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Winter Park Homes for Sale in Winter Park - 74 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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  • 330 ELKHORN CT, WINTER PARK, FL 32792

    $544,900155 Days on yellowkey   MLS ID: O6376757

    REDUCED by $5,000 (0.9%) on 06/26/2026

    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: $3,160 (change assumption)
    Mortgage ($2,986) + Taxes in 2025 ($174)


    Taxes:$2,086

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 910 ENCLAVE PL, WINTER PARK, FL 32792

    $1,899,00046 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


  • 926 ENCLAVE PL, WINTER PARK, FL 32792

    $2,235,00040 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


  • 2803 BANCHORY RD, WINTER PARK, FL 32792

    $474,00031 Days on yellowkey   MLS ID: O6404011

    REDUCED by $21,000 (4.2%) on 06/26/2026

    For Sale O6404011 - 2803 BANCHORY RD, WINTER PARK, FL 32792 31 photos

    Bed: 4   Bath: 2.0
    Liv Area Sq Ft: 1596
       Built: 1965
    Monthly Fee: $5
       Tax: $2,458 (2025)
    Community: Winter Park Pines
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,807 (change assumption)
    Mortgage ($2,597) + Fees ($5) + Taxes in 2025 ($205)


    Taxes:$2,458

    Elementary School: Aloma Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 946 ENCLAVE PL, WINTER PARK, FL 32792

    $2,175,00032 Days on yellowkey   MLS ID: O6411633

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

    Bed: 5   Bath: 4.5   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


  • 905 ENCLAVE PL, WINTER PARK, FL 32792

    $1,495,000101 Days on yellowkey   MLS ID: O6383679

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

    Bed: 4   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


  • 2889 ROUEN AVE, WINTER PARK, FL 32789

    $365,00069 Days on yellowkey   MLS ID: L4961275

    0 Days Off yellowkey (back on 6/24/2026)

    REDUCED by $10,000 (2.7%) on 06/23/2026

    For Sale L4961275 - 2889 ROUEN AVE, WINTER PARK, FL 32789 10 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1144
       Built: 1959   Tax: $5,061 (2025)
    Community: Winter Park Manor
    Single Family


    Estimated Monthly Payment: $2,422 (change assumption)
    Mortgage ($2,000) + Taxes in 2025 ($422)


    Taxes:$5,061

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 541 W CANTON AVE, WINTER PARK, FL 32789

    $2,650,000100 Days on yellowkey   MLS ID: O6389829

    REDUCED by $150,000 (5.4%) on 06/24/2026

    For Sale O6389829 - 541 W CANTON AVE, WINTER PARK, FL 32789 51 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3553
       Built: 2024   Tax: $4,692 (2024)
    Community: Winter Park
    Single Family


    Estimated Monthly Payment: $14,911 (change assumption)
    Mortgage ($14,520) + Taxes in 2024 ($391)


    Taxes:$4,692

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Maitland Middle


  • 751 WARRENTON RD, WINTER PARK, FL 32792

    $319,9006 Days on yellowkey   MLS ID: TB8522073

    For Sale TB8522073 - 751 WARRENTON RD, WINTER PARK, FL 32792 16 photos

    Bed: 3   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1196
       Built: 1989
    Monthly Fee: $86
       Tax: $2,795 (2025)
    Community: Winter Park Pines Patio Homes
    Spa: No

    Half Duplex


    Estimated Monthly Payment: $2,072 (change assumption)
    Mortgage ($1,753) + Fees ($86) + Taxes in 2025 ($233)


    Taxes:$2,795

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 413 W MORSE BLVD, WINTER PARK, FL 32789

    $2,695,00023 Days on yellowkey   MLS ID: O6412134

    For Sale O6412134 - 413 W MORSE BLVD, WINTER PARK, FL 32789 29 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


  • 332 FLEET RD, WINTER PARK, FL 32792

    $595,00011 Days on yellowkey   MLS ID: O6414829

    2 Days Off yellowkey (back on 6/23/2026)

    For Sale O6414829 - 332 FLEET RD, WINTER PARK, FL 32792 35 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2355
       Built: 1966   Tax: $4,919 (2025)
    Community: Winter Park Pines Merrie Oaks
    Single Family


    Estimated Monthly Payment: $3,670 (change assumption)
    Mortgage ($3,260) + Taxes in 2025 ($410)


    Taxes:$4,919

    Elementary School: Aloma Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 942 ENCLAVE PL, WINTER PARK, FL 32792

    $2,195,00032 Days on yellowkey   MLS ID: O6411550

    For Sale O6411550 - 942 ENCLAVE PL, WINTER PARK, FL 32792 4 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


  • 350 CORNWALL RD, WINTER PARK, FL 32792

    $765,00092 Days on yellowkey   MLS ID: O6394524

    0 Days Off yellowkey (back on 6/22/2026)

    REDUCED by $10,000 (1.3%) on 05/28/2026

    For Sale O6394524 - 350 CORNWALL RD, WINTER PARK, FL 32792 36 photos

    Bed: 4   Bath: 3.0
    Liv Area Sq Ft: 2038
       Built: 1963   Tax: $2,127 (2025)
    Community: Winter Park Pines Rep
    Single Family


    Estimated Monthly Payment: $4,369 (change assumption)
    Mortgage ($4,192) + Taxes in 2025 ($177)


    Taxes:$2,127

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 641 W LYMAN AVE, WINTER PARK, FL 32789

    $509,00027 Days on yellowkey   MLS ID: O6408078

    0 Days Off yellowkey (back on 6/21/2026)

    For Sale O6408078 - 641 W LYMAN AVE, WINTER PARK, FL 32789 36 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1120
       Built: 2003   Tax: $6,342 (2025)
    Community: Town/Winter Park
    Single Family


    Estimated Monthly Payment: $3,317 (change assumption)
    Mortgage ($2,789) + Taxes in 2025 ($529)


    Taxes:$6,342

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 2974 CHANTILLY AVE, WINTER PARK, FL 32789

    $499,00023 Days on yellowkey   MLS ID: O6412851

    REDUCED by $51,000 (9.3%) on 06/15/2026

    For Sale O6412851 - 2974 CHANTILLY AVE, WINTER PARK, FL 32789 26 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1433
       Built: 1960   Tax: $1,178 (2025)
    Community: Winter Park Manor
    Single Family


    Estimated Monthly Payment: $2,832 (change assumption)
    Mortgage ($2,734) + Taxes in 2025 ($98)


    Taxes:$1,178

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 2718 SANDWELL DR, WINTER PARK, FL 32792

    $525,00011 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


  • 950 ENCLAVE PL, WINTER PARK, FL 32792

    $2,125,00032 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

    $2,050,00046 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

    $1,495,000101 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


  • 914 ENCLAVE PL, WINTER PARK, FL 32792

    $1,895,000101 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




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.