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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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  • 1760 LEGION DR, WINTER PARK, FL 32789

    $2,295,000107 Days on yellowkey   MLS ID: O6383603

    For Sale O6383603 - 1760 LEGION DR, WINTER PARK, FL 32789 66 photos

    Bed: 4   Bath: 5.5   Gar: 2
    Liv Area Sq Ft: 4392
       Built: 1964   Tax: $13,622 (2025)
    Community: Green Oaks Rep
    Single Family


    Estimated Monthly Payment: $13,710 (change assumption)
    Mortgage ($12,575) + Taxes in 2025 ($1,135)


    Taxes:$13,622

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 2922 REEF KNOT PL, WINTER PARK, FL 32792

    $1,149,000362 Days on yellowkey   MLS ID: O6316445

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

    For Sale O6316445 - 2922 REEF KNOT PL, WINTER PARK, FL 32792 49 photos

    Bed: 4   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 3153
       Built: 2019
    Monthly Fee: $186
       Tax: $10,521 (2024)
    Community: Lake Florence Preserve
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $7,358 (change assumption)
    Mortgage ($6,296) + Fees ($186) + Taxes in 2024 ($877)


    Taxes:$10,521

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 2627 AMBERGATE RD, WINTER PARK, FL 32792

    $510,0001179 Days on yellowkey   MLS ID: O6093816

    For Sale O6093816 - 2627 AMBERGATE RD, WINTER PARK, FL 32792 19 photos

    Bed: 4   Bath: 3.0   Gar: 1
    Liv Area Sq Ft: 1805
       Built: 1959   Tax: $4,750 (2022)
    Community: Winter Park Estates
    Single Family


    Estimated Monthly Payment: $3,190 (change assumption)
    Mortgage ($2,794) + Taxes in 2022 ($396)


    Taxes:$4,750

    Elementary School: None

    High School: None

    Tax Year: 2022

    Middle School: None


  • 2237 WOODCREST DR, WINTER PARK, FL 32792

    $490,00035 Days on yellowkey   MLS ID: O6404115

    0 Days Off yellowkey (back on 5/1/2026)

    For Sale O6404115 - 2237 WOODCREST DR, WINTER PARK, FL 32792 1 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1492
       Built: 1959   Tax: $1,919 (2025)
    Community: Kenilworth Estates 1St Add
    Single Family


    Estimated Monthly Payment: $2,845 (change assumption)
    Mortgage ($2,685) + Taxes in 2025 ($160)


    Taxes:$1,919

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 150 DANA WAY, WINTER PARK, FL 32789

    $3,799,00070 Days on yellowkey   MLS ID: O6394012

    0 Days Off yellowkey (back on 5/1/2026)

    For Sale O6394012 - 150 DANA WAY, WINTER PARK, FL 32789 81 photos

    Bed: 5   Bath: 5.0   Gar: 2
    Liv Area Sq Ft: 4451
       Built: 2026   Tax: $14,010 (2025)
    Community: Charmont
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $21,983 (change assumption)
    Mortgage ($20,816) + Taxes in 2025 ($1,168)


    Taxes:$14,010

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 1354 INDIANA AVE, WINTER PARK, FL 32789

    $589,90092 Days on yellowkey   MLS ID: O6387500

    For Sale O6387500 - 1354 INDIANA AVE, WINTER PARK, FL 32789 39 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1269
       Built: 1947   Tax: $5,352 (2024)
    Community: Metzingers Add
    Single Family


    Estimated Monthly Payment: $3,678 (change assumption)
    Mortgage ($3,232) + Taxes in 2024 ($446)


    Taxes:$5,352

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 420 OHIO ST, WINTER PARK, FL 32789

    $1,360,00038 Days on yellowkey   MLS ID: O6399541

    For Sale O6399541 - 420 OHIO ST, WINTER PARK, FL 32789 8 photos

    Bed: 5   Bath: 5.5   Gar: 2
    Liv Area Sq Ft: 3735
       Built: 2026   Tax: $1,281 (2025)
    Community: Karolina On Killarney
    Single Family


    Estimated Monthly Payment: $7,559 (change assumption)
    Mortgage ($7,452) + Taxes in 2025 ($107)


    Taxes:$1,281

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 501 LAKEVIEW AVE, WINTER PARK, FL 32789

    $1,390,000322 Days on yellowkey   MLS ID: O6325192

    For Sale O6325192 - 501 LAKEVIEW AVE, WINTER PARK, FL 32789 59 photos

    Bed: 4   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3253
       Built: 2026   Tax: $2,820 (2024)
    Community: Killarney Estates
    Single Family


    Estimated Monthly Payment: $7,851 (change assumption)
    Mortgage ($7,616) + Taxes in 2024 ($235)


    Taxes:$2,820

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2024

    Middle School: College Park Middle


  • 3245 COLEUS CT, WINTER PARK, FL 32792

    $379,90068 Days on yellowkey   MLS ID: O6390829

    REDUCED by $10,000 (2.6%) on 04/28/2026

    For Sale O6390829 - 3245 COLEUS CT, WINTER PARK, FL 32792 18 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1529
       Built: 1968   Tax: $986 (2024)
    Community: Eastbrook Sub Unit 14
    Single Family


    Estimated Monthly Payment: $2,164 (change assumption)
    Mortgage ($2,082) + Taxes in 2024 ($82)


    Taxes:$986

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 2454 BROOKSHIRE AVE, WINTER PARK, FL 32792

    $1,399,00099 Days on yellowkey   MLS ID: O6384924

    1 Days Off yellowkey (back on 4/28/2026)

    For Sale O6384924 - 2454 BROOKSHIRE AVE, WINTER PARK, FL 32792 34 photos

    Bed: 4   Bath: 3.5   Gar: 1
    Liv Area Sq Ft: 2509
       Built: 2023   Tax: $11,586 (2024)
    Community: Brookshire Heights 1St Add
    Single Family


    Estimated Monthly Payment: $8,631 (change assumption)
    Mortgage ($7,666) + Taxes in 2024 ($966)


    Taxes:$11,586

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Glenridge Middle


  • 632 COUNTRY CLUB DR, WINTER PARK, FL 32789

    $1,050,000587 Days on yellowkey   MLS ID: O6250417

    0 Days Off yellowkey (back on 9/29/2025)

    For Sale O6250417 - 632 COUNTRY CLUB DR, WINTER PARK, FL 32789 36 photos

    Bed: 3   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 2342
       Built: 1952   Tax: $4,638 (2023)
    Community: Lords Sub
    Spa: No

    Single Family


    Estimated Monthly Payment: $6,140 (change assumption)
    Mortgage ($5,753) + Taxes in 2023 ($387)


    Taxes:$4,638

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2023

    Middle School: College Park Middle


  • 121 STEFANIK RD, WINTER PARK, FL 32792

    $317,500226 Days on yellowkey   MLS ID: A4669103

    For Sale A4669103 - 121 STEFANIK RD, WINTER PARK, FL 32792 11 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1392
       Built: 1949   Tax: $3,581 (2024)
    Community: Slovak Village
    Single Family


    Estimated Monthly Payment: $2,038 (change assumption)
    Mortgage ($1,740) + Taxes in 2024 ($298)


    Taxes:$3,581

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 2503 VERSAILLES AVE, WINTER PARK, FL 32789

    $2,184,000177 Days on yellowkey   MLS ID: O6365961

    0 Days Off yellowkey (back on 4/27/2026)

    REDUCED by $166,000 (7.1%) on 04/04/2026

    For Sale O6365961 - 2503 VERSAILLES AVE, WINTER PARK, FL 32789 53 photos

    Bed: 5   Bath: 4.0   Gar: 3
    Liv Area Sq Ft: 4026
       Built: 2015   Tax: $15,760 (2024)
    Community: Fontainebleau
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $13,280 (change assumption)
    Mortgage ($11,967) + Taxes in 2024 ($1,313)


    Taxes:$15,760

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Maitland Middle


  • 1540 MILLER AVE, WINTER PARK, FL 32789

    $1,399,90053 Days on yellowkey   MLS ID: O6398421

    For Sale O6398421 - 1540 MILLER AVE, WINTER PARK, FL 32789 55 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2984
       Built: 2026   Tax: $3,573 (2025)
    Community: Lawndale
    Spa: No

    Single Family


    Estimated Monthly Payment: $7,968 (change assumption)
    Mortgage ($7,670) + Taxes in 2025 ($298)


    Taxes:$3,573

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park Middle


  • 1807 MAGNOLIA AVE, WINTER PARK, FL 32789

    $1,199,00050 Days on yellowkey   MLS ID: O6396616

    0 Days Off yellowkey (back on 4/25/2026)

    For Sale O6396616 - 1807 MAGNOLIA AVE, WINTER PARK, FL 32789 38 photos

    Bed: 5   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2618
       Built: 2026   Tax: $4,720 (2025)
    Community: Temple Terrace
    Spa: No

    Single Family


    Estimated Monthly Payment: $6,963 (change assumption)
    Mortgage ($6,570) + Taxes in 2025 ($393)


    Taxes:$4,720

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 2020 COCOS CT, WINTER PARK, FL 32792

    $458,99084 Days on yellowkey   MLS ID: O6389901

    1 Days Off yellowkey (back on 4/24/2026)

    REDUCED by $1,000 (0.2%) on 04/17/2026

    For Sale O6389901 - 2020 COCOS CT, WINTER PARK, FL 32792 22 photos

    Bed: 3   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1715
       Built: 1966   Tax: $1,410 (2024)
    Community: Eastbrook Sub Unit 8
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,632 (change assumption)
    Mortgage ($2,515) + Taxes in 2024 ($117)


    Taxes:$1,410

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 1751 GOODRICH AVE, WINTER PARK, FL 32789

    $1,425,000127 Days on yellowkey   MLS ID: O6377936

    REDUCED by $50,000 (3.4%) on 04/23/2026

    For Sale O6377936 - 1751 GOODRICH AVE, WINTER PARK, FL 32789 50 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2170
       Built: 2016   Tax: $9,263 (2024)
    Community: Sylvan Heights
    Single Family


    Estimated Monthly Payment: $8,580 (change assumption)
    Mortgage ($7,808) + Taxes in 2024 ($772)


    Taxes:$9,263

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Glenridge Middle


  • 2305 COLDSTREAM DRIVE, WINTER PARK, FL 32792

    $1,825,00066 Days on yellowkey   MLS ID: O6393049

    1 Days Off yellowkey (back on 4/23/2026)

    For Sale O6393049 - 2305 COLDSTREAM DRIVE, WINTER PARK, FL 32792 23 photos

    Bed: 5   Bath: 5.5   Gar: 2
    Liv Area Sq Ft: 3655
       Built: 2026   Tax: $7,014 (2025)
    Community: Brookshire Heights
    Single Family


    Estimated Monthly Payment: $10,584 (change assumption)
    Mortgage ($10,000) + Taxes in 2025 ($585)


    Taxes:$7,014

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 1792 CHILEAN LN, WINTER PARK, FL 32792

    $325,000134 Days on yellowkey   MLS ID: O6375881

    1 Days Off yellowkey (back on 4/21/2026)

    For Sale O6375881 - 1792 CHILEAN LN, WINTER PARK, FL 32792 30 photos

    Bed: 3   Bath: 1.0
    Liv Area Sq Ft: 984
       Built: 1959   Tax: $2,677 (2024)
    Community: Eastbrook Sub Unit 05
    Single Family


    Estimated Monthly Payment: $2,004 (change assumption)
    Mortgage ($1,781) + Taxes in 2024 ($223)


    Taxes:$2,677

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 1849 VIBURNUM LN, WINTER PARK, FL 32792

    $425,000302 Days on yellowkey   MLS ID: O6333863

    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: $2,632 (change assumption)
    Mortgage ($2,329) + Taxes in 2024 ($304)


    Taxes:$3,645

    Elementary School: None

    High School: None

    Tax Year: 2024

    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.