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Winter Park Homes for Sale in Winter Park - 70 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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  • 938 ENCLAVE PL, WINTER PARK, FL 32792

    $2,099,00024 Days on yellowkey   MLS ID: O6408090

    For Sale O6408090 - 938 ENCLAVE PL, WINTER PARK, FL 32792 4 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


  • 942 ENCLAVE PL, WINTER PARK, FL 32792

    $2,195,00016 Days on yellowkey   MLS ID: O6411550

    For Sale O6411550 - 942 ENCLAVE PL, WINTER PARK, FL 32792 3 photos

    Bed: 5   Bath: 5.0   Gar: 2
    Liv Area Sq Ft: 3831
       Built: 2026
    Monthly Fee: $372
       Tax: $9,900 (2026)
    Community: The Enclave Winter Park
    Single Family


    Estimated Monthly Payment: $13,224 (change assumption)
    Mortgage ($12,027) + Fees ($372) + 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

    $2,125,00016 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


  • 946 ENCLAVE PL, WINTER PARK, FL 32792

    $2,175,00016 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


  • 738 S PENNSYLVANIA AVE, WINTER PARK, FL 32789

    $735,0005 Days on yellowkey   MLS ID: S5151458

    0 Days Off yellowkey (back on 6/10/2026)

    For Sale S5151458 - 738 S PENNSYLVANIA AVE, WINTER PARK, FL 32789 55 photos

    Bed: 3   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1739
       Built: 1925   Tax: $2,730 (2025)
    Community: Winter Park
    Single Family


    Estimated Monthly Payment: $4,255 (change assumption)
    Mortgage ($4,027) + Taxes in 2025 ($228)


    Taxes:$2,730

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 2715 PRINCE JOHN RD, WINTER PARK, FL 32792

    $519,9005 Days on yellowkey   MLS ID: O6415084

    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: $3,440 (change assumption)
    Mortgage ($2,849) + 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 #E116, WINTER PARK, FL 32789

    $110,00040 Days on yellowkey   MLS ID: O6399346

    0 Days Off yellowkey (back on 6/9/2026)

    REDUCED by $15,000 (12.0%) on 06/02/2026

    For Sale O6399346 - 1695 LEE RD #E116, WINTER PARK, FL 32789 29 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1149
       Built: 1966
    Monthly Fee: $624
       Tax: $2,263 (2025)
    Community: Waterfall Cove/Winter Park
    Condo


    Estimated Monthly Payment: $1,415 (change assumption)
    Mortgage ($603) + Fees ($624) + Taxes in 2025 ($189)


    Taxes:$2,263

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 119 OAK GROVE RD, WINTER PARK, FL 32789

    $285,00065 Days on yellowkey   MLS ID: O6397460

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

    For Sale O6397460 - 119 OAK GROVE RD, WINTER PARK, FL 32789 13 photos

    Bed: 3   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1134
       Built: 1994   Tax: $608 (2025)
    Community: Winter Park Oaks
    Single Family


    Estimated Monthly Payment: $1,612 (change assumption)
    Mortgage ($1,562) + Taxes in 2025 ($51)


    Taxes:$608

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 505 CORNWALL RD, WINTER PARK, FL 32792

    $675,00024 Days on yellowkey   MLS ID: O6408759

    1 Days Off yellowkey (back on 6/9/2026)

    For Sale O6408759 - 505 CORNWALL RD, WINTER PARK, FL 32792 42 photos

    Bed: 4   Bath: 2.0
    Liv Area Sq Ft: 1813
       Built: 1965   Tax: $7,194 (2025)
    Community: Winter Park Pines
    Single Family


    Estimated Monthly Payment: $4,298 (change assumption)
    Mortgage ($3,699) + Taxes in 2025 ($600)


    Taxes:$7,194

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 650 DOUGLAS AVE, WINTER PARK, FL 32789

    $550,0005 Days on yellowkey   MLS ID: O6414807

    0 Days Off yellowkey (back on 6/8/2026)

    For Sale O6414807 - 650 DOUGLAS AVE, WINTER PARK, FL 32789 2 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1280
       Built: 2003   Tax: $7,799 (2025)
    Community: Winter Park
    Single Family


    Estimated Monthly Payment: $3,664 (change assumption)
    Mortgage ($3,014) + Taxes in 2025 ($650)


    Taxes:$7,799

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 418 GILBERT RD, WINTER PARK, FL 32792

    $710,00079 Days on yellowkey   MLS ID: O6385950

    REDUCED by $9,000 (1.3%) on 06/02/2026

    For Sale O6385950 - 418 GILBERT RD, WINTER PARK, FL 32792 30 photos

    Bed: 3   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 1680
       Built: 1964   Tax: $9,094 (2025)
    Community: Winter Park Pines Ut 5
    Single Family


    Estimated Monthly Payment: $4,648 (change assumption)
    Mortgage ($3,890) + Taxes in 2025 ($758)


    Taxes:$9,094

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 1319 BESSMOR RD, WINTER PARK, FL 32789

    $589,00053 Days on yellowkey   MLS ID: O6400395

    REDUCED by $6,000 (1.0%) on 06/08/2026

    For Sale O6400395 - 1319 BESSMOR RD, WINTER PARK, FL 32789 13 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1126
       Built: 1956   Tax: $5,626 (2025)
    Community: Winter Park Village
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,696 (change assumption)
    Mortgage ($3,227) + Taxes in 2025 ($469)


    Taxes:$5,626

    Elementary School: Dream Lake Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 193 LEWFIELD CIR, WINTER PARK, FL 32792

    $248,90018 Days on yellowkey   MLS ID: O6409075

    For Sale O6409075 - 193 LEWFIELD CIR, WINTER PARK, FL 32792 33 photos

    Bed: 2   Bath: 2.5
    Liv Area Sq Ft: 1300
       Built: 1973
    Monthly Fee: $533
       Tax: $2,286 (2025)
    Community: Stratford A Winter Park Condo
    Condo


    Estimated Monthly Payment: $2,087 (change assumption)
    Mortgage ($1,364) + Fees ($533) + Taxes in 2025 ($191)


    Taxes:$2,286

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 413 W MORSE BLVD, WINTER PARK, FL 32789

    $2,695,0007 Days on yellowkey   MLS ID: O6412134

    For Sale O6412134 - 413 W MORSE BLVD, WINTER PARK, FL 32789 28 photos

    Bed: 3   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3048
       Built: 2018
    Monthly Fee: $386
       Tax: $19,919 (2026)
    Community: Town Of Winter Park
    Townhouse


    Estimated Monthly Payment: $16,813 (change assumption)
    Mortgage ($14,767) + Fees ($386) + Taxes in 2026 ($1,660)


    Taxes:$19,919

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2026

    Middle School: Maitland Middle


  • 1404 BORDER DR, WINTER PARK, FL 32789

    $1,200,00015 Days on yellowkey   MLS ID: O6412140

    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: $7,927 (change assumption)
    Mortgage ($6,575) + Taxes in 2025 ($1,352)


    Taxes:$16,220

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 2756 SHERIFF WAY, WINTER PARK, FL 32792

    $595,00046 Days on yellowkey   MLS ID: O6402570

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

    REDUCED by $30,000 (4.8%) on 06/05/2026

    For Sale O6402570 - 2756 SHERIFF WAY, WINTER PARK, FL 32792 48 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1812
       Built: 1965   Tax: $5,547 (2025)
    Community: Winter Park Pines
    Single Family


    Estimated Monthly Payment: $3,722 (change assumption)
    Mortgage ($3,260) + Taxes in 2025 ($462)


    Taxes:$5,547

    Elementary School: Aloma Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 2430 CHANTILLY AVE, WINTER PARK, FL 32789

    $1,665,00030 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


  • 2829 ALOMA, WINTER PARK, FL 32792

    $579,00043 Days on yellowkey   MLS ID: O6404107

    2 Days Off yellowkey (back on 6/5/2026)

    For Sale O6404107 - 2829 ALOMA, WINTER PARK, FL 32792 36 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1821
       Built: 1963   Tax: $4,277 (2025)
    Community: Winter Park Estates
    Single Family


    Estimated Monthly Payment: $3,529 (change assumption)
    Mortgage ($3,173) + Taxes in 2025 ($356)


    Taxes:$4,277

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 715 S RANGER BLVD, WINTER PARK, FL 32792

    $695,00018 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


  • 330 ELKHORN CT, WINTER PARK, FL 32792

    $549,900139 Days on yellowkey   MLS ID: O6376757

    REDUCED by $5,000 (0.9%) on 06/04/2026

    For Sale O6376757 - 330 ELKHORN CT, WINTER PARK, FL 32792 41 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1570
       Built: 1965   Tax: $2,086 (2025)
    Community: Winter Park Pines Merrie Oaks
    Single Family


    Estimated Monthly Payment: $3,187 (change assumption)
    Mortgage ($3,013) + Taxes in 2025 ($174)


    Taxes:$2,086

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None




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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.