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Winter Park Single Family Homes For Sale - 303 homes

Winter Park Single Family Homes for Sale are located in Seminole 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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  • 7577 DOCKSIDE ST, WINTER PARK, FL 32792

    $360,00042 Days on yellowkey   MLS ID: O6412514

    4 Days Off yellowkey (back on 7/7/2026)

    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


  • 333 CORNWALL RD, WINTER PARK, FL 32792

    $579,00053 Days on yellowkey   MLS ID: O6409379

    For Sale O6409379 - 333 CORNWALL RD, WINTER PARK, FL 32792 32 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1660
       Built: 1963
    Monthly Fee: $5
       Tax: $2,654 (2025)
    Community: Winter Park Pines
    Single Family


    Estimated Monthly Payment: $3,399 (change assumption)
    Mortgage ($3,173) + Fees ($5) + Taxes in 2025 ($221)


    Taxes:$2,654

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 2157 LAKE DR, WINTER PARK, FL 32789

    $689,00045 Days on yellowkey   MLS ID: O6412258

    3 Days Off yellowkey (back on 7/6/2026)

    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


  • 501 LAKEVIEW AVE, WINTER PARK, FL 32789

    $1,390,000361 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


  • 2022 EASTBROOK BLVD, WINTER PARK, FL 32792

    $353,00015 Days on yellowkey   MLS ID: S5152746

    1 Days Off yellowkey (back on 7/6/2026)

    For Sale S5152746 - 2022 EASTBROOK BLVD, WINTER PARK, FL 32792 21 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1420
       Built: 1966   Tax: $3,122 (2025)
    Community: Eastbrook Sub Unit 07
    Single Family


    Estimated Monthly Payment: $2,194 (change assumption)
    Mortgage ($1,934) + Taxes in 2025 ($260)


    Taxes:$3,122

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 1521 CAVENDISH RD, WINTER PARK, FL 32789

    $470,00033 Days on yellowkey   MLS ID: O6415985

    5 Days Off yellowkey (back on 7/6/2026)

    For Sale O6415985 - 1521 CAVENDISH RD, WINTER PARK, FL 32789 22 photos

    Bed: 2   Bath: 1.0
    Liv Area Sq Ft: 1036
       Built: 1946   Tax: $2,793 (2025)
    Community: Orwin Manor Westminster
    Single Family


    Estimated Monthly Payment: $2,808 (change assumption)
    Mortgage ($2,575) + Taxes in 2025 ($233)


    Taxes:$2,793

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park Middle


  • 1836 GRINNELL TER, WINTER PARK, FL 32789

    $999,000158 Days on yellowkey   MLS ID: O6380457

    4 Days Off yellowkey (back on 7/6/2026)

    REDUCED by $51,000 (4.9%) on 05/06/2026

    For Sale O6380457 - 1836 GRINNELL TER, WINTER PARK, FL 32789 24 photos

    Bed: 3   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1907
       Built: 1995   Tax: $11,979 (2025)
    Community: Lake Virginia
    Single Family


    Estimated Monthly Payment: $6,472 (change assumption)
    Mortgage ($5,474) + Taxes in 2025 ($998)


    Taxes:$11,979

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 1849 VIBURNUM LN, WINTER PARK, FL 32792

    $399,900341 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


  • 240 ORANGE TERRACE DR, WINTER PARK, FL 32789

    $470,000341 Days on yellowkey   MLS ID: O6330690

    REDUCED by $9,900 (2.1%) on 06/23/2026

    For Sale O6330690 - 240 ORANGE TERRACE DR, WINTER PARK, FL 32789 32 photos

    Bed: 4   Bath: 2.0
    Liv Area Sq Ft: 1718
       Built: 1955   Tax: $6,210 (2024)
    Community: Orange Terrace
    Single Family


    Estimated Monthly Payment: $3,093 (change assumption)
    Mortgage ($2,575) + Taxes in 2024 ($518)


    Taxes:$6,210

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2024

    Middle School: Robinswood Middle


  • 7509 GLENMOOR LN, WINTER PARK, FL 32792

    $499,50012 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


  • 1707 HARMON AVE, WINTER PARK, FL 32789

    $649,00056 Days on yellowkey   MLS ID: O6409180

    REDUCED by $38,000 (5.5%) on 06/24/2026

    For Sale O6409180 - 1707 HARMON AVE, WINTER PARK, FL 32789 37 photos

    Bed: 3   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1669
       Built: 1927   Tax: $4,658 (2025)
    Community: Lawndale
    Single Family


    Estimated Monthly Payment: $3,944 (change assumption)
    Mortgage ($3,556) + Taxes in 2025 ($388)


    Taxes:$4,658

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park Middle


  • 1260 ALABAMA DR, WINTER PARK, FL 32789

    $6,900,000133 Days on yellowkey   MLS ID: O6387200

    For Sale O6387200 - 1260 ALABAMA DR, WINTER PARK, FL 32789 58 photos

    Bed: 6   Bath: 6.0   Gar: 3
    Liv Area Sq Ft: 6396
       Built: 1991   Tax: $59,749 (2025)
    Community: J Kronenberger Sub
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $42,786 (change assumption)
    Mortgage ($37,807) + Taxes in 2025 ($4,979)


    Taxes:$59,749

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 321 SYLVAN BLVD, WINTER PARK, FL 32789

    $1,395,00027 Days on yellowkey   MLS ID: O6417674

    0 Days Off yellowkey (back on 7/2/2026)

    For Sale O6417674 - 321 SYLVAN BLVD, WINTER PARK, FL 32789 39 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2821
       Built: 1940   Tax: $6,544 (2025)
    Community: Sylvan Lake Shores
    Single Family


    Estimated Monthly Payment: $8,189 (change assumption)
    Mortgage ($7,644) + Taxes in 2025 ($545)


    Taxes:$6,544

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 501 HERITAGE BLVD, WINTER PARK, FL 32792

    $469,000123 Days on yellowkey   MLS ID: S5145746

    REDUCED by $5,900 (1.2%) on 07/04/2026

    For Sale S5145746 - 501 HERITAGE BLVD, WINTER PARK, FL 32792 20 photos

    Bed: 4   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1376
       Built: 1966   Tax: $10,434 (2025)
    Community: Georgetown Estates
    Single Family


    Estimated Monthly Payment: $3,439 (change assumption)
    Mortgage ($2,570) + Taxes in 2025 ($870)


    Taxes:$10,434

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 2600 EUSTON RD, WINTER PARK, FL 32789

    $630,00095 Days on yellowkey   MLS ID: O6397890

    For Sale O6397890 - 2600 EUSTON RD, WINTER PARK, FL 32789 36 photos

    Bed: 6   Bath: 3.0
    Liv Area Sq Ft: 3145
       Built: 1951   Tax: $7,446 (2024)
    Community: Glencoe Sub
    Single Family


    Estimated Monthly Payment: $4,072 (change assumption)
    Mortgage ($3,452) + Taxes in 2024 ($620)


    Taxes:$7,446

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 1612 LAWNDALE CIR, WINTER PARK, FL 32792

    $439,00012 Days on yellowkey   MLS ID: O6418472

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

    For Sale O6418472 - 1612 LAWNDALE CIR, WINTER PARK, FL 32792 2 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1592
       Built: 1984
    Monthly Fee: $49
       Tax: $1,425 (2025)
    Community: Country Lane
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,573 (change assumption)
    Mortgage ($2,405) + Fees ($49) + Taxes in 2025 ($119)


    Taxes:$1,425

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 120 BROADVIEW AVE, WINTER PARK, FL 32789

    $1,450,00053 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


  • 1751 GOODRICH AVE, WINTER PARK, FL 32789

    $1,380,000166 Days on yellowkey   MLS ID: O6377936

    REDUCED by $45,000 (3.2%) on 07/03/2026

    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: $8,333 (change assumption)
    Mortgage ($7,561) + Taxes in 2024 ($772)


    Taxes:$9,263

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Glenridge Middle


  • 3006 NORTHWOOD BLVD, WINTER PARK, FL 32789

    $1,249,00018 Days on yellowkey   MLS ID: O6419056

    REDUCED by $51,000 (3.9%) on 07/02/2026

    For Sale O6419056 - 3006 NORTHWOOD BLVD, WINTER PARK, FL 32789 46 photos

    Bed: 4   Bath: 3.0   Gar: 1
    Liv Area Sq Ft: 2075
       Built: 1953   Tax: $4,188 (2025)
    Community: Northwood Terrace
    Spa: No

    Single Family


    Estimated Monthly Payment: $7,193 (change assumption)
    Mortgage ($6,844) + Taxes in 2025 ($349)


    Taxes:$4,188

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 1565 FOREST AVE, WINTER PARK, FL 32789

    $1,495,00091 Days on yellowkey   MLS ID: O6398694

    0 Days Off yellowkey (back on 7/2/2026)

    REDUCED by $155,000 (9.4%) on 06/15/2026

    For Sale O6398694 - 1565 FOREST AVE, WINTER PARK, FL 32789 37 photos

    Bed: 4   Bath: 2.0
    Liv Area Sq Ft: 2163
       Built: 1925   Tax: $2,803 (2025)
    Community: Ellno Willo
    Single Family


    Estimated Monthly Payment: $8,425 (change assumption)
    Mortgage ($8,192) + Taxes in 2025 ($234)


    Taxes:$2,803

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8




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.