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Winter Park Homes For Sale & Real Estate - 416 homes

Winter Park homes for sale are located in Orange County, Florida. Find homes in Winter Park for sale with data from the Multiple Listing Service (MLS). Our REALTORS® can assist you in your real estate search for Winter Park houses.

Location: Winter Park

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  • 644 N KNOWLES AVE #3, WINTER PARK, FL 32789

    $475,00032 Days on yellowkey   MLS ID: O6420484

    For Sale O6420484 - 644 N KNOWLES AVE #3, WINTER PARK, FL 32789 32 photos

    Bed: 1   Bath: 1.0
    Liv Area Sq Ft: 767
       Built: 1974   Tax: $4,218 (2025)
    Community: Knowles Manor North Condo
    Condo


    Estimated Monthly Payment: $2,954 (change assumption)
    Mortgage ($2,603) + Taxes in 2025 ($352)


    Taxes:$4,218

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 346 S RANGER BLVD, WINTER PARK, FL 32792

    $475,000318 Days on yellowkey   MLS ID: S5134662

    For Sale S5134662 - 346 S RANGER BLVD, WINTER PARK, FL 32792 31 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1592
       Built: 1965   Tax: $5,339 (2024)
    Community: Winter Park Pines
    Single Family


    Estimated Monthly Payment: $3,048 (change assumption)
    Mortgage ($2,603) + Taxes in 2024 ($445)


    Taxes:$5,339

    Elementary School: Aloma Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Glenridge Middle


  • 729 MONMOUTH WAY, WINTER PARK, FL 32792

    $799,00026 Days on yellowkey   MLS ID: O6422168

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

    For Sale O6422168 - 729 MONMOUTH WAY, WINTER PARK, FL 32792 50 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2332
       Built: 1970   Tax: $8,433 (2025)
    Community: Winter Park Pines
    Spa: No

    Single Family


    Estimated Monthly Payment: $5,081 (change assumption)
    Mortgage ($4,378) + Taxes in 2025 ($703)


    Taxes:$8,433

    Elementary School: Aloma Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 7500 WAUNATTA CT, WINTER PARK, FL 32792

    $299,90026 Days on yellowkey   MLS ID: TB8525179

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

    For Sale TB8525179 - 7500 WAUNATTA CT, WINTER PARK, FL 32792 34 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1998
       Built: 1979   Tax: $6,383 (2025)
    Community: Lake Waunatta Village
    Single Family


    Estimated Monthly Payment: $2,175 (change assumption)
    Mortgage ($1,643) + Taxes in 2025 ($532)


    Taxes:$6,383

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 4768 TANGERINE AVE #4768, WINTER PARK, FL 32792

    $174,900155 Days on yellowkey   MLS ID: S5144503

    REDUCED by $4,100 (2.3%) on 07/07/2026

    For Sale S5144503 - 4768 TANGERINE AVE #4768, WINTER PARK, FL 32792 17 photos

    Bed: 1   Bath: 1.0
    Liv Area Sq Ft: 753
       Built: 1973
    Monthly Fee: $280
       Tax: $1,479 (2024)
    Community: Wrenwood Condo
    Condo


    Estimated Monthly Payment: $1,362 (change assumption)
    Mortgage ($958) + Fees ($280) + Taxes in 2024 ($123)


    Taxes:$1,479

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 333 CORNWALL RD, WINTER PARK, FL 32792

    $579,00068 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


  • 1250 S DENNING DR #109, WINTER PARK, FL 32789

    $190,00023 Days on yellowkey   MLS ID: R4911491

    For Sale R4911491 - 1250 S DENNING DR #109, WINTER PARK, FL 32789 27 photos

    Bed: 1   Bath: 1.0
    Liv Area Sq Ft: 658
       Built: 1967
    Monthly Fee: $350
       Tax: $1,669 (2025)
    Community: Mead Garden
    Spa: No

    Condo


    Estimated Monthly Payment: $1,530 (change assumption)
    Mortgage ($1,041) + Fees ($350) + Taxes in 2025 ($139)


    Taxes:$1,669

    Elementary School: Killarney Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 2157 LAKE DR, WINTER PARK, FL 32789

    $689,00060 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


  • 751 WARRENTON RD, WINTER PARK, FL 32792

    $319,90036 Days on yellowkey   MLS ID: TB8522073

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

    For Sale TB8522073 - 751 WARRENTON RD, WINTER PARK, FL 32792 16 photos

    Bed: 3   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1196
       Built: 1989
    Monthly Fee: $86
       Tax: $2,795 (2025)
    Community: Winter Park Pines Patio Homes
    Spa: No

    Half Duplex


    Estimated Monthly Payment: $2,072 (change assumption)
    Mortgage ($1,753) + Fees ($86) + Taxes in 2025 ($233)


    Taxes:$2,795

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2022 EASTBROOK BLVD, WINTER PARK, FL 32792

    $353,00030 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

    $470,00048 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


  • 1260 ALABAMA DR, WINTER PARK, FL 32789

    $6,900,000148 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


  • 252 SCOTTSDALE SQ #252, WINTER PARK, FL 32792

    $85,00027 Days on yellowkey   MLS ID: O6421977

    For Sale O6421977 - 252 SCOTTSDALE SQ #252, WINTER PARK, FL 32792 3 photos

    Bed: 2   Bath: 1.5
    Liv Area Sq Ft: 1085
       Built: 1974   Tax: $1,637 (2025)
    Community: Winter Park Woods Condo
    Condo


    Estimated Monthly Payment: $602 (change assumption)
    Mortgage ($466) + Taxes in 2025 ($136)


    Taxes:$1,637

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 5184 LAZY OAKS DR, WINTER PARK, FL 32792

    $280,00025 Days on yellowkey   MLS ID: O6422366

    For Sale O6422366 - 5184 LAZY OAKS DR, WINTER PARK, FL 32792 31 photos

    Bed: 2   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1008
       Built: 1984   Tax: $2,780 (2025)
    Community: Lazy Oaks Condo
    Condo


    Estimated Monthly Payment: $1,766 (change assumption)
    Mortgage ($1,534) + Taxes in 2025 ($232)


    Taxes:$2,780

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 120 BROADVIEW AVE, WINTER PARK, FL 32789

    $1,450,00068 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


  • 1695 LEE RD #B210, WINTER PARK, FL 32789

    $95,000188 Days on yellowkey   MLS ID: O6375872

    REDUCED by $3,000 (3.1%) on 07/03/2026

    For Sale O6375872 - 1695 LEE RD #B210, WINTER PARK, FL 32789 27 photos

    Bed: 1   Bath: 1.0
    Liv Area Sq Ft: 638
       Built: 1966   Tax: $1,493 (2024)
    Community: Waterfall Cove
    Spa: No

    Condo


    Estimated Monthly Payment: $645 (change assumption)
    Mortgage ($521) + Taxes in 2024 ($124)


    Taxes:$1,493

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 1751 GOODRICH AVE, WINTER PARK, FL 32789

    $1,380,000181 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


  • 1565 FOREST AVE, WINTER PARK, FL 32789

    $1,495,000106 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


  • 2361 MULBRY DR, WINTER PARK, FL 32789

    $2,249,000104 Days on yellowkey   MLS ID: O6396840

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

    REDUCED by $40,000 (1.7%) on 06/10/2026

    For Sale O6396840 - 2361 MULBRY DR, WINTER PARK, FL 32789 76 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 3130
       Built: 2026   Tax: $6,436 (2025)
    Community: Lake Forest Park
    Single Family


    Estimated Monthly Payment: $12,859 (change assumption)
    Mortgage ($12,323) + Taxes in 2025 ($536)


    Taxes:$6,436

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 1232 VALLEY CREEK RUN, WINTER PARK, FL 32792

    $535,00041 Days on yellowkey   MLS ID: O6417190

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

    For Sale O6417190 - 1232 VALLEY CREEK RUN, WINTER PARK, FL 32792 48 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2071
       Built: 1994
    Monthly Fee: $22
       Tax: $2,283 (2025)
    Community: Lost Creek
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,144 (change assumption)
    Mortgage ($2,931) + Fees ($22) + Taxes in 2025 ($190)


    Taxes:$2,283

    Elementary School: Red Bug Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle




Why Bother Searching Elsewhere for Winter Park Homes for Sale and Other Real Estate?

Winter Park home, townhome, condo, villa, and other listing sales 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 houses for sale in Winter Park . You can use our website to view Multiple Listing Service (MLS) data on Winter Park Real Estate. 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 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.