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Winter Park Single Family Homes For Sale - 311 homes

Winter Park Single Family Homes for Sale are located in Seminole 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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  • 3463 ARNEL DR, WINTER PARK, FL 32792

    $429,90099 Days on yellowkey   MLS ID: O6390301

    REDUCED by $20,000 (4.4%) on 06/01/2026

    For Sale O6390301 - 3463 ARNEL DR, WINTER PARK, FL 32792 36 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1770
       Built: 1967   Tax: $4,648 (2024)
    Community: Eastbrook Sub Unit 11
    Single Family


    Estimated Monthly Payment: $2,743 (change assumption)
    Mortgage ($2,356) + Taxes in 2024 ($387)


    Taxes:$4,648

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 1662 TREMONT LN, WINTER PARK, FL 32792

    $384,90019 Days on yellowkey   MLS ID: O6414180

    REDUCED by $5,000 (1.3%) on 06/19/2026

    For Sale O6414180 - 1662 TREMONT LN, WINTER PARK, FL 32792 56 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1534
       Built: 1986
    Monthly Fee: $49
       Tax: $4,339 (2025)
    Community: Country Lane
    Single Family


    Estimated Monthly Payment: $2,520 (change assumption)
    Mortgage ($2,109) + Fees ($49) + Taxes in 2025 ($362)


    Taxes:$4,339

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1434 VIA SANGRO PL, WINTER PARK, FL 32792

    $1,300,00011 Days on yellowkey   MLS ID: O6416325

    0 Days Off yellowkey (back on 6/13/2026)

    For Sale O6416325 - 1434 VIA SANGRO PL, WINTER PARK, FL 32792 1 photos

    Bed: 4   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 3063
       Built: 2016
    Monthly Fee: $182
       Tax: $9,764 (2025)
    Community: Lakeside Estates
    Single Family


    Estimated Monthly Payment: $8,119 (change assumption)
    Mortgage ($7,123) + Fees ($182) + Taxes in 2025 ($814)


    Taxes:$9,764

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1871 BRYAN AVE, WINTER PARK, FL 32789

    $499,00029 Days on yellowkey   MLS ID: O6410779

    0 Days Off yellowkey (back on 5/27/2026)

    For Sale O6410779 - 1871 BRYAN AVE, WINTER PARK, FL 32789 3 photos

    Bed: 3   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1232
       Built: 1985   Tax: $3,328 (2025)
    Community: Lakeview Terrace
    Single Family


    Estimated Monthly Payment: $3,012 (change assumption)
    Mortgage ($2,734) + Taxes in 2025 ($277)


    Taxes:$3,328

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 1177 KENWOOD AVE, WINTER PARK, FL 32789

    $1,800,000103 Days on yellowkey   MLS ID: O6390592

    0 Days Off yellowkey (back on 5/21/2026)

    REDUCED by $70,000 (3.7%) on 05/13/2026

    For Sale O6390592 - 1177 KENWOOD AVE, WINTER PARK, FL 32789 57 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 4363
       Built: 2007   Tax: $16,206 (2025)
    Community: Dixie Terrace
    Spa: No

    Single Family


    Estimated Monthly Payment: $11,213 (change assumption)
    Mortgage ($9,863) + Taxes in 2025 ($1,351)


    Taxes:$16,206

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2614 PARKLAND DR, WINTER PARK, FL 32789

    $1,890,000430 Days on yellowkey   MLS ID: O6301489

    REDUCED by $34,450 (1.8%) on 06/18/2026

    For Sale O6301489 - 2614 PARKLAND DR, WINTER PARK, FL 32789 54 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3307
       Built: 2007   Tax: $12,712 (2024)
    Community: Parklando 03
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $11,415 (change assumption)
    Mortgage ($10,356) + Taxes in 2024 ($1,059)


    Taxes:$12,712

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Audubon Park K-8


  • 1468 AUBURN GREEN LOOP, WINTER PARK, FL 32792

    $475,00065 Days on yellowkey   MLS ID: O6399199

    0 Days Off yellowkey (back on 5/17/2026)

    REDUCED by $5,000 (1.0%) on 05/06/2026

    For Sale O6399199 - 1468 AUBURN GREEN LOOP, WINTER PARK, FL 32792 43 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1676
       Built: 1984
    Monthly Fee: $49
       Tax: $6,243 (2024)
    Community: Country Lane
    Single Family


    Estimated Monthly Payment: $3,172 (change assumption)
    Mortgage ($2,603) + Fees ($49) + Taxes in 2024 ($520)


    Taxes:$6,243

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 2054 EASTBROOK BLVD, WINTER PARK, FL 32792

    $500,00022 Days on yellowkey   MLS ID: V4949389

    For Sale V4949389 - 2054 EASTBROOK BLVD, WINTER PARK, FL 32792 5 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


  • 2700 CADY WAY, WINTER PARK, FL 32792

    $649,000267 Days on yellowkey   MLS ID: O6347690

    For Sale O6347690 - 2700 CADY WAY, WINTER PARK, FL 32792 49 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1876
       Built: 1965   Tax: $8,335 (2024)
    Community: Winter Park Pines Unit 4
    Single Family


    Estimated Monthly Payment: $4,251 (change assumption)
    Mortgage ($3,556) + Taxes in 2024 ($695)


    Taxes:$8,335

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Glenridge Middle


  • 1605 PURITAN AVE, WINTER PARK, FL 32792

    $399,0007 Days on yellowkey   MLS ID: O6417098

    For Sale O6417098 - 1605 PURITAN AVE, WINTER PARK, FL 32792 19 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1285
       Built: 1963   Tax: $3,605 (2025)
    Community: Eastbrook Sub Unit 06 2Nd Rep
    Single Family


    Estimated Monthly Payment: $2,487 (change assumption)
    Mortgage ($2,186) + Taxes in 2025 ($300)


    Taxes:$3,605

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 2501 LAFAYETTE AVE, WINTER PARK, FL 32789

    $1,795,0007 Days on yellowkey   MLS ID: O6416565

    For Sale O6416565 - 2501 LAFAYETTE AVE, WINTER PARK, FL 32789 22 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 2819
       Built: 2026   Tax: $4,608 (2026)
    Community: Winter Park Village
    Single Family


    Estimated Monthly Payment: $10,219 (change assumption)
    Mortgage ($9,835) + Taxes in 2026 ($384)


    Taxes:$4,608

    Elementary School: None

    High School: None

    Tax Year: 2026

    Middle School: None


  • 2008 HOUNDSLAKE DR, WINTER PARK, FL 32792

    $515,0009 Days on yellowkey   MLS ID: O6414369

    For Sale O6414369 - 2008 HOUNDSLAKE DR, WINTER PARK, FL 32792 27 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2250
       Built: 1980   Tax: $5,253 (2025)
    Community: Cedar Ridge
    Single Family


    Estimated Monthly Payment: $3,260 (change assumption)
    Mortgage ($2,822) + Taxes in 2025 ($438)


    Taxes:$5,253

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 120 BROADVIEW AVE, WINTER PARK, FL 32789

    $1,450,00033 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


  • 1220 WOODMERE DR, WINTER PARK, FL 32789

    $1,700,00012 Days on yellowkey   MLS ID: O6415611

    0 Days Off yellowkey (back on 6/17/2026)

    For Sale O6415611 - 1220 WOODMERE DR, WINTER PARK, FL 32789 44 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2815
       Built: 1996   Tax: $7,845 (2025)
    Community: Woodmere Terrace Rep
    Single Family


    Estimated Monthly Payment: $9,969 (change assumption)
    Mortgage ($9,315) + Taxes in 2025 ($654)


    Taxes:$7,845

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 1849 VIBURNUM LN, WINTER PARK, FL 32792

    $408,000321 Days on yellowkey   MLS ID: O6333863

    2 Days Off yellowkey (back on 6/17/2026)

    REDUCED by $17,000 (4.0%) on 06/10/2026

    For Sale O6333863 - 1849 VIBURNUM LN, WINTER PARK, FL 32792 27 photos

    Bed: 4   Bath: 2.0
    Liv Area Sq Ft: 1627
       Built: 1961   Tax: $3,645 (2024)
    Community: Eastbrook Sub Unit 05
    Single Family


    Estimated Monthly Payment: $2,539 (change assumption)
    Mortgage ($2,236) + Taxes in 2024 ($304)


    Taxes:$3,645

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 2838 WRIGHT AVE, WINTER PARK, FL 32789

    $2,399,00063 Days on yellowkey   MLS ID: O6399931

    For Sale O6399931 - 2838 WRIGHT AVE, WINTER PARK, FL 32789 10 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3479
       Built: 2026   Tax: $6,037 (2025)
    Community: Lake Forest Park
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $13,648 (change assumption)
    Mortgage ($13,145) + Taxes in 2025 ($503)


    Taxes:$6,037

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 121 E FAWSETT RD, WINTER PARK, FL 32789

    $3,490,00012 Days on yellowkey   MLS ID: O6413910

    For Sale O6413910 - 121 E FAWSETT RD, WINTER PARK, FL 32789 11 photos

    Bed: 5   Bath: 5.5   Gar: 2
    Liv Area Sq Ft: 4191
       Built: 1954   Tax: $7,867 (2025)
    Community: Charmont
    Single Family


    Estimated Monthly Payment: $19,778 (change assumption)
    Mortgage ($19,123) + Taxes in 2025 ($656)


    Taxes:$7,867

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 1448 LAKE FLORENCE WAY, WINTER PARK, FL 32792

    $1,149,90028 Days on yellowkey   MLS ID: O6411164

    REDUCED by $49,100 (4.1%) on 06/17/2026

    For Sale O6411164 - 1448 LAKE FLORENCE WAY, WINTER PARK, FL 32792 51 photos

    Bed: 5   Bath: 4.5   Gar: 3
    Liv Area Sq Ft: 3652
       Built: 2018
    Monthly Fee: $186
       Tax: $7,277 (2025)
    Community: Lake Florence Preserve
    Spa: No

    Single Family


    Estimated Monthly Payment: $7,093 (change assumption)
    Mortgage ($6,301) + Fees ($186) + Taxes in 2025 ($606)


    Taxes:$7,277

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 313 SYLVAN DR, WINTER PARK, FL 32789

    $5,500,0009 Days on yellowkey   MLS ID: O6407606

    For Sale O6407606 - 313 SYLVAN DR, WINTER PARK, FL 32789 10 photos

    Bed: 4   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 4775
       Built: 2027   Tax: $11,409 (2025)
    Community: Sylvan Park
    Single Family


    Estimated Monthly Payment: $31,087 (change assumption)
    Mortgage ($30,136) + Taxes in 2025 ($951)


    Taxes:$11,409

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 1900 WINTER PARK RD, WINTER PARK, FL 32789

    $799,00058 Days on yellowkey   MLS ID: O6402566

    REDUCED by $50,900 (6.0%) on 06/16/2026

    For Sale O6402566 - 1900 WINTER PARK RD, WINTER PARK, FL 32789 22 photos

    Bed: 4   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1511
       Built: 1947   Tax: $2,803 (2025)
    Community: Charmont
    Single Family


    Estimated Monthly Payment: $4,612 (change assumption)
    Mortgage ($4,378) + Taxes in 2025 ($234)


    Taxes:$2,803

    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.