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Winter Park Single Family Homes For Sale - 310 homes

Winter Park Single Family Homes for Sale are located in Orange County, Florida. Find single family homes for sale in Winter Park with data from the Multiple Listing Service (MLS). Our REALTORS® can assist you in your real estate search for Winter Park single family houses.

Location: Winter Park

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  • 1649 HARMON AVE, WINTER PARK, FL 32789

    $1,349,90071 Days on yellowkey   MLS ID: O6392216

    REDUCED by $49,100 (3.5%) on 05/15/2026

    For Sale O6392216 - 1649 HARMON AVE, WINTER PARK, FL 32789 57 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3223
       Built: 2018   Tax: $11,908 (2025)
    Community: Lawndale
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $8,389 (change assumption)
    Mortgage ($7,397) + Taxes in 2025 ($992)


    Taxes:$11,908

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park Middle


  • 1090 WILDMEADOW RUN, WINTER PARK, FL 32792

    $845,00064 Days on yellowkey   MLS ID: O6394208

    For Sale O6394208 - 1090 WILDMEADOW RUN, WINTER PARK, FL 32792 37 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2589
       Built: 2021
    Monthly Fee: $243
       Tax: $6,258 (2024)
    Community: Hawks Crest
    Single Family


    Estimated Monthly Payment: $5,394 (change assumption)
    Mortgage ($4,630) + Fees ($243) + Taxes in 2024 ($521)


    Taxes:$6,258

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 2333 WESTMINSTER CT, WINTER PARK, FL 32789

    $719,00013 Days on yellowkey   MLS ID: O6407054

    For Sale O6407054 - 2333 WESTMINSTER CT, WINTER PARK, FL 32789 48 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1877
       Built: 1948   Tax: $6,723 (2025)
    Community: Glencoe Sub
    Single Family


    Estimated Monthly Payment: $4,500 (change assumption)
    Mortgage ($3,940) + Taxes in 2025 ($560)


    Taxes:$6,723

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park Middle


  • 5210 OHIO ST, WINTER PARK, FL 32792

    $445,00015 Days on yellowkey   MLS ID: O6408143

    0 Days Off yellowkey (back on 5/23/2026)

    For Sale O6408143 - 5210 OHIO ST, WINTER PARK, FL 32792 34 photos

    Bed: 4   Bath: 2.5   Gar: 1
    Liv Area Sq Ft: 1946
       Built: 1973   Tax: $4,869 (2024)
    Community: Suburban Homes Sec 2
    Single Family


    Estimated Monthly Payment: $2,844 (change assumption)
    Mortgage ($2,438) + Taxes in 2024 ($406)


    Taxes:$4,869

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 2232 BANCHORY ROAD, WINTER PARK, FL 32792

    $1,115,00026 Days on yellowkey   MLS ID: O6404702

    REDUCED by $45,000 (3.9%) on 05/21/2026

    For Sale O6404702 - 2232 BANCHORY ROAD, WINTER PARK, FL 32792 44 photos

    Bed: 4   Bath: 3.0   Gar: 1
    Liv Area Sq Ft: 2597
       Built: 1966   Tax: $11,186 (2025)
    Community: Brookshire Heights 4Th Add
    Single Family


    Estimated Monthly Payment: $7,042 (change assumption)
    Mortgage ($6,109) + Taxes in 2025 ($932)


    Taxes:$11,186

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2087 LAURELWOOD WAY, WINTER PARK, FL 32792

    $624,000256 Days on yellowkey   MLS ID: O6344482

    REDUCED by $35,000 (5.3%) on 05/06/2026

    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: $4,045 (change assumption)
    Mortgage ($3,419) + 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


  • 1617 CHILEAN LN, WINTER PARK, FL 32792

    $367,500135 Days on yellowkey   MLS ID: O6373026

    1 Days Off yellowkey (back on 5/15/2026)

    REDUCED by $2,400 (0.6%) on 04/30/2026

    For Sale O6373026 - 1617 CHILEAN LN, WINTER PARK, FL 32792 40 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1359
       Built: 1960   Tax: $3,432 (2024)
    Community: Eastbrook Sub Unit 05
    Single Family


    Estimated Monthly Payment: $2,300 (change assumption)
    Mortgage ($2,014) + Taxes in 2024 ($286)


    Taxes:$3,432

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 1354 TIERRA CIR, WINTER PARK, FL 32792

    $425,000502 Days on yellowkey   MLS ID: O6271121

    For Sale O6271121 - 1354 TIERRA CIR, WINTER PARK, FL 32792 31 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1827
       Built: 1969
    Monthly Fee: $2
       Tax: $3,812 (2023)
    Community: Casa Aloma
    Single Family


    Estimated Monthly Payment: $2,648 (change assumption)
    Mortgage ($2,329) + Fees ($2) + Taxes in 2023 ($318)


    Taxes:$3,812

    Elementary School: English Estates Elementary

    High School: Lake Howell High

    Tax Year: 2023

    Middle School: Tuskawilla Middle


  • 501 HERITAGE BLVD, WINTER PARK, FL 32792

    $479,90078 Days on yellowkey   MLS ID: S5145746

    REDUCED by $5,090 (1.0%) on 05/23/2026

    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: $3,499 (change assumption)
    Mortgage ($2,630) + Taxes in 2025 ($870)


    Taxes:$10,434

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 120 BROADVIEW AVE, WINTER PARK, FL 32789

    $1,450,0008 Days on yellowkey   MLS ID: O6409860

    For Sale O6409860 - 120 BROADVIEW AVE, WINTER PARK, FL 32789 6 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1747
       Built: 1947   Tax: $2,693 (2025)
    Community: Killarney Estates
    Single Family


    Estimated Monthly Payment: $8,169 (change assumption)
    Mortgage ($7,945) + Taxes in 2025 ($224)


    Taxes:$2,693

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park Middle


  • 1009 LAKE BELL DR, WINTER PARK, FL 32789

    $699,0008 Days on yellowkey   MLS ID: O6409849

    For Sale O6409849 - 1009 LAKE BELL DR, WINTER PARK, FL 32789 20 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1467
       Built: 1958   Tax: $5,448 (2025)
    Community: Albert Lee Ridge Add 02
    Single Family


    Estimated Monthly Payment: $4,284 (change assumption)
    Mortgage ($3,830) + Taxes in 2025 ($454)


    Taxes:$5,448

    Elementary School: Hungerford Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park Middle


  • 2707 TIERRA CIR, WINTER PARK, FL 32792

    $495,00031 Days on yellowkey   MLS ID: O6398979

    2 Days Off yellowkey (back on 5/22/2026)

    For Sale O6398979 - 2707 TIERRA CIR, WINTER PARK, FL 32792 42 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1710
       Built: 1970   Tax: $3,237 (2025)
    Community: Casa Aloma
    Single Family


    Estimated Monthly Payment: $2,982 (change assumption)
    Mortgage ($2,712) + Taxes in 2025 ($270)


    Taxes:$3,237

    Elementary School: English Estates Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 1725 CAROLLEE LN, WINTER PARK, FL 32789

    $1,005,00033 Days on yellowkey   MLS ID: O6402656

    0 Days Off yellowkey (back on 5/22/2026)

    REDUCED by $10,000 (1.0%) on 05/12/2026

    For Sale O6402656 - 1725 CAROLLEE LN, WINTER PARK, FL 32789 41 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2335
       Built: 1960   Tax: $8,445 (2025)
    Community: Green Terrace
    Single Family


    Estimated Monthly Payment: $6,210 (change assumption)
    Mortgage ($5,507) + Taxes in 2025 ($704)


    Taxes:$8,445

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 4469 OLD BEAR RUN, WINTER PARK, FL 32792

    $1,799,999110 Days on yellowkey   MLS ID: O6375415

    REDUCED by $50,001 (2.7%) on 05/22/2026

    For Sale O6375415 - 4469 OLD BEAR RUN, WINTER PARK, FL 32792 77 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 4288
       Built: 1978   Tax: $10,710 (2024)
    Community: Pervis Survey For R E
    Spa: No

    Single Family


    Estimated Monthly Payment: $10,755 (change assumption)
    Mortgage ($9,863) + Taxes in 2024 ($893)


    Taxes:$10,710

    Elementary School: Red Bug Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 2973 SANBINA ST, WINTER PARK, FL 32789

    $377,88015 Days on yellowkey   MLS ID: O6407521

    For Sale O6407521 - 2973 SANBINA ST, WINTER PARK, FL 32789 36 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1128
       Built: 1965   Tax: $5,253 (2025)
    Community: Howell Heights
    Single Family


    Estimated Monthly Payment: $2,508 (change assumption)
    Mortgage ($2,071) + Taxes in 2025 ($438)


    Taxes:$5,253

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 2756 SHERIFF WAY, WINTER PARK, FL 32792

    $625,00032 Days on yellowkey   MLS ID: O6402570

    For Sale O6402570 - 2756 SHERIFF WAY, WINTER PARK, FL 32792 48 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1812
       Built: 1965   Tax: $5,547 (2025)
    Community: Winter Park Pines
    Single Family


    Estimated Monthly Payment: $3,887 (change assumption)
    Mortgage ($3,425) + Taxes in 2025 ($462)


    Taxes:$5,547

    Elementary School: Aloma Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 841 W SWOOPE AVE, WINTER PARK, FL 32789

    $499,000121 Days on yellowkey   MLS ID: O6373287

    0 Days Off yellowkey (back on 4/30/2026)

    REDUCED by $241,000 (32.6%) on 04/13/2026

    For Sale O6373287 - 841 W SWOOPE AVE, WINTER PARK, FL 32789 31 photos

    Bed: 2   Bath: 1.0
    Liv Area Sq Ft: 1396
       Built: 1930   Tax: $3,824 (2024)
    Community: Capens Add
    Single Family


    Estimated Monthly Payment: $3,053 (change assumption)
    Mortgage ($2,734) + Taxes in 2024 ($319)


    Taxes:$3,824

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 2512 EASTBROOK BLVD, WINTER PARK, FL 32792

    $390,0009 Days on yellowkey   MLS ID: O6409544

    For Sale O6409544 - 2512 EASTBROOK BLVD, WINTER PARK, FL 32792 42 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1607
       Built: 1967   Tax: $4,171 (2025)
    Community: Eastbrook Sub Unit 8
    Single Family


    Estimated Monthly Payment: $2,485 (change assumption)
    Mortgage ($2,137) + Taxes in 2025 ($348)


    Taxes:$4,171

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1441 CARDINAL CT, WINTER PARK, FL 32789

    $4,285,00045 Days on yellowkey   MLS ID: O6399395

    For Sale O6399395 - 1441 CARDINAL CT, WINTER PARK, FL 32789 85 photos

    Bed: 4   Bath: 5.5   Gar: 2
    Liv Area Sq Ft: 4066
       Built: 2022   Tax: $47,740 (2025)
    Community: Winflor Court
    Spa: No

    Single Family


    Estimated Monthly Payment: $27,457 (change assumption)
    Mortgage ($23,479) + Taxes in 2025 ($3,978)


    Taxes:$47,740

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 2889 ROUEN AVE, WINTER PARK, FL 32789

    $399,50039 Days on yellowkey   MLS ID: L4961275

    For Sale L4961275 - 2889 ROUEN AVE, WINTER PARK, FL 32789 10 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1144
       Built: 1959   Tax: $5,061 (2025)
    Community: Winter Park Manor
    Single Family


    Estimated Monthly Payment: $2,611 (change assumption)
    Mortgage ($2,189) + Taxes in 2025 ($422)


    Taxes:$5,061

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None




Why Bother Searching Elsewhere for Winter Park Single Family Homes for Sale?

Winter Park home, townhome, and condo, villa, and other listing sale 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 single family homes for sale in Winter Park . You can use our website to view Multiple Listing Service (MLS) data on Winter Park single family homes. 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 single family home 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.