 32789

    $1,425,00096 Days on yellowkey   MLS ID: O6370568

    1 Days Off yellowkey (back on 1/12/2026)

    For Sale O6370568 - 850 JUANITA RAEL, WINTER PARK, FL 32789 50 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2306
       Built: 1966   Tax: $6,218 (2024)
    Community: Green Oaks Rep 03
    Spa: No

    Single Family


    Estimated Monthly Payment: $8,326 (change assumption)
    Mortgage ($7,808) + Taxes in 2024 ($518)


    Taxes:$6,218

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Maitland Middle


  • 3312 HEARTWOOD AVE, WINTER PARK, FL 32792

    $465,000177 Days on yellowkey   MLS ID: O6352582

    1 Days Off yellowkey (back on 4/13/2026)

    REDUCED by $19,000 (3.9%) on 04/08/2026

    For Sale O6352582 - 3312 HEARTWOOD AVE, WINTER PARK, FL 32792 36 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2878
       Built: 1983   Tax: $2,183 (2025)
    Community: Bel-Aire Pines
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,730 (change assumption)
    Mortgage ($2,548) + Taxes in 2025 ($182)


    Taxes:$2,183

    Elementary School: Aloma Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 3021 AARON BURR AVE #3, WINTER PARK, FL 32792

    $140,000Listed 04/12/2026 11:07PM   MLS ID: S5147382

    For Sale S5147382 - 3021 AARON BURR AVE #3, WINTER PARK, FL 32792 21 photos

    Bed: 2   Bath: 2.5
    Liv Area Sq Ft: 1090
       Built: 1974
    Monthly Fee: $479
       Tax: $1,992 (2025)
    Community: Colonies
    Condo


    Estimated Monthly Payment: $1,412 (change assumption)
    Mortgage ($767) + Fees ($479) + Taxes in 2025 ($166)


    Taxes:$1,992

    Elementary School: Cheney Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 851 MILES AVE #13, WINTER PARK, FL 32789

    $209,999116 Days on yellowkey   MLS ID: O6368234

    For Sale O6368234 - 851 MILES AVE #13, WINTER PARK, FL 32789 24 photos

    Bed: 2   Bath: 1.0
    Liv Area Sq Ft: 808
       Built: 1984   Tax: $2,694 (2025)
    Community: Aragon Condo
    Condo


    Estimated Monthly Payment: $1,375 (change assumption)
    Mortgage ($1,151) + Taxes in 2025 ($224)


    Taxes:$2,694

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 1507 GOLFSIDE DR, WINTER PARK, FL 32792

    $975,00011 Days on yellowkey   MLS ID: O6395355

    For Sale O6395355 - 1507 GOLFSIDE DR, WINTER PARK, FL 32792 44 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2003
       Built: 1981   Tax: $2,783 (2025)
    Community: Greenview At Winter Pines
    Single Family


    Estimated Monthly Payment: $5,574 (change assumption)
    Mortgage ($5,342) + Taxes in 2025 ($232)


    Taxes:$2,783

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 720 W WEBSTER AVE, WINTER PARK, FL 32789

    $550,00039 Days on yellowkey   MLS ID: G5108643

    For Sale G5108643 - 720 W WEBSTER AVE, WINTER PARK, FL 32789 43 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1356
       Built: 1950   Tax: $5,128 (2024)
    Community: Carver Town
    Single Family


    Estimated Monthly Payment: $3,441 (change assumption)
    Mortgage ($3,014) + Taxes in 2024 ($427)


    Taxes:$5,128

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Maitland Middle


  • 1108 FAIRWAY DR, WINTER PARK, FL 32792

    $725,00045 Days on yellowkey   MLS ID: O6386266

    For Sale O6386266 - 1108 FAIRWAY DR, WINTER PARK, FL 32792 46 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1677
       Built: 1978   Tax: $6,713 (2024)
    Community: Golfside Sec 03
    Single Family


    Estimated Monthly Payment: $4,532 (change assumption)
    Mortgage ($3,973) + Taxes in 2024 ($559)


    Taxes:$6,713

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Glenridge Middle


  • 676 DUNBLANE DR, WINTER PARK, FL 32792

    $750,000129 Days on yellowkey   MLS ID: O6365557

    For Sale O6365557 - 676 DUNBLANE DR, WINTER PARK, FL 32792 35 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1827
       Built: 1962   Tax: $5,584 (2024)
    Community: Kenilworth Shores Sec 04
    Single Family


    Estimated Monthly Payment: $4,575 (change assumption)
    Mortgage ($4,109) + Taxes in 2024 ($465)


    Taxes:$5,584

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Glenridge Middle


  • 2702 PARKLAND DR, WINTER PARK, FL 32789

    $1,175,0003 Days on yellowkey   MLS ID: O6397997

    For Sale O6397997 - 2702 PARKLAND DR, WINTER PARK, FL 32789 48 photos

    Bed: 5   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2656
       Built: 1949   Tax: $5,269 (2025)
    Community: Parklando
    Single Family


    Estimated Monthly Payment: $6,877 (change assumption)
    Mortgage ($6,438) + Taxes in 2025 ($439)


    Taxes:$5,269

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 318 VITORIA AVE, WINTER PARK, FL 32789

    $2,200,00017 Days on yellowkey   MLS ID: O6388489

    For Sale O6388489 - 318 VITORIA AVE, WINTER PARK, FL 32789 69 photos

    Bed: 3   Bath: 2.5
    Liv Area Sq Ft: 2433
       Built: 1922   Tax: $2,960 (2024)
    Community: College Quarter
    Spa: No

    Single Family


    Estimated Monthly Payment: $12,301 (change assumption)
    Mortgage ($12,054) + Taxes in 2024 ($247)


    Taxes:$2,960

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Glenridge Middle


  • 906 ENCLAVE PL, WINTER PARK, FL 32792

    $1,925,00024 Days on yellowkey   MLS ID: O6383092

    For Sale O6383092 - 906 ENCLAVE PL, WINTER PARK, FL 32792 5 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3618
       Built: 2026
    Monthly Fee: $372
       Tax: $9,900 (2026)
    Community: The Enclave Winter Park
    Single Family


    Estimated Monthly Payment: $11,745 (change assumption)
    Mortgage ($10,548) + Fees ($372) + Taxes in 2026 ($825)


    Taxes:$9,900

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2026

    Middle School: Maitland Middle


  • 1760 GREENWICH AVE, WINTER PARK, FL 32789

    $650,00025 Days on yellowkey   MLS ID: O6392001

    For Sale O6392001 - 1760 GREENWICH AVE, WINTER PARK, FL 32789 18 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1610
       Built: 1967   Tax: $2,779 (2025)
    Community: Golfview Heights
    Single Family


    Estimated Monthly Payment: $3,793 (change assumption)
    Mortgage ($3,562) + Taxes in 2025 ($232)


    Taxes:$2,779

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 1870 WALKER AVE, WINTER PARK, FL 32789

    $1,425,00031 Days on yellowkey   MLS ID: O6390504

    For Sale O6390504 - 1870 WALKER AVE, WINTER PARK, FL 32789 20 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2046
       Built: 2026   Tax: $3,981 (2025)
    Community: Osceola Heights
    Single Family


    Estimated Monthly Payment: $8,140 (change assumption)
    Mortgage ($7,808) + Taxes in 2025 ($332)


    Taxes:$3,981

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle




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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.