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Winter Park Homes For Sale & Real Estate - 446 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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  • 2612 ROXBURY RD, WINTER PARK, FL 32789

    $630,000223 Days on yellowkey   MLS ID: S5137596

    For Sale S5137596 - 2612 ROXBURY RD, WINTER PARK, FL 32789 30 photos

    Bed: 5   Bath: 3.0
    Liv Area Sq Ft: 2472
       Built: 1957   Tax: $6,425 (2024)
    Community: Glencoe Sub
    Single Family


    Estimated Monthly Payment: $3,987 (change assumption)
    Mortgage ($3,452) + Taxes in 2024 ($535)


    Taxes:$6,425

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2024

    Middle School: College Park Middle


  • 3021 AARON BURR AVE #3, WINTER PARK, FL 32792

    $140,00063 Days on yellowkey   MLS ID: S5147382

    For Sale S5147382 - 3021 AARON BURR AVE #3, WINTER PARK, FL 32792 21 photos

    Bed: 2   Bath: 2.5
    Liv Area Sq Ft: 1090
       Built: 1974
    Monthly Fee: $479
       Tax: $1,992 (2025)
    Community: Colonies
    Condo


    Estimated Monthly Payment: $1,412 (change assumption)
    Mortgage ($767) + Fees ($479) + Taxes in 2025 ($166)


    Taxes:$1,992

    Elementary School: Cheney Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 256 LEWFIELD CIR #256, WINTER PARK, FL 32792

    $184,900154 Days on yellowkey   MLS ID: O6367842

    For Sale O6367842 - 256 LEWFIELD CIR #256, WINTER PARK, FL 32792 55 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 927
       Built: 1973
    Monthly Fee: $465
       Tax: $1,916 (2025)
    Community: Stratford A Winter Park Condo
    Condo


    Estimated Monthly Payment: $1,638 (change assumption)
    Mortgage ($1,013) + Fees ($465) + Taxes in 2025 ($160)


    Taxes:$1,916

    Elementary School: English Estates Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 520 FITZWALTER DR, WINTER PARK, FL 32792

    $1,000,000102 Days on yellowkey   MLS ID: O6380171

    0 Days Off yellowkey (back on 4/11/2026)

    For Sale O6380171 - 520 FITZWALTER DR, WINTER PARK, FL 32792 47 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2111
       Built: 2022   Tax: $10,205 (2024)
    Community: Brookshire Heights 1St Add
    Single Family


    Estimated Monthly Payment: $6,330 (change assumption)
    Mortgage ($5,479) + Taxes in 2024 ($850)


    Taxes:$10,205

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Glenridge Middle


  • 675 OVERSPIN DR, WINTER PARK, FL 32789

    $775,000125 Days on yellowkey   MLS ID: O6378975

    0 Days Off yellowkey (back on 4/8/2026)

    For Sale O6378975 - 675 OVERSPIN DR, WINTER PARK, FL 32789 32 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3062
       Built: 2010   Tax: $11,578 (2025)
    Community: Dubsdread Heights
    Single Family


    Estimated Monthly Payment: $5,211 (change assumption)
    Mortgage ($4,246) + Taxes in 2025 ($965)


    Taxes:$11,578

    Elementary School: Princeton Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park Middle


  • 311 E MORSE BLVD #7-5, WINTER PARK, FL 32789

    $359,000345 Days on yellowkey   MLS ID: O6308664

    For Sale O6308664 - 311 E MORSE BLVD #7-5, WINTER PARK, FL 32789 40 photos

    Bed: 1   Bath: 1.0
    Liv Area Sq Ft: 482
       Built: 1960   Tax: $3,405 (2024)
    Community: Phillips Circle Rep
    Condo


    Estimated Monthly Payment: $2,251 (change assumption)
    Mortgage ($1,967) + Taxes in 2024 ($284)


    Taxes:$3,405

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 1870 STAUNTON AVE, WINTER PARK, FL 32789

    $1,250,00072 Days on yellowkey   MLS ID: O6391469

    For Sale O6391469 - 1870 STAUNTON AVE, WINTER PARK, FL 32789 10 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2525
       Built: 1935   Tax: $1,302 (2025)
    Community: Karolina On Killarney
    Single Family


    Estimated Monthly Payment: $6,958 (change assumption)
    Mortgage ($6,849) + Taxes in 2025 ($109)


    Taxes:$1,302

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park Middle


  • 1630 ELM AVE, WINTER PARK, FL 32789

    $2,385,00090 Days on yellowkey   MLS ID: O6388606

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

    For Sale O6388606 - 1630 ELM AVE, WINTER PARK, FL 32789 15 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3408
       Built: 2026   Tax: $1,673 (2024)
    Community: Temple Estates
    Single Family


    Estimated Monthly Payment: $13,208 (change assumption)
    Mortgage ($13,068) + Taxes in 2024 ($139)


    Taxes:$1,673

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Maitland Middle


  • 230 STRATHY LN, WINTER PARK, FL 32792

    $499,000158 Days on yellowkey   MLS ID: O6371054

    For Sale O6371054 - 230 STRATHY LN, WINTER PARK, FL 32792 12 photos

    Bed: 2   Bath: 1.0
    Liv Area Sq Ft: 920
       Built: 1957   Tax: $4,071 (2024)
    Community: Aloma
    Single Family


    Estimated Monthly Payment: $3,073 (change assumption)
    Mortgage ($2,734) + Taxes in 2024 ($339)


    Taxes:$4,071

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Glenridge Middle


  • 2231 NAIRN DR, WINTER PARK, FL 32792

    $499,000158 Days on yellowkey   MLS ID: O6369016

    For Sale O6369016 - 2231 NAIRN DR, WINTER PARK, FL 32792 19 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1088
       Built: 1956   Tax: $3,793 (2025)
    Community: Aloma
    Single Family


    Estimated Monthly Payment: $3,050 (change assumption)
    Mortgage ($2,734) + Taxes in 2025 ($316)


    Taxes:$3,793

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 2423 VIA SIENNA, WINTER PARK, FL 32789

    $2,200,000100 Days on yellowkey   MLS ID: O6386867

    For Sale O6386867 - 2423 VIA SIENNA, WINTER PARK, FL 32789 44 photos

    Bed: 4   Bath: 3.5
    Liv Area Sq Ft: 3472
       Built: 1990   Tax: $18,918 (2026)
    Community: Cinnamon Shores
    Single Family


    Estimated Monthly Payment: $13,631 (change assumption)
    Mortgage ($12,054) + Taxes in 2026 ($1,577)


    Taxes:$18,918

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2026

    Middle School: Maitland Middle


  • 512 N LAKEMONT AVE, WINTER PARK, FL 32792

    $500,00086 Days on yellowkey   MLS ID: O6392353

    For Sale O6392353 - 512 N LAKEMONT AVE, WINTER PARK, FL 32792 43 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1413
       Built: 1955   Tax: $2,136 (2025)
    Community: Eastgate Sub
    Single Family


    Estimated Monthly Payment: $2,918 (change assumption)
    Mortgage ($2,740) + Taxes in 2025 ($178)


    Taxes:$2,136

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 1996 INDIANA AVE, WINTER PARK, FL 32789

    $249,900157 Days on yellowkey   MLS ID: O6372229

    0 Days Off yellowkey (back on 3/27/2026)

    For Sale O6372229 - 1996 INDIANA AVE, WINTER PARK, FL 32789 18 photos

    Bed: 2   Bath: 1.0
    Liv Area Sq Ft: 818
       Built: 1938   Tax: $1,401 (2024)
    Community: Lawndale
    Single Family


    Estimated Monthly Payment: $1,486 (change assumption)
    Mortgage ($1,369) + Taxes in 2024 ($117)


    Taxes:$1,401

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 1000 S SEMORAN BLVD #715, WINTER PARK, FL 32792

    $122,990114 Days on yellowkey   MLS ID: S5144243

    For Sale S5144243 - 1000 S SEMORAN BLVD #715, WINTER PARK, FL 32792 14 photos

    Bed: 1   Bath: 1.0
    Liv Area Sq Ft: 735
       Built: 1969
    Monthly Fee: $350
       Tax: $1,641 (2024)
    Community: Golfside Villas Condo
    Condo


    Estimated Monthly Payment: $1,161 (change assumption)
    Mortgage ($674) + Fees ($350) + Taxes in 2024 ($137)


    Taxes:$1,641

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 7618 WAUNATTA CT, WINTER PARK, FL 32792

    $457,000144 Days on yellowkey   MLS ID: V4946886

    0 Days Off yellowkey (back on 3/26/2026)

    For Sale V4946886 - 7618 WAUNATTA CT, WINTER PARK, FL 32792 31 photos

    Bed: 3   Bath: 3.0
    Liv Area Sq Ft: 1970
       Built: 1981
    Community: Lake Waunatta Village
    Single Family


    Estimated Monthly Payment: $2,504 (change assumption)
    Mortgage ($2,504)


    Taxes:

    Elementary School: None

    High School: None

    Tax Year:

    Middle School: None


  • 1120 PRESERVE POINT DR, WINTER PARK, FL 32789

    $8,950,000251 Days on yellowkey   MLS ID: O6350054

    For Sale O6350054 - 1120 PRESERVE POINT DR, WINTER PARK, FL 32789 89 photos

    Bed: 7   Bath: 10.0
    Liv Area Sq Ft: 11255
       Built: 2009
    Community: Windsong-Preserve Point
    Single Family


    Estimated Monthly Payment: $49,040 (change assumption)
    Mortgage ($49,040)


    Taxes:

    Elementary School: None

    High School: None

    Tax Year:

    Middle School: None


  • 7468 CANFORD CT #24, WINTER PARK, FL 32792

    $189,999151 Days on yellowkey   MLS ID: O6373850

    For Sale O6373850 - 7468 CANFORD CT #24, WINTER PARK, FL 32792 49 photos

    Bed: 2   Bath: 1.5
    Liv Area Sq Ft: 1365
       Built: 1974
    Community: Whisperwood Condo
    Condo


    Estimated Monthly Payment: $1,041 (change assumption)
    Mortgage ($1,041)


    Taxes:

    Elementary School: None

    High School: None

    Tax Year:

    Middle School: None


  • 1695 LEE RD #B204, WINTER PARK, FL 32789

    $120,000141 Days on yellowkey   MLS ID: O6375348

    For Sale O6375348 - 1695 LEE RD #B204, WINTER PARK, FL 32789 2 photos

    Bed: 2   Bath: 1.0
    Built: 1966

    Community: Waterfall Cove At Winter Park Condo
    Condo


    Estimated Monthly Payment: $658 (change assumption)
    Mortgage ($658)


    Taxes:

    Elementary School: None

    High School: None

    Tax Year:

    Middle School: None


  • 1137 OAKS BLVD, WINTER PARK, FL 32789

    $634,900129 Days on yellowkey   MLS ID: O6379388

    0 Days Off yellowkey (back on 3/21/2026)

    For Sale O6379388 - 1137 OAKS BLVD, WINTER PARK, FL 32789 29 photos

    Bed: 2   Bath: 1.5
    Liv Area Sq Ft: 1149
       Built: 1958
    Community: Dixie Terrace
    Single Family


    Estimated Monthly Payment: $3,479 (change assumption)
    Mortgage ($3,479)


    Taxes:

    Elementary School: None

    High School: None

    Tax Year:

    Middle School: None


  • 200 SAINT ANDREWS BLVD #312, WINTER PARK, FL 32792

    $170,00088 Days on yellowkey   MLS ID: S5145794

    For Sale S5145794 - 200 SAINT ANDREWS BLVD #312, WINTER PARK, FL 32792 28 photos

    Bed: 1   Bath: 1.0
    Liv Area Sq Ft: 793
       Built: 1970
    Community: Four Seasons Condo
    Condo


    Estimated Monthly Payment: $931 (change assumption)
    Mortgage ($931)


    Taxes:

    Elementary School: None

    High School: None

    Tax Year:

    Middle School: None




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.