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Winter Park Homes For Sale & Real Estate - 446 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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  • 1535 LAWNDALE CIR, WINTER PARK, FL 32792

    $450,0003 Days on yellowkey   MLS ID: C7527235

    For Sale C7527235 - 1535 LAWNDALE CIR, WINTER PARK, FL 32792 15 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1676
       Built: 1986
    Monthly Fee: $50
       Tax: $5,433 (2025)
    Community: Country Lane
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,968 (change assumption)
    Mortgage ($2,466) + Fees ($50) + Taxes in 2025 ($453)


    Taxes:$5,433

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 1521 CAVENDISH RD, WINTER PARK, FL 32789

    $470,0003 Days on yellowkey   MLS ID: O6415985

    For Sale O6415985 - 1521 CAVENDISH RD, WINTER PARK, FL 32789 22 photos

    Bed: 2   Bath: 1.0
    Liv Area Sq Ft: 1036
       Built: 1946   Tax: $2,793 (2025)
    Community: Orwin Manor Westminster
    Single Family


    Estimated Monthly Payment: $2,808 (change assumption)
    Mortgage ($2,575) + Taxes in 2025 ($233)


    Taxes:$2,793

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park Middle


  • 2032 KIMBRACE PL, WINTER PARK, FL 32792

    $2,188,8885 Days on yellowkey   MLS ID: O6414862

    For Sale O6414862 - 2032 KIMBRACE PL, WINTER PARK, FL 32792 83 photos

    Bed: 5   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 3382
       Built: 2021   Tax: $16,035 (2025)
    Community: Kenilworth Shores Sec 03
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $13,330 (change assumption)
    Mortgage ($11,994) + Taxes in 2025 ($1,336)


    Taxes:$16,035

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 1300 MAYFIELD AVE, WINTER PARK, FL 32789

    $2,695,00079 Days on yellowkey   MLS ID: O6393777

    For Sale O6393777 - 1300 MAYFIELD AVE, WINTER PARK, FL 32789 50 photos

    Bed: 5   Bath: 5.5   Gar: 4
    Liv Area Sq Ft: 4389
       Built: 1958   Tax: $26,658 (2025)
    Community: Temple Heights
    Spa: No

    Single Family


    Estimated Monthly Payment: $16,988 (change assumption)
    Mortgage ($14,767) + Taxes in 2025 ($2,221)


    Taxes:$26,658

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 231 CHELTON CIR, WINTER PARK, FL 32789

    $4,950,0004 Days on yellowkey   MLS ID: O6414890

    For Sale O6414890 - 231 CHELTON CIR, WINTER PARK, FL 32789 67 photos

    Bed: 4   Bath: 6.0   Gar: 3
    Liv Area Sq Ft: 5550
       Built: 2018   Tax: $56,866 (2025)
    Community: Forest Hills
    Spa: No

    Single Family


    Estimated Monthly Payment: $31,861 (change assumption)
    Mortgage ($27,123) + Taxes in 2025 ($4,739)


    Taxes:$56,866

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 1032 MANCHESTER CIR, WINTER PARK, FL 32792

    $464,900116 Days on yellowkey   MLS ID: O6383113

    REDUCED by $5,100 (1.1%) on 06/11/2026

    For Sale O6383113 - 1032 MANCHESTER CIR, WINTER PARK, FL 32792 27 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1787
       Built: 1976   Tax: $1,535 (2025)
    Community: Howell Estates Rep
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,675 (change assumption)
    Mortgage ($2,547) + Taxes in 2025 ($128)


    Taxes:$1,535

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 1651 WESTCHESTER AVE, WINTER PARK, FL 32789

    $1,175,00072 Days on yellowkey   MLS ID: O6384358

    0 Days Off yellowkey (back on 6/9/2026)

    REDUCED by $100,000 (7.8%) on 06/01/2026

    For Sale O6384358 - 1651 WESTCHESTER AVE, WINTER PARK, FL 32789 47 photos

    Bed: 3   Bath: 2.5   Gar: 1
    Liv Area Sq Ft: 2426
       Built: 1938   Tax: $10,973 (2025)
    Community: Orwin Manor Westminster Sec
    Single Family


    Estimated Monthly Payment: $7,353 (change assumption)
    Mortgage ($6,438) + Taxes in 2025 ($914)


    Taxes:$10,973

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park Middle


  • 2500 LEE RD #220, WINTER PARK, FL 32789

    $199,9006 Days on yellowkey   MLS ID: O6411927

    For Sale O6411927 - 2500 LEE RD #220, WINTER PARK, FL 32789 28 photos

    Bed: 2   Bath: 1.0
    Liv Area Sq Ft: 851
       Built: 1969
    Monthly Fee: $292
       Tax: $2,015 (2025)
    Community: Lakeside Manor Apts Condo
    Condo


    Estimated Monthly Payment: $1,555 (change assumption)
    Mortgage ($1,095) + Fees ($292) + Taxes in 2025 ($168)


    Taxes:$2,015

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park Middle


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

    $172,00092 Days on yellowkey   MLS ID: O6390713

    1 Days Off yellowkey (back on 6/11/2026)

    REDUCED by $3,000 (1.7%) on 06/04/2026

    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: $1,185 (change assumption)
    Mortgage ($942) + Taxes in 2025 ($242)


    Taxes:$2,909

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1750 CAROLLEE LANE, WINTER PARK, FL 32789

    $1,820,00086 Days on yellowkey   MLS ID: O6391179

    REDUCED by $70,000 (3.7%) on 05/26/2026

    For Sale O6391179 - 1750 CAROLLEE LANE, WINTER PARK, FL 32789 46 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3249
       Built: 2012   Tax: $24,658 (2025)
    Community: Green Terrace V/140 Lot 3 Blk B
    Single Family


    Estimated Monthly Payment: $12,027 (change assumption)
    Mortgage ($9,972) + Taxes in 2025 ($2,055)


    Taxes:$24,658

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 1944 NATALEN RD, WINTER PARK, FL 32792

    $519,00013 Days on yellowkey   MLS ID: O6405802

    0 Days Off yellowkey (back on 6/11/2026)

    For Sale O6405802 - 1944 NATALEN RD, WINTER PARK, FL 32792 27 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1380
       Built: 1957   Tax: $7,067 (2025)
    Community: Kenilworth Shores Sec 07
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,433 (change assumption)
    Mortgage ($2,844) + Taxes in 2025 ($589)


    Taxes:$7,067

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


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

    $235,9009 Days on yellowkey   MLS ID: O6413612

    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


  • 1511 GLADIOLAS DR, WINTER PARK, FL 32792

    $470,0006 Days on yellowkey   MLS ID: O6412441

    1 Days Off yellowkey (back on 6/11/2026)

    For Sale O6412441 - 1511 GLADIOLAS DR, WINTER PARK, FL 32792 45 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1594
       Built: 1979   Tax: $2,543 (2025)
    Community: Garden Lake Estates Unit 1
    Single Family


    Estimated Monthly Payment: $2,787 (change assumption)
    Mortgage ($2,575) + Taxes in 2025 ($212)


    Taxes:$2,543

    Elementary School: Red Bug Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 2465 BANCHORY RD, WINTER PARK, FL 32792

    $1,295,00037 Days on yellowkey   MLS ID: O6403997

    3 Days Off yellowkey (back on 6/11/2026)

    For Sale O6403997 - 2465 BANCHORY RD, WINTER PARK, FL 32792 42 photos

    Bed: 4   Bath: 5.0   Gar: 2
    Liv Area Sq Ft: 3971
       Built: 2007   Tax: $8,540 (2025)
    Community: Brookshire Heights 1St Add
    Spa: No

    Single Family


    Estimated Monthly Payment: $7,807 (change assumption)
    Mortgage ($7,096) + Taxes in 2025 ($712)


    Taxes:$8,540

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 1849 VIBURNUM LN, WINTER PARK, FL 32792

    $408,000311 Days on yellowkey   MLS ID: O6333863

    REDUCED by $17,000 (4.0%) on 06/10/2026

    For Sale O6333863 - 1849 VIBURNUM LN, WINTER PARK, FL 32792 27 photos

    Bed: 4   Bath: 2.0
    Liv Area Sq Ft: 1627
       Built: 1961   Tax: $3,645 (2024)
    Community: Eastbrook Sub Unit 05
    Single Family


    Estimated Monthly Payment: $2,539 (change assumption)
    Mortgage ($2,236) + Taxes in 2024 ($304)


    Taxes:$3,645

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 2384 SUN VALLEY CIR, WINTER PARK, FL 32792

    $269,900104 Days on yellowkey   MLS ID: O6386755

    1 Days Off yellowkey (back on 6/11/2026)

    REDUCED by $5,000 (1.8%) on 04/28/2026

    For Sale O6386755 - 2384 SUN VALLEY CIR, WINTER PARK, FL 32792 36 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1311
       Built: 1983   Tax: $688 (2024)
    Community: Cedarwood Village 1
    Condo


    Estimated Monthly Payment: $1,536 (change assumption)
    Mortgage ($1,479) + Taxes in 2024 ($57)


    Taxes:$688

    Elementary School: English Estates Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 1914 BONANZA CT, WINTER PARK, FL 32792

    $429,99930 Days on yellowkey   MLS ID: O6408461

    For Sale O6408461 - 1914 BONANZA CT, WINTER PARK, FL 32792 30 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1727
       Built: 1968   Tax: $4,497 (2025)
    Community: Eastbrook Sub Unit 13
    Single Family


    Estimated Monthly Payment: $2,731 (change assumption)
    Mortgage ($2,356) + Taxes in 2025 ($375)


    Taxes:$4,497

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 3651 N GOLDENROD RD #D102, WINTER PARK, FL 32792

    $158,00054 Days on yellowkey   MLS ID: O6401114

    REDUCED by $1,000 (0.6%) on 06/11/2026

    For Sale O6401114 - 3651 N GOLDENROD RD #D102, WINTER PARK, FL 32792 15 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 840
       Built: 1990
    Monthly Fee: $370
       Tax: $2,461 (2025)
    Community: Lancelot/Winter Park
    Condo


    Estimated Monthly Payment: $1,441 (change assumption)
    Mortgage ($866) + Fees ($370) + Taxes in 2025 ($205)


    Taxes:$2,461

    Elementary School: Aloma Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 3949 COOL WATER CT, WINTER PARK, FL 32792

    $399,9004 Days on yellowkey   MLS ID: O6415880

    FORECLOSURE O6415880 - 3949 COOL WATER CT, WINTER PARK, FL 32792 26 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1979
       Built: 1994
    Monthly Fee: $28
       Tax: $2,894 (2025)
    Community: Oxford Cove
    Single Family


    Estimated Monthly Payment: $2,460 (change assumption)
    Mortgage ($2,191) + Fees ($28) + Taxes in 2025 ($241)


    Taxes:$2,894

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 685 OVERSPIN DR, WINTER PARK, FL 32789

    $629,0004 Days on yellowkey   MLS ID: O6415537

    For Sale O6415537 - 685 OVERSPIN DR, WINTER PARK, FL 32789 26 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2112
       Built: 2003   Tax: $8,533 (2025)
    Community: Dubsdread Heights
    Single Family


    Estimated Monthly Payment: $4,158 (change assumption)
    Mortgage ($3,446) + Taxes in 2025 ($711)


    Taxes:$8,533

    Elementary School: Princeton Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park Middle




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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.