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Homes for Sale Near Winter Park High in Winter Park - 217 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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  • 2614 PARKLAND DR, WINTER PARK, FL 32789

    $1,899,000452 Days on yellowkey   MLS ID: O6301489

    REDUCED by $11,000 (0.6%) on 07/12/2026

    For Sale O6301489 - 2614 PARKLAND DR, WINTER PARK, FL 32789 54 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3307
       Built: 2007   Tax: $12,712 (2024)
    Community: Parklando 03
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $11,465 (change assumption)
    Mortgage ($10,405) + Taxes in 2024 ($1,059)


    Taxes:$12,712

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Audubon Park K-8


  • 101 S NEW YORK AVE #311, WINTER PARK, FL 32789

    $1,849,90029 Days on yellowkey   MLS ID: O6416927

    For Sale O6416927 - 101 S NEW YORK AVE #311, WINTER PARK, FL 32789 39 photos

    Bed: 3   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3112
       Built: 2008
    Monthly Fee: $1,303
       Tax: $20,039 (2025)
    Community: Winter Park Residential
    Condo


    Estimated Monthly Payment: $13,109 (change assumption)
    Mortgage ($10,136) + Fees ($1,303) + Taxes in 2025 ($1,670)


    Taxes:$20,039

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 437 N CAPEN AVE, WINTER PARK, FL 32789

    $849,00031 Days on yellowkey   MLS ID: O6414283

    For Sale O6414283 - 437 N CAPEN AVE, WINTER PARK, FL 32789 36 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1904
       Built: 2016
    Monthly Fee: $400
       Tax: $11,943 (2025)
    Community: Canton Ave Cottages 1
    Single Family


    Estimated Monthly Payment: $6,047 (change assumption)
    Mortgage ($4,652) + Fees ($400) + Taxes in 2025 ($995)


    Taxes:$11,943

    Elementary School: Killarney Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 446 MELROSE AVE, WINTER PARK, FL 32789

    $1,625,00080 Days on yellowkey   MLS ID: O6402113

    REDUCED by $70,000 (4.1%) on 06/18/2026

    For Sale O6402113 - 446 MELROSE AVE, WINTER PARK, FL 32789 39 photos

    Bed: 4   Bath: 2.0
    Liv Area Sq Ft: 2640
       Built: 1987   Tax: $20,217 (2025)
    Community: Virginia Heights Rep
    Spa: No

    Single Family


    Estimated Monthly Payment: $10,589 (change assumption)
    Mortgage ($8,904) + Taxes in 2025 ($1,685)


    Taxes:$20,217

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 2625 PARK PLACE DR, WINTER PARK, FL 32789

    $1,799,00027 Days on yellowkey   MLS ID: O6413031

    REDUCED by $151,000 (7.7%) on 07/09/2026

    For Sale O6413031 - 2625 PARK PLACE DR, WINTER PARK, FL 32789 55 photos

    Bed: 4   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3460
       Built: 2002
    Monthly Fee: $146
       Tax: $9,695 (2025)
    Community: Winter Park Place 45/148
    Single Family


    Estimated Monthly Payment: $10,811 (change assumption)
    Mortgage ($9,857) + Fees ($146) + Taxes in 2025 ($808)


    Taxes:$9,695

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: None


  • 715 S RANGER BLVD, WINTER PARK, FL 32792

    $695,00051 Days on yellowkey   MLS ID: O6410899

    For Sale O6410899 - 715 S RANGER BLVD, WINTER PARK, FL 32792 48 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2312
       Built: 1967
    Monthly Fee: $4
       Tax: $2,773 (2025)
    Community: Winter Park Pines
    Single Family


    Estimated Monthly Payment: $4,043 (change assumption)
    Mortgage ($3,808) + Fees ($4) + Taxes in 2025 ($231)


    Taxes:$2,773

    Elementary School: Aloma Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 1611 CHESTNUT AVE, WINTER PARK, FL 32789

    $1,040,00077 Days on yellowkey   MLS ID: O6402502

    REDUCED by $30,000 (2.8%) on 07/10/2026

    For Sale O6402502 - 1611 CHESTNUT AVE, WINTER PARK, FL 32789 50 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 2916
       Built: 1973   Tax: $3,590 (2025)
    Community: Lake Knowles Terrace
    Single Family


    Estimated Monthly Payment: $5,998 (change assumption)
    Mortgage ($5,698) + Taxes in 2025 ($299)


    Taxes:$3,590

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 2501 WINTER PARK RD, WINTER PARK, FL 32789

    $1,649,000134 Days on yellowkey   MLS ID: O6384756

    REDUCED by $41,000 (2.4%) on 05/14/2026

    For Sale O6384756 - 2501 WINTER PARK RD, WINTER PARK, FL 32789 63 photos

    Bed: 5   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3304
       Built: 2014   Tax: $10,938 (2024)
    Community: Parklando #3
    Single Family


    Estimated Monthly Payment: $9,947 (change assumption)
    Mortgage ($9,035) + Taxes in 2024 ($912)


    Taxes:$10,938

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2024

    Middle School: None


  • 528 SAINT DUNSTAN WAY, WINTER PARK, FL 32792

    $524,99036 Days on yellowkey   MLS ID: O6414677

    REDUCED by $10,010 (1.9%) on 07/11/2026

    For Sale O6414677 - 528 SAINT DUNSTAN WAY, WINTER PARK, FL 32792 35 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1656
       Built: 1964   Tax: $6,000 (2025)
    Community: Winter Park Pines
    Single Family


    Estimated Monthly Payment: $3,377 (change assumption)
    Mortgage ($2,877) + Taxes in 2025 ($500)


    Taxes:$6,000

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 1807 HAMMERLIN AVE #G, WINTER PARK, FL 32789

    $515,000121 Days on yellowkey   MLS ID: O6391277

    REDUCED by $10,000 (1.9%) on 06/15/2026

    For Sale O6391277 - 1807 HAMMERLIN AVE #G, WINTER PARK, FL 32789 29 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1818
       Built: 2006   Tax: $6,197 (2025)
    Community: Terrazo Del Sol
    Condo


    Estimated Monthly Payment: $3,338 (change assumption)
    Mortgage ($2,822) + Taxes in 2025 ($516)


    Taxes:$6,197

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 1265 ARLINGTON PL, WINTER PARK, FL 32789

    $849,90035 Days on yellowkey   MLS ID: O6415981

    REDUCED by $29,100 (3.3%) on 07/11/2026

    For Sale O6415981 - 1265 ARLINGTON PL, WINTER PARK, FL 32789 38 photos

    Bed: 3   Bath: 3.5   Gar: 1
    Liv Area Sq Ft: 2030
       Built: 2014   Tax: $8,450 (2025)
    Community: Virginia Hgts Rep
    Spa: No

    Townhouse


    Estimated Monthly Payment: $5,361 (change assumption)
    Mortgage ($4,657) + Taxes in 2025 ($704)


    Taxes:$8,450

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 512 W SWOOPE AVE, WINTER PARK, FL 32789

    $1,399,00028 Days on yellowkey   MLS ID: O6417375

    For Sale O6417375 - 512 W SWOOPE AVE, WINTER PARK, FL 32789 46 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2585
       Built: 2023
    Monthly Fee: $659
       Tax: $15,833 (2025)
    Community: Vilasa Twnhms
    Townhouse


    Estimated Monthly Payment: $9,644 (change assumption)
    Mortgage ($7,666) + Fees ($659) + Taxes in 2025 ($1,319)


    Taxes:$15,833

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 641 NORTHWOOD CIRCLE, WINTER PARK, FL 32789

    $1,725,00045 Days on yellowkey   MLS ID: O6412554

    REDUCED by $70,000 (3.9%) on 07/09/2026

    For Sale O6412554 - 641 NORTHWOOD CIRCLE, WINTER PARK, FL 32789 41 photos

    Bed: 3   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 2756
       Built: 2023   Tax: $18,393 (2025)
    Community: Winter Park Oasis
    Single Family


    Estimated Monthly Payment: $10,985 (change assumption)
    Mortgage ($9,452) + Taxes in 2025 ($1,533)


    Taxes:$18,393

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 950 ENCLAVE PL, WINTER PARK, FL 32792

    $2,125,00049 Days on yellowkey   MLS ID: O6410963

    For Sale O6410963 - 950 ENCLAVE PL, WINTER PARK, FL 32792 3 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3797
       Built: 2027
    Monthly Fee: $124
       Tax: $9,900 (2026)
    Community: The Enclave Winter Park
    Single Family


    Estimated Monthly Payment: $12,593 (change assumption)
    Mortgage ($11,644) + Fees ($124) + Taxes in 2026 ($825)


    Taxes:$9,900

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2026

    Middle School: Maitland Middle


  • 926 ENCLAVE PL, WINTER PARK, FL 32792

    $2,235,00057 Days on yellowkey   MLS ID: O6408030

    For Sale O6408030 - 926 ENCLAVE PL, WINTER PARK, FL 32792 6 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 4150
       Built: 2026
    Monthly Fee: $124
       Tax: $9,900 (2026)
    Community: The Enclave Winter Park
    Single Family


    Estimated Monthly Payment: $13,195 (change assumption)
    Mortgage ($12,246) + Fees ($124) + Taxes in 2026 ($825)


    Taxes:$9,900

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2026

    Middle School: Maitland Middle


  • 938 ENCLAVE PL, WINTER PARK, FL 32792

    $2,099,00057 Days on yellowkey   MLS ID: O6408090

    For Sale O6408090 - 938 ENCLAVE PL, WINTER PARK, FL 32792 7 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3865
       Built: 2026
    Monthly Fee: $124
       Tax: $9,900 (2026)
    Community: The Enclave Winter Park
    Single Family


    Estimated Monthly Payment: $12,450 (change assumption)
    Mortgage ($11,501) + Fees ($124) + Taxes in 2026 ($825)


    Taxes:$9,900

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2026

    Middle School: Maitland Middle


  • 910 ENCLAVE PL, WINTER PARK, FL 32792

    $1,899,00063 Days on yellowkey   MLS ID: O6406803

    For Sale O6406803 - 910 ENCLAVE PL, WINTER PARK, FL 32792 4 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3620
       Built: 2027
    Monthly Fee: $124
       Tax: $9,900 (2026)
    Community: The Enclave Winter Park
    Single Family


    Estimated Monthly Payment: $11,354 (change assumption)
    Mortgage ($10,405) + Fees ($124) + Taxes in 2026 ($825)


    Taxes:$9,900

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2026

    Middle School: Maitland Middle


  • 930 ENCLAVE PL, WINTER PARK, FL 32792

    $2,050,00063 Days on yellowkey   MLS ID: O6403032

    For Sale O6403032 - 930 ENCLAVE PL, WINTER PARK, FL 32792 4 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3813
       Built: 2026
    Monthly Fee: $124
       Tax: $9,900 (2026)
    Community: The Enclave Winter Park
    Single Family


    Estimated Monthly Payment: $12,182 (change assumption)
    Mortgage ($11,233) + Fees ($124) + Taxes in 2026 ($825)


    Taxes:$9,900

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2026

    Middle School: Maitland Middle


  • 2430 CHANTILLY AVE, WINTER PARK, FL 32789

    $1,599,00063 Days on yellowkey   MLS ID: O6401352

    REDUCED by $66,000 (4.0%) on 07/07/2026

    For Sale O6401352 - 2430 CHANTILLY AVE, WINTER PARK, FL 32789 49 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 2916
       Built: 2026   Tax: $4,730 (2025)
    Community: Winter Park Village
    Spa: No

    Single Family


    Estimated Monthly Payment: $9,156 (change assumption)
    Mortgage ($8,761) + Taxes in 2025 ($394)


    Taxes:$4,730

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 901 ENCLAVE PL, WINTER PARK, FL 32792

    $1,495,000118 Days on yellowkey   MLS ID: O6383602

    For Sale O6383602 - 901 ENCLAVE PL, WINTER PARK, FL 32792 2 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2738
       Built: 2026
    Monthly Fee: $247
       Tax: $9,900 (2026)
    Community: The Enclave Winter Park
    Townhouse


    Estimated Monthly Payment: $9,264 (change assumption)
    Mortgage ($8,192) + Fees ($247) + Taxes in 2026 ($825)


    Taxes:$9,900

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2026

    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, 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.