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Winter Park Homes For Sale & Real Estate - 410 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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  • 1500 GAY RD #3C, WINTER PARK, FL 32789

    $244,90043 Days on yellowkey   MLS ID: O6417533

    REDUCED by $3,100 (1.3%) on 07/21/2026

    For Sale O6417533 - 1500 GAY RD #3C, WINTER PARK, FL 32789 26 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1026
       Built: 1972
    Monthly Fee: $425
       Tax: $3,244 (2025)
    Community: Chateaux Du Lac
    Condo


    Estimated Monthly Payment: $2,037 (change assumption)
    Mortgage ($1,342) + Fees ($425) + Taxes in 2025 ($270)


    Taxes:$3,244

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park Middle


  • 1870 WALKER AVE, WINTER PARK, FL 32789

    $1,225,000140 Days on yellowkey   MLS ID: O6390504

    REDUCED by $74,000 (5.7%) on 07/07/2026

    For Sale O6390504 - 1870 WALKER AVE, WINTER PARK, FL 32789 32 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2046
       Built: 2026   Tax: $3,981 (2025)
    Community: Osceola Heights
    Single Family


    Estimated Monthly Payment: $7,044 (change assumption)
    Mortgage ($6,712) + Taxes in 2025 ($332)


    Taxes:$3,981

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 281 BREWER AVE, WINTER PARK, FL 32789

    $1,800,00011 Days on yellowkey   MLS ID: O6424364

    SHORT SALE O6424364 - 281 BREWER AVE, WINTER PARK, FL 32789 54 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 4029
       Built: 2022   Tax: $26,908 (2025)
    Community: Osceola Shores Sec 02
    Single Family


    Estimated Monthly Payment: $12,105 (change assumption)
    Mortgage ($9,863) + Taxes in 2025 ($2,242)


    Taxes:$26,908

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 501 LAKEVIEW AVE, WINTER PARK, FL 32789

    $1,390,000378 Days on yellowkey   MLS ID: O6325192

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

    For Sale O6325192 - 501 LAKEVIEW AVE, WINTER PARK, FL 32789 59 photos

    Bed: 4   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3253
       Built: 2026   Tax: $2,820 (2024)
    Community: Killarney Estates
    Single Family


    Estimated Monthly Payment: $7,851 (change assumption)
    Mortgage ($7,616) + Taxes in 2024 ($235)


    Taxes:$2,820

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2024

    Middle School: College Park Middle


  • Lot #21 KAROLINA AVE, WINTER PARK, FL 32789

    $918,000140 Days on yellowkey   MLS ID: O6387812

    REDUCED by $26,890 (2.8%) on 07/20/2026

    For Sale O6387812 - Lot #21 KAROLINA AVE, WINTER PARK, FL 32789 9 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2662
       Built: 2025   Tax: $2,207 (2024)
    Community: Karolina On Killarney
    Single Family


    Estimated Monthly Payment: $5,214 (change assumption)
    Mortgage ($5,030) + Taxes in 2024 ($184)


    Taxes:$2,207

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2024

    Middle School: Maitland Middle


  • 1778 MONDRIAN CIR, WINTER PARK, FL 32789

    $1,339,00018 Days on yellowkey   MLS ID: O6422941

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

    For Sale O6422941 - 1778 MONDRIAN CIR, WINTER PARK, FL 32789 52 photos

    Bed: 3   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2377
       Built: 2023
    Monthly Fee: $395
       Tax: $12,451 (2025)
    Community: Mondrian/Winter Park Twnhms
    Spa: No

    Townhouse


    Estimated Monthly Payment: $8,769 (change assumption)
    Mortgage ($7,337) + Fees ($395) + Taxes in 2025 ($1,038)


    Taxes:$12,451

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park Middle


  • 3381 CEDAR SPRINGS PL #151, WINTER PARK, FL 32792

    $179,90036 Days on yellowkey   MLS ID: O6419959

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

    For Sale O6419959 - 3381 CEDAR SPRINGS PL #151, WINTER PARK, FL 32792 32 photos

    Bed: 2   Bath: 2.5
    Liv Area Sq Ft: 1031
       Built: 1984   Tax: $197 (2025)
    Community: Hidden. Oaks
    Spa: No

    Condo


    Estimated Monthly Payment: $1,002 (change assumption)
    Mortgage ($986) + Taxes in 2025 ($16)


    Taxes:$197

    Elementary School: Aloma Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 1695 LEE RD #E215, WINTER PARK, FL 32789

    $135,000164 Days on yellowkey   MLS ID: O6383089

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

    REDUCED by $14,990 (10.0%) on 06/17/2026

    For Sale O6383089 - 1695 LEE RD #E215, WINTER PARK, FL 32789 82 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1149
       Built: 1966
    Monthly Fee: $624
       Tax: $2,472 (2024)
    Community: Waterfall Cove
    Condo


    Estimated Monthly Payment: $1,570 (change assumption)
    Mortgage ($740) + Fees ($624) + Taxes in 2024 ($206)


    Taxes:$2,472

    Elementary School: Hungerford Elem

    High School: Edgewater High

    Tax Year: 2024

    Middle School: College Park Middle


  • 1287 VERDANT GLADE PL, WINTER PARK, FL 32792

    $799,90098 Days on yellowkey   MLS ID: O6400331

    REDUCED by $25,100 (3.0%) on 07/20/2026

    For Sale O6400331 - 1287 VERDANT GLADE PL, WINTER PARK, FL 32792 50 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3020
       Built: 2020
    Monthly Fee: $413
       Tax: $6,133 (2025)
    Community: Meadows At Hawks Crest
    Single Family


    Estimated Monthly Payment: $5,307 (change assumption)
    Mortgage ($4,383) + Fees ($413) + Taxes in 2025 ($511)


    Taxes:$6,133

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 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


  • 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


  • 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




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.