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Winter Park Homes For Sale & Real Estate - 382 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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  • 1780 MONDRIAN CIR, WINTER PARK, FL 32789

    $1,395,00041 Days on yellowkey   MLS ID: O6389472

    For Sale O6389472 - 1780 MONDRIAN CIR, WINTER PARK, FL 32789 51 photos

    Bed: 3   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2310
       Built: 2023
    Monthly Fee: $395
       Tax: $10,448 (2024)
    Community: Mondrian/Winder Park Twnhms
    Spa: No

    Townhouse


    Estimated Monthly Payment: $8,909 (change assumption)
    Mortgage ($7,644) + Fees ($395) + Taxes in 2024 ($871)


    Taxes:$10,448

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2024

    Middle School: College Park Middle


  • 2501 TAHOE CIR, WINTER PARK, FL 32792

    $259,90084 Days on yellowkey   MLS ID: O6378209

    2 Days Off yellowkey (back on 4/21/2026)

    REDUCED by $10,000 (3.7%) on 04/05/2026

    For Sale O6378209 - 2501 TAHOE CIR, WINTER PARK, FL 32792 36 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1495
       Built: 1981   Tax: $3,757 (2025)
    Community: Cedarwood Village 1
    Condo


    Estimated Monthly Payment: $1,737 (change assumption)
    Mortgage ($1,424) + Taxes in 2025 ($313)


    Taxes:$3,757

    Elementary School: English Estates Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 7301 CEDAR CREEK CT #66, WINTER PARK, FL 32792

    $187,50014 Days on yellowkey   MLS ID: O6397477

    For Sale O6397477 - 7301 CEDAR CREEK CT #66, WINTER PARK, FL 32792 44 photos

    Bed: 2   Bath: 2.5
    Liv Area Sq Ft: 1031
       Built: 1983
    Monthly Fee: $10
       Tax: $2,731 (2025)
    Community: Hidden Oaks Condo Ph 04
    Condo


    Estimated Monthly Payment: $1,265 (change assumption)
    Mortgage ($1,027) + Fees ($10) + Taxes in 2025 ($228)


    Taxes:$2,731

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1923 LINDEN RD, WINTER PARK, FL 32792

    $475,00024 Days on yellowkey   MLS ID: O6393643

    REDUCED by $24,999 (5.0%) on 04/17/2026

    For Sale O6393643 - 1923 LINDEN RD, WINTER PARK, FL 32792 33 photos

    Bed: 4   Bath: 3.0
    Liv Area Sq Ft: 2117
       Built: 1955   Tax: $340 (2024)
    Community: Tanglewood Sec 4
    Single Family


    Estimated Monthly Payment: $2,631 (change assumption)
    Mortgage ($2,603) + Taxes in 2024 ($28)


    Taxes:$340

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 259 E CANTON AVE #259, WINTER PARK, FL 32789

    $619,00044 Days on yellowkey   MLS ID: O6389246

    REDUCED by $10,000 (1.6%) on 04/19/2026

    For Sale O6389246 - 259 E CANTON AVE #259, WINTER PARK, FL 32789 36 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1040
       Built: 1971   Tax: $3,603 (2025)
    Community: Village Winterset Inc
    Condo


    Estimated Monthly Payment: $3,692 (change assumption)
    Mortgage ($3,392) + Taxes in 2025 ($300)


    Taxes:$3,603

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 3028 GEORGE MASON AVE #J-7E, WINTER PARK, FL 32792

    $105,0008 Days on yellowkey   MLS ID: O6398380

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

    For Sale O6398380 - 3028 GEORGE MASON AVE #J-7E, WINTER PARK, FL 32792 25 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1088
       Built: 1974
    Monthly Fee: $427
       Tax: $1,989 (2025)
    Community: Colonies
    Condo


    Estimated Monthly Payment: $1,168 (change assumption)
    Mortgage ($575) + Fees ($427) + Taxes in 2025 ($166)


    Taxes:$1,989

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2401 ANTILLES DR, WINTER PARK, FL 32792

    $320,000169 Days on yellowkey   MLS ID: O6357934

    For Sale O6357934 - 2401 ANTILLES DR, WINTER PARK, FL 32792 33 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1719
       Built: 1977
    Monthly Fee: $95

    Community: Windward Square Sec 1
    Townhouse


    Estimated Monthly Payment: $1,848 (change assumption)
    Mortgage ($1,753) + Fees ($95) + Taxes in 2024 ($0)


    Taxes:$0

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 1792 CHILEAN LN, WINTER PARK, FL 32792

    $325,00091 Days on yellowkey   MLS ID: O6375881

    1 Days Off yellowkey (back on 4/21/2026)

    For Sale O6375881 - 1792 CHILEAN LN, WINTER PARK, FL 32792 30 photos

    Bed: 3   Bath: 1.0
    Liv Area Sq Ft: 984
       Built: 1959   Tax: $2,677 (2024)
    Community: Eastbrook Sub Unit 05
    Single Family


    Estimated Monthly Payment: $2,004 (change assumption)
    Mortgage ($1,781) + Taxes in 2024 ($223)


    Taxes:$2,677

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 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


  • 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




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.