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Winter Park Homes For Sale & Real Estate - 378 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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  • 1354 TIERRA CIR, WINTER PARK, FL 32792

    $425,000466 Days on yellowkey   MLS ID: O6271121

    For Sale O6271121 - 1354 TIERRA CIR, WINTER PARK, FL 32792 31 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1827
       Built: 1969
    Monthly Fee: $2
       Tax: $3,812 (2023)
    Community: Casa Aloma
    Single Family


    Estimated Monthly Payment: $2,648 (change assumption)
    Mortgage ($2,329) + Fees ($2) + Taxes in 2023 ($318)


    Taxes:$3,812

    Elementary School: English Estates Elementary

    High School: Lake Howell High

    Tax Year: 2023

    Middle School: Tuskawilla Middle


  • 240 N PHELPS AVE, WINTER PARK, FL 32789

    $2,279,00046 Days on yellowkey   MLS ID: O6389035

    For Sale O6389035 - 240 N PHELPS AVE, WINTER PARK, FL 32789 68 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 2889
       Built: 2026   Tax: $6,605 (2025)
    Community: Sylvan Heights
    Spa: No

    Single Family


    Estimated Monthly Payment: $13,038 (change assumption)
    Mortgage ($12,487) + Taxes in 2025 ($550)


    Taxes:$6,605

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 3172 CROWN JEWEL CT, WINTER PARK, FL 32792

    $339,9009 Days on yellowkey   MLS ID: O6397498

    0 Days Off yellowkey (back on 4/17/2026)

    For Sale O6397498 - 3172 CROWN JEWEL CT, WINTER PARK, FL 32792 24 photos

    Bed: 3   Bath: 2.5   Gar: 1
    Liv Area Sq Ft: 1406
       Built: 2019
    Monthly Fee: $146
       Tax: $4,977 (2025)
    Community: Coronado Twnhms
    Townhouse


    Estimated Monthly Payment: $2,423 (change assumption)
    Mortgage ($1,862) + Fees ($146) + Taxes in 2025 ($415)


    Taxes:$4,977

    Elementary School: Cheney Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 525 LAKEVIEW AVE, WINTER PARK, FL 32789

    $1,390,000280 Days on yellowkey   MLS ID: O6325165

    1 Days Off yellowkey (back on 3/30/2026)

    For Sale O6325165 - 525 LAKEVIEW AVE, WINTER PARK, FL 32789 7 photos

    Bed: 4   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3253
       Built: 2026   Tax: $2,814 (2024)
    Community: Killarney Estates
    Single Family


    Estimated Monthly Payment: $7,851 (change assumption)
    Mortgage ($7,616) + Taxes in 2024 ($234)


    Taxes:$2,814

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2024

    Middle School: College Park Middle


  • 1473 BERKSHIRE AVE, WINTER PARK, FL 32789

    $1,499,000306 Days on yellowkey   MLS ID: O6320741

    For Sale O6320741 - 1473 BERKSHIRE AVE, WINTER PARK, FL 32789 53 photos

    Bed: 5   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 2895
       Built: 2025   Tax: $5,730 (2024)
    Community: Orwin Manor Westminster Sec
    Single Family


    Estimated Monthly Payment: $8,691 (change assumption)
    Mortgage ($8,213) + Taxes in 2024 ($478)


    Taxes:$5,730

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2024

    Middle School: College Park Middle


  • 2015 N PARK AVE, WINTER PARK, FL 32789

    $2,295,00081 Days on yellowkey   MLS ID: O6372603

    0 Days Off yellowkey (back on 4/17/2026)

    For Sale O6372603 - 2015 N PARK AVE, WINTER PARK, FL 32789 64 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3963
       Built: 2023   Tax: $27,508 (2024)
    Community: Twin Acres
    Spa: No

    Single Family


    Estimated Monthly Payment: $14,867 (change assumption)
    Mortgage ($12,575) + Taxes in 2024 ($2,292)


    Taxes:$27,508

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Maitland Middle


  • 1523 MILLER AVE, WINTER PARK, FL 32789

    $1,550,000107 Days on yellowkey   MLS ID: O6371649

    For Sale O6371649 - 1523 MILLER AVE, WINTER PARK, FL 32789 65 photos

    Bed: 5   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 3164
       Built: 2026   Tax: $3,620 (2025)
    Community: Lawndale
    Single Family


    Estimated Monthly Payment: $8,795 (change assumption)
    Mortgage ($8,493) + Taxes in 2025 ($302)


    Taxes:$3,620

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park Middle


  • 1661 WOODLAND AVE, WINTER PARK, FL 32789

    $1,300,0008 Days on yellowkey   MLS ID: O6399348

    1 Days Off yellowkey (back on 4/17/2026)

    For Sale O6399348 - 1661 WOODLAND AVE, WINTER PARK, FL 32789 58 photos

    Bed: 3   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3215
       Built: 1948   Tax: $17,067 (2025)
    Community: Comstock Park
    Single Family


    Estimated Monthly Payment: $8,545 (change assumption)
    Mortgage ($7,123) + Taxes in 2025 ($1,422)


    Taxes:$17,067

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 811 OVERSPIN DR, WINTER PARK, FL 32789

    $349,0008 Days on yellowkey   MLS ID: O6400009

    For Sale O6400009 - 811 OVERSPIN DR, WINTER PARK, FL 32789 9 photos

    Bed: 2   Bath: 1.0   Gar: 1
    Liv Area Sq Ft: 749
       Built: 1950   Tax: $3,998 (2025)
    Community: Dubsdread Heights
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,245 (change assumption)
    Mortgage ($1,912) + Taxes in 2025 ($333)


    Taxes:$3,998

    Elementary School: Princeton Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park Middle


  • 814 DENSMORE DR, WINTER PARK, FL 32792

    $425,0008 Days on yellowkey   MLS ID: O6399773

    For Sale O6399773 - 814 DENSMORE DR, WINTER PARK, FL 32792 24 photos

    Bed: 4   Bath: 2.0
    Liv Area Sq Ft: 1610
       Built: 1960   Tax: $5,402 (2025)
    Community: Winter Park Estates
    Single Family


    Estimated Monthly Payment: $2,779 (change assumption)
    Mortgage ($2,329) + Taxes in 2025 ($450)


    Taxes:$5,402

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 3204 NETHERWOOD, WINTER PARK, FL 32792

    $299,99974 Days on yellowkey   MLS ID: O6380637

    0 Days Off yellowkey (back on 4/16/2026)

    For Sale O6380637 - 3204 NETHERWOOD, WINTER PARK, FL 32792 35 photos

    Bed: 2   Bath: 1.5
    Liv Area Sq Ft: 1056
       Built: 1983   Tax: $3,426 (2024)
    Community: Coronation Add
    Spa: No

    Half Duplex


    Estimated Monthly Payment: $1,929 (change assumption)
    Mortgage ($1,644) + Taxes in 2024 ($286)


    Taxes:$3,426

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 5503 ALBERT DR, WINTER PARK, FL 32792

    $405,00025 Days on yellowkey   MLS ID: S5146768

    3 Days Off yellowkey (back on 4/16/2026)

    For Sale S5146768 - 5503 ALBERT DR, WINTER PARK, FL 32792 55 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1366
       Built: 1978   Tax: $4,241 (2024)
    Community: Howell Branch Woods
    Single Family


    Estimated Monthly Payment: $2,573 (change assumption)
    Mortgage ($2,219) + Taxes in 2024 ($353)


    Taxes:$4,241

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 311 E MORSE BLVD #2 - 5, WINTER PARK, FL 32789

    $2,100,000109 Days on yellowkey   MLS ID: O6370558

    0 Days Off yellowkey (back on 4/16/2026)

    For Sale O6370558 - 311 E MORSE BLVD #2 - 5, WINTER PARK, FL 32789 32 photos

    Bed: 2   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1900
       Built: 1960
    Monthly Fee: $2,622
       Tax: $6,719 (2025)
    Community: Whispering Waters/Phillips Circle Rep
    Condo


    Estimated Monthly Payment: $14,688 (change assumption)
    Mortgage ($11,507) + Fees ($2,622) + Taxes in 2025 ($560)


    Taxes:$6,719

    Elementary School: None

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 7336 FOREST HILL CT #240, WINTER PARK, FL 32792

    $169,90056 Days on yellowkey   MLS ID: O6386461

    REDUCED by $10,000 (5.6%) on 04/08/2026

    For Sale O6386461 - 7336 FOREST HILL CT #240, WINTER PARK, FL 32792 26 photos

    Bed: 2   Bath: 1.5
    Liv Area Sq Ft: 990
       Built: 1984
    Monthly Fee: $450
       Tax: $2,899 (2025)
    Community: Hidden Oaks Condo Ph 12
    Condo


    Estimated Monthly Payment: $1,622 (change assumption)
    Mortgage ($931) + Fees ($450) + Taxes in 2025 ($242)


    Taxes:$2,899

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 3374 HAMLET LOOP, WINTER PARK, FL 32792

    $375,00052 Days on yellowkey   MLS ID: O6386907

    For Sale O6386907 - 3374 HAMLET LOOP, WINTER PARK, FL 32792 37 photos

    Bed: 3   Bath: 2.5   Gar: 1
    Liv Area Sq Ft: 1397
       Built: 1994
    Monthly Fee: $63
       Tax: $5,326 (2024)
    Community: Villas Of Casselberry Ph 3
    Single Family


    Estimated Monthly Payment: $2,562 (change assumption)
    Mortgage ($2,055) + Fees ($63) + Taxes in 2024 ($444)


    Taxes:$5,326

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 3217 OAK LAWN PL #211, WINTER PARK, FL 32792

    $179,00041 Days on yellowkey   MLS ID: O6390713

    For Sale O6390713 - 3217 OAK LAWN PL #211, WINTER PARK, FL 32792 21 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1117
       Built: 1984   Tax: $2,909 (2025)
    Community: Hidden Oaks Condo Ph 11
    Condo


    Estimated Monthly Payment: $1,223 (change assumption)
    Mortgage ($981) + Taxes in 2025 ($242)


    Taxes:$2,909

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 647 RANDY LN, WINTER PARK, FL 32789

    $1,795,00046 Days on yellowkey   MLS ID: O6387217

    For Sale O6387217 - 647 RANDY LN, WINTER PARK, FL 32789 64 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2851
       Built: 1957   Tax: $5,627 (2025)
    Community: Timberlane
    Single Family


    Estimated Monthly Payment: $10,304 (change assumption)
    Mortgage ($9,835) + Taxes in 2025 ($469)


    Taxes:$5,627

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 721 PANSY AVE, WINTER PARK, FL 32789

    $1,925,000185 Days on yellowkey   MLS ID: O6352857

    For Sale O6352857 - 721 PANSY AVE, WINTER PARK, FL 32789 29 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 2653
       Built: 2018   Tax: $15,480 (2025)
    Community: Villa View Park
    Single Family


    Estimated Monthly Payment: $11,838 (change assumption)
    Mortgage ($10,548) + Taxes in 2025 ($1,290)


    Taxes:$15,480

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 800 JUANITA RAEL, WINTER PARK, FL 32789

    $2,300,00016 Days on yellowkey   MLS ID: O6396611

    For Sale O6396611 - 800 JUANITA RAEL, WINTER PARK, FL 32789 37 photos

    Bed: 5   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 4021
       Built: 1961   Tax: $9,773 (2025)
    Community: Green Oaks Rep 02
    Spa: No

    Single Family


    Estimated Monthly Payment: $13,417 (change assumption)
    Mortgage ($12,602) + Taxes in 2025 ($814)


    Taxes:$9,773

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 3720 JONQUIL LN, WINTER PARK, FL 32792

    $445,0009 Days on yellowkey   MLS ID: O6399628

    0 Days Off yellowkey (back on 4/16/2026)

    For Sale O6399628 - 3720 JONQUIL LN, WINTER PARK, FL 32792 1 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1647
       Built: 1982   Tax: $1,835 (2024)
    Community: Garden Lake Estates Unit 2
    Single Family


    Estimated Monthly Payment: $2,591 (change assumption)
    Mortgage ($2,438) + Taxes in 2024 ($153)


    Taxes:$1,835

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None




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.