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Winter Park Homes for Sale in Winter Park - 44 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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  • 814 DENSMORE DR, WINTER PARK, FL 32792

    $425,0008 Days on yellowkey   MLS ID: O6399773

    For Sale O6399773 - 814 DENSMORE DR, WINTER PARK, FL 32792 24 photos

    Bed: 4   Bath: 2.0
    Liv Area Sq Ft: 1610
       Built: 1960   Tax: $5,402 (2025)
    Community: Winter Park Estates
    Single Family


    Estimated Monthly Payment: $2,779 (change assumption)
    Mortgage ($2,329) + Taxes in 2025 ($450)


    Taxes:$5,402

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • WINTER PARK, FL 32792

    $430,00043 Days on yellowkey   MLS ID: S5145631

    REDUCED by $10,000 (2.3%) on 04/15/2026

    For Sale S5145631 - WINTER PARK, FL 32792 11 photos

    Bed: 4   Bath: 2.0
    Liv Area Sq Ft: 1296
       Built: 1958   Tax: $4,968 (2025)
    Community: Winter Park Estates
    Single Family


    Estimated Monthly Payment: $2,770 (change assumption)
    Mortgage ($2,356) + Taxes in 2025 ($414)


    Taxes:$4,968

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 541 W CANTON AVE, WINTER PARK, FL 32789

    $2,800,00034 Days on yellowkey   MLS ID: O6389829

    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: $15,733 (change assumption)
    Mortgage ($15,342) + Taxes in 2024 ($391)


    Taxes:$4,692

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Maitland Middle


  • 2919 BOWER RD, WINTER PARK, FL 32792

    $779,00036 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


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

    $184,900103 Days on yellowkey   MLS ID: O6367842

    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


  • 906 ENCLAVE PL, WINTER PARK, FL 32792

    $1,925,00035 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


  • 302 LEWFIELD CIR #302, WINTER PARK, FL 32792

    $146,00078 Days on yellowkey   MLS ID: O6380160

    REDUCED by $4,000 (2.7%) on 04/11/2026

    For Sale O6380160 - 302 LEWFIELD CIR #302, WINTER PARK, FL 32792 23 photos

    Bed: 1   Bath: 1.0
    Liv Area Sq Ft: 678
       Built: 1973
    Monthly Fee: $350
       Tax: $1,942 (2025)
    Community: Stratford A Winter Park Condo
    Condo


    Estimated Monthly Payment: $1,312 (change assumption)
    Mortgage ($800) + Fees ($350) + Taxes in 2025 ($162)


    Taxes:$1,942

    Elementary School: English Estates Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 119 OAK GROVE RD, WINTER PARK, FL 32789

    $285,00015 Days on yellowkey   MLS ID: O6397460

    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


  • 1695 LEE RD #D211, WINTER PARK, FL 32789

    $115,00016 Days on yellowkey   MLS ID: O6396190

    For Sale O6396190 - 1695 LEE RD #D211, WINTER PARK, FL 32789 28 photos

    Bed: 2   Bath: 1.0
    Liv Area Sq Ft: 881
       Built: 1966   Tax: $2,051 (2025)
    Community: Waterfall Cove/Winter Park
    Condo


    Estimated Monthly Payment: $801 (change assumption)
    Mortgage ($630) + Taxes in 2025 ($171)


    Taxes:$2,051

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 901 ENCLAVE PL, WINTER PARK, FL 32792

    $1,495,00035 Days on yellowkey   MLS ID: O6383602

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

    Bed: 3   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

    $1,495,00035 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

    $1,895,00035 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


  • 291 LEWFIELD CIR #291, WINTER PARK, FL 32792

    $144,00067 Days on yellowkey   MLS ID: O6382547

    For Sale O6382547 - 291 LEWFIELD CIR #291, WINTER PARK, FL 32792 32 photos

    Bed: 1   Bath: 1.0
    Liv Area Sq Ft: 678
       Built: 1973
    Monthly Fee: $350
       Tax: $1,942 (2025)
    Community: Stratford Winter Park
    Condo


    Estimated Monthly Payment: $1,301 (change assumption)
    Mortgage ($789) + Fees ($350) + Taxes in 2025 ($162)


    Taxes:$1,942

    Elementary School: English Estates Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 621 HUNTINGTON AVE, WINTER PARK, FL 32789

    $1,795,00024 Days on yellowkey   MLS ID: O6394464

    For Sale O6394464 - 621 HUNTINGTON AVE, WINTER PARK, FL 32789 38 photos

    Bed: 3   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2399
       Built: 2008   Tax: $12,854 (2025)
    Community: Winter Park Rev
    Spa: No

    Single Family


    Estimated Monthly Payment: $10,907 (change assumption)
    Mortgage ($9,835) + Taxes in 2025 ($1,071)


    Taxes:$12,854

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 781 NORTHWOOD CIR, WINTER PARK, FL 32789

    $775,00023 Days on yellowkey   MLS ID: O6394119

    0 Days Off yellowkey (back on 4/5/2026)

    For Sale O6394119 - 781 NORTHWOOD CIR, WINTER PARK, FL 32789 33 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1566
       Built: 1971   Tax: $6,931 (2025)
    Community: Winter Park Oasis
    Single Family


    Estimated Monthly Payment: $4,824 (change assumption)
    Mortgage ($4,246) + Taxes in 2025 ($578)


    Taxes:$6,931

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 1134 WASHINGTON AVE #13, WINTER PARK, FL 32789

    $625,000151 Days on yellowkey   MLS ID: O6362206

    For Sale O6362206 - 1134 WASHINGTON AVE #13, WINTER PARK, FL 32789 32 photos

    Bed: 3   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2083
       Built: 1981   Tax: $7,472 (2025)
    Community: Quarters At Winter Park Condo
    Condo


    Estimated Monthly Payment: $4,047 (change assumption)
    Mortgage ($3,425) + Taxes in 2025 ($623)


    Taxes:$7,472

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 700 MELROSE AVE #J1, WINTER PARK, FL 32789

    $350,00028 Days on yellowkey   MLS ID: O6394372

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

    For Sale O6394372 - 700 MELROSE AVE #J1, WINTER PARK, FL 32789 20 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1074
       Built: 1964   Tax: $4,205 (2025)
    Community: Winter Park Gardens Condo
    Condo


    Estimated Monthly Payment: $2,268 (change assumption)
    Mortgage ($1,918) + Taxes in 2025 ($350)


    Taxes:$4,205

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 151 LEWFIELD CIR #4, WINTER PARK, FL 32792

    $139,000137 Days on yellowkey   MLS ID: O6365536

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

    For Sale O6365536 - 151 LEWFIELD CIR #4, WINTER PARK, FL 32792 30 photos

    Bed: 1   Bath: 1.0
    Liv Area Sq Ft: 678
       Built: 1973   Tax: $1,278 (2024)
    Community: Stratford A Winter Park Condo
    Condo


    Estimated Monthly Payment: $868 (change assumption)
    Mortgage ($762) + Taxes in 2024 ($106)


    Taxes:$1,278

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 758 WARRENTON RD, WINTER PARK, FL 32792

    $318,98523 Days on yellowkey   MLS ID: O6395298

    For Sale O6395298 - 758 WARRENTON RD, WINTER PARK, FL 32792 52 photos

    Bed: 3   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1196
       Built: 1988
    Monthly Fee: $86
       Tax: $3,689 (2025)
    Community: Winter Park Pines Patio Homes
    Half Duplex


    Estimated Monthly Payment: $2,141 (change assumption)
    Mortgage ($1,748) + Fees ($86) + Taxes in 2025 ($307)


    Taxes:$3,689

    Elementary School: Aloma Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 837 APPALACHEE AVE, WINTER PARK, FL 32792

    $439,00028 Days on yellowkey   MLS ID: O6393151

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

    For Sale O6393151 - 837 APPALACHEE AVE, WINTER PARK, FL 32792 33 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1771
       Built: 1968   Tax: $6,834 (2025)
    Community: Winter Park Forest
    Single Family


    Estimated Monthly Payment: $2,975 (change assumption)
    Mortgage ($2,405) + Taxes in 2025 ($570)


    Taxes:$6,834

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge 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.