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Winter Park Homes For Sale & Real Estate - 438 homes

Winter Park homes for sale are located in Orange 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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  • 1900 WINTER PARK RD, WINTER PARK, FL 32789

    $799,00078 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


  • 731 BONGART ROAD, WINTER PARK, FL 32792

    $499,00068 Days on yellowkey   MLS ID: O6406004

    3 Days Off yellowkey (back on 6/27/2026)

    For Sale O6406004 - 731 BONGART ROAD, WINTER PARK, FL 32792 44 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 1526
       Built: 1961   Tax: $5,910 (2025)
    Community: Winter Park Estates
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,227 (change assumption)
    Mortgage ($2,734) + Taxes in 2025 ($493)


    Taxes:$5,910

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 2923 ANTIQUE OAKS CIR #39, WINTER PARK, FL 32792

    $184,999509 Days on yellowkey   MLS ID: OM695642

    0 Days Off yellowkey (back on 6/26/2026)

    For Sale OM695642 - 2923 ANTIQUE OAKS CIR #39, WINTER PARK, FL 32792 22 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1105
       Built: 1984
    Monthly Fee: $442
       Tax: $2,702 (2024)
    Community: Parkview Village
    Condo


    Estimated Monthly Payment: $1,681 (change assumption)
    Mortgage ($1,014) + Fees ($442) + Taxes in 2024 ($225)


    Taxes:$2,702

    Elementary School: Aloma Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Glenridge Middle


  • 2676 BARBADOS DR, WINTER PARK, FL 32792

    $340,00046 Days on yellowkey   MLS ID: O6411958

    2 Days Off yellowkey (back on 6/26/2026)

    For Sale O6411958 - 2676 BARBADOS DR, WINTER PARK, FL 32792 29 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1743
       Built: 1978
    Monthly Fee: $98
       Tax: $4,131 (2025)
    Community: Windward Square Sec 2
    Townhouse


    Estimated Monthly Payment: $2,305 (change assumption)
    Mortgage ($1,863) + Fees ($98) + Taxes in 2025 ($344)


    Taxes:$4,131

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 2228 HOWARD DR, WINTER PARK, FL 32789

    $2,460,00062 Days on yellowkey   MLS ID: O6407733

    For Sale O6407733 - 2228 HOWARD DR, WINTER PARK, FL 32789 9 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3294
       Built: 2026   Tax: $3,647 (2025)
    Community: Lake Forest Park
    Single Family


    Estimated Monthly Payment: $13,783 (change assumption)
    Mortgage ($13,479) + Taxes in 2025 ($304)


    Taxes:$3,647

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 3641 OAK VISTA LN, WINTER PARK, FL 32792

    $475,00036 Days on yellowkey   MLS ID: O6412855

    0 Days Off yellowkey (back on 6/26/2026)

    For Sale O6412855 - 3641 OAK VISTA LN, WINTER PARK, FL 32792 46 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1645
       Built: 1981   Tax: $1,562 (2025)
    Community: Garden Lake Estates Unit 2
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,733 (change assumption)
    Mortgage ($2,603) + Taxes in 2025 ($130)


    Taxes:$1,562

    Elementary School: Red Bug Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 700 MELROSE AVE #F 21, WINTER PARK, FL 32789

    $235,90039 Days on yellowkey   MLS ID: O6413612

    1 Days Off yellowkey (back on 6/26/2026)

    For Sale O6413612 - 700 MELROSE AVE #F 21, WINTER PARK, FL 32789 27 photos

    Bed: 1   Bath: 1.0
    Liv Area Sq Ft: 787
       Built: 1964   Tax: $1,123 (2025)
    Community: Winter Park Gdns Condo
    Condo


    Estimated Monthly Payment: $1,386 (change assumption)
    Mortgage ($1,293) + Taxes in 2025 ($94)


    Taxes:$1,123

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 330 ELKHORN CT, WINTER PARK, FL 32792

    $544,900170 Days on yellowkey   MLS ID: O6376757

    REDUCED by $5,000 (0.9%) on 06/26/2026

    For Sale O6376757 - 330 ELKHORN CT, WINTER PARK, FL 32792 41 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1570
       Built: 1965   Tax: $2,086 (2025)
    Community: Winter Park Pines Merrie Oaks
    Single Family


    Estimated Monthly Payment: $3,160 (change assumption)
    Mortgage ($2,986) + Taxes in 2025 ($174)


    Taxes:$2,086

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 3037 ANTIQUE OAKS CIR #156, WINTER PARK, FL 32792

    $154,90019 Days on yellowkey   MLS ID: O6420008

    For Sale O6420008 - 3037 ANTIQUE OAKS CIR #156, WINTER PARK, FL 32792 21 photos

    Bed: 1   Bath: 1.0
    Liv Area Sq Ft: 749
       Built: 1984   Tax: $2,058 (2025)
    Community: Parkview Village
    Condo


    Estimated Monthly Payment: $1,020 (change assumption)
    Mortgage ($849) + Taxes in 2025 ($172)


    Taxes:$2,058

    Elementary School: Aloma Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 313 SYLVAN DR, WINTER PARK, FL 32789

    $5,500,00029 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


  • 2712 TORTOISE CV, WINTER PARK, FL 32792

    $235,00021 Days on yellowkey   MLS ID: O6419150

    For Sale O6419150 - 2712 TORTOISE CV, WINTER PARK, FL 32792 22 photos

    Bed: 2   Bath: 1.0   Gar: 1
    Liv Area Sq Ft: 924
       Built: 1981   Tax: $2,442 (2025)
    Community: Slovak Village
    Half Duplex


    Estimated Monthly Payment: $1,491 (change assumption)
    Mortgage ($1,288) + Taxes in 2025 ($204)


    Taxes:$2,442

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 541 W CANTON AVE, WINTER PARK, FL 32789

    $2,650,000115 Days on yellowkey   MLS ID: O6389829

    REDUCED by $150,000 (5.4%) on 06/24/2026

    For Sale O6389829 - 541 W CANTON AVE, WINTER PARK, FL 32789 51 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3553
       Built: 2024   Tax: $4,692 (2024)
    Community: Winter Park
    Single Family


    Estimated Monthly Payment: $14,911 (change assumption)
    Mortgage ($14,520) + Taxes in 2024 ($391)


    Taxes:$4,692

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Maitland Middle


  • 2648 GALLIANO CIR, WINTER PARK, FL 32792

    $355,000140 Days on yellowkey   MLS ID: S5144547

    For Sale S5144547 - 2648 GALLIANO CIR, WINTER PARK, FL 32792 39 photos

    Bed: 2   Bath: 2.5   Gar: 1
    Liv Area Sq Ft: 1550
       Built: 2004
    Monthly Fee: $175
       Tax: $4,736 (2024)
    Community: Vistas At Lake Howell
    Townhouse


    Estimated Monthly Payment: $2,515 (change assumption)
    Mortgage ($1,945) + Fees ($175) + Taxes in 2024 ($395)


    Taxes:$4,736

    Elementary School: Sterling Park Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 7514 LAUREL SPRINGS DR, WINTER PARK, FL 32792

    $400,000186 Days on yellowkey   MLS ID: O6372653

    1 Days Off yellowkey (back on 6/24/2026)

    For Sale O6372653 - 7514 LAUREL SPRINGS DR, WINTER PARK, FL 32792 30 photos

    Bed: 4   Bath: 2.0
    Liv Area Sq Ft: 1677
       Built: 1972   Tax: $1,289 (2024)
    Community: Laurel Spgs
    Single Family


    Estimated Monthly Payment: $2,299 (change assumption)
    Mortgage ($2,192) + Taxes in 2024 ($107)


    Taxes:$1,289

    Elementary School: Aloma Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Glenridge Middle


  • 2231 NAIRN DR, WINTER PARK, FL 32792

    $499,000188 Days on yellowkey   MLS ID: O6369016

    For Sale O6369016 - 2231 NAIRN DR, WINTER PARK, FL 32792 19 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1088
       Built: 1956   Tax: $3,793 (2025)
    Community: Aloma
    Single Family


    Estimated Monthly Payment: $3,050 (change assumption)
    Mortgage ($2,734) + Taxes in 2025 ($316)


    Taxes:$3,793

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 230 STRATHY LN, WINTER PARK, FL 32792

    $499,000188 Days on yellowkey   MLS ID: O6371054

    For Sale O6371054 - 230 STRATHY LN, WINTER PARK, FL 32792 12 photos

    Bed: 2   Bath: 1.0
    Liv Area Sq Ft: 920
       Built: 1957   Tax: $4,071 (2024)
    Community: Aloma
    Single Family


    Estimated Monthly Payment: $3,073 (change assumption)
    Mortgage ($2,734) + Taxes in 2024 ($339)


    Taxes:$4,071

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Glenridge Middle


  • 1826 BANCHORY RD, WINTER PARK, FL 32789

    $779,00021 Days on yellowkey   MLS ID: O6419474

    0 Days Off yellowkey (back on 6/23/2026)

    For Sale O6419474 - 1826 BANCHORY RD, WINTER PARK, FL 32789 1 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2391
       Built: 1962   Tax: $7,662 (2025)
    Community: Kenilworth Shores Sec 06
    Single Family


    Estimated Monthly Payment: $4,907 (change assumption)
    Mortgage ($4,268) + Taxes in 2025 ($639)


    Taxes:$7,662

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1630 LASBURY AVE, WINTER PARK, FL 32789

    $2,750,00073 Days on yellowkey   MLS ID: O6404300

    4 Days Off yellowkey (back on 6/24/2026)

    For Sale O6404300 - 1630 LASBURY AVE, WINTER PARK, FL 32789 37 photos

    Bed: 5   Bath: 4.0   Gar: 3
    Liv Area Sq Ft: 4917
       Built: 2003   Tax: $14,204 (2025)
    Community: Comstock Park
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $16,252 (change assumption)
    Mortgage ($15,068) + Taxes in 2025 ($1,184)


    Taxes:$14,204

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 413 W MORSE BLVD, WINTER PARK, FL 32789

    $2,695,00038 Days on yellowkey   MLS ID: O6412134

    For Sale O6412134 - 413 W MORSE BLVD, WINTER PARK, FL 32789 29 photos

    Bed: 3   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3048
       Built: 2018
    Monthly Fee: $386
       Tax: $19,919 (2026)
    Community: Town Of Winter Park
    Townhouse


    Estimated Monthly Payment: $16,813 (change assumption)
    Mortgage ($14,767) + Fees ($386) + Taxes in 2026 ($1,660)


    Taxes:$19,919

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2026

    Middle School: Maitland Middle


  • 2500 LEE RD #208, WINTER PARK, FL 32789

    $175,000459 Days on yellowkey   MLS ID: O6297570

    REDUCED by $5,000 (2.8%) on 05/14/2026

    For Sale O6297570 - 2500 LEE RD #208, WINTER PARK, FL 32789 49 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 956
       Built: 1969
    Monthly Fee: $432
       Tax: $1,519 (2025)
    Community: Lakeside Manor Apts Condo
    Condo


    Estimated Monthly Payment: $1,517 (change assumption)
    Mortgage ($959) + Fees ($432) + Taxes in 2025 ($127)


    Taxes:$1,519

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park Middle




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.