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Winter Park Single Family Homes For Sale - 255 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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  • 1742 TEMPLE DR, WINTER PARK, FL 32789

    $3,449,99983 Days on yellowkey   MLS ID: O6378905

    REDUCED by $99,991 (2.8%) on 04/05/2026

    For Sale O6378905 - 1742 TEMPLE DR, WINTER PARK, FL 32789 73 photos

    Bed: 4   Bath: 5.0   Gar: 2
    Liv Area Sq Ft: 3658
       Built: 2003   Tax: $22,077 (2024)
    Community: Lake Knowles Terrace Add 02
    Single Family


    Estimated Monthly Payment: $20,743 (change assumption)
    Mortgage ($18,904) + Taxes in 2024 ($1,840)


    Taxes:$22,077

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 781 NORTHWOOD CIR, WINTER PARK, FL 32789

    $775,00025 Days on yellowkey   MLS ID: O6394119

    0 Days Off yellowkey (back on 4/5/2026)

    For Sale O6394119 - 781 NORTHWOOD CIR, WINTER PARK, FL 32789 33 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1566
       Built: 1971   Tax: $6,931 (2025)
    Community: Winter Park Oasis
    Single Family


    Estimated Monthly Payment: $4,824 (change assumption)
    Mortgage ($4,246) + Taxes in 2025 ($578)


    Taxes:$6,931

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 2175 MARSH SEDGE LN, WINTER PARK, FL 32792

    $845,00032 Days on yellowkey   MLS ID: O6393503

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

    For Sale O6393503 - 2175 MARSH SEDGE LN, WINTER PARK, FL 32792 44 photos

    Bed: 5   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3188
       Built: 2019
    Monthly Fee: $236
       Tax: $9,100 (2025)
    Community: Hawks Crest
    Single Family


    Estimated Monthly Payment: $5,624 (change assumption)
    Mortgage ($4,630) + Fees ($236) + Taxes in 2025 ($758)


    Taxes:$9,100

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 7445 BETTY ST, WINTER PARK, FL 32792

    $435,00025 Days on yellowkey   MLS ID: OM721366

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

    For Sale OM721366 - 7445 BETTY ST, WINTER PARK, FL 32792 76 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1576
       Built: 1983   Tax: $3,769 (2025)
    Community: Wrenwood Unit 3 4Th Add
    Single Family


    Estimated Monthly Payment: $2,698 (change assumption)
    Mortgage ($2,384) + Taxes in 2025 ($314)


    Taxes:$3,769

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 643 DUNBLANE DR, WINTER PARK, FL 32792

    $699,80058 Days on yellowkey   MLS ID: O6386136

    For Sale O6386136 - 643 DUNBLANE DR, WINTER PARK, FL 32792 62 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1575
       Built: 1962   Tax: $4,598 (2024)
    Community: Kenilworth Shores Section Four Y/71 Lot 21 Blk B
    Single Family


    Estimated Monthly Payment: $4,218 (change assumption)
    Mortgage ($3,834) + Taxes in 2024 ($383)


    Taxes:$4,598

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Glenridge Middle


  • 2820 BEAR ISLAND POINTE, WINTER PARK, FL 32792

    $2,095,00023 Days on yellowkey   MLS ID: O6395836

    For Sale O6395836 - 2820 BEAR ISLAND POINTE, WINTER PARK, FL 32792 75 photos

    Bed: 3   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 5138
       Built: 1998
    Monthly Fee: $158
       Tax: $13,815 (2024)
    Community: Cypress Reserve
    Single Family


    Estimated Monthly Payment: $12,788 (change assumption)
    Mortgage ($11,479) + Fees ($158) + Taxes in 2024 ($1,151)


    Taxes:$13,815

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 1870 STAUNTON AVE, WINTER PARK, FL 32789

    $1,250,00023 Days on yellowkey   MLS ID: O6391469

    For Sale O6391469 - 1870 STAUNTON AVE, WINTER PARK, FL 32789 10 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2525
       Built: 1935   Tax: $1,302 (2025)
    Community: Karolina On Killarney
    Single Family


    Estimated Monthly Payment: $6,958 (change assumption)
    Mortgage ($6,849) + Taxes in 2025 ($109)


    Taxes:$1,302

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park Middle


  • 1340 PLACE PICARDY, WINTER PARK, FL 32789

    $1,599,00073 Days on yellowkey   MLS ID: O6382113

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

    For Sale O6382113 - 1340 PLACE PICARDY, WINTER PARK, FL 32789 34 photos

    Bed: 3   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3459
       Built: 1997   Tax: $7,515 (2025)
    Community: Fontainebleau
    Single Family


    Estimated Monthly Payment: $9,388 (change assumption)
    Mortgage ($8,761) + Taxes in 2025 ($626)


    Taxes:$7,515

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 3642 PERIWINKLE DR, WINTER PARK, FL 32792

    $440,000234 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


  • 1418 LONE FEATHER TRL, WINTER PARK, FL 32792

    $759,99985 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

    $899,00025 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


  • 1098 WILDMEADOW RUN, WINTER PARK, FL 32792

    $625,00073 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

    $725,000297 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

    $2,385,00041 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

    $439,00030 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


  • 230 STRATHY LN, WINTER PARK, FL 32792

    $499,000109 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

    $499,000109 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

    $2,200,00031 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


  • 3127 ASH PARK LOOP, WINTER PARK, FL 32792

    $400,00051 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

    $440,000155 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




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.