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Winter Park Homes For Sale & Real Estate - 378 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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  • 1830 EDWIN BLVD, WINTER PARK, FL 32789

    $679,8007 Days on yellowkey   MLS ID: O6400055

    For Sale O6400055 - 1830 EDWIN BLVD, WINTER PARK, FL 32789 52 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1287
       Built: 1957   Tax: $3,955 (2025)
    Community: Campo Bello
    Single Family


    Estimated Monthly Payment: $4,054 (change assumption)
    Mortgage ($3,725) + Taxes in 2025 ($330)


    Taxes:$3,955

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 1529 HOLTS GROVE CIR, WINTER PARK, FL 32789

    $2,795,00022 Days on yellowkey   MLS ID: O6395062

    REDUCED by $55,000 (1.9%) on 04/21/2026

    For Sale O6395062 - 1529 HOLTS GROVE CIR, WINTER PARK, FL 32789 84 photos

    Bed: 4   Bath: 5.0   Gar: 3
    Liv Area Sq Ft: 4356
       Built: 2005
    Monthly Fee: $262
       Tax: $21,342 (2025)
    Community: Windsong Lakeside Sec 02 43/71
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $17,355 (change assumption)
    Mortgage ($15,315) + Fees ($262) + Taxes in 2025 ($1,779)


    Taxes:$21,342

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 7506 CRANES CREEK CT #30, WINTER PARK, FL 32792

    $365,0003 Days on yellowkey   MLS ID: S5148231

    For Sale S5148231 - 7506 CRANES CREEK CT #30, WINTER PARK, FL 32792 20 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1861
       Built: 2006
    Monthly Fee: $181
       Tax: $1,974 (2025)
    Community: Cranes Creek
    Townhouse


    Estimated Monthly Payment: $2,345 (change assumption)
    Mortgage ($2,000) + Fees ($181) + Taxes in 2025 ($165)


    Taxes:$1,974

    Elementary School: Aloma Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 5330 TANGERINE AVE, WINTER PARK, FL 32792

    $354,9008 Days on yellowkey   MLS ID: O6399019

    0 Days Off yellowkey (back on 4/15/2026)

    For Sale O6399019 - 5330 TANGERINE AVE, WINTER PARK, FL 32792 32 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1642
       Built: 1976   Tax: $1,296 (2024)
    Community: Wrenwood
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,053 (change assumption)
    Mortgage ($1,945) + Taxes in 2024 ($108)


    Taxes:$1,296

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 446 ALBERTA DR, WINTER PARK, FL 32789

    $1,675,000308 Days on yellowkey   MLS ID: O6319233

    0 Days Off yellowkey (back on 3/17/2026)

    For Sale O6319233 - 446 ALBERTA DR, WINTER PARK, FL 32789 69 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 3263
       Built: 1968   Tax: $6,789 (2024)
    Community: Osceola Summit
    Single Family


    Estimated Monthly Payment: $9,744 (change assumption)
    Mortgage ($9,178) + Taxes in 2024 ($566)


    Taxes:$6,789

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Maitland Middle


  • 2681 FITZHUGH RD, WINTER PARK, FL 32792

    $750,00063 Days on yellowkey   MLS ID: O6383699

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

    For Sale O6383699 - 2681 FITZHUGH RD, WINTER PARK, FL 32792 55 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2375
       Built: 1966   Tax: $5,903 (2024)
    Community: Winter Park Pines Merrie Oaks
    Single Family


    Estimated Monthly Payment: $4,601 (change assumption)
    Mortgage ($4,109) + Taxes in 2024 ($492)


    Taxes:$5,903

    Elementary School: Aloma Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Glenridge Middle


  • 1809 HAMMERLIN AVE, WINTER PARK, FL 32789

    $585,00099 Days on yellowkey   MLS ID: O6373616

    For Sale O6373616 - 1809 HAMMERLIN AVE, WINTER PARK, FL 32789 44 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1818
       Built: 2006   Tax: $5,826 (2024)
    Community: Terazzo Del Sol Condo Assn Inc
    Condo


    Estimated Monthly Payment: $3,691 (change assumption)
    Mortgage ($3,205) + Taxes in 2024 ($486)


    Taxes:$5,826

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Audubon Park K-8


  • 1849 VIBURNUM LN, WINTER PARK, FL 32792

    $425,000259 Days on yellowkey   MLS ID: O6333863

    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: $2,632 (change assumption)
    Mortgage ($2,329) + Taxes in 2024 ($304)


    Taxes:$3,645

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 1905 BONANZA CT, WINTER PARK, FL 32792

    $490,0007 Days on yellowkey   MLS ID: O6398772

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

    For Sale O6398772 - 1905 BONANZA CT, WINTER PARK, FL 32792 35 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1774
       Built: 1968   Tax: $5,015 (2024)
    Community: Eastbrook Sub Unit 13
    Single Family


    Estimated Monthly Payment: $3,103 (change assumption)
    Mortgage ($2,685) + Taxes in 2024 ($418)


    Taxes:$5,015

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 1177 KENWOOD AVE, WINTER PARK, FL 32789

    $1,870,00041 Days on yellowkey   MLS ID: O6390592

    REDUCED by $100,000 (5.1%) on 04/01/2026

    For Sale O6390592 - 1177 KENWOOD AVE, WINTER PARK, FL 32789 57 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 4363
       Built: 2007   Tax: $16,206 (2025)
    Community: Dixie Terrace
    Spa: No

    Single Family


    Estimated Monthly Payment: $11,597 (change assumption)
    Mortgage ($10,246) + Taxes in 2025 ($1,351)


    Taxes:$16,206

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


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

    $180,000377 Days on yellowkey   MLS ID: O6297570

    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: $1,545 (change assumption)
    Mortgage ($986) + 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


  • 2299 VIA TUSCANY, WINTER PARK, FL 32789

    $2,200,000170 Days on yellowkey   MLS ID: O6355858

    For Sale O6355858 - 2299 VIA TUSCANY, WINTER PARK, FL 32789 60 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3986
       Built: 1953   Tax: $26,035 (2025)
    Community: Maitland Shores
    Single Family


    Estimated Monthly Payment: $14,224 (change assumption)
    Mortgage ($12,054) + Taxes in 2025 ($2,170)


    Taxes:$26,035

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 1840 BRYAN AVE, WINTER PARK, FL 32789

    $1,849,00034 Days on yellowkey   MLS ID: O6391922

    REDUCED by $50,500 (2.7%) on 04/20/2026

    For Sale O6391922 - 1840 BRYAN AVE, WINTER PARK, FL 32789 46 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3727
       Built: 2014   Tax: $19,607 (2025)
    Community: Lakeview Terrace
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $11,765 (change assumption)
    Mortgage ($10,131) + Taxes in 2025 ($1,634)


    Taxes:$19,607

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 1841 HARLAND PARK DR, WINTER PARK, FL 32789

    $1,895,000115 Days on yellowkey   MLS ID: O6369653

    0 Days Off yellowkey (back on 4/11/2026)

    For Sale O6369653 - 1841 HARLAND PARK DR, WINTER PARK, FL 32789 78 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3470
       Built: 2014
    Monthly Fee: $262
       Tax: $21,031 (2024)
    Community: Windsong-Knowles Place
    Single Family


    Estimated Monthly Payment: $12,398 (change assumption)
    Mortgage ($10,383) + Fees ($262) + Taxes in 2024 ($1,753)


    Taxes:$21,031

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Glenridge Middle


  • 3220 NETHERWOOD DR, WINTER PARK, FL 32792

    $269,00097 Days on yellowkey   MLS ID: O6374172

    REDUCED by $10,990 (3.9%) on 04/20/2026

    For Sale O6374172 - 3220 NETHERWOOD DR, WINTER PARK, FL 32792 18 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1036
       Built: 1982   Tax: $1,222 (2025)
    Community: Coronation Add
    Half Duplex


    Estimated Monthly Payment: $1,576 (change assumption)
    Mortgage ($1,474) + Taxes in 2025 ($102)


    Taxes:$1,222

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 5331 OAK CT, WINTER PARK, FL 32792

    $460,000281 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

    $470,00089 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

    $1,399,00041 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

    $200,00065 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

    $4,195,0007 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




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.