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Winter Park Homes For Sale & Real Estate - 438 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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  • 1813 HARLAND PARK DR, WINTER PARK, FL 32789

    $1,875,00074 Days on yellowkey   MLS ID: O6403483

    1 Days Off yellowkey (back on 7/8/2026)

    REDUCED by $120,000 (6.0%) on 05/28/2026

    For Sale O6403483 - 1813 HARLAND PARK DR, WINTER PARK, FL 32789 55 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3551
       Built: 2013
    Monthly Fee: $268
       Tax: $23,539 (2025)
    Community: Windsong - Knowles Place
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $12,503 (change assumption)
    Mortgage ($10,274) + Fees ($268) + Taxes in 2025 ($1,962)


    Taxes:$23,539

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 1823 SUNSET DR, WINTER PARK, FL 32789

    $2,549,0007 Days on yellowkey   MLS ID: O6421690

    For Sale O6421690 - 1823 SUNSET DR, WINTER PARK, FL 32789 14 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3479
       Built: 2026   Tax: $3,358 (2025)
    Community: Lake Knowles Terrace Add 02
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $14,247 (change assumption)
    Mortgage ($13,967) + Taxes in 2025 ($280)


    Taxes:$3,358

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 644 N KNOWLES AVE #3, WINTER PARK, FL 32789

    $475,00017 Days on yellowkey   MLS ID: O6420484

    For Sale O6420484 - 644 N KNOWLES AVE #3, WINTER PARK, FL 32789 32 photos

    Bed: 1   Bath: 1.0
    Liv Area Sq Ft: 767
       Built: 1974   Tax: $4,218 (2025)
    Community: Knowles Manor North Condo
    Condo


    Estimated Monthly Payment: $2,954 (change assumption)
    Mortgage ($2,603) + Taxes in 2025 ($352)


    Taxes:$4,218

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 346 S RANGER BLVD, WINTER PARK, FL 32792

    $475,000303 Days on yellowkey   MLS ID: S5134662

    For Sale S5134662 - 346 S RANGER BLVD, WINTER PARK, FL 32792 31 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1592
       Built: 1965   Tax: $5,339 (2024)
    Community: Winter Park Pines
    Single Family


    Estimated Monthly Payment: $3,048 (change assumption)
    Mortgage ($2,603) + Taxes in 2024 ($445)


    Taxes:$5,339

    Elementary School: Aloma Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Glenridge Middle


  • 2708 LION HEART RD, WINTER PARK, FL 32792

    $615,000132 Days on yellowkey   MLS ID: O6387685

    REDUCED by $2,500 (0.4%) on 07/07/2026

    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: $3,954 (change assumption)
    Mortgage ($3,370) + Taxes in 2024 ($584)


    Taxes:$7,007

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Glenridge Middle


  • 729 MONMOUTH WAY, WINTER PARK, FL 32792

    $799,00011 Days on yellowkey   MLS ID: O6422168

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

    For Sale O6422168 - 729 MONMOUTH WAY, WINTER PARK, FL 32792 50 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2332
       Built: 1970   Tax: $8,433 (2025)
    Community: Winter Park Pines
    Spa: No

    Single Family


    Estimated Monthly Payment: $5,081 (change assumption)
    Mortgage ($4,378) + Taxes in 2025 ($703)


    Taxes:$8,433

    Elementary School: Aloma Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 840 W CANTON AVE, WINTER PARK, FL 32789

    $675,00043 Days on yellowkey   MLS ID: O6412754

    For Sale O6412754 - 840 W CANTON AVE, WINTER PARK, FL 32789 63 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1370
       Built: 1952   Tax: $5,722 (2025)
    Community: N/A
    Single Family


    Estimated Monthly Payment: $4,175 (change assumption)
    Mortgage ($3,699) + Taxes in 2025 ($477)


    Taxes:$5,722

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 7500 WAUNATTA CT, WINTER PARK, FL 32792

    $299,90011 Days on yellowkey   MLS ID: TB8525179

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

    For Sale TB8525179 - 7500 WAUNATTA CT, WINTER PARK, FL 32792 34 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1998
       Built: 1979   Tax: $6,383 (2025)
    Community: Lake Waunatta Village
    Single Family


    Estimated Monthly Payment: $2,175 (change assumption)
    Mortgage ($1,643) + Taxes in 2025 ($532)


    Taxes:$6,383

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1870 WALKER AVE, WINTER PARK, FL 32789

    $1,225,000123 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


  • 7577 DOCKSIDE ST, WINTER PARK, FL 32792

    $360,00042 Days on yellowkey   MLS ID: O6412514

    4 Days Off yellowkey (back on 7/7/2026)

    REDUCED by $10,000 (2.7%) on 06/25/2026

    For Sale O6412514 - 7577 DOCKSIDE ST, WINTER PARK, FL 32792 30 photos

    Bed: 3   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1245
       Built: 1977   Tax: $3,722 (2025)
    Community: Woodcrest Unit 6
    Single Family


    Estimated Monthly Payment: $2,283 (change assumption)
    Mortgage ($1,973) + Taxes in 2025 ($310)


    Taxes:$3,722

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 4768 TANGERINE AVE #4768, WINTER PARK, FL 32792

    $174,900140 Days on yellowkey   MLS ID: S5144503

    REDUCED by $4,100 (2.3%) on 07/07/2026

    For Sale S5144503 - 4768 TANGERINE AVE #4768, WINTER PARK, FL 32792 17 photos

    Bed: 1   Bath: 1.0
    Liv Area Sq Ft: 753
       Built: 1973
    Monthly Fee: $280
       Tax: $1,479 (2024)
    Community: Wrenwood Condo
    Condo


    Estimated Monthly Payment: $1,362 (change assumption)
    Mortgage ($958) + Fees ($280) + Taxes in 2024 ($123)


    Taxes:$1,479

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 7733 COUNTRY PL #G2, WINTER PARK, FL 32792

    $234,50022 Days on yellowkey   MLS ID: O6418682

    REDUCED by $5,000 (2.1%) on 07/07/2026

    For Sale O6418682 - 7733 COUNTRY PL #G2, WINTER PARK, FL 32792 21 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1068
       Built: 1982   Tax: $371 (2025)
    Community: Goldenrod Villas Condo
    Condo


    Estimated Monthly Payment: $1,316 (change assumption)
    Mortgage ($1,285) + Taxes in 2025 ($31)


    Taxes:$371

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2317 SUN VALLEY CIR #2317, WINTER PARK, FL 32792

    $249,00088 Days on yellowkey   MLS ID: O6398500

    REDUCED by $10,000 (3.9%) on 07/02/2026

    For Sale O6398500 - 2317 SUN VALLEY CIR #2317, WINTER PARK, FL 32792 20 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1295
       Built: 1987   Tax: $1,107 (2025)
    Community: Cedarwood Village 1
    Condo


    Estimated Monthly Payment: $1,457 (change assumption)
    Mortgage ($1,364) + Taxes in 2025 ($92)


    Taxes:$1,107

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 333 CORNWALL RD, WINTER PARK, FL 32792

    $579,00053 Days on yellowkey   MLS ID: O6409379

    For Sale O6409379 - 333 CORNWALL RD, WINTER PARK, FL 32792 32 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1660
       Built: 1963
    Monthly Fee: $5
       Tax: $2,654 (2025)
    Community: Winter Park Pines
    Single Family


    Estimated Monthly Payment: $3,399 (change assumption)
    Mortgage ($3,173) + Fees ($5) + Taxes in 2025 ($221)


    Taxes:$2,654

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 1250 S DENNING DR #109, WINTER PARK, FL 32789

    $190,0008 Days on yellowkey   MLS ID: R4911491

    For Sale R4911491 - 1250 S DENNING DR #109, WINTER PARK, FL 32789 27 photos

    Bed: 1   Bath: 1.0
    Liv Area Sq Ft: 658
       Built: 1967
    Monthly Fee: $350
       Tax: $1,669 (2025)
    Community: Mead Garden
    Spa: No

    Condo


    Estimated Monthly Payment: $1,530 (change assumption)
    Mortgage ($1,041) + Fees ($350) + Taxes in 2025 ($139)


    Taxes:$1,669

    Elementary School: Killarney Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 2157 LAKE DR, WINTER PARK, FL 32789

    $689,00045 Days on yellowkey   MLS ID: O6412258

    3 Days Off yellowkey (back on 7/6/2026)

    REDUCED by $70,000 (9.2%) on 05/31/2026

    For Sale O6412258 - 2157 LAKE DR, WINTER PARK, FL 32789 45 photos

    Bed: 3   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2124
       Built: 1962   Tax: $1,605 (2025)
    Community: Killarney Point
    Single Family


    Estimated Monthly Payment: $3,909 (change assumption)
    Mortgage ($3,775) + Taxes in 2025 ($134)


    Taxes:$1,605

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 751 WARRENTON RD, WINTER PARK, FL 32792

    $319,90021 Days on yellowkey   MLS ID: TB8522073

    0 Days Off yellowkey (back on 7/6/2026)

    For Sale TB8522073 - 751 WARRENTON RD, WINTER PARK, FL 32792 16 photos

    Bed: 3   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1196
       Built: 1989
    Monthly Fee: $86
       Tax: $2,795 (2025)
    Community: Winter Park Pines Patio Homes
    Spa: No

    Half Duplex


    Estimated Monthly Payment: $2,072 (change assumption)
    Mortgage ($1,753) + Fees ($86) + Taxes in 2025 ($233)


    Taxes:$2,795

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 501 LAKEVIEW AVE, WINTER PARK, FL 32789

    $1,390,000361 Days on yellowkey   MLS ID: O6325192

    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


  • 1695 LEE RD #A116, WINTER PARK, FL 32789

    $135,00013 Days on yellowkey   MLS ID: O6420863

    For Sale O6420863 - 1695 LEE RD #A116, WINTER PARK, FL 32789 18 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1149
       Built: 1966   Tax: $2,263 (2025)
    Community: Waterfall Cove
    Condo


    Estimated Monthly Payment: $928 (change assumption)
    Mortgage ($740) + Taxes in 2025 ($189)


    Taxes:$2,263

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2022 EASTBROOK BLVD, WINTER PARK, FL 32792

    $353,00015 Days on yellowkey   MLS ID: S5152746

    1 Days Off yellowkey (back on 7/6/2026)

    For Sale S5152746 - 2022 EASTBROOK BLVD, WINTER PARK, FL 32792 21 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1420
       Built: 1966   Tax: $3,122 (2025)
    Community: Eastbrook Sub Unit 07
    Single Family


    Estimated Monthly Payment: $2,194 (change assumption)
    Mortgage ($1,934) + Taxes in 2025 ($260)


    Taxes:$3,122

    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.