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Winter Park Homes For Sale & Real Estate - 438 homes

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

Location: Winter Park

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  • 240 N PHELPS AVE, WINTER PARK, FL 32789

    $2,250,00033 Days on yellowkey   MLS ID: O6415360

    For Sale O6415360 - 240 N PHELPS AVE, WINTER PARK, FL 32789 39 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 2889
       Built: 2026   Tax: $6,605 (2025)
    Community: Sylvan Heights
    Single Family


    Estimated Monthly Payment: $12,879 (change assumption)
    Mortgage ($12,328) + Taxes in 2025 ($550)


    Taxes:$6,605

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


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

    $515,000119 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


  • 283 LEWFIELD CIR #283, WINTER PARK, FL 32792

    $142,50012 Days on yellowkey   MLS ID: O6420915

    1 Days Off yellowkey (back on 7/12/2026)

    For Sale O6420915 - 283 LEWFIELD CIR #283, WINTER PARK, FL 32792 23 photos

    Bed: 1   Bath: 1.0
    Liv Area Sq Ft: 678
       Built: 1973   Tax: $1,729 (2025)
    Community: Stratford A Winter Park Condo
    Condo


    Estimated Monthly Payment: $925 (change assumption)
    Mortgage ($781) + Taxes in 2025 ($144)


    Taxes:$1,729

    Elementary School: English Estates Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 1540 FLORENTINO LN, WINTER PARK, FL 32792

    $315,00052 Days on yellowkey   MLS ID: O6408841

    REDUCED by $20,000 (6.0%) on 07/12/2026

    For Sale O6408841 - 1540 FLORENTINO LN, WINTER PARK, FL 32792 20 photos

    Bed: 3   Bath: 2.5   Gar: 1
    Liv Area Sq Ft: 1682
       Built: 2004
    Monthly Fee: $175
       Tax: $5,340 (2025)
    Community: Vistas At Lake Howell
    Townhouse


    Estimated Monthly Payment: $2,346 (change assumption)
    Mortgage ($1,726) + Fees ($175) + Taxes in 2025 ($445)


    Taxes:$5,340

    Elementary School: Sterling Park Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 5530 S LAKE BURKETT LN, WINTER PARK, FL 32792

    $430,00040 Days on yellowkey   MLS ID: O6409433

    1 Days Off yellowkey (back on 7/12/2026)

    INCREASED by $5,000 (1.2%) on 07/05/2026

    For Sale O6409433 - 5530 S LAKE BURKETT LN, WINTER PARK, FL 32792 36 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1669
       Built: 1985
    Monthly Fee: $69
       Tax: $3,871 (2025)
    Community: Trinity Bay
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,748 (change assumption)
    Mortgage ($2,356) + Fees ($69) + Taxes in 2025 ($323)


    Taxes:$3,871

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2008 HOUNDSLAKE DR, WINTER PARK, FL 32792

    $515,00029 Days on yellowkey   MLS ID: O6414369

    For Sale O6414369 - 2008 HOUNDSLAKE DR, WINTER PARK, FL 32792 33 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2250
       Built: 1980   Tax: $5,253 (2025)
    Community: Cedar Ridge
    Single Family


    Estimated Monthly Payment: $3,260 (change assumption)
    Mortgage ($2,822) + Taxes in 2025 ($438)


    Taxes:$5,253

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 1090 WILDMEADOW RUN, WINTER PARK, FL 32792

    $835,000109 Days on yellowkey   MLS ID: O6394208

    REDUCED by $10,000 (1.2%) on 06/02/2026

    For Sale O6394208 - 1090 WILDMEADOW RUN, WINTER PARK, FL 32792 37 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2589
       Built: 2021
    Monthly Fee: $243
       Tax: $6,258 (2024)
    Community: Hawks Crest
    Single Family


    Estimated Monthly Payment: $5,340 (change assumption)
    Mortgage ($4,575) + Fees ($243) + Taxes in 2024 ($521)


    Taxes:$6,258

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 1265 ARLINGTON PL, WINTER PARK, FL 32789

    $849,90033 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


  • 2217 SUSSEX RD, WINTER PARK, FL 32792

    $499,000235 Days on yellowkey   MLS ID: O6362648

    REDUCED by $20,999 (4.0%) on 07/07/2026

    For Sale O6362648 - 2217 SUSSEX RD, WINTER PARK, FL 32792 34 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2092
       Built: 1968   Tax: $4,939 (2024)
    Community: Winter Woods Unit 01
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,146 (change assumption)
    Mortgage ($2,734) + Taxes in 2024 ($412)


    Taxes:$4,939

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 1150 VIA SALERNO, WINTER PARK, FL 32789

    $4,195,000381 Days on yellowkey   MLS ID: O6321143

    REDUCED by $555,000 (11.7%) on 04/25/2026

    For Sale O6321143 - 1150 VIA SALERNO, WINTER PARK, FL 32789 62 photos

    Bed: 4   Bath: 5.5   Gar: 2
    Liv Area Sq Ft: 3850
       Built: 2025   Tax: $10,158 (2024)
    Community: Cloister Grove Sub
    Spa: No

    Single Family


    Estimated Monthly Payment: $23,832 (change assumption)
    Mortgage ($22,986) + Taxes in 2024 ($847)


    Taxes:$10,158

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Maitland Middle


  • 512 W SWOOPE AVE, WINTER PARK, FL 32789

    $1,399,00026 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

    $1,725,00043 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


  • 946 ENCLAVE PL, WINTER PARK, FL 32792

    $2,175,00047 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


  • 950 ENCLAVE PL, WINTER PARK, FL 32792

    $2,125,00047 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


  • 942 ENCLAVE PL, WINTER PARK, FL 32792

    $2,195,00047 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


  • 926 ENCLAVE PL, WINTER PARK, FL 32792

    $2,235,00055 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

    $2,099,00055 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

    $1,899,00061 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

    $2,050,00061 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

    $1,599,00061 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




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

Winter Park home, townhome, condo, villa, and other listing sales data is continuously updated on yellowkeyrealty.com. yellowkeyrealty.com offers one of the most exhaustive, current, and relevant set of data you can find on houses for sale in Winter Park. You can use our website to view Multiple Listing Service (MLS) data on Winter Park Real Estate. 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 Winter Park listings.



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.