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Winter Park Single Family Homes For Sale - 314 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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  • 1813 HARLAND PARK DR, WINTER PARK, FL 32789

    $1,875,00033 Days on yellowkey   MLS ID: O6403483

    REDUCED by $120,000 (6.0%) on 05/28/2026

    For Sale O6403483 - 1813 HARLAND PARK DR, WINTER PARK, FL 32789 59 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3551
       Built: 2013
    Monthly Fee: $268
       Tax: $23,539 (2025)
    Community: Windsong - Knowles Place
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $12,503 (change assumption)
    Mortgage ($10,274) + Fees ($268) + Taxes in 2025 ($1,962)


    Taxes:$23,539

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 5275 PINE LILY CIR, WINTER PARK, FL 32792

    $665,000124 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


  • 2823 WRIGHT AVE, WINTER PARK, FL 32789

    $899,90082 Days on yellowkey   MLS ID: O6390670

    0 Days Off yellowkey (back on 6/3/2026)

    REDUCED by $30,000 (3.2%) on 05/07/2026

    For Sale O6390670 - 2823 WRIGHT AVE, WINTER PARK, FL 32789 19 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1536
       Built: 1958   Tax: $9,119 (2025)
    Community: Lake Forest Park
    Single Family


    Estimated Monthly Payment: $5,691 (change assumption)
    Mortgage ($4,931) + Taxes in 2025 ($760)


    Taxes:$9,119

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 5503 ALBERT DR, WINTER PARK, FL 32792

    $405,000Listed 06/03/2026 11:04AM   MLS ID: S5151098

    For Sale S5151098 - 5503 ALBERT DR, WINTER PARK, FL 32792 57 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1366
       Built: 1978   Tax: $4,123 (2025)
    Community: Howell Branch Woods
    Single Family


    Estimated Monthly Payment: $2,563 (change assumption)
    Mortgage ($2,219) + Taxes in 2025 ($344)


    Taxes:$4,123

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1510 MILLER AVE, WINTER PARK, FL 32789

    $1,599,900239 Days on yellowkey   MLS ID: O6350503

    REDUCED by $35,000 (2.1%) on 05/13/2026

    For Sale O6350503 - 1510 MILLER AVE, WINTER PARK, FL 32789 70 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3252
       Built: 2026   Tax: $3,573 (2025)
    Community: Lawndale
    Single Family


    Estimated Monthly Payment: $9,064 (change assumption)
    Mortgage ($8,766) + Taxes in 2025 ($298)


    Taxes:$3,573

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park Middle


  • 1920 HEATHWOOD DR, WINTER PARK, FL 32792

    $370,00070 Days on yellowkey   MLS ID: O6393303

    For Sale O6393303 - 1920 HEATHWOOD DR, WINTER PARK, FL 32792 37 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1978
       Built: 1980   Tax: $4,895 (2025)
    Community: Cedar Ridge Unit 1
    Single Family


    Estimated Monthly Payment: $2,435 (change assumption)
    Mortgage ($2,027) + Taxes in 2025 ($408)


    Taxes:$4,895

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2648 GALLIANO CIR, WINTER PARK, FL 32792

    $355,00099 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


  • 1351 MAGNOLIA AVE, WINTER PARK, FL 32789

    $3,100,00033 Days on yellowkey   MLS ID: O6404105

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

    For Sale O6404105 - 1351 MAGNOLIA AVE, WINTER PARK, FL 32789 1 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3460
       Built: 2026   Tax: $9,720 (2025)
    Community: Lake Knowles Terrace Add 02
    Single Family


    Estimated Monthly Payment: $17,796 (change assumption)
    Mortgage ($16,986) + Taxes in 2025 ($810)


    Taxes:$9,720

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 240 ORANGE TERRACE DR, WINTER PARK, FL 32789

    $479,900300 Days on yellowkey   MLS ID: O6330690

    REDUCED by $100 (0.0%) on 06/03/2026

    For Sale O6330690 - 240 ORANGE TERRACE DR, WINTER PARK, FL 32789 32 photos

    Bed: 4   Bath: 2.0
    Liv Area Sq Ft: 1718
       Built: 1955   Tax: $6,210 (2024)
    Community: Orange Terrace
    Single Family


    Estimated Monthly Payment: $3,147 (change assumption)
    Mortgage ($2,630) + Taxes in 2024 ($518)


    Taxes:$6,210

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2024

    Middle School: Robinswood Middle


  • 1437 MILLER AVE, WINTER PARK, FL 32789

    $750,00034 Days on yellowkey   MLS ID: O6403858

    1 Days Off yellowkey (back on 5/3/2026)

    For Sale O6403858 - 1437 MILLER AVE, WINTER PARK, FL 32789 1 photos

    Bed: 5   Bath: 4.0
    Liv Area Sq Ft: 2150
       Built: 1932   Tax: $6,987 (2025)
    Community: Lawndale
    Single Family


    Estimated Monthly Payment: $4,692 (change assumption)
    Mortgage ($4,109) + Taxes in 2025 ($582)


    Taxes:$6,987

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1082 WILDMEADOW RUN, WINTER PARK, FL 32792

    $650,00013 Days on yellowkey   MLS ID: O6408825

    For Sale O6408825 - 1082 WILDMEADOW RUN, WINTER PARK, FL 32792 40 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1770
       Built: 2021
    Monthly Fee: $170
       Tax: $5,154 (2025)
    Community: Meadows At Hawks Crest
    Single Family


    Estimated Monthly Payment: $4,161 (change assumption)
    Mortgage ($3,562) + Fees ($170) + Taxes in 2025 ($430)


    Taxes:$5,154

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 1651 WESTCHESTER AVE, WINTER PARK, FL 32789

    $1,175,00061 Days on yellowkey   MLS ID: O6384358

    REDUCED by $100,000 (7.8%) on 06/01/2026

    For Sale O6384358 - 1651 WESTCHESTER AVE, WINTER PARK, FL 32789 48 photos

    Bed: 3   Bath: 2.5   Gar: 1
    Liv Area Sq Ft: 2426
       Built: 1938   Tax: $10,973 (2025)
    Community: Orwin Manor Westminster Sec
    Single Family


    Estimated Monthly Payment: $7,353 (change assumption)
    Mortgage ($6,438) + Taxes in 2025 ($914)


    Taxes:$10,973

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park Middle


  • 1260 ALABAMA DR, WINTER PARK, FL 32789

    $6,900,00092 Days on yellowkey   MLS ID: O6387200

    For Sale O6387200 - 1260 ALABAMA DR, WINTER PARK, FL 32789 58 photos

    Bed: 6   Bath: 6.0   Gar: 3
    Liv Area Sq Ft: 6396
       Built: 1991   Tax: $59,749 (2025)
    Community: J Kronenberger Sub
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $42,786 (change assumption)
    Mortgage ($37,807) + Taxes in 2025 ($4,979)


    Taxes:$59,749

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 7577 DOCKSIDE ST, WINTER PARK, FL 32792

    $370,0001 Day on yellowkey   MLS ID: O6412514

    For Sale O6412514 - 7577 DOCKSIDE ST, WINTER PARK, FL 32792 30 photos

    Bed: 3   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1245
       Built: 1977   Tax: $3,722 (2025)
    Community: Woodcrest Unit 6
    Single Family


    Estimated Monthly Payment: $2,338 (change assumption)
    Mortgage ($2,027) + Taxes in 2025 ($310)


    Taxes:$3,722

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 2054 EASTBROOK BLVD, WINTER PARK, FL 32792

    $500,0001 Day on yellowkey   MLS ID: V4949389

    For Sale V4949389 - 2054 EASTBROOK BLVD, WINTER PARK, FL 32792 2 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2031
       Built: 1966   Tax: $5,054 (2025)
    Community: Eastbrook Sub Unit 8
    Single Family


    Estimated Monthly Payment: $3,161 (change assumption)
    Mortgage ($2,740) + Taxes in 2025 ($421)


    Taxes:$5,054

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 508 DUNRAVEN DR, WINTER PARK, FL 32792

    $595,0001 Day on yellowkey   MLS ID: O6412363

    For Sale O6412363 - 508 DUNRAVEN DR, WINTER PARK, FL 32792 34 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1370
       Built: 1958   Tax: $2,281 (2025)
    Community: Kenilworth Shores Sec 03
    Single Family


    Estimated Monthly Payment: $3,450 (change assumption)
    Mortgage ($3,260) + Taxes in 2025 ($190)


    Taxes:$2,281

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 2006 CORNELL AVE, WINTER PARK, FL 32789

    $338,0001 Day on yellowkey   MLS ID: O6412789

    For Sale O6412789 - 2006 CORNELL AVE, WINTER PARK, FL 32789 28 photos

    Bed: 2   Bath: 1.0
    Liv Area Sq Ft: 797
       Built: 1940   Tax: $4,795 (2025)
    Community: Stansbury Estates
    Single Family


    Estimated Monthly Payment: $2,252 (change assumption)
    Mortgage ($1,852) + Taxes in 2025 ($400)


    Taxes:$4,795

    Elementary School: Princeton Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park Middle


  • 1850 ASTER DR, WINTER PARK, FL 32792

    $500,0001 Day on yellowkey   MLS ID: TB8513990

    For Sale TB8513990 - 1850 ASTER DR, WINTER PARK, FL 32792 50 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1656
       Built: 1978   Tax: $1,584 (2025)
    Community: Garden Lake Estates Unit 1
    Single Family


    Estimated Monthly Payment: $2,872 (change assumption)
    Mortgage ($2,740) + Taxes in 2025 ($132)


    Taxes:$1,584

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 715 S RANGER BLVD, WINTER PARK, FL 32792

    $695,0008 Days on yellowkey   MLS ID: O6410899

    For Sale O6410899 - 715 S RANGER BLVD, WINTER PARK, FL 32792 48 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2312
       Built: 1967
    Monthly Fee: $4
       Tax: $2,773 (2025)
    Community: Winter Park Pines
    Single Family


    Estimated Monthly Payment: $4,043 (change assumption)
    Mortgage ($3,808) + Fees ($4) + Taxes in 2025 ($231)


    Taxes:$2,773

    Elementary School: Aloma Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 3312 HEARTWOOD AVE, WINTER PARK, FL 32792

    $465,000228 Days on yellowkey   MLS ID: O6352582

    REDUCED by $19,000 (3.9%) on 04/08/2026

    For Sale O6352582 - 3312 HEARTWOOD AVE, WINTER PARK, FL 32792 36 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2878
       Built: 1983   Tax: $2,183 (2025)
    Community: Bel-Aire Pines
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,730 (change assumption)
    Mortgage ($2,548) + Taxes in 2025 ($182)


    Taxes:$2,183

    Elementary School: Aloma Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge 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.