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Winter Park Single Family Homes For Sale - 235 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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  • 1750 CAROLLEE LANE, WINTER PARK, FL 32789

    $1,890,00028 Days on yellowkey   MLS ID: O6391179

    REDUCED by $105,000 (5.3%) on 04/08/2026

    For Sale O6391179 - 1750 CAROLLEE LANE, WINTER PARK, FL 32789 47 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3249
       Built: 2012   Tax: $24,658 (2025)
    Community: Green Terrace V/140 Lot 3 Blk B
    Single Family


    Estimated Monthly Payment: $12,411 (change assumption)
    Mortgage ($10,356) + Taxes in 2025 ($2,055)


    Taxes:$24,658

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 675 OVERSPIN DR, WINTER PARK, FL 32789

    $775,00067 Days on yellowkey   MLS ID: O6378975

    0 Days Off yellowkey (back on 4/8/2026)

    For Sale O6378975 - 675 OVERSPIN DR, WINTER PARK, FL 32789 32 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3062
       Built: 2010   Tax: $11,578 (2025)
    Community: Dubsdread Heights
    Single Family


    Estimated Monthly Payment: $5,211 (change assumption)
    Mortgage ($4,246) + Taxes in 2025 ($965)


    Taxes:$11,578

    Elementary School: Princeton Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park Middle


  • 4923 N MAGNOLIA AVE, WINTER PARK, FL 32792

    $390,00010 Days on yellowkey   MLS ID: O6396378

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

    For Sale O6396378 - 4923 N MAGNOLIA AVE, WINTER PARK, FL 32792 2 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1559
       Built: 1953   Tax: $2,479 (2025)
    Community: Suburban Homes
    Single Family


    Estimated Monthly Payment: $2,344 (change assumption)
    Mortgage ($2,137) + Taxes in 2025 ($207)


    Taxes:$2,479

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 1127 WILDMEADOW RUN, WINTER PARK, FL 32792

    $675,000135 Days on yellowkey   MLS ID: O6364368

    0 Days Off yellowkey (back on 3/19/2026)

    For Sale O6364368 - 1127 WILDMEADOW RUN, WINTER PARK, FL 32792 82 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2196
       Built: 2020
    Monthly Fee: $243
       Tax: $6,882 (2024)
    Community: Meadows At Hawks Crest
    Single Family


    Estimated Monthly Payment: $4,515 (change assumption)
    Mortgage ($3,699) + Fees ($243) + Taxes in 2024 ($574)


    Taxes:$6,882

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 1617 CHILEAN LN, WINTER PARK, FL 32792

    $369,90092 Days on yellowkey   MLS ID: O6373026

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

    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: $2,313 (change assumption)
    Mortgage ($2,027) + Taxes in 2024 ($286)


    Taxes:$3,432

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 5275 PINE LILY CIR, WINTER PARK, FL 32792

    $665,00077 Days on yellowkey   MLS ID: O6377988

    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


  • 1500 HARRIS CIR, WINTER PARK, FL 32789

    $1,295,00065 Days on yellowkey   MLS ID: O6379012

    For Sale O6379012 - 1500 HARRIS CIR, WINTER PARK, FL 32789 26 photos

    Bed: 2   Bath: 3.0
    Liv Area Sq Ft: 2096
       Built: 1994   Tax: $11,846 (2024)
    Community: Sylvan Lake Shores
    Single Family


    Estimated Monthly Payment: $8,083 (change assumption)
    Mortgage ($7,096) + Taxes in 2024 ($987)


    Taxes:$11,846

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Glenridge Middle


  • 823 GRANVILLE DR, WINTER PARK, FL 32789

    $1,400,00018 Days on yellowkey   MLS ID: O6394306

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

    For Sale O6394306 - 823 GRANVILLE DR, WINTER PARK, FL 32789 63 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2544
       Built: 1963   Tax: $7,623 (2025)
    Community: Park Grove
    Single Family


    Estimated Monthly Payment: $8,306 (change assumption)
    Mortgage ($7,671) + Taxes in 2025 ($635)


    Taxes:$7,623

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 518 SHOREVIEW AVE, WINTER PARK, FL 32789

    $490,09024 Days on yellowkey   MLS ID: O6392797

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

    For Sale O6392797 - 518 SHOREVIEW AVE, WINTER PARK, FL 32789 35 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1609
       Built: 1920   Tax: $3,919 (2025)
    Community: Killarney Estates
    Single Family


    Estimated Monthly Payment: $3,012 (change assumption)
    Mortgage ($2,685) + Taxes in 2025 ($327)


    Taxes:$3,919

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park Middle


  • 1760 PERUVIAN LN, WINTER PARK, FL 32792

    $339,00041 Days on yellowkey   MLS ID: A4685217

    For Sale A4685217 - 1760 PERUVIAN LN, WINTER PARK, FL 32792 23 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1160
       Built: 1960   Tax: $3,470 (2025)
    Community: Eastbrook Sub Unit 06
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,147 (change assumption)
    Mortgage ($1,857) + Taxes in 2025 ($289)


    Taxes:$3,470

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 432 WORTHINGTON DR, WINTER PARK, FL 32789

    $2,719,00016 Days on yellowkey   MLS ID: O6390186

    For Sale O6390186 - 432 WORTHINGTON DR, WINTER PARK, FL 32789 17 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3845
       Built: 2026   Tax: $8,705 (2025)
    Community: Kenilworth Shores Sec 01
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $15,624 (change assumption)
    Mortgage ($14,898) + Taxes in 2025 ($725)


    Taxes:$8,705

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 3245 COLEUS CT, WINTER PARK, FL 32792

    $389,90019 Days on yellowkey   MLS ID: O6390829

    For Sale O6390829 - 3245 COLEUS CT, WINTER PARK, FL 32792 14 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1529
       Built: 1968   Tax: $986 (2024)
    Community: Eastbrook Sub Unit 14
    Single Family


    Estimated Monthly Payment: $2,219 (change assumption)
    Mortgage ($2,136) + Taxes in 2024 ($82)


    Taxes:$986

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 621 HUNTINGTON AVE, WINTER PARK, FL 32789

    $1,795,00017 Days on yellowkey   MLS ID: O6394464

    For Sale O6394464 - 621 HUNTINGTON AVE, WINTER PARK, FL 32789 38 photos

    Bed: 3   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2399
       Built: 2008   Tax: $12,854 (2025)
    Community: Winter Park Rev
    Spa: No

    Single Family


    Estimated Monthly Payment: $10,907 (change assumption)
    Mortgage ($9,835) + Taxes in 2025 ($1,071)


    Taxes:$12,854

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 141 GLENRIDGE WAY, WINTER PARK, FL 32789

    $3,250,00021 Days on yellowkey   MLS ID: O6393616

    For Sale O6393616 - 141 GLENRIDGE WAY, WINTER PARK, FL 32789 66 photos

    Bed: 5   Bath: 4.5   Gar: 3
    Liv Area Sq Ft: 5243
       Built: 2008   Tax: $40,155 (2025)
    Community: Charmont
    Single Family


    Estimated Monthly Payment: $21,154 (change assumption)
    Mortgage ($17,808) + Taxes in 2025 ($3,346)


    Taxes:$40,155

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 1117 KENWOOD AVE, WINTER PARK, FL 32789

    $3,978,90028 Days on yellowkey   MLS ID: O6389970

    For Sale O6389970 - 1117 KENWOOD AVE, WINTER PARK, FL 32789 67 photos

    Bed: 4   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 4353
       Built: 2024   Tax: $13,467 (2024)
    Community: Dixie Terrace
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $22,924 (change assumption)
    Mortgage ($21,802) + Taxes in 2024 ($1,122)


    Taxes:$13,467

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Maitland Middle


  • 1742 TEMPLE DR, WINTER PARK, FL 32789

    $3,449,99974 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


  • 4872 ORANGE AVE, WINTER PARK, FL 32792

    $375,00071 Days on yellowkey   MLS ID: O6380333

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

    For Sale O6380333 - 4872 ORANGE AVE, WINTER PARK, FL 32792 18 photos

    Bed: 3   Bath: 2.5
    Liv Area Sq Ft: 1881
       Built: 1960   Tax: $4,494 (2024)
    Community: Suburban Homes First Add
    Single Family


    Estimated Monthly Payment: $2,429 (change assumption)
    Mortgage ($2,055) + Taxes in 2024 ($374)


    Taxes:$4,494

    Elementary School: Lakemont Elem

    High School: None

    Tax Year: 2024

    Middle School: Maitland Middle


  • 781 NORTHWOOD CIR, WINTER PARK, FL 32789

    $775,00016 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

    $845,00023 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

    $435,00016 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




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.