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Winter Park Homes For Sale & Real Estate - 350 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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  • 2361 MULBRY DR, WINTER PARK, FL 32789

    $2,395,000Listed 04/16/2026 12:39AM   MLS ID: O6396840

    For Sale O6396840 - 2361 MULBRY DR, WINTER PARK, FL 32789 87 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 3111
       Built: 2026   Tax: $6,436 (2025)
    Community: Lake Forest Park
    Single Family


    Estimated Monthly Payment: $13,659 (change assumption)
    Mortgage ($13,123) + 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


  • 1661 WOODLAND AVE, WINTER PARK, FL 32789

    $1,300,000Listed 04/16/2026 12:03AM   MLS ID: O6399348

    For Sale O6399348 - 1661 WOODLAND AVE, WINTER PARK, FL 32789 58 photos

    Bed: 3   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3215
       Built: 1948   Tax: $17,067 (2025)
    Community: Comstock Park
    Single Family


    Estimated Monthly Payment: $8,545 (change assumption)
    Mortgage ($7,123) + Taxes in 2025 ($1,422)


    Taxes:$17,067

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 3720 JONQUIL LN, WINTER PARK, FL 32792

    $445,000Listed 04/15/2026 10:42PM   MLS ID: O6399628

    For Sale O6399628 - 3720 JONQUIL LN, WINTER PARK, FL 32792 1 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1647
       Built: 1982   Tax: $1,835 (2024)
    Community: Garden Lake Estates Unit 2
    Single Family


    Estimated Monthly Payment: $2,591 (change assumption)
    Mortgage ($2,438) + Taxes in 2024 ($153)


    Taxes:$1,835

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 1441 CARDINAL CT, WINTER PARK, FL 32789

    $4,285,000Listed 04/15/2026 2:18PM   MLS ID: O6399395

    For Sale O6399395 - 1441 CARDINAL CT, WINTER PARK, FL 32789 85 photos

    Bed: 4   Bath: 5.5   Gar: 2
    Liv Area Sq Ft: 4066
       Built: 2022   Tax: $47,740 (2025)
    Community: Winflor Court
    Spa: No

    Single Family


    Estimated Monthly Payment: $27,457 (change assumption)
    Mortgage ($23,479) + Taxes in 2025 ($3,978)


    Taxes:$47,740

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 1905 BONANZA CT, WINTER PARK, FL 32789

    $490,000Listed 04/16/2026 12:08AM   MLS ID: O6398772

    For Sale O6398772 - 1905 BONANZA CT, WINTER PARK, FL 32789 34 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1774
       Built: 1968   Tax: $5,015 (2024)
    Community: Eastbrook Sub Unit 13
    Single Family


    Estimated Monthly Payment: $3,103 (change assumption)
    Mortgage ($2,685) + Taxes in 2024 ($418)


    Taxes:$5,015

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 7454 WYNNEWOOD SQ #188, WINTER PARK, FL 32792

    $229,000Listed 04/15/2026 6:42PM   MLS ID: O6386578

    For Sale O6386578 - 7454 WYNNEWOOD SQ #188, WINTER PARK, FL 32792 29 photos

    Bed: 3   Bath: 2.5
    Liv Area Sq Ft: 1151
       Built: 1984
    Monthly Fee: $450
       Tax: $2,858 (2025)
    Community: Hidden Oaks Condo Ph 10
    Condo


    Estimated Monthly Payment: $1,943 (change assumption)
    Mortgage ($1,255) + Fees ($450) + Taxes in 2025 ($238)


    Taxes:$2,858

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2052 LEANNE CT, WINTER PARK, FL 32792

    $450,00072 Days on yellowkey   MLS ID: O6379323

    REDUCED by $6,000 (1.3%) on 04/15/2026

    For Sale O6379323 - 2052 LEANNE CT, WINTER PARK, FL 32792 30 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2264
       Built: 1969   Tax: $1,581 (2024)
    Community: Eastbrook Sub Unit 15
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,597 (change assumption)
    Mortgage ($2,466) + Taxes in 2024 ($132)


    Taxes:$1,581

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 405 LAKE FAIR LN, WINTER PARK, FL 32789

    $459,99922 Days on yellowkey   MLS ID: O6393594

    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: $2,633 (change assumption)
    Mortgage ($2,520) + Taxes in 2025 ($113)


    Taxes:$1,355

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 3172 CROWN JEWEL CT, WINTER PARK, FL 32792

    $339,900Listed 04/15/2026 12:39PM   MLS ID: O6397498

    For Sale O6397498 - 3172 CROWN JEWEL CT, WINTER PARK, FL 32792 24 photos

    Bed: 3   Bath: 2.5   Gar: 1
    Liv Area Sq Ft: 1406
       Built: 2019
    Monthly Fee: $146
       Tax: $4,977 (2025)
    Community: Coronado Twnhms
    Townhouse


    Estimated Monthly Payment: $2,423 (change assumption)
    Mortgage ($1,862) + Fees ($146) + Taxes in 2025 ($415)


    Taxes:$4,977

    Elementary School: Cheney Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • WINTER PARK, FL 32792

    $430,00035 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


  • 640 ARJAY WAY, WINTER PARK, FL 32789

    $1,925,00086 Days on yellowkey   MLS ID: O6372947

    REDUCED by $49,900 (2.5%) on 04/15/2026

    For Sale O6372947 - 640 ARJAY WAY, WINTER PARK, FL 32789 46 photos

    Bed: 5   Bath: 4.0   Gar: 3
    Liv Area Sq Ft: 3953
       Built: 1958   Tax: $11,586 (2024)
    Community: Timberlane Shores
    Single Family


    Estimated Monthly Payment: $11,513 (change assumption)
    Mortgage ($10,548) + Taxes in 2024 ($965)


    Taxes:$11,586

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Audubon Park K-8


  • 1515 WINTER GREEN BLVD, WINTER PARK, FL 32792

    $315,00042 Days on yellowkey   MLS ID: O6384755

    For Sale O6384755 - 1515 WINTER GREEN BLVD, WINTER PARK, FL 32792 26 photos

    Bed: 3   Bath: 3.5
    Liv Area Sq Ft: 1652
       Built: 1984
    Monthly Fee: $188
       Tax: $3,993 (2024)
    Community: Winter Green
    Townhouse


    Estimated Monthly Payment: $2,247 (change assumption)
    Mortgage ($1,726) + Fees ($188) + Taxes in 2024 ($333)


    Taxes:$3,993

    Elementary School: English Estates Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 5473 BRACKEN CT, WINTER PARK, FL 32792

    $295,000111 Days on yellowkey   MLS ID: O6368415

    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


  • 4864 TANGERINE AVE #4864, WINTER PARK, FL 32792

    $200,00058 Days on yellowkey   MLS ID: O6383320

    INCREASED by $1,000 (0.5%) on 04/09/2026

    For Sale O6383320 - 4864 TANGERINE AVE #4864, WINTER PARK, FL 32792 25 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1059
       Built: 1973
    Monthly Fee: $441
       Tax: $2,828 (2025)
    Community: Wrenwood Condo
    Condo


    Estimated Monthly Payment: $1,773 (change assumption)
    Mortgage ($1,096) + Fees ($441) + Taxes in 2025 ($236)


    Taxes:$2,828

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 250 CORTLAND AVE, WINTER PARK, FL 32789

    $950,00013 Days on yellowkey   MLS ID: O6395137

    For Sale O6395137 - 250 CORTLAND AVE, WINTER PARK, FL 32789 46 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2114
       Built: 1981   Tax: $4,370 (2024)
    Community: Cortland Park
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $5,569 (change assumption)
    Mortgage ($5,205) + Taxes in 2024 ($364)


    Taxes:$4,370

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 2330 COLDSTREAM DR, WINTER PARK, FL 32792

    $650,00024 Days on yellowkey   MLS ID: O6384436

    0 Days Off yellowkey (back on 4/15/2026)

    For Sale O6384436 - 2330 COLDSTREAM DR, WINTER PARK, FL 32792 20 photos

    Bed: 4   Bath: 2.0
    Liv Area Sq Ft: 1750
       Built: 1958   Tax: $6,951 (2024)
    Community: Brookshire Heights
    Single Family


    Estimated Monthly Payment: $4,141 (change assumption)
    Mortgage ($3,562) + Taxes in 2024 ($579)


    Taxes:$6,951

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Glenridge Middle


  • 2007 EDWIN BLVD, WINTER PARK, FL 32792

    $369,90010 Days on yellowkey   MLS ID: O6396498

    REDUCED by $5,100 (1.4%) on 04/15/2026

    For Sale O6396498 - 2007 EDWIN BLVD, WINTER PARK, FL 32792 16 photos

    Bed: 4   Bath: 1.5
    Liv Area Sq Ft: 1296
       Built: 1955   Tax: $3,535 (2025)
    Community: Eastgate Sub
    Single Family


    Estimated Monthly Payment: $2,321 (change assumption)
    Mortgage ($2,027) + Taxes in 2025 ($295)


    Taxes:$3,535

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 3312 HEARTWOOD AVE, WINTER PARK, FL 32792

    $465,000180 Days on yellowkey   MLS ID: O6352582

    1 Days Off yellowkey (back on 4/13/2026)

    REDUCED by $19,000 (3.9%) on 04/08/2026

    For Sale O6352582 - 3312 HEARTWOOD AVE, WINTER PARK, FL 32792 36 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2878
       Built: 1983   Tax: $2,183 (2025)
    Community: Bel-Aire Pines
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,730 (change assumption)
    Mortgage ($2,548) + Taxes in 2025 ($182)


    Taxes:$2,183

    Elementary School: Aloma Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 135 W SWOOPE AVE, WINTER PARK, FL 32789

    $2,540,0008 Days on yellowkey   MLS ID: O6396594

    0 Days Off yellowkey (back on 4/15/2026)

    For Sale O6396594 - 135 W SWOOPE AVE, WINTER PARK, FL 32789 36 photos

    Bed: 3   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2667
       Built: 1998   Tax: $21,641 (2025)
    Community: Stovins Sub
    Townhouse


    Estimated Monthly Payment: $15,721 (change assumption)
    Mortgage ($13,917) + Taxes in 2025 ($1,803)


    Taxes:$21,641

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 3028 GEORGE MASON AVE #J-7E, WINTER PARK, FL 32792

    $105,000Listed 04/15/2026 10:01AM   MLS ID: O6398380

    For Sale O6398380 - 3028 GEORGE MASON AVE #J-7E, WINTER PARK, FL 32792 25 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1088
       Built: 1974
    Monthly Fee: $427
       Tax: $1,989 (2025)
    Community: Colonies
    Condo


    Estimated Monthly Payment: $1,168 (change assumption)
    Mortgage ($575) + Fees ($427) + Taxes in 2025 ($166)


    Taxes:$1,989

    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.