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Winter Park Homes For Sale & Real Estate - 413 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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  • 2189 SUSSEX RD, WINTER PARK, FL 32792

    $375,00022 Days on yellowkey   MLS ID: O6423782

    0 Days Off yellowkey (back on 7/20/2026)

    FORECLOSURE O6423782 - 2189 SUSSEX RD, WINTER PARK, FL 32792 29 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1776
       Built: 1968
    Monthly Fee: $2
       Tax: $4,646 (2025)
    Community: Winter Woods Unit 01
    Single Family


    Estimated Monthly Payment: $2,444 (change assumption)
    Mortgage ($2,055) + Fees ($2) + Taxes in 2025 ($387)


    Taxes:$4,646

    Elementary School: English Estates Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 2651 CAYMAN WAY, WINTER PARK, FL 32792

    $255,000192 Days on yellowkey   MLS ID: O6375086

    For Sale O6375086 - 2651 CAYMAN WAY, WINTER PARK, FL 32792 30 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1020
       Built: 1978
    Monthly Fee: $99
       Tax: $3,553 (2024)
    Community: Windward Square Sec 2
    Townhouse


    Estimated Monthly Payment: $1,792 (change assumption)
    Mortgage ($1,397) + Fees ($99) + Taxes in 2024 ($296)


    Taxes:$3,553

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 3019 ANTIQUE OAKS CIR #124, WINTER PARK, FL 32792

    $142,500343 Days on yellowkey   MLS ID: O6337083

    REDUCED by $2,000 (1.4%) on 07/10/2026

    For Sale O6337083 - 3019 ANTIQUE OAKS CIR #124, WINTER PARK, FL 32792 26 photos

    Bed: 1   Bath: 1.0
    Liv Area Sq Ft: 749
       Built: 1984
    Monthly Fee: $300
       Tax: $2,050 (2024)
    Community: Parkview Village
    Spa: No

    Condo


    Estimated Monthly Payment: $1,252 (change assumption)
    Mortgage ($781) + Fees ($300) + Taxes in 2024 ($171)


    Taxes:$2,050

    Elementary School: Aloma Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Glenridge Middle


  • 291 LEWFIELD CIR #291, WINTER PARK, FL 32792

    $144,000165 Days on yellowkey   MLS ID: O6382547

    For Sale O6382547 - 291 LEWFIELD CIR #291, WINTER PARK, FL 32792 32 photos

    Bed: 1   Bath: 1.0
    Liv Area Sq Ft: 678
       Built: 1973
    Monthly Fee: $350
       Tax: $1,942 (2025)
    Community: Stratford Winter Park
    Condo


    Estimated Monthly Payment: $1,301 (change assumption)
    Mortgage ($789) + Fees ($350) + Taxes in 2025 ($162)


    Taxes:$1,942

    Elementary School: English Estates Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 2008 HOUNDSLAKE DR, WINTER PARK, FL 32792

    $490,00046 Days on yellowkey   MLS ID: O6414369

    REDUCED by $25,000 (4.9%) on 07/20/2026

    For Sale O6414369 - 2008 HOUNDSLAKE DR, WINTER PARK, FL 32792 33 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2250
       Built: 1980   Tax: $5,253 (2025)
    Community: Cedar Ridge
    Single Family


    Estimated Monthly Payment: $3,123 (change assumption)
    Mortgage ($2,685) + Taxes in 2025 ($438)


    Taxes:$5,253

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 316 BECKETT CT, WINTER PARK, FL 32792

    $450,00065 Days on yellowkey   MLS ID: O6411108

    For Sale O6411108 - 316 BECKETT CT, WINTER PARK, FL 32792 33 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1651
       Built: 1966   Tax: $2,232 (2025)
    Community: Winter Park Pines Merrie Oaks
    Single Family


    Estimated Monthly Payment: $2,652 (change assumption)
    Mortgage ($2,466) + Taxes in 2025 ($186)


    Taxes:$2,232

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 501 HERITAGE BLVD, WINTER PARK, FL 32792

    $458,000140 Days on yellowkey   MLS ID: S5145746

    REDUCED by $11,000 (2.3%) on 07/20/2026

    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: $3,379 (change assumption)
    Mortgage ($2,510) + Taxes in 2025 ($870)


    Taxes:$10,434

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 700 MELROSE AVE #J24, WINTER PARK, FL 32789

    $380,00070 Days on yellowkey   MLS ID: R4911307

    REDUCED by $10,000 (2.6%) on 07/20/2026

    For Sale R4911307 - 700 MELROSE AVE #J24, WINTER PARK, FL 32789 28 photos

    Bed: 1   Bath: 1.0
    Liv Area Sq Ft: 987
       Built: 1964   Tax: $3,874 (2025)
    Community: Winter Park Gardens Condo
    Condo


    Estimated Monthly Payment: $2,405 (change assumption)
    Mortgage ($2,082) + Taxes in 2025 ($323)


    Taxes:$3,874

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 3321 ROYAL ST, WINTER PARK, FL 32792

    $280,00012 Days on yellowkey   MLS ID: A4700206

    For Sale A4700206 - 3321 ROYAL ST, WINTER PARK, FL 32792 20 photos

    Bed: 3   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1197
       Built: 1982   Tax: $4,462 (2025)
    Community: Coronation Add
    Spa: No

    Half Duplex


    Estimated Monthly Payment: $1,906 (change assumption)
    Mortgage ($1,534) + Taxes in 2025 ($372)


    Taxes:$4,462

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1600 LEGION DR, WINTER PARK, FL 32789

    $3,795,00048 Days on yellowkey   MLS ID: O6415591

    REDUCED by $200,000 (5.0%) on 07/13/2026

    For Sale O6415591 - 1600 LEGION DR, WINTER PARK, FL 32789 70 photos

    Bed: 5   Bath: 5.5   Gar: 3
    Liv Area Sq Ft: 4483
       Built: 2008   Tax: $20,740 (2025)
    Community: Green Oaks Rep
    Spa: No

    Single Family


    Estimated Monthly Payment: $22,522 (change assumption)
    Mortgage ($20,794) + Taxes in 2025 ($1,728)


    Taxes:$20,740

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 1864 GRINNELL TER, WINTER PARK, FL 32789

    $1,599,00091 Days on yellowkey   MLS ID: O6403822

    For Sale O6403822 - 1864 GRINNELL TER, WINTER PARK, FL 32789 43 photos

    Bed: 5   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3028
       Built: 2006   Tax: $16,615 (2025)
    Community: Fremar
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $10,146 (change assumption)
    Mortgage ($8,761) + Taxes in 2025 ($1,385)


    Taxes:$16,615

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 2503 TAHOE CIR #2503, WINTER PARK, FL 32792

    $250,000120 Days on yellowkey   MLS ID: O6395130

    For Sale O6395130 - 2503 TAHOE CIR #2503, WINTER PARK, FL 32792 20 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1173
       Built: 1981   Tax: $506 (2025)
    Community: Cedarwood Village 1
    Condo


    Estimated Monthly Payment: $1,412 (change assumption)
    Mortgage ($1,370) + Taxes in 2025 ($42)


    Taxes:$506

    Elementary School: English Estates Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 311 E MORSE BLVD #7-11, WINTER PARK, FL 32789

    $299,000338 Days on yellowkey   MLS ID: O6337061

    REDUCED by $10,900 (3.5%) on 05/24/2026

    For Sale O6337061 - 311 E MORSE BLVD #7-11, WINTER PARK, FL 32789 25 photos

    Bed: 1   Bath: 1.0   Gar: 1
    Liv Area Sq Ft: 570
       Built: 1960   Tax: $668 (2024)
    Community: Phillips Circle Rep
    Condo


    Estimated Monthly Payment: $1,694 (change assumption)
    Mortgage ($1,638) + Taxes in 2024 ($56)


    Taxes:$668

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 5143 LAZY OAKS DR #5143, WINTER PARK, FL 32792

    $275,000108 Days on yellowkey   MLS ID: O6398856

    REDUCED by $5,000 (1.8%) on 06/29/2026

    For Sale O6398856 - 5143 LAZY OAKS DR #5143, WINTER PARK, FL 32792 38 photos

    Bed: 2   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1008
       Built: 1984   Tax: $668 (2024)
    Community: Lazy Oaks Condo
    Condo


    Estimated Monthly Payment: $1,563 (change assumption)
    Mortgage ($1,507) + Taxes in 2024 ($56)


    Taxes:$668

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 1562 ARBOR PARK DR, WINTER PARK, FL 32789

    $775,00015 Days on yellowkey   MLS ID: O6425628

    For Sale O6425628 - 1562 ARBOR PARK DR, WINTER PARK, FL 32789 49 photos

    Bed: 4   Bath: 2.5
    Liv Area Sq Ft: 1899
       Built: 1957   Tax: $9,725 (2025)
    Community: Conwill Estates
    Single Family


    Estimated Monthly Payment: $5,057 (change assumption)
    Mortgage ($4,246) + Taxes in 2025 ($810)


    Taxes:$9,725

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 4756 TANGERINE AVE #4756, WINTER PARK, FL 32792

    $185,00044 Days on yellowkey   MLS ID: R4911483

    REDUCED by $10,000 (5.1%) on 07/19/2026

    For Sale R4911483 - 4756 TANGERINE AVE #4756, WINTER PARK, FL 32792 6 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1058
       Built: 1973   Tax: $2,244 (2025)
    Community: Wrenwood Condo
    Spa: No

    Condo


    Estimated Monthly Payment: $1,201 (change assumption)
    Mortgage ($1,014) + Taxes in 2025 ($187)


    Taxes:$2,244

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 2600 EUSTON RD, WINTER PARK, FL 32789

    $630,000112 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


  • 1420 MAGNOLIA AVE, WINTER PARK, FL 32789

    $1,695,00086 Days on yellowkey   MLS ID: O6404564

    REDUCED by $55,000 (3.1%) on 07/14/2026

    For Sale O6404564 - 1420 MAGNOLIA AVE, WINTER PARK, FL 32789 67 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3174
       Built: 2015   Tax: $21,173 (2025)
    Community: Lake Knowles Terrace Add 02
    Spa: No

    Single Family


    Estimated Monthly Payment: $11,052 (change assumption)
    Mortgage ($9,287) + Taxes in 2025 ($1,764)


    Taxes:$21,173

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 2568 LOTAFUN AVE, WINTER PARK, FL 32789

    $409,90014 Days on yellowkey   MLS ID: W7887744

    For Sale W7887744 - 2568 LOTAFUN AVE, WINTER PARK, FL 32789 25 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1201
       Built: 1978   Tax: $4,415 (2025)
    Community: Justamere Camp Rep
    Single Family


    Estimated Monthly Payment: $2,614 (change assumption)
    Mortgage ($2,246) + Taxes in 2025 ($368)


    Taxes:$4,415

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1418 LONE FEATHER TRL, WINTER PARK, FL 32792

    $750,00045 Days on yellowkey   MLS ID: O6417341

    For Sale O6417341 - 1418 LONE FEATHER TRL, WINTER PARK, FL 32792 46 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2197
       Built: 2022
    Monthly Fee: $244
       Tax: $6,224 (2025)
    Community: Landings At Hawks Crest
    Single Family


    Estimated Monthly Payment: $4,872 (change assumption)
    Mortgage ($4,109) + Fees ($244) + Taxes in 2025 ($519)


    Taxes:$6,224

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla 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.