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Winter Park Single Family Homes For Sale - 306 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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  • 914 ENCLAVE PL, WINTER PARK, FL 32792

    $1,895,00096 Days on yellowkey   MLS ID: O6391825

    For Sale O6391825 - 914 ENCLAVE PL, WINTER PARK, FL 32792 3 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3617
       Built: 2026
    Monthly Fee: $372
       Tax: $10,000 (2025)
    Community: The Enclave Winter Park
    Single Family


    Estimated Monthly Payment: $11,589 (change assumption)
    Mortgage ($10,383) + Fees ($372) + Taxes in 2025 ($833)


    Taxes:$10,000

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 1927 ELAND AVE, WINTER PARK, FL 32789

    $820,000133 Days on yellowkey   MLS ID: O6381009

    REDUCED by $5,000 (0.6%) on 06/15/2026

    For Sale O6381009 - 1927 ELAND AVE, WINTER PARK, FL 32789 68 photos

    Bed: 5   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2242
       Built: 1957   Tax: $3,190 (2024)
    Community: Lake Bell Terrace
    Single Family


    Estimated Monthly Payment: $4,759 (change assumption)
    Mortgage ($4,493) + Taxes in 2024 ($266)


    Taxes:$3,190

    Elementary School: Hungerford Elem

    High School: Edgewater High

    Tax Year: 2024

    Middle School: College Park Middle


  • 1316 BLUE STEM LN, WINTER PARK, FL 32792

    $725,00010 Days on yellowkey   MLS ID: O6416828

    For Sale O6416828 - 1316 BLUE STEM LN, WINTER PARK, FL 32792 42 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2196
       Built: 2022
    Monthly Fee: $243
       Tax: $6,788 (2025)
    Community: Landings At Hawks Crest
    Single Family


    Estimated Monthly Payment: $4,781 (change assumption)
    Mortgage ($3,973) + Fees ($243) + Taxes in 2025 ($566)


    Taxes:$6,788

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 2831 MULFORD AVE, WINTER PARK, FL 32789

    $735,00017 Days on yellowkey   MLS ID: O6414319

    For Sale O6414319 - 2831 MULFORD AVE, WINTER PARK, FL 32789 22 photos

    Bed: 4   Bath: 2.5
    Liv Area Sq Ft: 1647
       Built: 1952   Tax: $3,192 (2025)
    Community: Orangewood Park
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,293 (change assumption)
    Mortgage ($4,027) + Taxes in 2025 ($266)


    Taxes:$3,192

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2914 REEF KNOT PL, WINTER PARK, FL 32792

    $1,725,0006 Days on yellowkey   MLS ID: O6418185

    For Sale O6418185 - 2914 REEF KNOT PL, WINTER PARK, FL 32792 63 photos

    Bed: 6   Bath: 5.0   Gar: 3
    Liv Area Sq Ft: 4173
       Built: 2019
    Monthly Fee: $186
       Tax: $17,688 (2025)
    Community: Lake Florence Preserve
    Spa: No

    Single Family


    Estimated Monthly Payment: $11,112 (change assumption)
    Mortgage ($9,452) + Fees ($186) + Taxes in 2025 ($1,474)


    Taxes:$17,688

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 2625 PARK PLACE DR, WINTER PARK, FL 32789

    $1,950,0005 Days on yellowkey   MLS ID: O6413031

    For Sale O6413031 - 2625 PARK PLACE DR, WINTER PARK, FL 32789 55 photos

    Bed: 4   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3460
       Built: 2002
    Monthly Fee: $146
       Tax: $9,695 (2025)
    Community: Winter Park Place 45/148
    Single Family


    Estimated Monthly Payment: $11,639 (change assumption)
    Mortgage ($10,685) + Fees ($146) + Taxes in 2025 ($808)


    Taxes:$9,695

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: None


  • 1287 VERDANT GLADE PL, WINTER PARK, FL 32792

    $825,00061 Days on yellowkey   MLS ID: O6400331

    REDUCED by $22,000 (2.6%) on 06/19/2026

    For Sale O6400331 - 1287 VERDANT GLADE PL, WINTER PARK, FL 32792 50 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3020
       Built: 2020
    Monthly Fee: $413
       Tax: $6,133 (2025)
    Community: Meadows At Hawks Crest
    Single Family


    Estimated Monthly Payment: $5,444 (change assumption)
    Mortgage ($4,520) + Fees ($413) + Taxes in 2025 ($511)


    Taxes:$6,133

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 1946 STRATHAVEN RD, WINTER PARK, FL 32792

    $650,00028 Days on yellowkey   MLS ID: O6411329

    REDUCED by $25,000 (3.7%) on 06/19/2026

    For Sale O6411329 - 1946 STRATHAVEN RD, WINTER PARK, FL 32792 37 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2102
       Built: 1960   Tax: $8,540 (2025)
    Community: Kenilworth Shores Sec 07
    Single Family


    Estimated Monthly Payment: $4,273 (change assumption)
    Mortgage ($3,562) + Taxes in 2025 ($712)


    Taxes:$8,540

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 1571 WOODLAND AVE, WINTER PARK, FL 32789

    $6,000,00026 Days on yellowkey   MLS ID: O6411706

    For Sale O6411706 - 1571 WOODLAND AVE, WINTER PARK, FL 32789 75 photos

    Bed: 5   Bath: 7.0   Gar: 3
    Liv Area Sq Ft: 7397
       Built: 2007   Tax: $31,040 (2025)
    Community: Comstock Park
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $35,463 (change assumption)
    Mortgage ($32,876) + Taxes in 2025 ($2,587)


    Taxes:$31,040

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 2715 PRINCE JOHN RD, WINTER PARK, FL 32792

    $504,90016 Days on yellowkey   MLS ID: O6415084

    REDUCED by $15,000 (2.9%) on 06/19/2026

    For Sale O6415084 - 2715 PRINCE JOHN RD, WINTER PARK, FL 32792 29 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1565
       Built: 1963   Tax: $7,101 (2025)
    Community: Winter Park Pines Rep
    Single Family


    Estimated Monthly Payment: $3,358 (change assumption)
    Mortgage ($2,767) + Taxes in 2025 ($592)


    Taxes:$7,101

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 1110 ALABAMA DR, WINTER PARK, FL 32789

    $1,699,00083 Days on yellowkey   MLS ID: O6395692

    0 Days Off yellowkey (back on 6/19/2026)

    REDUCED by $51,000 (2.9%) on 05/19/2026

    For Sale O6395692 - 1110 ALABAMA DR, WINTER PARK, FL 32789 53 photos

    Bed: 3   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2488
       Built: 1958   Tax: $12,858 (2025)
    Community: J Kronenberger Sub
    Spa: No

    Single Family


    Estimated Monthly Payment: $10,381 (change assumption)
    Mortgage ($9,309) + Taxes in 2025 ($1,072)


    Taxes:$12,858

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 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


  • 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


  • 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




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.