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Winter Park Single Family Homes For Sale - 303 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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  • 2758 BANCHORY RD, WINTER PARK, FL 32792

    $598,000351 Days on yellowkey   MLS ID: O6329628

    For Sale O6329628 - 2758 BANCHORY RD, WINTER PARK, FL 32792 37 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1539
       Built: 1965   Tax: $7,325 (2024)
    Community: Winter Park Pines
    Single Family


    Estimated Monthly Payment: $3,887 (change assumption)
    Mortgage ($3,277) + Taxes in 2024 ($610)


    Taxes:$7,325

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 3949 COOL WATER CT, WINTER PARK, FL 32792

    $399,90034 Days on yellowkey   MLS ID: O6415880

    0 Days Off yellowkey (back on 6/30/2026)

    FORECLOSURE O6415880 - 3949 COOL WATER CT, WINTER PARK, FL 32792 26 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1979
       Built: 1994
    Monthly Fee: $28
       Tax: $2,894 (2025)
    Community: Oxford Cove
    Single Family


    Estimated Monthly Payment: $2,460 (change assumption)
    Mortgage ($2,191) + Fees ($28) + Taxes in 2025 ($241)


    Taxes:$2,894

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1807 YORKSHIRE DR, WINTER PARK, FL 32792

    $1,450,000232 Days on yellowkey   MLS ID: TB8451098

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

    For Sale TB8451098 - 1807 YORKSHIRE DR, WINTER PARK, FL 32792 18 photos

    Bed: 4   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3565
       Built: 2025   Tax: $5,446 (2025)
    Community: Park Manor
    Single Family


    Estimated Monthly Payment: $8,399 (change assumption)
    Mortgage ($7,945) + Taxes in 2025 ($454)


    Taxes:$5,446

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 4348 STEED TER, WINTER PARK, FL 32792

    $824,00067 Days on yellowkey   MLS ID: O6406018

    0 Days Off yellowkey (back on 5/26/2026)

    For Sale O6406018 - 4348 STEED TER, WINTER PARK, FL 32792 74 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 3040
       Built: 1989
    Monthly Fee: $29
       Tax: $3,652 (2024)
    Community: Kings Cove
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,848 (change assumption)
    Mortgage ($4,515) + Fees ($29) + Taxes in 2024 ($304)


    Taxes:$3,652

    Elementary School: Red Bug Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 231 CHELTON CIR, WINTER PARK, FL 32789

    $4,950,00034 Days on yellowkey   MLS ID: O6414890

    For Sale O6414890 - 231 CHELTON CIR, WINTER PARK, FL 32789 67 photos

    Bed: 4   Bath: 6.0   Gar: 3
    Liv Area Sq Ft: 5550
       Built: 2018   Tax: $56,866 (2025)
    Community: Forest Hills
    Spa: No

    Single Family


    Estimated Monthly Payment: $31,861 (change assumption)
    Mortgage ($27,123) + Taxes in 2025 ($4,739)


    Taxes:$56,866

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 5503 ALBERT DR, WINTER PARK, FL 32792

    $402,50041 Days on yellowkey   MLS ID: S5151098

    REDUCED by $2,500 (0.6%) on 06/15/2026

    For Sale S5151098 - 5503 ALBERT DR, WINTER PARK, FL 32792 57 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1366
       Built: 1978   Tax: $4,123 (2025)
    Community: Howell Branch Woods
    Single Family


    Estimated Monthly Payment: $2,549 (change assumption)
    Mortgage ($2,205) + Taxes in 2025 ($344)


    Taxes:$4,123

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2261 MULBRY DRIVE, WINTER PARK, FL 32789

    $1,995,00046 Days on yellowkey   MLS ID: O6410979

    3 Days Off yellowkey (back on 6/29/2026)

    For Sale O6410979 - 2261 MULBRY DRIVE, WINTER PARK, FL 32789 77 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 3696
       Built: 2020   Tax: $11,789 (2025)
    Community: Lake Forest Park
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $11,914 (change assumption)
    Mortgage ($10,931) + Taxes in 2025 ($982)


    Taxes:$11,789

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 2652 ABBEY RD, WINTER PARK, FL 32792

    $625,00022 Days on yellowkey   MLS ID: O6419026

    0 Days Off yellowkey (back on 6/29/2026)

    For Sale O6419026 - 2652 ABBEY RD, WINTER PARK, FL 32792 44 photos

    Bed: 5   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1938
       Built: 1967   Tax: $7,337 (2025)
    Community: Winter Park Pines Merrie Oaks
    Single Family


    Estimated Monthly Payment: $4,036 (change assumption)
    Mortgage ($3,425) + Taxes in 2025 ($611)


    Taxes:$7,337

    Elementary School: Aloma Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 744 CORNWALL RD, WINTER PARK, FL 32792

    $675,000347 Days on yellowkey   MLS ID: O6332168

    REDUCED by $20,000 (2.9%) on 06/29/2026

    For Sale O6332168 - 744 CORNWALL RD, WINTER PARK, FL 32792 59 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1968
       Built: 1968   Tax: $5,359 (2024)
    Community: Winter Park Pines
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,145 (change assumption)
    Mortgage ($3,699) + Taxes in 2024 ($447)


    Taxes:$5,359

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Glenridge Middle


  • 1885 TEMPLE DR, WINTER PARK, FL 32789

    $2,225,000244 Days on yellowkey   MLS ID: O6359471

    For Sale O6359471 - 1885 TEMPLE DR, WINTER PARK, FL 32789 56 photos

    Bed: 5   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3691
       Built: 1963   Tax: $6,073 (2025)
    Community: Lugano Terrace
    Spa: No

    Single Family


    Estimated Monthly Payment: $12,698 (change assumption)
    Mortgage ($12,191) + Taxes in 2025 ($506)


    Taxes:$6,073

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 616 BRECHIN DR, WINTER PARK, FL 32792

    $1,045,00053 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


  • 950 HANOVER AVE, WINTER PARK, FL 32789

    $460,00094 Days on yellowkey   MLS ID: O6398273

    REDUCED by $10,000 (2.1%) on 06/01/2026

    For Sale O6398273 - 950 HANOVER AVE, WINTER PARK, FL 32789 28 photos

    Bed: 3   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1606
       Built: 1956   Tax: $3,525 (2025)
    Community: Albert Lee Ridge 1St Add
    Single Family


    Estimated Monthly Payment: $2,814 (change assumption)
    Mortgage ($2,520) + Taxes in 2025 ($294)


    Taxes:$3,525

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 3135 HEARTLEAF PL, WINTER PARK, FL 32792

    $649,00053 Days on yellowkey   MLS ID: O6410276

    5 Days Off yellowkey (back on 6/28/2026)

    REDUCED by $10,900 (1.7%) on 06/17/2026

    For Sale O6410276 - 3135 HEARTLEAF PL, WINTER PARK, FL 32792 36 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2749
       Built: 1994
    Monthly Fee: $20
       Tax: $2,825 (2025)
    Community: Lost Creek
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,812 (change assumption)
    Mortgage ($3,556) + Fees ($20) + Taxes in 2025 ($235)


    Taxes:$2,825

    Elementary School: Red Bug Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 1581 FOREST AVE, WINTER PARK, FL 32789

    $3,393,000124 Days on yellowkey   MLS ID: O6382377

    REDUCED by $102,000 (2.9%) on 05/21/2026

    For Sale O6382377 - 1581 FOREST AVE, WINTER PARK, FL 32789 57 photos

    Bed: 4   Bath: 5.0   Gar: 2
    Liv Area Sq Ft: 4683
       Built: 1954   Tax: $20,042 (2024)
    Community: Ellno Willo
    Spa: No

    Single Family


    Estimated Monthly Payment: $20,261 (change assumption)
    Mortgage ($18,591) + Taxes in 2024 ($1,670)


    Taxes:$20,042

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Audubon Park K-8


  • 860 N DENNING DR, WINTER PARK, FL 32789

    $699,90043 Days on yellowkey   MLS ID: O6412589

    REDUCED by $25,000 (3.4%) on 06/25/2026

    For Sale O6412589 - 860 N DENNING DR, WINTER PARK, FL 32789 52 photos

    Bed: 3   Bath: 2.5
    Liv Area Sq Ft: 1411
       Built: 1954   Tax: $4,595 (2025)
    Community: Magnolia Gardens Sub
    Single Family


    Estimated Monthly Payment: $4,218 (change assumption)
    Mortgage ($3,835) + Taxes in 2025 ($383)


    Taxes:$4,595

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 1009 LAKE BELL DR, WINTER PARK, FL 32789

    $650,00053 Days on yellowkey   MLS ID: O6409849

    REDUCED by $49,000 (7.0%) on 06/15/2026

    For Sale O6409849 - 1009 LAKE BELL DR, WINTER PARK, FL 32789 41 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1467
       Built: 1958   Tax: $5,448 (2025)
    Community: Albert Lee Ridge Add 02
    Single Family


    Estimated Monthly Payment: $4,016 (change assumption)
    Mortgage ($3,562) + Taxes in 2025 ($454)


    Taxes:$5,448

    Elementary School: Hungerford Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park Middle


  • 4353 STEED TER, WINTER PARK, FL 32792

    $614,99019 Days on yellowkey   MLS ID: TB8517548

    For Sale TB8517548 - 4353 STEED TER, WINTER PARK, FL 32792 30 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2275
       Built: 1989
    Monthly Fee: $29
       Tax: $7,031 (2024)
    Community: Kings Cove
    Single Family


    Estimated Monthly Payment: $3,985 (change assumption)
    Mortgage ($3,370) + Fees ($29) + Taxes in 2024 ($586)


    Taxes:$7,031

    Elementary School: Red Bug Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 2715 PRINCE JOHN RD, WINTER PARK, FL 32792

    $498,90036 Days on yellowkey   MLS ID: O6415084

    REDUCED by $6,000 (1.2%) on 06/27/2026

    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: $3,325 (change assumption)
    Mortgage ($2,734) + Taxes in 2025 ($592)


    Taxes:$7,101

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 1287 VERDANT GLADE PL, WINTER PARK, FL 32792

    $825,00081 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


  • 1900 WINTER PARK RD, WINTER PARK, FL 32789

    $799,00078 Days on yellowkey   MLS ID: O6402566

    REDUCED by $50,900 (6.0%) on 06/16/2026

    For Sale O6402566 - 1900 WINTER PARK RD, WINTER PARK, FL 32789 22 photos

    Bed: 4   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1511
       Built: 1947   Tax: $2,803 (2025)
    Community: Charmont
    Single Family


    Estimated Monthly Payment: $4,612 (change assumption)
    Mortgage ($4,378) + Taxes in 2025 ($234)


    Taxes:$2,803

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None




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.