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Winter Park Homes For Sale & Real Estate - 342 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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  • 1405 MILLER AVE, WINTER PARK, FL 32789

    $950,00043 Days on yellowkey   MLS ID: O6386405

    For Sale O6386405 - 1405 MILLER AVE, WINTER PARK, FL 32789 46 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1884
       Built: 2023
    Monthly Fee: $400
       Tax: $8,200 (2025)
    Community: H Vanwies Sub
    Townhouse


    Estimated Monthly Payment: $6,289 (change assumption)
    Mortgage ($5,205) + Fees ($400) + Taxes in 2025 ($683)


    Taxes:$8,200

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park Middle


  • 200 SAINT ANDREWS BLVD #315, WINTER PARK, FL 32792

    $169,00060 Days on yellowkey   MLS ID: V4947283

    For Sale V4947283 - 200 SAINT ANDREWS BLVD #315, WINTER PARK, FL 32792 43 photos

    Bed: 1   Bath: 1.0
    Liv Area Sq Ft: 793
       Built: 1970
    Monthly Fee: $451
       Tax: $873 (2024)
    Community: Four Seasons Condo
    Condo


    Estimated Monthly Payment: $1,450 (change assumption)
    Mortgage ($926) + Fees ($451) + Taxes in 2024 ($73)


    Taxes:$873

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Glenridge Middle


  • 432 W SWOOPE AVE, WINTER PARK, FL 32789

    $695,00083 Days on yellowkey   MLS ID: O6375719

    For Sale O6375719 - 432 W SWOOPE AVE, WINTER PARK, FL 32789 20 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2317
       Built: 2014
    Monthly Fee: $463
       Tax: $9,138 (2025)
    Community: Swoope Park
    Townhouse


    Estimated Monthly Payment: $5,033 (change assumption)
    Mortgage ($3,808) + Fees ($463) + Taxes in 2025 ($761)


    Taxes:$9,138

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 640 ARJAY WAY, WINTER PARK, FL 32789

    $1,974,90084 Days on yellowkey   MLS ID: O6372947

    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: $11,787 (change assumption)
    Mortgage ($10,821) + 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


  • 5473 BRACKEN CT, WINTER PARK, FL 32792

    $295,000109 Days on yellowkey   MLS ID: O6368415

    For Sale O6368415 - 5473 BRACKEN CT, WINTER PARK, FL 32792 27 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


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

    $359,000284 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


  • 700 MELROSE AVE #J1, WINTER PARK, FL 32789

    $350,00018 Days on yellowkey   MLS ID: O6394372

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

    For Sale O6394372 - 700 MELROSE AVE #J1, WINTER PARK, FL 32789 20 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1074
       Built: 1964   Tax: $4,205 (2025)
    Community: Winter Park Gardens Condo
    Condo


    Estimated Monthly Payment: $2,268 (change assumption)
    Mortgage ($1,918) + Taxes in 2025 ($350)


    Taxes:$4,205

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2420 FIRSTLIGHT WAY, WINTER PARK, FL 32792

    $450,000184 Days on yellowkey   MLS ID: O6351808

    3 Days Off yellowkey (back on 4/4/2026)

    For Sale O6351808 - 2420 FIRSTLIGHT WAY, WINTER PARK, FL 32792 49 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2312
       Built: 2019
    Monthly Fee: $320
       Tax: $5,397 (2024)
    Community: Enclave At Hawks Crest
    Townhouse


    Estimated Monthly Payment: $3,235 (change assumption)
    Mortgage ($2,466) + Fees ($320) + Taxes in 2024 ($450)


    Taxes:$5,397

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 2820 BEAR ISLAND POINTE, WINTER PARK, FL 32792

    $2,095,00011 Days on yellowkey   MLS ID: O6395836

    For Sale O6395836 - 2820 BEAR ISLAND POINTE, WINTER PARK, FL 32792 75 photos

    Bed: 3   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 5138
       Built: 1998
    Monthly Fee: $158
       Tax: $13,815 (2024)
    Community: Cypress Reserve
    Single Family


    Estimated Monthly Payment: $12,788 (change assumption)
    Mortgage ($11,479) + Fees ($158) + Taxes in 2024 ($1,151)


    Taxes:$13,815

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 1870 STAUNTON AVE, WINTER PARK, FL 32789

    $1,250,00011 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


  • 330 ELKHORN CT, WINTER PARK, FL 32792

    $569,90079 Days on yellowkey   MLS ID: O6376757

    REDUCED by $5,099 (0.9%) on 04/03/2026

    For Sale O6376757 - 330 ELKHORN CT, WINTER PARK, FL 32792 34 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1570
       Built: 1965   Tax: $2,086 (2025)
    Community: Winter Park Pines Merrie Oaks
    Single Family


    Estimated Monthly Payment: $3,297 (change assumption)
    Mortgage ($3,123) + Taxes in 2025 ($174)


    Taxes:$2,086

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 7471 CANFORD CT #19, WINTER PARK, FL 32792

    $199,000187 Days on yellowkey   MLS ID: G5103114

    For Sale G5103114 - 7471 CANFORD CT #19, WINTER PARK, FL 32792 15 photos

    Bed: 2   Bath: 1.5
    Liv Area Sq Ft: 1393
       Built: 1974   Tax: $2,750 (2024)
    Community: Whisperwood Condo
    Condo


    Estimated Monthly Payment: $1,320 (change assumption)
    Mortgage ($1,090) + Taxes in 2024 ($229)


    Taxes:$2,750

    Elementary School: Cheney Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Glenridge Middle


  • 1110 ALABAMA DR, WINTER PARK, FL 32789

    $1,750,00012 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
    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


  • 7117 SWALLOW RUN #G1, WINTER PARK, FL 32792

    $249,80047 Days on yellowkey   MLS ID: O6385942

    For Sale O6385942 - 7117 SWALLOW RUN #G1, WINTER PARK, FL 32792 22 photos

    Bed: 3   Bath: 2.5   Gar: 1
    Liv Area Sq Ft: 1565
       Built: 2011
    Monthly Fee: $385
       Tax: $3,776 (2024)
    Community: Village/Whisperwood
    Condo


    Estimated Monthly Payment: $2,068 (change assumption)
    Mortgage ($1,369) + Fees ($385) + Taxes in 2024 ($315)


    Taxes:$3,776

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 1340 PLACE PICARDY, WINTER PARK, FL 32789

    $1,599,00061 Days on yellowkey   MLS ID: O6382113

    3 Days Off yellowkey (back on 3/30/2026)

    For Sale O6382113 - 1340 PLACE PICARDY, WINTER PARK, FL 32789 34 photos

    Bed: 3   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3459
       Built: 1997   Tax: $7,515 (2025)
    Community: Fontainebleau
    Single Family


    Estimated Monthly Payment: $9,388 (change assumption)
    Mortgage ($8,761) + Taxes in 2025 ($626)


    Taxes:$7,515

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 184 SANDLEWOOD TRL ##2, WINTER PARK, FL 32789

    $314,00066 Days on yellowkey   MLS ID: O6380753

    For Sale O6380753 - 184 SANDLEWOOD TRL ##2, WINTER PARK, FL 32789 29 photos

    Bed: 2   Bath: 2.5
    Liv Area Sq Ft: 1133
       Built: 1985
    Monthly Fee: $310
       Tax: $2,915 (2025)
    Community: Sandlewood Creek Condo Ph 10
    Condo


    Estimated Monthly Payment: $2,273 (change assumption)
    Mortgage ($1,721) + Fees ($310) + Taxes in 2025 ($243)


    Taxes:$2,915

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 147 S INTERLACHEN AVE #202, WINTER PARK, FL 32789

    $2,450,00073 Days on yellowkey   MLS ID: L4959060

    For Sale L4959060 - 147 S INTERLACHEN AVE #202, WINTER PARK, FL 32789 31 photos

    Bed: 3   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3272
       Built: 1990   Tax: $18,439 (2024)
    Community: 147 Interlachen Place
    Condo


    Estimated Monthly Payment: $14,961 (change assumption)
    Mortgage ($13,424) + Taxes in 2024 ($1,537)


    Taxes:$18,439

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 151 LEWFIELD CIR #4, WINTER PARK, FL 32792

    $139,000127 Days on yellowkey   MLS ID: O6365536

    1 Days Off yellowkey (back on 4/3/2026)

    For Sale O6365536 - 151 LEWFIELD CIR #4, WINTER PARK, FL 32792 30 photos

    Bed: 1   Bath: 1.0
    Liv Area Sq Ft: 678
       Built: 1973   Tax: $1,278 (2024)
    Community: Stratford A Winter Park Condo
    Condo


    Estimated Monthly Payment: $868 (change assumption)
    Mortgage ($762) + Taxes in 2024 ($106)


    Taxes:$1,278

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 1952 SPRING ST, WINTER PARK, FL 32792

    $270,00082 Days on yellowkey   MLS ID: O6373082

    For Sale O6373082 - 1952 SPRING ST, WINTER PARK, FL 32792 26 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1050
       Built: 1983
    Monthly Fee: $57
       Tax: $2,652 (2024)
    Community: Villas Of Casselberry Ph 2
    Townhouse


    Estimated Monthly Payment: $1,757 (change assumption)
    Mortgage ($1,479) + Fees ($57) + Taxes in 2024 ($221)


    Taxes:$2,652

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 660 OSCEOLA AVE #101, WINTER PARK, FL 32789

    $2,195,000158 Days on yellowkey   MLS ID: O6353495

    2 Days Off yellowkey (back on 4/3/2026)

    For Sale O6353495 - 660 OSCEOLA AVE #101, WINTER PARK, FL 32789 64 photos

    Bed: 3   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2714
       Built: 1999
    Monthly Fee: $1,870
       Tax: $13,257 (2024)
    Community: Perle Du Lac
    Condo


    Estimated Monthly Payment: $15,002 (change assumption)
    Mortgage ($12,027) + Fees ($1,870) + Taxes in 2024 ($1,105)


    Taxes:$13,257

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Glenridge 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.