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Winter Park Single Family Homes For Sale - 250 homes

Winter Park Single Family Homes for Sale are located in Seminole County, Florida. Find single family homes for sale in Winter Park with data from the Multiple Listing Service (MLS). Our REALTORS® can assist you in your real estate search for Winter Park single family houses.

Location: Winter Park

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  • 1923 LINDEN RD, WINTER PARK, FL 32792

    $475,00023 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


  • 1398 GROVE TER, WINTER PARK, FL 32789

    $2,195,0006 Days on yellowkey   MLS ID: O6399698

    For Sale O6399698 - 1398 GROVE TER, WINTER PARK, FL 32789 59 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3450
       Built: 2004   Tax: $24,548 (2025)
    Community: Sylvan Lake Shores
    Spa: No

    Single Family


    Estimated Monthly Payment: $14,073 (change assumption)
    Mortgage ($12,027) + Taxes in 2025 ($2,046)


    Taxes:$24,548

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 1161 VALENCIA AVE, WINTER PARK, FL 32789

    $4,270,000244 Days on yellowkey   MLS ID: O6330736

    REDUCED by $25,000 (0.6%) on 04/21/2026

    For Sale O6330736 - 1161 VALENCIA AVE, WINTER PARK, FL 32789 65 photos

    Bed: 4   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 4181
       Built: 2021   Tax: $30,421 (2024)
    Community: Valencia Terrace
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $25,932 (change assumption)
    Mortgage ($23,397) + Taxes in 2024 ($2,535)


    Taxes:$30,421

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Maitland Middle


  • 1792 CHILEAN LN, WINTER PARK, FL 32792

    $325,00090 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

    $679,8006 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

    $2,795,00021 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


  • 5330 TANGERINE AVE, WINTER PARK, FL 32792

    $354,9007 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

    $1,675,000307 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

    $750,00062 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


  • 1849 VIBURNUM LN, WINTER PARK, FL 32792

    $425,000258 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

    $490,0006 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

    $1,870,00040 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


  • 2299 VIA TUSCANY, WINTER PARK, FL 32789

    $2,200,000169 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

    $1,849,00033 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

    $1,895,000114 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


  • 5331 OAK CT, WINTER PARK, FL 32792

    $460,000280 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

    $470,00088 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

    $1,399,00040 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


  • 2020 VIA TUSCANY, WINTER PARK, FL 32789

    $4,195,0006 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


  • 731 BONGART RD, WINTER PARK, FL 32792

    $499,999110 Days on yellowkey   MLS ID: S5140952

    For Sale S5140952 - 731 BONGART RD, WINTER PARK, FL 32792 25 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 1826
       Built: 1961   Tax: $5,910 (2025)
    Community: Winter Park Estates
    Single Family


    Estimated Monthly Payment: $3,232 (change assumption)
    Mortgage ($2,740) + Taxes in 2025 ($493)


    Taxes:$5,910

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle




Why Bother Searching Elsewhere for Winter Park Single Family Homes for Sale?

Winter Park home, townhome, and condo, villa, and other listing sale 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 single family homes for sale in Winter Park . You can use our website to view Multiple Listing Service (MLS) data on Winter Park single family homes. 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 single family home 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.