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Winter Park Single Family Homes For Sale - 280 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

    $1,599,00077 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


  • 1751 GLENCOE RD, WINTER PARK, FL 32789

    $3,390,000268 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


  • 2217 SUSSEX RD, WINTER PARK, FL 32792

    $499,000251 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


  • 721 PANSY AVE, WINTER PARK, FL 32789

    $1,850,000282 Days on yellowkey   MLS ID: O6352857

    3 Days Off yellowkey (back on 7/29/2026)

    REDUCED by $75,000 (3.9%) on 06/10/2026

    For Sale O6352857 - 721 PANSY AVE, WINTER PARK, FL 32789 29 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 2653
       Built: 2018   Tax: $15,480 (2025)
    Community: Villa View Park
    Single Family


    Estimated Monthly Payment: $11,427 (change assumption)
    Mortgage ($10,137) + Taxes in 2025 ($1,290)


    Taxes:$15,480

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 1649 HARMON AVE, WINTER PARK, FL 32789

    $1,250,000132 Days on yellowkey   MLS ID: O6392216

    REDUCED by $99,900 (7.4%) on 06/12/2026

    For Sale O6392216 - 1649 HARMON AVE, WINTER PARK, FL 32789 57 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3223
       Built: 2018   Tax: $11,908 (2025)
    Community: Lawndale
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $7,841 (change assumption)
    Mortgage ($6,849) + Taxes in 2025 ($992)


    Taxes:$11,908

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park Middle


  • 1885 TEMPLE DR, WINTER PARK, FL 32789

    $2,195,000260 Days on yellowkey   MLS ID: O6359471

    REDUCED by $30,000 (1.3%) on 07/23/2026

    For Sale O6359471 - 1885 TEMPLE DR, WINTER PARK, FL 32789 62 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: $12,533 (change assumption)
    Mortgage ($12,027) + Taxes in 2025 ($506)


    Taxes:$6,073

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 2525 LAFAYETTE AVE, WINTER PARK, FL 32789

    $1,749,0001 Day on yellowkey   MLS ID: O6428823

    For Sale O6428823 - 2525 LAFAYETTE AVE, WINTER PARK, FL 32789 10 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2715
       Built: 2026   Tax: $4,700 (2025)
    Community: Winter Park Village
    Single Family


    Estimated Monthly Payment: $9,975 (change assumption)
    Mortgage ($9,583) + Taxes in 2025 ($392)


    Taxes:$4,700

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 5117 CYPRESS CT, WINTER PARK, FL 32792

    $449,99077 Days on yellowkey   MLS ID: O6407713

    1 Days Off yellowkey (back on 6/20/2026)

    For Sale O6407713 - 5117 CYPRESS CT, WINTER PARK, FL 32792 26 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1534
       Built: 1972   Tax: $3,877 (2025)
    Community: Wrenwood Heights
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,789 (change assumption)
    Mortgage ($2,466) + Taxes in 2025 ($323)


    Taxes:$3,877

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 7509 GLENMOOR LN, WINTER PARK, FL 32792

    $499,50028 Days on yellowkey   MLS ID: O6421887

    0 Days Off yellowkey (back on 7/5/2026)

    For Sale O6421887 - 7509 GLENMOOR LN, WINTER PARK, FL 32792 45 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2067
       Built: 1986   Tax: $2,931 (2025)
    Community: Glenmoor
    Single Family


    Estimated Monthly Payment: $2,981 (change assumption)
    Mortgage ($2,737) + Taxes in 2025 ($244)


    Taxes:$2,931

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1849 VIBURNUM LN, WINTER PARK, FL 32792

    $399,900357 Days on yellowkey   MLS ID: O6333863

    REDUCED by $8,100 (2.0%) on 07/02/2026

    For Sale O6333863 - 1849 VIBURNUM LN, WINTER PARK, FL 32792 27 photos

    Bed: 4   Bath: 2.0
    Liv Area Sq Ft: 1627
       Built: 1961   Tax: $3,645 (2024)
    Community: Eastbrook Sub Unit 05
    Single Family


    Estimated Monthly Payment: $2,495 (change assumption)
    Mortgage ($2,191) + Taxes in 2024 ($304)


    Taxes:$3,645

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 7577 DOCKSIDE ST, WINTER PARK, FL 32792

    $360,00058 Days on yellowkey   MLS ID: O6412514

    REDUCED by $10,000 (2.7%) on 06/25/2026

    For Sale O6412514 - 7577 DOCKSIDE ST, WINTER PARK, FL 32792 30 photos

    Bed: 3   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1245
       Built: 1977   Tax: $3,722 (2025)
    Community: Woodcrest Unit 6
    Single Family


    Estimated Monthly Payment: $2,283 (change assumption)
    Mortgage ($1,973) + Taxes in 2025 ($310)


    Taxes:$3,722

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 1840 LAUREL RD, WINTER PARK, FL 32789

    $2,299,0001 Day on yellowkey   MLS ID: O6428841

    For Sale O6428841 - 1840 LAUREL RD, WINTER PARK, FL 32789 12 photos

    Bed: 5   Bath: 5.0   Gar: 2
    Liv Area Sq Ft: 2868
       Built: 2026   Tax: $12,141 (2025)
    Community: Charmont
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $13,609 (change assumption)
    Mortgage ($12,597) + Taxes in 2025 ($1,012)


    Taxes:$12,141

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 1133 BELLA LAGO CV, WINTER PARK, FL 32792

    $2,100,00015 Days on yellowkey   MLS ID: O6425181

    For Sale O6425181 - 1133 BELLA LAGO CV, WINTER PARK, FL 32792 21 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1765
       Built: 1945   Tax: $4,801 (2025)
    Community: None
    Single Family


    Estimated Monthly Payment: $11,907 (change assumption)
    Mortgage ($11,507) + Taxes in 2025 ($400)


    Taxes:$4,801

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 3463 ARNEL DR, WINTER PARK, FL 32792

    $404,900135 Days on yellowkey   MLS ID: O6390301

    0 Days Off yellowkey (back on 7/28/2026)

    REDUCED by $5,000 (1.2%) on 07/24/2026

    For Sale O6390301 - 3463 ARNEL DR, WINTER PARK, FL 32792 35 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1770
       Built: 1967   Tax: $4,648 (2024)
    Community: Eastbrook Sub Unit 11
    Single Family


    Estimated Monthly Payment: $2,606 (change assumption)
    Mortgage ($2,219) + Taxes in 2024 ($387)


    Taxes:$4,648

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 1840 ASTER DR, WINTER PARK, FL 32792

    $414,90059 Days on yellowkey   MLS ID: O6412364

    REDUCED by $5,000 (1.2%) on 07/28/2026

    For Sale O6412364 - 1840 ASTER DR, WINTER PARK, FL 32792 20 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1667
       Built: 1978   Tax: $864 (2025)
    Community: Garden Lake Estates Unit 1
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,345 (change assumption)
    Mortgage ($2,273) + Taxes in 2025 ($72)


    Taxes:$864

    Elementary School: Red Bug Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 1404 BORDER DR, WINTER PARK, FL 32789

    $1,150,00062 Days on yellowkey   MLS ID: O6412140

    REDUCED by $25,000 (2.1%) on 07/01/2026

    For Sale O6412140 - 1404 BORDER DR, WINTER PARK, FL 32789 38 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 2469
       Built: 2023   Tax: $16,220 (2025)
    Community: Winter Park Village
    Single Family


    Estimated Monthly Payment: $7,653 (change assumption)
    Mortgage ($6,301) + Taxes in 2025 ($1,352)


    Taxes:$16,220

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 102 BELL PL, WINTER PARK, FL 32792

    $1,399,000107 Days on yellowkey   MLS ID: O6398118

    For Sale O6398118 - 102 BELL PL, WINTER PARK, FL 32792 46 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2459
       Built: 2025   Tax: $4,224 (2025)
    Community: Eastgate Sub
    Spa: No

    Single Family


    Estimated Monthly Payment: $8,018 (change assumption)
    Mortgage ($7,666) + Taxes in 2025 ($352)


    Taxes:$4,224

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 723 SYMONDS AVE, WINTER PARK, FL 32789

    $1,800,00063 Days on yellowkey   MLS ID: O6406823

    For Sale O6406823 - 723 SYMONDS AVE, WINTER PARK, FL 32789 50 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 3065
       Built: 2023   Tax: $15,884 (2025)
    Community: Horton Aaron
    Single Family


    Estimated Monthly Payment: $11,186 (change assumption)
    Mortgage ($9,863) + Taxes in 2025 ($1,324)


    Taxes:$15,884

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 433 GILBERT RD, WINTER PARK, FL 32792

    $675,0003 Days on yellowkey   MLS ID: O6428430

    For Sale O6428430 - 433 GILBERT RD, WINTER PARK, FL 32792 36 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1770
       Built: 1965   Tax: $4,032 (2025)
    Community: Winter Park Pines
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,035 (change assumption)
    Mortgage ($3,699) + Taxes in 2025 ($336)


    Taxes:$4,032

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 338 BLUE HERON DR, WINTER PARK, FL 32789

    $840,00061 Days on yellowkey   MLS ID: O6410174

    REDUCED by $25,000 (2.9%) on 07/28/2026

    For Sale O6410174 - 338 BLUE HERON DR, WINTER PARK, FL 32789 44 photos

    Bed: 3   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2017
       Built: 1960   Tax: $6,647 (2025)
    Community: Flamingo Shores
    Single Family


    Estimated Monthly Payment: $5,157 (change assumption)
    Mortgage ($4,603) + Taxes in 2025 ($554)


    Taxes:$6,647

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park 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.