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Winter Park Single Family Homes For Sale - 310 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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  • 607 ELLEN DR, WINTER PARK, FL 32789

    $1,449,900239 Days on yellowkey   MLS ID: O6354269

    REDUCED by $50,000 (3.3%) on 05/23/2026

    For Sale O6354269 - 607 ELLEN DR, WINTER PARK, FL 32789 34 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 2812
       Built: 2025
    Monthly Fee: $76
       Tax: $4,224 (2024)
    Community: Lake Killarney Shores
    Spa: No

    Single Family


    Estimated Monthly Payment: $8,372 (change assumption)
    Mortgage ($7,944) + Fees ($76) + Taxes in 2024 ($352)


    Taxes:$4,224

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2024

    Middle School: College Park Middle


  • 5117 CYPRESS CT, WINTER PARK, FL 32792

    $449,99034 Days on yellowkey   MLS ID: O6407713

    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


  • 120 BROADVIEW AVE, WINTER PARK, FL 32789

    $1,450,00026 Days on yellowkey   MLS ID: O6409860

    For Sale O6409860 - 120 BROADVIEW AVE, WINTER PARK, FL 32789 6 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1747
       Built: 1947   Tax: $2,693 (2025)
    Community: Killarney Estates
    Single Family


    Estimated Monthly Payment: $8,169 (change assumption)
    Mortgage ($7,945) + Taxes in 2025 ($224)


    Taxes:$2,693

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park Middle


  • 2157 LAKE DR, WINTER PARK, FL 32789

    $689,00018 Days on yellowkey   MLS ID: O6412258

    REDUCED by $70,000 (9.2%) on 05/31/2026

    For Sale O6412258 - 2157 LAKE DR, WINTER PARK, FL 32789 45 photos

    Bed: 3   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2124
       Built: 1962   Tax: $1,605 (2025)
    Community: Killarney Point
    Single Family


    Estimated Monthly Payment: $3,909 (change assumption)
    Mortgage ($3,775) + Taxes in 2025 ($134)


    Taxes:$1,605

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 338 BLUE HERON DR, WINTER PARK, FL 32789

    $865,00018 Days on yellowkey   MLS ID: O6410174

    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: $5,294 (change assumption)
    Mortgage ($4,740) + Taxes in 2025 ($554)


    Taxes:$6,647

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park Middle


  • 1821 ENGLEWOOD RD, WINTER PARK, FL 32789

    $3,135,000271 Days on yellowkey   MLS ID: O6345085

    For Sale O6345085 - 1821 ENGLEWOOD RD, WINTER PARK, FL 32789 36 photos

    Bed: 5   Bath: 5.5   Gar: 2
    Liv Area Sq Ft: 3863
       Built: 2025   Tax: $11,127 (2024)
    Community: Forest Hills
    Spa: No

    Single Family


    Estimated Monthly Payment: $18,105 (change assumption)
    Mortgage ($17,178) + Taxes in 2024 ($927)


    Taxes:$11,127

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Audubon Park K-8


  • 2501 WINTER PARK RD, WINTER PARK, FL 32789

    $1,649,000105 Days on yellowkey   MLS ID: O6384756

    REDUCED by $41,000 (2.4%) on 05/14/2026

    For Sale O6384756 - 2501 WINTER PARK RD, WINTER PARK, FL 32789 63 photos

    Bed: 5   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3304
       Built: 2014   Tax: $10,938 (2024)
    Community: Parklando #3
    Single Family


    Estimated Monthly Payment: $9,947 (change assumption)
    Mortgage ($9,035) + Taxes in 2024 ($912)


    Taxes:$10,938

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2024

    Middle School: None


  • 2228 HOWARD DR, WINTER PARK, FL 32789

    $2,460,00035 Days on yellowkey   MLS ID: O6407733

    For Sale O6407733 - 2228 HOWARD DR, WINTER PARK, FL 32789 9 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3294
       Built: 2026   Tax: $3,647 (2025)
    Community: Lake Forest Park
    Single Family


    Estimated Monthly Payment: $13,783 (change assumption)
    Mortgage ($13,479) + Taxes in 2025 ($304)


    Taxes:$3,647

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1571 WOODLAND AVE, WINTER PARK, FL 32789

    $6,000,00019 Days on yellowkey   MLS ID: O6411706

    For Sale O6411706 - 1571 WOODLAND AVE, WINTER PARK, FL 32789 73 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


  • 2614 PARKLAND DR, WINTER PARK, FL 32789

    $1,924,450423 Days on yellowkey   MLS ID: O6301489

    REDUCED by $24,550 (1.3%) on 05/29/2026

    For Sale O6301489 - 2614 PARKLAND DR, WINTER PARK, FL 32789 54 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3307
       Built: 2007   Tax: $12,712 (2024)
    Community: Parklando 03
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $11,604 (change assumption)
    Mortgage ($10,545) + Taxes in 2024 ($1,059)


    Taxes:$12,712

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Audubon Park K-8


  • 151 OAKWOOD WAY, WINTER PARK, FL 32789

    $2,850,000132 Days on yellowkey   MLS ID: O6380037

    0 Days Off yellowkey (back on 5/29/2026)

    REDUCED by $100,000 (3.4%) on 05/26/2026

    For Sale O6380037 - 151 OAKWOOD WAY, WINTER PARK, FL 32789 68 photos

    Bed: 4   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 4129
       Built: 2023   Tax: $34,218 (2025)
    Community: Charmont
    Spa: No

    Single Family


    Estimated Monthly Payment: $18,468 (change assumption)
    Mortgage ($15,616) + Taxes in 2025 ($2,852)


    Taxes:$34,218

    Elementary School: None

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 1433 ASTER CT, WINTER PARK, FL 32792

    $389,00034 Days on yellowkey   MLS ID: O6407873

    0 Days Off yellowkey (back on 5/29/2026)

    REDUCED by $10,000 (2.5%) on 05/21/2026

    For Sale O6407873 - 1433 ASTER CT, WINTER PARK, FL 32792 30 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1363
       Built: 1984   Tax: $1,057 (2025)
    Community: Garden Lake Estates Unit 3
    Single Family


    Estimated Monthly Payment: $2,220 (change assumption)
    Mortgage ($2,131) + Taxes in 2025 ($88)


    Taxes:$1,057

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 234 DETMAR DR, WINTER PARK, FL 32789

    $1,599,000127 Days on yellowkey   MLS ID: O6379927

    2 Days Off yellowkey (back on 5/29/2026)

    REDUCED by $46,000 (2.8%) on 04/29/2026

    For Sale O6379927 - 234 DETMAR DR, WINTER PARK, FL 32789 49 photos

    Bed: 4   Bath: 5.5   Gar: 1
    Liv Area Sq Ft: 3609
       Built: 1935   Tax: $13,664 (2025)
    Community: Osceola Shores Sec 1
    Spa: No

    Single Family


    Estimated Monthly Payment: $9,900 (change assumption)
    Mortgage ($8,761) + Taxes in 2025 ($1,139)


    Taxes:$13,664

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 4190 BEAR GULLY RD, WINTER PARK, FL 32792

    $499,900162 Days on yellowkey   MLS ID: O6371014

    REDUCED by $25,000 (4.8%) on 05/29/2026

    For Sale O6371014 - 4190 BEAR GULLY RD, WINTER PARK, FL 32792 30 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2058
       Built: 2003
    Monthly Fee: $52
       Tax: $5,630 (2024)
    Community: Bear Gully Forest
    Single Family


    Estimated Monthly Payment: $3,260 (change assumption)
    Mortgage ($2,739) + Fees ($52) + Taxes in 2024 ($469)


    Taxes:$5,630

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 1340 PLACE PICARDY, WINTER PARK, FL 32789

    $1,599,000125 Days on yellowkey   MLS ID: O6382113

    3 Days Off yellowkey (back on 3/30/2026)

    For Sale O6382113 - 1340 PLACE PICARDY, WINTER PARK, FL 32789 34 photos

    Bed: 3   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3459
       Built: 1997   Tax: $7,515 (2025)
    Community: Fontainebleau
    Single Family


    Estimated Monthly Payment: $9,388 (change assumption)
    Mortgage ($8,761) + Taxes in 2025 ($626)


    Taxes:$7,515

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 1760 GREENWICH AVE, WINTER PARK, FL 32789

    $625,00090 Days on yellowkey   MLS ID: O6392001

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

    REDUCED by $25,000 (3.8%) on 05/05/2026

    For Sale O6392001 - 1760 GREENWICH AVE, WINTER PARK, FL 32789 18 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1610
       Built: 1967   Tax: $2,779 (2025)
    Community: Golfview Heights
    Single Family


    Estimated Monthly Payment: $3,656 (change assumption)
    Mortgage ($3,425) + Taxes in 2025 ($232)


    Taxes:$2,779

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 2838 WRIGHT AVE, WINTER PARK, FL 32789

    $2,399,00056 Days on yellowkey   MLS ID: O6399931

    For Sale O6399931 - 2838 WRIGHT AVE, WINTER PARK, FL 32789 10 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3479
       Built: 2026   Tax: $6,037 (2025)
    Community: Lake Forest Park
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $13,648 (change assumption)
    Mortgage ($13,145) + Taxes in 2025 ($503)


    Taxes:$6,037

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 1946 STRATHAVEN RD, WINTER PARK, FL 32792

    $675,00021 Days on yellowkey   MLS ID: O6411329

    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: $4,410 (change assumption)
    Mortgage ($3,699) + Taxes in 2025 ($712)


    Taxes:$8,540

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 316 BECKETT CT, WINTER PARK, FL 32792

    $450,00021 Days on yellowkey   MLS ID: O6411108

    For Sale O6411108 - 316 BECKETT CT, WINTER PARK, FL 32792 33 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1651
       Built: 1966   Tax: $2,232 (2025)
    Community: Winter Park Pines Merrie Oaks
    Single Family


    Estimated Monthly Payment: $2,652 (change assumption)
    Mortgage ($2,466) + Taxes in 2025 ($186)


    Taxes:$2,232

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1177 KENWOOD AVE, WINTER PARK, FL 32789

    $1,800,00096 Days on yellowkey   MLS ID: O6390592

    0 Days Off yellowkey (back on 5/21/2026)

    REDUCED by $70,000 (3.7%) on 05/13/2026

    For Sale O6390592 - 1177 KENWOOD AVE, WINTER PARK, FL 32789 57 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 4363
       Built: 2007   Tax: $16,206 (2025)
    Community: Dixie Terrace
    Spa: No

    Single Family


    Estimated Monthly Payment: $11,213 (change assumption)
    Mortgage ($9,863) + Taxes in 2025 ($1,351)


    Taxes:$16,206

    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.