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Winter Park Homes For Sale & Real Estate - 443 homes

Winter Park homes for sale are located in Seminole County, Florida. Find homes in Winter Park for sale with data from the Multiple Listing Service (MLS). Our REALTORS® can assist you in your real estate search for Winter Park houses.

Location: Winter Park

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  • 3440 ALLSTON LN, WINTER PARK, FL 32792

    $405,00037 Days on yellowkey   MLS ID: O6401731

    REDUCED by $15,000 (3.6%) on 05/26/2026

    For Sale O6401731 - 3440 ALLSTON LN, WINTER PARK, FL 32792 36 photos

    Bed: 3   Bath: 2.5   Gar: 1
    Liv Area Sq Ft: 1533
       Built: 1993
    Monthly Fee: $65
       Tax: $1,364 (2024)
    Community: Villas Of Casselberry Ph 4
    Single Family


    Estimated Monthly Payment: $2,398 (change assumption)
    Mortgage ($2,219) + Fees ($65) + Taxes in 2024 ($114)


    Taxes:$1,364

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 3370 CEDAR SPRINGS PL #156, WINTER PARK, FL 32792

    $185,000325 Days on yellowkey   MLS ID: O6326460

    REDUCED by $4,000 (2.1%) on 05/11/2026

    For Sale O6326460 - 3370 CEDAR SPRINGS PL #156, WINTER PARK, FL 32792 26 photos

    Bed: 2   Bath: 2.5
    Liv Area Sq Ft: 1031
       Built: 1984
    Monthly Fee: $420
       Tax: $2,549 (2024)
    Community: Hidden Oaks Condo Ph 09
    Condo


    Estimated Monthly Payment: $1,646 (change assumption)
    Mortgage ($1,014) + Fees ($420) + Taxes in 2024 ($212)


    Taxes:$2,549

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 151 N ORLANDO AVE #259, WINTER PARK, FL 32789

    $239,00012 Days on yellowkey   MLS ID: O6409651

    For Sale O6409651 - 151 N ORLANDO AVE #259, WINTER PARK, FL 32789 31 photos

    Bed: 1   Bath: 1.0
    Liv Area Sq Ft: 582
       Built: 1960   Tax: $2,552 (2025)
    Community: Lake Killarney Condo
    Condo


    Estimated Monthly Payment: $1,522 (change assumption)
    Mortgage ($1,310) + Taxes in 2025 ($213)


    Taxes:$2,552

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park Middle


  • 2500 LEE RD. #222, WINTER PARK, FL 32789

    $189,500163 Days on yellowkey   MLS ID: O6368580

    For Sale O6368580 - 2500 LEE RD. #222, WINTER PARK, FL 32789 26 photos

    Bed: 1   Bath: 1.0
    Liv Area Sq Ft: 645
       Built: 1969
    Monthly Fee: $245
       Tax: $926 (2024)
    Community: Lakeside Manor Apts Condo
    Condo


    Estimated Monthly Payment: $1,360 (change assumption)
    Mortgage ($1,038) + Fees ($245) + Taxes in 2024 ($77)


    Taxes:$926

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 3018 NORTHWOOD BLVD, WINTER PARK, FL 32789

    $649,000221 Days on yellowkey   MLS ID: G5103499

    0 Days Off yellowkey (back on 5/28/2026)

    REDUCED by $10,000 (1.5%) on 05/22/2026

    For Sale G5103499 - 3018 NORTHWOOD BLVD, WINTER PARK, FL 32789 47 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1761
       Built: 1954   Tax: $6,623 (2024)
    Community: Northwood Terrace
    Single Family


    Estimated Monthly Payment: $4,108 (change assumption)
    Mortgage ($3,556) + Taxes in 2024 ($552)


    Taxes:$6,623

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Audubon Park K-8


  • 1995 CANNY CV, WINTER PARK, FL 32792

    $425,00016 Days on yellowkey   MLS ID: G5112476

    For Sale G5112476 - 1995 CANNY CV, WINTER PARK, FL 32792 26 photos

    Bed: 3   Bath: 2.5   Gar: 1
    Liv Area Sq Ft: 1907
       Built: 2023
    Monthly Fee: $375
       Tax: $5,957 (2025)
    Community: Grayson Square
    Townhouse


    Estimated Monthly Payment: $3,200 (change assumption)
    Mortgage ($2,329) + Fees ($375) + Taxes in 2025 ($496)


    Taxes:$5,957

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 5806 MARBLE CT, WINTER PARK, FL 32792

    $289,00029 Days on yellowkey   MLS ID: O6399228

    REDUCED by $6,000 (2.0%) on 05/28/2026

    For Sale O6399228 - 5806 MARBLE CT, WINTER PARK, FL 32792 20 photos

    Bed: 2   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1140
       Built: 1989
    Monthly Fee: $69
       Tax: $3,411 (2025)
    Community: Aloma Park
    Half Duplex


    Estimated Monthly Payment: $1,937 (change assumption)
    Mortgage ($1,584) + Fees ($69) + Taxes in 2025 ($284)


    Taxes:$3,411

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 901 ENCLAVE PL, WINTER PARK, FL 32792

    $1,495,00074 Days on yellowkey   MLS ID: O6383602

    For Sale O6383602 - 901 ENCLAVE PL, WINTER PARK, FL 32792 2 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2738
       Built: 2026
    Monthly Fee: $247
       Tax: $9,900 (2026)
    Community: The Enclave Winter Park
    Townhouse


    Estimated Monthly Payment: $9,264 (change assumption)
    Mortgage ($8,192) + Fees ($247) + Taxes in 2026 ($825)


    Taxes:$9,900

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2026

    Middle School: Maitland Middle


  • 1319 BESSMOR RD, WINTER PARK, FL 32789

    $595,00042 Days on yellowkey   MLS ID: O6400395

    For Sale O6400395 - 1319 BESSMOR RD, WINTER PARK, FL 32789 13 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1126
       Built: 1956   Tax: $5,626 (2025)
    Community: Winter Park Village
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,729 (change assumption)
    Mortgage ($3,260) + Taxes in 2025 ($469)


    Taxes:$5,626

    Elementary School: Dream Lake Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 2838 WRIGHT AVE, WINTER PARK, FL 32789

    $2,399,00041 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


  • 7505 LAUREL SPRINGS DR, WINTER PARK, FL 32792

    $400,00015 Days on yellowkey   MLS ID: O6405854

    For Sale O6405854 - 7505 LAUREL SPRINGS DR, WINTER PARK, FL 32792 26 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1471
       Built: 1972   Tax: $1,205 (2025)
    Community: Laurel Springs
    Single Family


    Estimated Monthly Payment: $2,292 (change assumption)
    Mortgage ($2,192) + Taxes in 2025 ($100)


    Taxes:$1,205

    Elementary School: Aloma Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 2142 BLOSSOM LN, WINTER PARK, FL 32789

    $399,90012 Days on yellowkey   MLS ID: O6409144

    0 Days Off yellowkey (back on 5/28/2026)

    For Sale O6409144 - 2142 BLOSSOM LN, WINTER PARK, FL 32789 14 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1363
       Built: 1957   Tax: $2,217 (2025)
    Community: Acreage
    Single Family


    Estimated Monthly Payment: $2,376 (change assumption)
    Mortgage ($2,191) + Taxes in 2025 ($185)


    Taxes:$2,217

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park Middle


  • 1946 STRATHAVEN RD, WINTER PARK, FL 32792

    $675,0006 Days on yellowkey   MLS ID: O6411329

    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: $4,410 (change assumption)
    Mortgage ($3,699) + Taxes in 2025 ($712)


    Taxes:$8,540

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 316 BECKETT CT, WINTER PARK, FL 32792

    $450,0006 Days on yellowkey   MLS ID: O6411108

    For Sale O6411108 - 316 BECKETT CT, WINTER PARK, FL 32792 33 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1651
       Built: 1966   Tax: $2,232 (2025)
    Community: Winter Park Pines Merrie Oaks
    Single Family


    Estimated Monthly Payment: $2,652 (change assumption)
    Mortgage ($2,466) + Taxes in 2025 ($186)


    Taxes:$2,232

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1841 LAKE SPIER DRIVE, WINTER PARK, FL 32789

    $1,650,0006 Days on yellowkey   MLS ID: O6407841

    For Sale O6407841 - 1841 LAKE SPIER DRIVE, WINTER PARK, FL 32789 32 photos

    Bed: 3   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 2467
       Built: 1964   Tax: $4,844 (2025)
    Community: South Lakemont Shores
    Spa: No

    Single Family


    Estimated Monthly Payment: $9,445 (change assumption)
    Mortgage ($9,041) + Taxes in 2025 ($404)


    Taxes:$4,844

    Elementary School: Baldwin Park Elementary

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 1177 KENWOOD AVE, WINTER PARK, FL 32789

    $1,800,00081 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


  • 450 LAKEWOOD DR, WINTER PARK, FL 32789

    $2,500,00032 Days on yellowkey   MLS ID: O6403490

    For Sale O6403490 - 450 LAKEWOOD DR, WINTER PARK, FL 32789 78 photos

    Bed: 5   Bath: 5.0   Gar: 3
    Liv Area Sq Ft: 4572
       Built: 2000   Tax: $11,393 (2025)
    Community: Osceola Shores Sec 03
    Single Family


    Estimated Monthly Payment: $14,648 (change assumption)
    Mortgage ($13,698) + Taxes in 2025 ($949)


    Taxes:$11,393

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 7794 COUNTRY PL #2, WINTER PARK, FL 32792

    $237,00046 Days on yellowkey   MLS ID: O6397587

    REDUCED by $1,500 (0.6%) on 05/27/2026

    For Sale O6397587 - 7794 COUNTRY PL #2, WINTER PARK, FL 32792 17 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1068
       Built: 1988
    Monthly Fee: $296
       Tax: $2,620 (2024)
    Community: Goldenrod Villas Condo
    Spa: No

    Condo


    Estimated Monthly Payment: $1,813 (change assumption)
    Mortgage ($1,299) + Fees ($296) + Taxes in 2024 ($218)


    Taxes:$2,620

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 1871 BRYAN AVE, WINTER PARK, FL 32789

    $499,0007 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


  • 1581 FOREST AVE, WINTER PARK, FL 32789

    $3,393,00082 Days on yellowkey   MLS ID: O6382377

    REDUCED by $102,000 (2.9%) on 05/21/2026

    For Sale O6382377 - 1581 FOREST AVE, WINTER PARK, FL 32789 57 photos

    Bed: 4   Bath: 5.0   Gar: 2
    Liv Area Sq Ft: 4683
       Built: 1954   Tax: $20,042 (2024)
    Community: Ellno Willo
    Spa: No

    Single Family


    Estimated Monthly Payment: $20,261 (change assumption)
    Mortgage ($18,591) + Taxes in 2024 ($1,670)


    Taxes:$20,042

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Audubon Park K-8




Why Bother Searching Elsewhere for Winter Park Homes for Sale and Other Real Estate?

Winter Park home, townhome, condo, villa, and other listing sales 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 houses for sale in Winter Park . You can use our website to view Multiple Listing Service (MLS) data on Winter Park Real Estate. 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 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.