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Winter Park Single Family Homes For Sale - 221 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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  • 1810 HOLLYWOOD AVE, WINTER PARK, FL 32789

    $1,689,00078 Days on yellowkey   MLS ID: O6377320

    For Sale O6377320 - 1810 HOLLYWOOD AVE, WINTER PARK, FL 32789 10 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2604
       Built: 2026   Tax: $6,903 (2024)
    Community: Lake Monte Sub
    Single Family


    Estimated Monthly Payment: $9,830 (change assumption)
    Mortgage ($9,255) + Taxes in 2024 ($575)


    Taxes:$6,903

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 2454 BROOKSHIRE AVE, WINTER PARK, FL 32792

    $1,399,00048 Days on yellowkey   MLS ID: O6384924

    For Sale O6384924 - 2454 BROOKSHIRE AVE, WINTER PARK, FL 32792 34 photos

    Bed: 4   Bath: 3.5   Gar: 1
    Liv Area Sq Ft: 2509
       Built: 2023   Tax: $11,586 (2024)
    Community: Brookshire Heights 1St Add
    Single Family


    Estimated Monthly Payment: $8,631 (change assumption)
    Mortgage ($7,666) + Taxes in 2024 ($966)


    Taxes:$11,586

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Glenridge Middle


  • 3642 PERIWINKLE DR, WINTER PARK, FL 32792

    $440,000223 Days on yellowkey   MLS ID: O6341725

    For Sale O6341725 - 3642 PERIWINKLE DR, WINTER PARK, FL 32792 28 photos

    Bed: 5   Bath: 3.0
    Liv Area Sq Ft: 1945
       Built: 1964   Tax: $5,131 (2024)
    Community: Eastbrook Sub
    Single Family


    Estimated Monthly Payment: $2,838 (change assumption)
    Mortgage ($2,411) + Taxes in 2024 ($428)


    Taxes:$5,131

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 2708 LION HEART RD, WINTER PARK, FL 32792

    $629,50042 Days on yellowkey   MLS ID: O6387685

    REDUCED by $5,000 (0.8%) on 04/02/2026

    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
    Single Family


    Estimated Monthly Payment: $4,033 (change assumption)
    Mortgage ($3,449) + Taxes in 2024 ($584)


    Taxes:$7,007

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Glenridge Middle


  • 1418 LONE FEATHER TRL, WINTER PARK, FL 32792

    $759,99974 Days on yellowkey   MLS ID: O6378636

    For Sale O6378636 - 1418 LONE FEATHER TRL, WINTER PARK, FL 32792 45 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2197
       Built: 2022
    Monthly Fee: $235
       Tax: $5,856 (2024)
    Community: Landings At Hawks Crest
    Single Family


    Estimated Monthly Payment: $4,887 (change assumption)
    Mortgage ($4,164) + Fees ($235) + Taxes in 2024 ($488)


    Taxes:$5,856

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 422 BALMORAL RD, WINTER PARK, FL 32789

    $899,00014 Days on yellowkey   MLS ID: R4910985

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

    For Sale R4910985 - 422 BALMORAL RD, WINTER PARK, FL 32789 3 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1800
       Built: 1957   Tax: $11,451 (2025)
    Community: Kenilworth Shores Sec 02
    Single Family


    Estimated Monthly Payment: $5,880 (change assumption)
    Mortgage ($4,926) + Taxes in 2025 ($954)


    Taxes:$11,451

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 3330 COLEUS CT, WINTER PARK, FL 32792

    $384,90064 Days on yellowkey   MLS ID: O6378218

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

    For Sale O6378218 - 3330 COLEUS CT, WINTER PARK, FL 32792 36 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1988
       Built: 1968   Tax: $5,410 (2024)
    Community: Eastbrook Sub Unit 14
    Single Family


    Estimated Monthly Payment: $2,560 (change assumption)
    Mortgage ($2,109) + Taxes in 2024 ($451)


    Taxes:$5,410

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 1098 WILDMEADOW RUN, WINTER PARK, FL 32792

    $625,00062 Days on yellowkey   MLS ID: O6380923

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

    For Sale O6380923 - 1098 WILDMEADOW RUN, WINTER PARK, FL 32792 42 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1770
       Built: 2020
    Monthly Fee: $244
       Tax: $4,088 (2024)
    Community: Meadows At Hawks Crest
    Single Family


    Estimated Monthly Payment: $4,009 (change assumption)
    Mortgage ($3,425) + Fees ($244) + Taxes in 2024 ($341)


    Taxes:$4,088

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 770 W WEBSTER AVE, WINTER PARK, FL 32789

    $725,000286 Days on yellowkey   MLS ID: O6323574

    For Sale O6323574 - 770 W WEBSTER AVE, WINTER PARK, FL 32789 34 photos

    Bed: 4   Bath: 2.0
    Liv Area Sq Ft: 1008
       Built: 1967   Tax: $4,856 (2024)
    Community: Capens Add
    Single Family


    Estimated Monthly Payment: $4,377 (change assumption)
    Mortgage ($3,973) + Taxes in 2024 ($405)


    Taxes:$4,856

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Maitland Middle


  • 1630 ELM AVE, WINTER PARK, FL 32789

    $2,385,00030 Days on yellowkey   MLS ID: O6388606

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

    For Sale O6388606 - 1630 ELM AVE, WINTER PARK, FL 32789 15 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3408
       Built: 2026   Tax: $1,673 (2024)
    Community: Temple Estates
    Single Family


    Estimated Monthly Payment: $13,208 (change assumption)
    Mortgage ($13,068) + Taxes in 2024 ($139)


    Taxes:$1,673

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Maitland Middle


  • 837 APPALACHEE AVE, WINTER PARK, FL 32792

    $439,00019 Days on yellowkey   MLS ID: O6393151

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

    For Sale O6393151 - 837 APPALACHEE AVE, WINTER PARK, FL 32792 33 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1771
       Built: 1968   Tax: $6,834 (2025)
    Community: Winter Park Forest
    Single Family


    Estimated Monthly Payment: $2,975 (change assumption)
    Mortgage ($2,405) + Taxes in 2025 ($570)


    Taxes:$6,834

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 770 CARVER ST, WINTER PARK, FL 32789

    $375,000194 Days on yellowkey   MLS ID: O6349509

    0 Days Off yellowkey (back on 10/15/2025)

    For Sale O6349509 - 770 CARVER ST, WINTER PARK, FL 32789 6 photos

    Bed: 4   Bath: 1.5
    Liv Area Sq Ft: 1248
       Built: 1954   Tax: $634 (2024)
    Community: Magnolia Gardens Sub
    Single Family


    Estimated Monthly Payment: $2,108 (change assumption)
    Mortgage ($2,055) + Taxes in 2024 ($53)


    Taxes:$634

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 230 STRATHY LN, WINTER PARK, FL 32792

    $499,00098 Days on yellowkey   MLS ID: O6371054

    For Sale O6371054 - 230 STRATHY LN, WINTER PARK, FL 32792 12 photos

    Bed: 2   Bath: 1.0
    Liv Area Sq Ft: 920
       Built: 1957   Tax: $4,071 (2024)
    Community: Aloma
    Single Family


    Estimated Monthly Payment: $3,073 (change assumption)
    Mortgage ($2,734) + Taxes in 2024 ($339)


    Taxes:$4,071

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Glenridge Middle


  • 2231 NAIRN DR, WINTER PARK, FL 32792

    $499,00098 Days on yellowkey   MLS ID: O6369016

    For Sale O6369016 - 2231 NAIRN DR, WINTER PARK, FL 32792 19 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1088
       Built: 1956   Tax: $3,793 (2025)
    Community: Aloma
    Single Family


    Estimated Monthly Payment: $3,050 (change assumption)
    Mortgage ($2,734) + Taxes in 2025 ($316)


    Taxes:$3,793

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 872 GRANVILLE DR, WINTER PARK, FL 32789

    $2,200,00020 Days on yellowkey   MLS ID: O6391464

    0 Days Off yellowkey (back on 3/31/2026)

    For Sale O6391464 - 872 GRANVILLE DR, WINTER PARK, FL 32789 40 photos

    Bed: 4   Bath: 3.5
    Liv Area Sq Ft: 3195
       Built: 1961   Tax: $12,465 (2025)
    Community: Park Grove W/125 Lot 10 Blk D
    Single Family


    Estimated Monthly Payment: $13,093 (change assumption)
    Mortgage ($12,054) + Taxes in 2025 ($1,039)


    Taxes:$12,465

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 1885 TEMPLE DR, WINTER PARK, FL 32789

    $2,265,000154 Days on yellowkey   MLS ID: O6359471

    For Sale O6359471 - 1885 TEMPLE DR, WINTER PARK, FL 32789 53 photos

    Bed: 5   Bath: 3.5
    Liv Area Sq Ft: 3691
       Built: 1963   Tax: $6,073 (2025)
    Community: Lugano Terrace
    Single Family


    Estimated Monthly Payment: $12,917 (change assumption)
    Mortgage ($12,411) + Taxes in 2025 ($506)


    Taxes:$6,073

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 1624 BARCELONA WAY, WINTER PARK, FL 32789

    $2,275,000146 Days on yellowkey   MLS ID: O6362124

    For Sale O6362124 - 1624 BARCELONA WAY, WINTER PARK, FL 32789 62 photos

    Bed: 4   Bath: 3.0
    Liv Area Sq Ft: 3828
       Built: 1972
    Monthly Fee: $87
       Tax: $12,501 (2024)
    Community: Sevilla
    Single Family


    Estimated Monthly Payment: $13,594 (change assumption)
    Mortgage ($12,465) + Fees ($87) + Taxes in 2024 ($1,042)


    Taxes:$12,501

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Audubon Park K-8


  • 3127 ASH PARK LOOP, WINTER PARK, FL 32792

    $400,00040 Days on yellowkey   MLS ID: O6388568

    0 Days Off yellowkey (back on 3/30/2026)

    For Sale O6388568 - 3127 ASH PARK LOOP, WINTER PARK, FL 32792 36 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1518
       Built: 1986
    Monthly Fee: $37
       Tax: $3,995 (2025)
    Community: Hyde Park
    Single Family


    Estimated Monthly Payment: $2,562 (change assumption)
    Mortgage ($2,192) + Fees ($37) + Taxes in 2025 ($333)


    Taxes:$3,995

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 1909 EDWIN BLVD, WINTER PARK, FL 32792

    $440,000144 Days on yellowkey   MLS ID: O6362682

    1 Days Off yellowkey (back on 12/2/2025)

    For Sale O6362682 - 1909 EDWIN BLVD, WINTER PARK, FL 32792 11 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1355
       Built: 1955   Tax: $4,703 (2024)
    Community: Eastgate Sub
    Single Family


    Estimated Monthly Payment: $2,803 (change assumption)
    Mortgage ($2,411) + Taxes in 2024 ($392)


    Taxes:$4,703

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Maitland Middle


  • 560 OLOLU DR, WINTER PARK, FL 32789

    $949,000197 Days on yellowkey   MLS ID: O6344540

    For Sale O6344540 - 560 OLOLU DR, WINTER PARK, FL 32789 29 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1086
       Built: 1953   Tax: $8,617 (2024)
    Community: Killarney Circle
    Single Family


    Estimated Monthly Payment: $5,918 (change assumption)
    Mortgage ($5,200) + Taxes in 2024 ($718)


    Taxes:$8,617

    Elementary School: None

    High School: None

    Tax Year: 2024

    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.