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Winter Park Homes for Sale in Winter Park - 73 homes

Winter Park homes for sale are located in Orange County, Florida. Find Winter Park Homes in Winter Park for sale with data from the Multiple Listing Service (MLS). Our REALTORS® can assist you in your search for Winter Park, Winter Park homes.

Location: Winter Park, Winter Park

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  • 3651 N GOLDENROD RD #D102, WINTER PARK, FL 32792

    $157,90064 Days on yellowkey   MLS ID: O6401114

    REDUCED by $100 (0.1%) on 06/17/2026

    For Sale O6401114 - 3651 N GOLDENROD RD #D102, WINTER PARK, FL 32792 16 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 840
       Built: 1990
    Monthly Fee: $370
       Tax: $2,461 (2025)
    Community: Lancelot/Winter Park
    Condo


    Estimated Monthly Payment: $1,440 (change assumption)
    Mortgage ($865) + Fees ($370) + Taxes in 2025 ($205)


    Taxes:$2,461

    Elementary School: Aloma Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 2718 SANDWELL DR, WINTER PARK, FL 32792

    $525,0006 Days on yellowkey   MLS ID: O6410283

    0 Days Off yellowkey (back on 6/20/2026)

    For Sale O6410283 - 2718 SANDWELL DR, WINTER PARK, FL 32792 56 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1597
       Built: 1968
    Monthly Fee: $5
       Tax: $2,105 (2025)
    Community: Winter Park Pines
    Single Family


    Estimated Monthly Payment: $3,057 (change assumption)
    Mortgage ($2,877) + Fees ($5) + Taxes in 2025 ($175)


    Taxes:$2,105

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 700 MELROSE AVE #J24, WINTER PARK, FL 32789

    $390,00033 Days on yellowkey   MLS ID: R4911307

    For Sale R4911307 - 700 MELROSE AVE #J24, WINTER PARK, FL 32789 28 photos

    Bed: 2   Bath: 1.0
    Liv Area Sq Ft: 987
       Built: 1964   Tax: $3,874 (2025)
    Community: Winter Park Gardens Condo
    Condo


    Estimated Monthly Payment: $2,460 (change assumption)
    Mortgage ($2,137) + Taxes in 2025 ($323)


    Taxes:$3,874

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2430 CHANTILLY AVE, WINTER PARK, FL 32789

    $1,665,00041 Days on yellowkey   MLS ID: O6401352

    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: $9,517 (change assumption)
    Mortgage ($9,123) + Taxes in 2025 ($394)


    Taxes:$4,730

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 700 MELROSE AVE #F 21, WINTER PARK, FL 32789

    $235,90019 Days on yellowkey   MLS ID: O6413612

    For Sale O6413612 - 700 MELROSE AVE #F 21, WINTER PARK, FL 32789 27 photos

    Bed: 1   Bath: 1.0
    Liv Area Sq Ft: 787
       Built: 1964   Tax: $1,123 (2025)
    Community: Winter Park Gdns Condo
    Condo


    Estimated Monthly Payment: $1,386 (change assumption)
    Mortgage ($1,293) + Taxes in 2025 ($94)


    Taxes:$1,123

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 946 ENCLAVE PL, WINTER PARK, FL 32792

    $2,175,00027 Days on yellowkey   MLS ID: O6411633

    For Sale O6411633 - 946 ENCLAVE PL, WINTER PARK, FL 32792 3 photos

    Bed: 5   Bath: 5.5   Gar: 2
    Liv Area Sq Ft: 3989
       Built: 2026
    Monthly Fee: $375
       Tax: $9,900 (2026)
    Community: The Enclave Winter Park
    Single Family


    Estimated Monthly Payment: $13,118 (change assumption)
    Mortgage ($11,918) + Fees ($375) + Taxes in 2026 ($825)


    Taxes:$9,900

    Elementary School: None

    High School: None

    Tax Year: 2026

    Middle School: None


  • 950 ENCLAVE PL, WINTER PARK, FL 32792

    $2,125,00027 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


  • 930 ENCLAVE PL, WINTER PARK, FL 32792

    $2,050,00041 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


  • 901 ENCLAVE PL, WINTER PARK, FL 32792

    $1,495,00096 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


  • 905 ENCLAVE PL, WINTER PARK, FL 32792

    $1,495,00096 Days on yellowkey   MLS ID: O6383679

    For Sale O6383679 - 905 ENCLAVE PL, WINTER PARK, FL 32792 2 photos

    Bed: 3   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2756
       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


  • 914 ENCLAVE PL, WINTER PARK, FL 32792

    $1,895,00096 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


  • 205 LEWFIELD CIR #205, WINTER PARK, FL 32792

    $182,900163 Days on yellowkey   MLS ID: S5141588

    REDUCED by $37,100 (16.9%) on 06/20/2026

    For Sale S5141588 - 205 LEWFIELD CIR #205, WINTER PARK, FL 32792 24 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 927
       Built: 1973   Tax: $796 (2024)
    Community: Stratford A Winter Park Condo
    Condo


    Estimated Monthly Payment: $1,069 (change assumption)
    Mortgage ($1,002) + Taxes in 2024 ($66)


    Taxes:$796

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 2625 PARK PLACE DR, WINTER PARK, FL 32789

    $1,950,0005 Days on yellowkey   MLS ID: O6413031

    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: $11,639 (change assumption)
    Mortgage ($10,685) + 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


  • 256 LEWFIELD CIR #256, WINTER PARK, FL 32792

    $184,900164 Days on yellowkey   MLS ID: O6367842

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

    For Sale O6367842 - 256 LEWFIELD CIR #256, WINTER PARK, FL 32792 55 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 927
       Built: 1973
    Monthly Fee: $465
       Tax: $1,916 (2025)
    Community: Stratford A Winter Park Condo
    Condo


    Estimated Monthly Payment: $1,638 (change assumption)
    Mortgage ($1,013) + Fees ($465) + Taxes in 2025 ($160)


    Taxes:$1,916

    Elementary School: English Estates Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 2715 PRINCE JOHN RD, WINTER PARK, FL 32792

    $504,90016 Days on yellowkey   MLS ID: O6415084

    REDUCED by $15,000 (2.9%) on 06/19/2026

    For Sale O6415084 - 2715 PRINCE JOHN RD, WINTER PARK, FL 32792 29 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1565
       Built: 1963   Tax: $7,101 (2025)
    Community: Winter Park Pines Rep
    Single Family


    Estimated Monthly Payment: $3,358 (change assumption)
    Mortgage ($2,767) + Taxes in 2025 ($592)


    Taxes:$7,101

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 1695 LEE RD #B204, WINTER PARK, FL 32789

    $130,000151 Days on yellowkey   MLS ID: O6375348

    INCREASED by $10,000 (8.3%) on 06/18/2026

    For Sale O6375348 - 1695 LEE RD #B204, WINTER PARK, FL 32789 21 photos

    Bed: 2   Bath: 1.0
    Built: 1966
       Tax: $2,084 (2025)
    Community: Waterfall Cove At Winter Park Condo
    Condo


    Estimated Monthly Payment: $886 (change assumption)
    Mortgage ($712) + Taxes in 2025 ($174)


    Taxes:$2,084

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2700 CADY WAY, WINTER PARK, FL 32792

    $649,000267 Days on yellowkey   MLS ID: O6347690

    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


  • 140 E MORSE BLVD #J, WINTER PARK, FL 32789

    $2,350,0007 Days on yellowkey   MLS ID: O6414891

    For Sale O6414891 - 140 E MORSE BLVD #J, WINTER PARK, FL 32789 38 photos

    Bed: 3   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2143
       Built: 2008   Tax: $18,655 (2025)
    Community: Landmark Winter Park Condo
    Condo


    Estimated Monthly Payment: $14,431 (change assumption)
    Mortgage ($12,876) + Taxes in 2025 ($1,555)


    Taxes:$18,655

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 2501 LAFAYETTE AVE, WINTER PARK, FL 32789

    $1,795,0007 Days on yellowkey   MLS ID: O6416565

    For Sale O6416565 - 2501 LAFAYETTE AVE, WINTER PARK, FL 32789 22 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 2819
       Built: 2026   Tax: $4,608 (2026)
    Community: Winter Park Village
    Single Family


    Estimated Monthly Payment: $10,219 (change assumption)
    Mortgage ($9,835) + Taxes in 2026 ($384)


    Taxes:$4,608

    Elementary School: None

    High School: None

    Tax Year: 2026

    Middle School: None


  • 1404 BORDER DR, WINTER PARK, FL 32789

    $1,175,00026 Days on yellowkey   MLS ID: O6412140

    REDUCED by $25,000 (2.1%) on 06/16/2026

    For Sale O6412140 - 1404 BORDER DR, WINTER PARK, FL 32789 38 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 2469
       Built: 2023   Tax: $16,220 (2025)
    Community: Winter Park Village
    Single Family


    Estimated Monthly Payment: $7,790 (change assumption)
    Mortgage ($6,438) + Taxes in 2025 ($1,352)


    Taxes:$16,220

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle




Why Bother Searching Elsewhere for Winter Park Homes for Sale and Other Winter Park Real Estate?

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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.