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Winter Park Homes For Sale & Real Estate - 442 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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  • 1037 N VIRGINIA AVE, WINTER PARK, FL 32789

    $649,0003 Days on yellowkey   MLS ID: O6419694

    For Sale O6419694 - 1037 N VIRGINIA AVE, WINTER PARK, FL 32789 35 photos

    Bed: 3   Bath: 1.0   Gar: 1
    Liv Area Sq Ft: 1101
       Built: 1960   Tax: $7,186 (2024)
    Community: Tantum Add
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,155 (change assumption)
    Mortgage ($3,556) + Taxes in 2024 ($599)


    Taxes:$7,186

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Maitland Middle


  • 7733 COUNTRY PL #G2, WINTER PARK, FL 32792

    $244,0006 Days on yellowkey   MLS ID: O6418682

    For Sale O6418682 - 7733 COUNTRY PL #G2, WINTER PARK, FL 32792 21 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1068
       Built: 1982   Tax: $371 (2025)
    Community: Goldenrod Villas Condo
    Condo


    Estimated Monthly Payment: $1,368 (change assumption)
    Mortgage ($1,337) + Taxes in 2025 ($31)


    Taxes:$371

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 948 POINCIANA LN, WINTER PARK, FL 32789

    $2,899,900167 Days on yellowkey   MLS ID: O6372165

    REDUCED by $274,100 (8.6%) on 06/13/2026

    For Sale O6372165 - 948 POINCIANA LN, WINTER PARK, FL 32789 57 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3676
       Built: 2001   Tax: $19,753 (2025)
    Community: Maitland Shores First Add
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $17,536 (change assumption)
    Mortgage ($15,889) + Taxes in 2025 ($1,646)


    Taxes:$19,753

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 2652 ABBEY RD, WINTER PARK, FL 32792

    $625,0006 Days on yellowkey   MLS ID: O6419026

    For Sale O6419026 - 2652 ABBEY RD, WINTER PARK, FL 32792 44 photos

    Bed: 5   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1938
       Built: 1967   Tax: $7,337 (2025)
    Community: Winter Park Pines Merrie Oaks
    Single Family


    Estimated Monthly Payment: $4,036 (change assumption)
    Mortgage ($3,425) + Taxes in 2025 ($611)


    Taxes:$7,337

    Elementary School: Aloma Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 1421 CHAPMAN CIR, WINTER PARK, FL 32789

    $1,550,00016 Days on yellowkey   MLS ID: O6415941

    For Sale O6415941 - 1421 CHAPMAN CIR, WINTER PARK, FL 32789 49 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3578
       Built: 2005
    Monthly Fee: $268
       Tax: $10,592 (2025)
    Community: Windsong Elizabeths Walk 43/81
    Single Family


    Estimated Monthly Payment: $9,644 (change assumption)
    Mortgage ($8,493) + Fees ($268) + Taxes in 2025 ($883)


    Taxes:$10,592

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 1761 GLADIOLAS DR, WINTER PARK, FL 32792

    $375,00030 Days on yellowkey   MLS ID: O6411912

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

    For Sale O6411912 - 1761 GLADIOLAS DR, WINTER PARK, FL 32792 7 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1656
       Built: 1979   Tax: $1,453 (2025)
    Community: Garden Lake Estates Unit 1
    Single Family


    Estimated Monthly Payment: $2,176 (change assumption)
    Mortgage ($2,055) + Taxes in 2025 ($121)


    Taxes:$1,453

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 275 N RANGER BLVD, WINTER PARK, FL 32792

    $775,00018 Days on yellowkey   MLS ID: O6415904

    For Sale O6415904 - 275 N RANGER BLVD, WINTER PARK, FL 32792 32 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 1950
       Built: 1965   Tax: $6,817 (2025)
    Community: Winter Park Pines Merrie Oaks
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,815 (change assumption)
    Mortgage ($4,246) + Taxes in 2025 ($568)


    Taxes:$6,817

    Elementary School: Aloma Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 1871 CASSELWOOD ST, WINTER PARK, FL 32792

    $419,90057 Days on yellowkey   MLS ID: O6404306

    0 Days Off yellowkey (back on 5/26/2026)

    REDUCED by $5,000 (1.2%) on 05/12/2026

    For Sale O6404306 - 1871 CASSELWOOD ST, WINTER PARK, FL 32792 37 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1616
       Built: 1988
    Monthly Fee: $39
       Tax: $1,223 (2024)
    Community: Villas Of Casselberry Ph 2
    Townhouse


    Estimated Monthly Payment: $2,442 (change assumption)
    Mortgage ($2,301) + Fees ($39) + Taxes in 2024 ($102)


    Taxes:$1,223

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 1411 MILLER AVE, WINTER PARK, FL 32789

    $899,00012 Days on yellowkey   MLS ID: O6416926

    For Sale O6416926 - 1411 MILLER AVE, WINTER PARK, FL 32789 37 photos

    Bed: 3   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 1824
       Built: 2023
    Monthly Fee: $200
       Tax: $8,005 (2025)
    Community: H Vanwies Sub
    Townhouse


    Estimated Monthly Payment: $5,793 (change assumption)
    Mortgage ($4,926) + Fees ($200) + Taxes in 2025 ($667)


    Taxes:$8,005

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park Middle


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

    $235,90023 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

    $544,900154 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


  • 910 ENCLAVE PL, WINTER PARK, FL 32792

    $1,899,00045 Days on yellowkey   MLS ID: O6406803

    For Sale O6406803 - 910 ENCLAVE PL, WINTER PARK, FL 32792 4 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3620
       Built: 2027
    Monthly Fee: $124
       Tax: $9,900 (2026)
    Community: The Enclave Winter Park
    Single Family


    Estimated Monthly Payment: $11,354 (change assumption)
    Mortgage ($10,405) + Fees ($124) + Taxes in 2026 ($825)


    Taxes:$9,900

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2026

    Middle School: Maitland Middle


  • 926 ENCLAVE PL, WINTER PARK, FL 32792

    $2,235,00039 Days on yellowkey   MLS ID: O6408030

    For Sale O6408030 - 926 ENCLAVE PL, WINTER PARK, FL 32792 6 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 4150
       Built: 2026
    Monthly Fee: $124
       Tax: $9,900 (2026)
    Community: The Enclave Winter Park
    Single Family


    Estimated Monthly Payment: $13,195 (change assumption)
    Mortgage ($12,246) + Fees ($124) + Taxes in 2026 ($825)


    Taxes:$9,900

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2026

    Middle School: Maitland Middle


  • 938 ENCLAVE PL, WINTER PARK, FL 32792

    $2,099,00039 Days on yellowkey   MLS ID: O6408090

    For Sale O6408090 - 938 ENCLAVE PL, WINTER PARK, FL 32792 7 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3865
       Built: 2026
    Monthly Fee: $124
       Tax: $9,900 (2026)
    Community: The Enclave Winter Park
    Single Family


    Estimated Monthly Payment: $12,450 (change assumption)
    Mortgage ($11,501) + Fees ($124) + Taxes in 2026 ($825)


    Taxes:$9,900

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2026

    Middle School: Maitland Middle


  • 1000 S SEMORAN BLVD BLVD #603, WINTER PARK, FL 32792

    $99,9003 Days on yellowkey   MLS ID: O6420027

    For Sale O6420027 - 1000 S SEMORAN BLVD BLVD #603, WINTER PARK, FL 32792 17 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1003
       Built: 1969   Tax: $1,878 (2025)
    Community: Golfside Villas Condo
    Condo


    Estimated Monthly Payment: $704 (change assumption)
    Mortgage ($547) + Taxes in 2025 ($157)


    Taxes:$1,878

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


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

    $154,9003 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


  • 4053 COOL WATER CT, WINTER PARK, FL 32792

    $549,0003 Days on yellowkey   MLS ID: O6419831

    For Sale O6419831 - 4053 COOL WATER CT, WINTER PARK, FL 32792 41 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1930
       Built: 1979
    Monthly Fee: $28
       Tax: $6,373 (2025)
    Community: Lake Waunatta Woods
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,567 (change assumption)
    Mortgage ($3,008) + Fees ($28) + Taxes in 2025 ($531)


    Taxes:$6,373

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 660 W MORSE BLVD, WINTER PARK, FL 32789

    $2,800,0003 Days on yellowkey   MLS ID: O6419377

    For Sale O6419377 - 660 W MORSE BLVD, WINTER PARK, FL 32789 47 photos

    Bed: 3   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 3286
       Built: 2021   Tax: $24,472 (2025)
    Community: Morse & Pennsylvania Twnhms
    Townhouse


    Estimated Monthly Payment: $17,381 (change assumption)
    Mortgage ($15,342) + Taxes in 2025 ($2,039)


    Taxes:$24,472

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2774 BANCHORY RD, WINTER PARK, FL 32792

    $645,0003 Days on yellowkey   MLS ID: O6418821

    For Sale O6418821 - 2774 BANCHORY RD, WINTER PARK, FL 32792 34 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1560
       Built: 1965   Tax: $7,220 (2025)
    Community: Winter Park Pines
    Single Family


    Estimated Monthly Payment: $4,136 (change assumption)
    Mortgage ($3,534) + Taxes in 2025 ($602)


    Taxes:$7,220

    Elementary School: Aloma Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 4353 STEED TER, WINTER PARK, FL 32792

    $614,9903 Days on yellowkey   MLS ID: TB8517548

    For Sale TB8517548 - 4353 STEED TER, WINTER PARK, FL 32792 30 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2275
       Built: 1989
    Monthly Fee: $29
       Tax: $7,031 (2024)
    Community: Kings Cove
    Single Family


    Estimated Monthly Payment: $3,985 (change assumption)
    Mortgage ($3,370) + Fees ($29) + Taxes in 2024 ($586)


    Taxes:$7,031

    Elementary School: Red Bug Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla 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.