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Winter Park Homes For Sale & Real Estate - 393 homes

Winter Park homes for sale are located in Seminole 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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  • 5473 BRACKEN CT, WINTER PARK, FL 32792

    $295,000125 Days on yellowkey   MLS ID: O6368415

    2 Days Off yellowkey (back on 4/26/2026)

    For Sale O6368415 - 5473 BRACKEN CT, WINTER PARK, FL 32792 30 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1178
       Built: 1986
    Monthly Fee: $101
       Tax: $2,205 (2024)
    Community: Fernbrook Trails
    Townhouse


    Estimated Monthly Payment: $1,901 (change assumption)
    Mortgage ($1,616) + Fees ($101) + Taxes in 2024 ($184)


    Taxes:$2,205

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • WINTER PARK, FL 32792

    $430,00049 Days on yellowkey   MLS ID: S5145631

    REDUCED by $10,000 (2.3%) on 04/15/2026

    For Sale S5145631 - WINTER PARK, FL 32792 11 photos

    Bed: 4   Bath: 2.0
    Liv Area Sq Ft: 1296
       Built: 1958   Tax: $4,968 (2025)
    Community: Winter Park Estates
    Single Family


    Estimated Monthly Payment: $2,770 (change assumption)
    Mortgage ($2,356) + Taxes in 2025 ($414)


    Taxes:$4,968

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1951 CANNY CV, WINTER PARK, FL 32792

    $444,900138 Days on yellowkey   MLS ID: O6367023

    For Sale O6367023 - 1951 CANNY CV, WINTER PARK, FL 32792 64 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1782
       Built: 2023
    Monthly Fee: $375
       Tax: $6,889 (2025)
    Community: Grayson Square
    Townhouse


    Estimated Monthly Payment: $3,387 (change assumption)
    Mortgage ($2,438) + Fees ($375) + Taxes in 2025 ($574)


    Taxes:$6,889

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 1809 HAMMERLIN AVE, WINTER PARK, FL 32789

    $585,000106 Days on yellowkey   MLS ID: O6373616

    For Sale O6373616 - 1809 HAMMERLIN AVE, WINTER PARK, FL 32789 44 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1818
       Built: 2006   Tax: $5,826 (2024)
    Community: Terazzo Del Sol Condo Assn Inc
    Condo


    Estimated Monthly Payment: $3,691 (change assumption)
    Mortgage ($3,205) + Taxes in 2024 ($486)


    Taxes:$5,826

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Audubon Park K-8


  • 1807 MAGNOLIA AVE, WINTER PARK, FL 32789

    $1,199,00014 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


  • 1760 GREENWICH AVE, WINTER PARK, FL 32789

    $650,00042 Days on yellowkey   MLS ID: O6392001

    For Sale O6392001 - 1760 GREENWICH AVE, WINTER PARK, FL 32789 18 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1610
       Built: 1967   Tax: $2,779 (2025)
    Community: Golfview Heights
    Single Family


    Estimated Monthly Payment: $3,793 (change assumption)
    Mortgage ($3,562) + Taxes in 2025 ($232)


    Taxes:$2,779

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 2708 LION HEART RD, WINTER PARK, FL 32792

    $627,50057 Days on yellowkey   MLS ID: O6387685

    REDUCED by $2,000 (0.3%) on 04/21/2026

    For Sale O6387685 - 2708 LION HEART RD, WINTER PARK, FL 32792 47 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1785
       Built: 1963   Tax: $7,007 (2024)
    Community: Winter Park Pines Rep
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,022 (change assumption)
    Mortgage ($3,438) + Taxes in 2024 ($584)


    Taxes:$7,007

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Glenridge Middle


  • 1541 WESTCHESTER AVE, WINTER PARK, FL 32789

    $1,090,000100 Days on yellowkey   MLS ID: O6374409

    REDUCED by $10,000 (0.9%) on 04/23/2026

    For Sale O6374409 - 1541 WESTCHESTER AVE, WINTER PARK, FL 32789 47 photos

    Bed: 3   Bath: 2.5
    Liv Area Sq Ft: 2578
       Built: 1935   Tax: $5,932 (2024)
    Community: Orwin Manor Westminster Sec
    Spa: No

    Single Family


    Estimated Monthly Payment: $6,467 (change assumption)
    Mortgage ($5,972) + Taxes in 2024 ($494)


    Taxes:$5,932

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2024

    Middle School: College Park Middle


  • 1110 ALABAMA DR, WINTER PARK, FL 32789

    $1,750,00028 Days on yellowkey   MLS ID: O6395692

    For Sale O6395692 - 1110 ALABAMA DR, WINTER PARK, FL 32789 53 photos

    Bed: 3   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2488
       Built: 1958   Tax: $12,858 (2025)
    Community: J Kronenberger Sub
    Spa: No

    Single Family


    Estimated Monthly Payment: $10,660 (change assumption)
    Mortgage ($9,589) + Taxes in 2025 ($1,072)


    Taxes:$12,858

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 7761 FOX KNOLL PL, WINTER PARK, FL 32792

    $425,0007 Days on yellowkey   MLS ID: O6401159

    For Sale O6401159 - 7761 FOX KNOLL PL, WINTER PARK, FL 32792 34 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1485
       Built: 1989
    Monthly Fee: $20
       Tax: $4,308 (2024)
    Community: Bridgewater
    Single Family


    Estimated Monthly Payment: $2,708 (change assumption)
    Mortgage ($2,329) + Fees ($20) + Taxes in 2024 ($359)


    Taxes:$4,308

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 2408 LAFAYETTE AVE, WINTER PARK, FL 32789

    $1,495,00020 Days on yellowkey   MLS ID: O6397694

    For Sale O6397694 - 2408 LAFAYETTE AVE, WINTER PARK, FL 32789 31 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2838
       Built: 2024   Tax: $3,770 (2024)
    Community: Winter Park Village
    Spa: No

    Single Family


    Estimated Monthly Payment: $8,506 (change assumption)
    Mortgage ($8,192) + Taxes in 2024 ($314)


    Taxes:$3,770

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Maitland Middle


  • 405 LAKE FAIR LN, WINTER PARK, FL 32789

    $459,00036 Days on yellowkey   MLS ID: O6393594

    REDUCED by $999 (0.2%) on 04/25/2026

    For Sale O6393594 - 405 LAKE FAIR LN, WINTER PARK, FL 32789 45 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1491
       Built: 1957   Tax: $1,355 (2025)
    Community: Fairbanks Shores 5Th Add
    Single Family


    Estimated Monthly Payment: $2,628 (change assumption)
    Mortgage ($2,515) + Taxes in 2025 ($113)


    Taxes:$1,355

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 151 OAKWOOD WAY, WINTER PARK, FL 32789

    $2,950,00084 Days on yellowkey   MLS ID: O6380037

    REDUCED by $105,000 (3.4%) on 04/01/2026

    For Sale O6380037 - 151 OAKWOOD WAY, WINTER PARK, FL 32789 68 photos

    Bed: 4   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 4129
       Built: 2023   Tax: $34,218 (2025)
    Community: Charmont
    Spa: No

    Single Family


    Estimated Monthly Payment: $19,015 (change assumption)
    Mortgage ($16,164) + Taxes in 2025 ($2,852)


    Taxes:$34,218

    Elementary School: None

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 1768 MONDRIAN CIR, WINTER PARK, FL 32789

    $1,099,00055 Days on yellowkey   MLS ID: O6375723

    For Sale O6375723 - 1768 MONDRIAN CIR, WINTER PARK, FL 32789 26 photos

    Bed: 3   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2193
       Built: 2023
    Monthly Fee: $395
       Tax: $10,379 (2024)
    Community: Mondrian/Winder Park Twnhms
    Townhouse


    Estimated Monthly Payment: $7,282 (change assumption)
    Mortgage ($6,022) + Fees ($395) + Taxes in 2024 ($865)


    Taxes:$10,379

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2024

    Middle School: College Park Middle


  • 1036 ARAGON AVE, WINTER PARK, FL 32789

    $510,00076 Days on yellowkey   MLS ID: O6382491

    REDUCED by $15,000 (2.9%) on 04/11/2026

    For Sale O6382491 - 1036 ARAGON AVE, WINTER PARK, FL 32789 41 photos

    Bed: 2   Bath: 1.0
    Liv Area Sq Ft: 1073
       Built: 1957   Tax: $5,764 (2024)
    Community: Seville Park
    Single Family


    Estimated Monthly Payment: $3,275 (change assumption)
    Mortgage ($2,794) + Taxes in 2024 ($480)


    Taxes:$5,764

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Audubon Park K-8


  • 150 DANA WAY, WINTER PARK, FL 32789

    $3,799,00034 Days on yellowkey   MLS ID: O6394012

    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


  • 501 HERITAGE BLVD, WINTER PARK, FL 32792

    $489,99048 Days on yellowkey   MLS ID: S5145746

    REDUCED by $10,000 (2.0%) on 04/15/2026

    For Sale S5145746 - 501 HERITAGE BLVD, WINTER PARK, FL 32792 17 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: $3,554 (change assumption)
    Mortgage ($2,685) + Taxes in 2025 ($870)


    Taxes:$10,434

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 3054 BLUEBROOK DR, WINTER PARK, FL 32792

    $427,50018 Days on yellowkey   MLS ID: O6398450

    For Sale O6398450 - 3054 BLUEBROOK DR, WINTER PARK, FL 32792 27 photos

    Bed: 3   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1939
       Built: 1973   Tax: $6,422 (2025)
    Community: Laurel Spgs
    Single Family


    Estimated Monthly Payment: $2,878 (change assumption)
    Mortgage ($2,342) + Taxes in 2025 ($535)


    Taxes:$6,422

    Elementary School: Aloma Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 1468 AUBURN GREEN LOOP, WINTER PARK, FL 32792

    $480,00010 Days on yellowkey   MLS ID: O6399199

    For Sale O6399199 - 1468 AUBURN GREEN LOOP, WINTER PARK, FL 32792 43 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1676
       Built: 1984
    Monthly Fee: $49
       Tax: $6,243 (2024)
    Community: Country Lane
    Single Family


    Estimated Monthly Payment: $3,199 (change assumption)
    Mortgage ($2,630) + Fees ($49) + Taxes in 2024 ($520)


    Taxes:$6,243

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 259 E CANTON AVE #259, WINTER PARK, FL 32789

    $619,00051 Days on yellowkey   MLS ID: O6389246

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

    REDUCED by $10,000 (1.6%) on 04/19/2026

    For Sale O6389246 - 259 E CANTON AVE #259, WINTER PARK, FL 32789 36 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1040
       Built: 1971   Tax: $3,603 (2025)
    Community: Village Winterset Inc
    Condo


    Estimated Monthly Payment: $3,692 (change assumption)
    Mortgage ($3,392) + Taxes in 2025 ($300)


    Taxes:$3,603

    Elementary School: None

    High School: None

    Tax Year: 2025

    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.