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Winter Park Single Family Homes For Sale - 311 homes

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

Location: Winter Park

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  • 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


  • 2702 PARKLAND DR, WINTER PARK, FL 32789

    $1,139,75075 Days on yellowkey   MLS ID: O6397997

    REDUCED by $35,250 (3.0%) on 05/18/2026

    For Sale O6397997 - 2702 PARKLAND DR, WINTER PARK, FL 32789 48 photos

    Bed: 5   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2656
       Built: 1949   Tax: $5,269 (2025)
    Community: Parklando
    Single Family


    Estimated Monthly Payment: $6,684 (change assumption)
    Mortgage ($6,245) + Taxes in 2025 ($439)


    Taxes:$5,269

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 785 N PHELPS AVE, WINTER PARK, FL 32789

    $1,900,00091 Days on yellowkey   MLS ID: O6393117

    REDUCED by $89,000 (4.5%) on 06/05/2026

    For Sale O6393117 - 785 N PHELPS AVE, WINTER PARK, FL 32789 41 photos

    Bed: 5   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2964
       Built: 2026   Tax: $9,172 (2025)
    Community: Comstock Park
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $11,175 (change assumption)
    Mortgage ($10,411) + Taxes in 2025 ($764)


    Taxes:$9,172

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 1870 WALKER AVE, WINTER PARK, FL 32789

    $1,299,000103 Days on yellowkey   MLS ID: O6390504

    REDUCED by $100,000 (7.1%) on 05/29/2026

    For Sale O6390504 - 1870 WALKER AVE, WINTER PARK, FL 32789 32 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2046
       Built: 2026   Tax: $3,981 (2025)
    Community: Osceola Heights
    Single Family


    Estimated Monthly Payment: $7,449 (change assumption)
    Mortgage ($7,118) + Taxes in 2025 ($332)


    Taxes:$3,981

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 1751 GLENCOE RD, WINTER PARK, FL 32789

    $3,390,000232 Days on yellowkey   MLS ID: O6339739

    REDUCED by $100,000 (2.9%) on 06/06/2026

    For Sale O6339739 - 1751 GLENCOE RD, WINTER PARK, FL 32789 45 photos

    Bed: 5   Bath: 6.0   Gar: 2
    Liv Area Sq Ft: 4520
       Built: 2025   Tax: $12,895 (2024)
    Community: Forest Hills
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $19,649 (change assumption)
    Mortgage ($18,575) + Taxes in 2024 ($1,075)


    Taxes:$12,895

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Audubon Park K-8


  • 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


  • 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


  • 1927 ELAND AVE, WINTER PARK, FL 32789

    $820,000133 Days on yellowkey   MLS ID: O6381009

    REDUCED by $5,000 (0.6%) on 06/15/2026

    For Sale O6381009 - 1927 ELAND AVE, WINTER PARK, FL 32789 68 photos

    Bed: 5   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2242
       Built: 1957   Tax: $3,190 (2024)
    Community: Lake Bell Terrace
    Single Family


    Estimated Monthly Payment: $4,759 (change assumption)
    Mortgage ($4,493) + Taxes in 2024 ($266)


    Taxes:$3,190

    Elementary School: Hungerford Elem

    High School: Edgewater High

    Tax Year: 2024

    Middle School: College Park Middle


  • 1316 BLUE STEM LN, WINTER PARK, FL 32792

    $725,00010 Days on yellowkey   MLS ID: O6416828

    For Sale O6416828 - 1316 BLUE STEM LN, WINTER PARK, FL 32792 42 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2196
       Built: 2022
    Monthly Fee: $243
       Tax: $6,788 (2025)
    Community: Landings At Hawks Crest
    Single Family


    Estimated Monthly Payment: $4,781 (change assumption)
    Mortgage ($3,973) + Fees ($243) + Taxes in 2025 ($566)


    Taxes:$6,788

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 2831 MULFORD AVE, WINTER PARK, FL 32789

    $735,00017 Days on yellowkey   MLS ID: O6414319

    For Sale O6414319 - 2831 MULFORD AVE, WINTER PARK, FL 32789 22 photos

    Bed: 4   Bath: 2.5
    Liv Area Sq Ft: 1647
       Built: 1952   Tax: $3,192 (2025)
    Community: Orangewood Park
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,293 (change assumption)
    Mortgage ($4,027) + Taxes in 2025 ($266)


    Taxes:$3,192

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2914 REEF KNOT PL, WINTER PARK, FL 32792

    $1,725,0006 Days on yellowkey   MLS ID: O6418185

    For Sale O6418185 - 2914 REEF KNOT PL, WINTER PARK, FL 32792 63 photos

    Bed: 6   Bath: 5.0   Gar: 3
    Liv Area Sq Ft: 4173
       Built: 2019
    Monthly Fee: $186
       Tax: $17,688 (2025)
    Community: Lake Florence Preserve
    Spa: No

    Single Family


    Estimated Monthly Payment: $11,112 (change assumption)
    Mortgage ($9,452) + Fees ($186) + Taxes in 2025 ($1,474)


    Taxes:$17,688

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 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


  • 1287 VERDANT GLADE PL, WINTER PARK, FL 32792

    $825,00061 Days on yellowkey   MLS ID: O6400331

    REDUCED by $22,000 (2.6%) on 06/19/2026

    For Sale O6400331 - 1287 VERDANT GLADE PL, WINTER PARK, FL 32792 50 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3020
       Built: 2020
    Monthly Fee: $413
       Tax: $6,133 (2025)
    Community: Meadows At Hawks Crest
    Single Family


    Estimated Monthly Payment: $5,444 (change assumption)
    Mortgage ($4,520) + Fees ($413) + Taxes in 2025 ($511)


    Taxes:$6,133

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 616 BRECHIN DR, WINTER PARK, FL 32792

    $1,045,00033 Days on yellowkey   MLS ID: O6409911

    For Sale O6409911 - 616 BRECHIN DR, WINTER PARK, FL 32792 44 photos

    Bed: 4   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 2638
       Built: 1961   Tax: $4,251 (2025)
    Community: Kenilworth Shores Sec 04
    Single Family


    Estimated Monthly Payment: $6,080 (change assumption)
    Mortgage ($5,726) + Taxes in 2025 ($354)


    Taxes:$4,251

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 1946 STRATHAVEN RD, WINTER PARK, FL 32792

    $650,00028 Days on yellowkey   MLS ID: O6411329

    REDUCED by $25,000 (3.7%) on 06/19/2026

    For Sale O6411329 - 1946 STRATHAVEN RD, WINTER PARK, FL 32792 37 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2102
       Built: 1960   Tax: $8,540 (2025)
    Community: Kenilworth Shores Sec 07
    Single Family


    Estimated Monthly Payment: $4,273 (change assumption)
    Mortgage ($3,562) + Taxes in 2025 ($712)


    Taxes:$8,540

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 1571 WOODLAND AVE, WINTER PARK, FL 32789

    $6,000,00026 Days on yellowkey   MLS ID: O6411706

    For Sale O6411706 - 1571 WOODLAND AVE, WINTER PARK, FL 32789 75 photos

    Bed: 5   Bath: 7.0   Gar: 3
    Liv Area Sq Ft: 7397
       Built: 2007   Tax: $31,040 (2025)
    Community: Comstock Park
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $35,463 (change assumption)
    Mortgage ($32,876) + Taxes in 2025 ($2,587)


    Taxes:$31,040

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland 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


  • 1110 ALABAMA DR, WINTER PARK, FL 32789

    $1,699,00083 Days on yellowkey   MLS ID: O6395692

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

    REDUCED by $51,000 (2.9%) on 05/19/2026

    For Sale O6395692 - 1110 ALABAMA DR, WINTER PARK, FL 32789 53 photos

    Bed: 3   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2488
       Built: 1958   Tax: $12,858 (2025)
    Community: J Kronenberger Sub
    Spa: No

    Single Family


    Estimated Monthly Payment: $10,381 (change assumption)
    Mortgage ($9,309) + Taxes in 2025 ($1,072)


    Taxes:$12,858

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle




Why Bother Searching Elsewhere for Winter Park Single Family Homes for Sale?

Winter Park home, townhome, and condo, villa, and other listing sale 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 single family homes for sale in Winter Park . You can use our website to view Multiple Listing Service (MLS) data on Winter Park single family homes. 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 single family home 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.