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Winter Park Homes For Sale & Real Estate - 376 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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  • 5331 OAK CT, WINTER PARK, FL 32792

    $460,000280 Days on yellowkey   MLS ID: S5130868

    For Sale S5130868 - 5331 OAK CT, WINTER PARK, FL 32792 41 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1263
       Built: 1976   Tax: $2,311 (2024)
    Community: Wrenwood Heights Unit 2
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,713 (change assumption)
    Mortgage ($2,520) + Taxes in 2024 ($193)


    Taxes:$2,311

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 1052 MANCHESTER CIR, WINTER PARK, FL 32792

    $470,00088 Days on yellowkey   MLS ID: O6376260

    REDUCED by $5,000 (1.1%) on 04/13/2026

    For Sale O6376260 - 1052 MANCHESTER CIR, WINTER PARK, FL 32792 41 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1703
       Built: 1983   Tax: $5,216 (2025)
    Community: Howell Estates 1St Add
    Single Family


    Estimated Monthly Payment: $3,010 (change assumption)
    Mortgage ($2,575) + Taxes in 2025 ($435)


    Taxes:$5,216

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 1870 WALKER AVE, WINTER PARK, FL 32789

    $1,399,00040 Days on yellowkey   MLS ID: O6390504

    REDUCED by $26,000 (1.8%) on 04/19/2026

    For Sale O6390504 - 1870 WALKER AVE, WINTER PARK, FL 32789 21 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2046
       Built: 2026   Tax: $3,981 (2025)
    Community: Osceola Heights
    Single Family


    Estimated Monthly Payment: $7,997 (change assumption)
    Mortgage ($7,666) + Taxes in 2025 ($332)


    Taxes:$3,981

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 4864 TANGERINE AVE #4864, WINTER PARK, FL 32792

    $200,00064 Days on yellowkey   MLS ID: O6383320

    INCREASED by $1,000 (0.5%) on 04/09/2026

    For Sale O6383320 - 4864 TANGERINE AVE #4864, WINTER PARK, FL 32792 25 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1059
       Built: 1973
    Monthly Fee: $441
       Tax: $2,828 (2025)
    Community: Wrenwood Condo
    Townhouse


    Estimated Monthly Payment: $1,773 (change assumption)
    Mortgage ($1,096) + Fees ($441) + Taxes in 2025 ($236)


    Taxes:$2,828

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2020 VIA TUSCANY, WINTER PARK, FL 32789

    $4,195,0006 Days on yellowkey   MLS ID: O6400063

    0 Days Off yellowkey (back on 4/20/2026)

    For Sale O6400063 - 2020 VIA TUSCANY, WINTER PARK, FL 32789 94 photos

    Bed: 4   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 4665
       Built: 2026   Tax: $12,585 (2025)
    Community: Tuscania
    Single Family


    Estimated Monthly Payment: $24,034 (change assumption)
    Mortgage ($22,986) + Taxes in 2025 ($1,049)


    Taxes:$12,585

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 1510 MILLER AVE, WINTER PARK, FL 32789

    $1,634,900197 Days on yellowkey   MLS ID: O6350503

    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: $9,256 (change assumption)
    Mortgage ($8,958) + Taxes in 2025 ($298)


    Taxes:$3,573

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park Middle


  • 731 BONGART RD, WINTER PARK, FL 32792

    $499,999110 Days on yellowkey   MLS ID: S5140952

    For Sale S5140952 - 731 BONGART RD, WINTER PARK, FL 32792 25 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 1826
       Built: 1961   Tax: $5,910 (2025)
    Community: Winter Park Estates
    Single Family


    Estimated Monthly Payment: $3,232 (change assumption)
    Mortgage ($2,740) + Taxes in 2025 ($493)


    Taxes:$5,910

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 639 FRIAR RD, WINTER PARK, FL 32792

    $795,00020 Days on yellowkey   MLS ID: O6395715

    1 Days Off yellowkey (back on 4/20/2026)

    For Sale O6395715 - 639 FRIAR RD, WINTER PARK, FL 32792 50 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 1950
       Built: 1967   Tax: $3,415 (2025)
    Community: Winter Park Pines
    Single Family


    Estimated Monthly Payment: $4,641 (change assumption)
    Mortgage ($4,356) + Taxes in 2025 ($285)


    Taxes:$3,415

    Elementary School: Aloma Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 188 LEWFIELD CIR #188, WINTER PARK, FL 32792

    $129,99050 Days on yellowkey   MLS ID: O6387291

    REDUCED by $9,010 (6.5%) on 04/20/2026

    For Sale O6387291 - 188 LEWFIELD CIR #188, WINTER PARK, FL 32792 27 photos

    Bed: 1   Bath: 1.0
    Liv Area Sq Ft: 678
       Built: 1973   Tax: $424 (2024)
    Community: Stratford A Winter Park Condo
    Condo


    Estimated Monthly Payment: $748 (change assumption)
    Mortgage ($712) + Taxes in 2024 ($35)


    Taxes:$424

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 2087 LAURELWOOD WAY, WINTER PARK, FL 32792

    $659,000218 Days on yellowkey   MLS ID: O6344482

    REDUCED by $5,000 (0.8%) on 04/20/2026

    For Sale O6344482 - 2087 LAURELWOOD WAY, WINTER PARK, FL 32792 30 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1920
       Built: 2019
    Monthly Fee: $236
       Tax: $4,680 (2024)
    Community: Preserve At Hawks Crest
    Single Family


    Estimated Monthly Payment: $4,237 (change assumption)
    Mortgage ($3,611) + Fees ($236) + Taxes in 2024 ($390)


    Taxes:$4,680

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 2361 MULBRY DR, WINTER PARK, FL 32789

    $2,395,0006 Days on yellowkey   MLS ID: O6396840

    For Sale O6396840 - 2361 MULBRY DR, WINTER PARK, FL 32789 87 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 3111
       Built: 2026   Tax: $6,436 (2025)
    Community: Lake Forest Park
    Single Family


    Estimated Monthly Payment: $13,659 (change assumption)
    Mortgage ($13,123) + Taxes in 2025 ($536)


    Taxes:$6,436

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 2779 SANBINA ST, WINTER PARK, FL 32789

    $460,00040 Days on yellowkey   MLS ID: O6388746

    For Sale O6388746 - 2779 SANBINA ST, WINTER PARK, FL 32789 29 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1405
       Built: 1960   Tax: $5,629 (2024)
    Community: Howell Heights
    Single Family


    Estimated Monthly Payment: $2,990 (change assumption)
    Mortgage ($2,520) + Taxes in 2024 ($469)


    Taxes:$5,629

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Maitland Middle


  • 2500 LEE RD #202, WINTER PARK, FL 32789

    $234,999440 Days on yellowkey   MLS ID: O6277579

    For Sale O6277579 - 2500 LEE RD #202, WINTER PARK, FL 32789 44 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 956
       Built: 1969
    Monthly Fee: $398
       Tax: $2,327 (2025)
    Community: Lakeside Manor Condominium Association, Inc.
    Condo


    Estimated Monthly Payment: $1,880 (change assumption)
    Mortgage ($1,288) + Fees ($398) + Taxes in 2025 ($194)


    Taxes:$2,327

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park Middle


  • 661 SELKIRK DR, WINTER PARK, FL 32792

    $650,000182 Days on yellowkey   MLS ID: O6354700

    REDUCED by $25,000 (3.7%) on 04/16/2026

    For Sale O6354700 - 661 SELKIRK DR, WINTER PARK, FL 32792 23 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2150
       Built: 1962   Tax: $2,353 (2024)
    Community: Kenilworth Shores Sec 05
    Single Family


    Estimated Monthly Payment: $3,758 (change assumption)
    Mortgage ($3,562) + Taxes in 2024 ($196)


    Taxes:$2,353

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 3057 AARON BURR AVE #1, WINTER PARK, FL 32792

    $116,000140 Days on yellowkey   MLS ID: O6364189

    For Sale O6364189 - 3057 AARON BURR AVE #1, WINTER PARK, FL 32792 11 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1066
       Built: 1974
    Monthly Fee: $409
       Tax: $1,911 (2024)
    Community: Colonies
    Condo


    Estimated Monthly Payment: $1,204 (change assumption)
    Mortgage ($636) + Fees ($409) + Taxes in 2024 ($159)


    Taxes:$1,911

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 1565 FOREST AVE, WINTER PARK, FL 32789

    $1,750,0008 Days on yellowkey   MLS ID: O6398694

    For Sale O6398694 - 1565 FOREST AVE, WINTER PARK, FL 32789 37 photos

    Bed: 4   Bath: 2.0
    Liv Area Sq Ft: 2163
       Built: 1925   Tax: $2,803 (2025)
    Community: Ellno Willo
    Single Family


    Estimated Monthly Payment: $9,822 (change assumption)
    Mortgage ($9,589) + Taxes in 2025 ($234)


    Taxes:$2,803

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 1540 MILLER AVE, WINTER PARK, FL 32789

    $1,399,9009 Days on yellowkey   MLS ID: O6398421

    For Sale O6398421 - 1540 MILLER AVE, WINTER PARK, FL 32789 55 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2984
       Built: 2026   Tax: $3,573 (2025)
    Community: Lawndale
    Spa: No

    Single Family


    Estimated Monthly Payment: $7,968 (change assumption)
    Mortgage ($7,670) + Taxes in 2025 ($298)


    Taxes:$3,573

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park Middle


  • 1649 HARMON AVE, WINTER PARK, FL 32789

    $1,399,00033 Days on yellowkey   MLS ID: O6392216

    REDUCED by $51,000 (3.5%) on 04/17/2026

    For Sale O6392216 - 1649 HARMON AVE, WINTER PARK, FL 32789 51 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3223
       Built: 2018   Tax: $11,908 (2025)
    Community: Lawndale
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $8,658 (change assumption)
    Mortgage ($7,666) + Taxes in 2025 ($992)


    Taxes:$11,908

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park Middle


  • 1800 MAGNOLIA AVE, WINTER PARK, FL 32789

    $1,148,00037 Days on yellowkey   MLS ID: NS1087637

    REDUCED by $1,000 (0.1%) on 04/14/2026

    For Sale NS1087637 - 1800 MAGNOLIA AVE, WINTER PARK, FL 32789 65 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2431
       Built: 1996   Tax: $11,730 (2025)
    Community: Temple Terrace
    Spa: No

    Single Family


    Estimated Monthly Payment: $7,268 (change assumption)
    Mortgage ($6,290) + Taxes in 2025 ($978)


    Taxes:$11,730

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 2823 WRIGHT AVE, WINTER PARK, FL 32789

    $929,90040 Days on yellowkey   MLS ID: O6390670

    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: $5,855 (change assumption)
    Mortgage ($5,095) + 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




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.