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Winter Park Homes For Sale & Real Estate - 439 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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  • 1521 CAVENDISH RD, WINTER PARK, FL 32789

    $470,00034 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

    $999,000159 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

    $399,900342 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

    $470,000342 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

    $499,50013 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

    $649,00057 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

    $6,900,000134 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

    $85,00013 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

    $280,00011 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


  • 321 SYLVAN BLVD, WINTER PARK, FL 32789

    $1,395,00028 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


  • 1122 WASHINGTON AVE #7B, WINTER PARK, FL 32789

    $575,00014 Days on yellowkey   MLS ID: O6421299

    For Sale O6421299 - 1122 WASHINGTON AVE #7B, WINTER PARK, FL 32789 53 photos

    Bed: 2   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1556
       Built: 1978
    Monthly Fee: $504
       Tax: $5,786 (2025)
    Community: Quarters At Winter Park Condo
    Townhouse


    Estimated Monthly Payment: $4,137 (change assumption)
    Mortgage ($3,151) + Fees ($504) + Taxes in 2025 ($482)


    Taxes:$5,786

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 501 HERITAGE BLVD, WINTER PARK, FL 32792

    $469,000124 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

    $630,00096 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

    $439,00013 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


  • 1000 S SEMORAN BLVD BLVD #603, WINTER PARK, FL 32792

    $99,90020 Days on yellowkey   MLS ID: O6420027

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

    For Sale O6420027 - 1000 S SEMORAN BLVD BLVD #603, WINTER PARK, FL 32792 17 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1003
       Built: 1969   Tax: $1,878 (2025)
    Community: Golfside Villas Condo
    Condo


    Estimated Monthly Payment: $704 (change assumption)
    Mortgage ($547) + Taxes in 2025 ($157)


    Taxes:$1,878

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 2305 SUN VALLEY CIR, WINTER PARK, FL 32792, WINTER PARK, FL 32792

    $279,90013 Days on yellowkey   MLS ID: O6421422

    For Sale O6421422 - 2305 SUN VALLEY CIR, WINTER PARK, FL 32792, WINTER PARK, FL 32792 42 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1295
       Built: 1985
    Monthly Fee: $499

    Community: Cedarwood Village
    Condo


    Estimated Monthly Payment: $2,033 (change assumption)
    Mortgage ($1,534) + Fees ($499) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 120 BROADVIEW AVE, WINTER PARK, FL 32789

    $1,450,00054 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

    $95,000174 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

    $1,380,000167 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

    $1,495,00092 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 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.