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Winter Park Homes For Sale & Real Estate - 393 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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  • 1565 FOREST AVE, WINTER PARK, FL 32789

    $1,750,00016 Days on yellowkey   MLS ID: O6398694

    For Sale O6398694 - 1565 FOREST AVE, WINTER PARK, FL 32789 37 photos

    Bed: 4   Bath: 2.0
    Liv Area Sq Ft: 2163
       Built: 1925   Tax: $2,803 (2025)
    Community: Ellno Willo
    Single Family


    Estimated Monthly Payment: $9,822 (change assumption)
    Mortgage ($9,589) + Taxes in 2025 ($234)


    Taxes:$2,803

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 629 COUNTRY CLUB DR, WINTER PARK, FL 32789

    $1,695,00061 Days on yellowkey   MLS ID: O6386610

    0 Days Off yellowkey (back on 4/27/2026)

    For Sale O6386610 - 629 COUNTRY CLUB DR, WINTER PARK, FL 32789 46 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3031
       Built: 2026   Tax: $2,028 (2025)
    Community: Lords Sub
    Spa: No

    Single Family


    Estimated Monthly Payment: $9,456 (change assumption)
    Mortgage ($9,287) + Taxes in 2025 ($169)


    Taxes:$2,028

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


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

    $309,900246 Days on yellowkey   MLS ID: O6337061

    REDUCED by $5,000 (1.6%) on 04/25/2026

    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: $1,754 (change assumption)
    Mortgage ($1,698) + Taxes in 2024 ($56)


    Taxes:$668

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 1521 HERON WOOD PL, WINTER PARK, FL 32792

    $925,00083 Days on yellowkey   MLS ID: O6379884

    For Sale O6379884 - 1521 HERON WOOD PL, WINTER PARK, FL 32792 74 photos

    Bed: 4   Bath: 2.0
    Liv Area Sq Ft: 3950
       Built: 1983   Tax: $6,494 (2024)
    Community: None
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $5,610 (change assumption)
    Mortgage ($5,068) + Taxes in 2024 ($541)


    Taxes:$6,494

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 1832 E CHERYL DR, WINTER PARK, FL 32792

    $439,9956 Days on yellowkey   MLS ID: O6402209

    INCREASED by $10,000 (2.3%) on 04/27/2026

    For Sale O6402209 - 1832 E CHERYL DR, WINTER PARK, FL 32792 22 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1808
       Built: 1983
    Monthly Fee: $8
       Tax: $1,847 (2024)
    Community: Carolyn Estates
    Single Family


    Estimated Monthly Payment: $2,573 (change assumption)
    Mortgage ($2,411) + Fees ($8) + Taxes in 2024 ($154)


    Taxes:$1,847

    Elementary School: Red Bug Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 121 STEFANIK RD, WINTER PARK, FL 32792

    $317,500190 Days on yellowkey   MLS ID: A4669103

    For Sale A4669103 - 121 STEFANIK RD, WINTER PARK, FL 32792 11 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1392
       Built: 1949   Tax: $3,581 (2024)
    Community: Slovak Village
    Single Family


    Estimated Monthly Payment: $2,038 (change assumption)
    Mortgage ($1,740) + Taxes in 2024 ($298)


    Taxes:$3,581

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 1130 PARK NORTH PLACE, WINTER PARK, FL 32789

    $2,495,00035 Days on yellowkey   MLS ID: O6392394

    REDUCED by $155,000 (5.8%) on 04/22/2026

    For Sale O6392394 - 1130 PARK NORTH PLACE, WINTER PARK, FL 32789 41 photos

    Bed: 5   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 4011
       Built: 1968   Tax: $9,744 (2025)
    Community: Park North
    Single Family


    Estimated Monthly Payment: $14,483 (change assumption)
    Mortgage ($13,671) + Taxes in 2025 ($812)


    Taxes:$9,744

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 350 CORNWALL RD, WINTER PARK, FL 32792

    $775,00032 Days on yellowkey   MLS ID: O6394524

    For Sale O6394524 - 350 CORNWALL RD, WINTER PARK, FL 32792 34 photos

    Bed: 4   Bath: 3.0
    Liv Area Sq Ft: 2038
       Built: 1963   Tax: $2,127 (2025)
    Community: Winter Park Pines Rep
    Single Family


    Estimated Monthly Payment: $4,424 (change assumption)
    Mortgage ($4,246) + Taxes in 2025 ($177)


    Taxes:$2,127

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2087 LAURELWOOD WAY, WINTER PARK, FL 32792

    $659,000226 Days on yellowkey   MLS ID: O6344482

    REDUCED by $5,000 (0.8%) on 04/20/2026

    For Sale O6344482 - 2087 LAURELWOOD WAY, WINTER PARK, FL 32792 30 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1920
       Built: 2019
    Monthly Fee: $236
       Tax: $4,680 (2024)
    Community: Hawks Crest
    Single Family


    Estimated Monthly Payment: $4,237 (change assumption)
    Mortgage ($3,611) + Fees ($236) + Taxes in 2024 ($390)


    Taxes:$4,680

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 2015 SUMMERFIELD RD, WINTER PARK, FL 32792

    $1,375,000175 Days on yellowkey   MLS ID: O6357615

    For Sale O6357615 - 2015 SUMMERFIELD RD, WINTER PARK, FL 32792 50 photos

    Bed: 4   Bath: 4.0   Gar: 1
    Liv Area Sq Ft: 3024
       Built: 1957   Tax: $7,243 (2025)
    Community: Kenilworth Shores Sec 07
    Spa: No

    Single Family


    Estimated Monthly Payment: $8,138 (change assumption)
    Mortgage ($7,534) + Taxes in 2025 ($604)


    Taxes:$7,243

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 5275 PINE LILY CIR, WINTER PARK, FL 32792

    $665,00090 Days on yellowkey   MLS ID: O6377988

    0 Days Off yellowkey (back on 4/27/2026)

    For Sale O6377988 - 5275 PINE LILY CIR, WINTER PARK, FL 32792 34 photos

    Bed: 5   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 3152
       Built: 2014
    Monthly Fee: $182
       Tax: $7,425 (2024)
    Community: Sanctuary At Aloma
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $4,444 (change assumption)
    Mortgage ($3,644) + Fees ($182) + Taxes in 2024 ($619)


    Taxes:$7,425

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 2503 VERSAILLES AVE, WINTER PARK, FL 32789

    $2,184,000141 Days on yellowkey   MLS ID: O6365961

    0 Days Off yellowkey (back on 4/27/2026)

    REDUCED by $166,000 (7.1%) on 04/04/2026

    For Sale O6365961 - 2503 VERSAILLES AVE, WINTER PARK, FL 32789 53 photos

    Bed: 5   Bath: 4.0   Gar: 3
    Liv Area Sq Ft: 4026
       Built: 2015   Tax: $15,760 (2024)
    Community: Fontainebleau
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $13,280 (change assumption)
    Mortgage ($11,967) + Taxes in 2024 ($1,313)


    Taxes:$15,760

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Maitland Middle


  • 1210 FAIRWAY DR, WINTER PARK, FL 32792

    $549,00017 Days on yellowkey   MLS ID: O6398533

    3 Days Off yellowkey (back on 4/27/2026)

    For Sale O6398533 - 1210 FAIRWAY DR, WINTER PARK, FL 32792 38 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1737
       Built: 1979   Tax: $7,265 (2025)
    Community: Golfside Sec 3
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,614 (change assumption)
    Mortgage ($3,008) + Taxes in 2025 ($605)


    Taxes:$7,265

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 200 SAINT ANDREWS BLVD #2901, WINTER PARK, FL 32792

    $225,00028 Days on yellowkey   MLS ID: O6395720

    1 Days Off yellowkey (back on 4/27/2026)

    For Sale O6395720 - 200 SAINT ANDREWS BLVD #2901, WINTER PARK, FL 32792 29 photos

    Bed: 2   Bath: 1.5
    Liv Area Sq Ft: 1266
       Built: 1970
    Monthly Fee: $451
       Tax: $2,131 (2025)
    Community: Four Seasons Condo
    Condo


    Estimated Monthly Payment: $1,861 (change assumption)
    Mortgage ($1,233) + Fees ($451) + Taxes in 2025 ($178)


    Taxes:$2,131

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 2648 GALLIANO CIR, WINTER PARK, FL 32792

    $355,00065 Days on yellowkey   MLS ID: S5144547

    For Sale S5144547 - 2648 GALLIANO CIR, WINTER PARK, FL 32792 39 photos

    Bed: 2   Bath: 2.5   Gar: 1
    Liv Area Sq Ft: 1550
       Built: 2004
    Monthly Fee: $175
       Tax: $4,736 (2024)
    Community: Vistas At Lake Howell
    Single Family


    Estimated Monthly Payment: $2,515 (change assumption)
    Mortgage ($1,945) + Fees ($175) + Taxes in 2024 ($395)


    Taxes:$4,736

    Elementary School: Sterling Park Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 5331 OAK CT, WINTER PARK, FL 32792

    $460,000288 Days on yellowkey   MLS ID: S5130868

    For Sale S5130868 - 5331 OAK CT, WINTER PARK, FL 32792 41 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1263
       Built: 1976   Tax: $2,311 (2024)
    Community: Wrenwood Heights Unit 2
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,713 (change assumption)
    Mortgage ($2,520) + Taxes in 2024 ($193)


    Taxes:$2,311

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 1660 PALMER AVE, WINTER PARK, FL 32789

    $4,950,000434 Days on yellowkey   MLS ID: O6282425

    For Sale O6282425 - 1660 PALMER AVE, WINTER PARK, FL 32789 53 photos

    Bed: 5   Bath: 6.5   Gar: 3
    Liv Area Sq Ft: 6406
       Built: 2024   Tax: $6,144 (2024)
    Community: Comstock Park
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $27,635 (change assumption)
    Mortgage ($27,123) + Taxes in 2024 ($512)


    Taxes:$6,144

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Maitland Middle


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

    $279,00013 Days on yellowkey   MLS ID: O6398500

    For Sale O6398500 - 2317 SUN VALLEY CIR #2317, WINTER PARK, FL 32792 17 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: $1,621 (change assumption)
    Mortgage ($1,529) + Taxes in 2025 ($92)


    Taxes:$1,107

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 661 SELKIRK DR, WINTER PARK, FL 32792

    $650,000190 Days on yellowkey   MLS ID: O6354700

    2 Days Off yellowkey (back on 4/27/2026)

    REDUCED by $25,000 (3.7%) on 04/16/2026

    For Sale O6354700 - 661 SELKIRK DR, WINTER PARK, FL 32792 23 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2150
       Built: 1962   Tax: $2,353 (2024)
    Community: Kenilworth Shores Sec 05
    Single Family


    Estimated Monthly Payment: $3,758 (change assumption)
    Mortgage ($3,562) + Taxes in 2024 ($196)


    Taxes:$2,353

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 2009 SHADYHILL TER, WINTER PARK, FL 32792

    $535,0004 Days on yellowkey   MLS ID: O6402256

    For Sale O6402256 - 2009 SHADYHILL TER, WINTER PARK, FL 32792 26 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1670
       Built: 1987
    Monthly Fee: $56
       Tax: $1,742 (2025)
    Community: Autumn Glen Ph 2
    Single Family


    Estimated Monthly Payment: $3,133 (change assumption)
    Mortgage ($2,931) + Fees ($56) + Taxes in 2025 ($145)


    Taxes:$1,742

    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.