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Winter Park Single Family Homes For Sale - 283 homes

Winter Park Single Family Homes for Sale are located in Orange 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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  • 2715 PRINCE JOHN RD, WINTER PARK, FL 32792

    $494,90051 Days on yellowkey   MLS ID: O6415084

    REDUCED by $4,000 (0.8%) on 07/22/2026

    For Sale O6415084 - 2715 PRINCE JOHN RD, WINTER PARK, FL 32792 29 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1565
       Built: 1963   Tax: $7,101 (2025)
    Community: Winter Park Pines Rep
    Single Family


    Estimated Monthly Payment: $3,303 (change assumption)
    Mortgage ($2,712) + Taxes in 2025 ($592)


    Taxes:$7,101

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 2087 LAURELWOOD WAY, WINTER PARK, FL 32792

    $625,00048 Days on yellowkey   MLS ID: O6415387

    1 Days Off yellowkey (back on 7/22/2026)

    For Sale O6415387 - 2087 LAURELWOOD WAY, WINTER PARK, FL 32792 48 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1920
       Built: 2019
    Monthly Fee: $244
       Tax: $4,970 (2025)
    Community: Hawks Crest
    Single Family


    Estimated Monthly Payment: $4,083 (change assumption)
    Mortgage ($3,425) + Fees ($244) + Taxes in 2025 ($414)


    Taxes:$4,970

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 550 PALMER AVE, WINTER PARK, FL 32789

    $6,495,000280 Days on yellowkey   MLS ID: O6349188

    REDUCED by $400,000 (5.8%) on 05/07/2026

    For Sale O6349188 - 550 PALMER AVE, WINTER PARK, FL 32789 76 photos

    Bed: 5   Bath: 6.5   Gar: 3
    Liv Area Sq Ft: 5939
       Built: 2025   Tax: $10,292 (2025)
    Community: Osceola Place
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $36,446 (change assumption)
    Mortgage ($35,588) + Taxes in 2025 ($858)


    Taxes:$10,292

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 1189 LAZY HOLLOW PL, WINTER PARK, FL 32792

    $445,00026 Days on yellowkey   MLS ID: O6422142

    3 Days Off yellowkey (back on 7/22/2026)

    REDUCED by $5,000 (1.1%) on 07/15/2026

    For Sale O6422142 - 1189 LAZY HOLLOW PL, WINTER PARK, FL 32792 59 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1525
       Built: 1984   Tax: $2,369 (2025)
    Community: Springview
    Single Family


    Estimated Monthly Payment: $2,636 (change assumption)
    Mortgage ($2,438) + Taxes in 2025 ($197)


    Taxes:$2,369

    Elementary School: Red Bug Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 338 BLUE HERON DR, WINTER PARK, FL 32789

    $865,00060 Days on yellowkey   MLS ID: O6410174

    For Sale O6410174 - 338 BLUE HERON DR, WINTER PARK, FL 32789 44 photos

    Bed: 3   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2017
       Built: 1960   Tax: $6,647 (2025)
    Community: Flamingo Shores
    Single Family


    Estimated Monthly Payment: $5,294 (change assumption)
    Mortgage ($4,740) + Taxes in 2025 ($554)


    Taxes:$6,647

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park Middle


  • 40 PALMER AVE, WINTER PARK, FL 32789

    $7,250,000170 Days on yellowkey   MLS ID: O6380444

    INCREASED by $300,000 (4.3%) on 07/09/2026

    For Sale O6380444 - 40 PALMER AVE, WINTER PARK, FL 32789 18 photos

    Bed: 5   Bath: 5.5   Gar: 4
    Liv Area Sq Ft: 5905
       Built: 2026   Tax: $12,774 (2024)
    Community: Robert Dhu Macdonald Park
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $40,790 (change assumption)
    Mortgage ($39,725) + Taxes in 2024 ($1,065)


    Taxes:$12,774

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Maitland Middle


  • 2831 MULFORD AVE, WINTER PARK, FL 32789

    $675,00052 Days on yellowkey   MLS ID: O6414319

    REDUCED by $20,000 (2.9%) on 07/21/2026

    For Sale O6414319 - 2831 MULFORD AVE, WINTER PARK, FL 32789 28 photos

    Bed: 4   Bath: 2.5
    Liv Area Sq Ft: 1647
       Built: 1952   Tax: $3,192 (2025)
    Community: Orangewood Park
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,965 (change assumption)
    Mortgage ($3,699) + Taxes in 2025 ($266)


    Taxes:$3,192

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1610 GLADIOLAS DR, WINTER PARK, FL 32792

    $410,00032 Days on yellowkey   MLS ID: O6420292

    REDUCED by $20,000 (4.7%) on 07/21/2026

    For Sale O6420292 - 1610 GLADIOLAS DR, WINTER PARK, FL 32792 42 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1808
       Built: 1979   Tax: $1,442 (2025)
    Community: Garden Lake Estates Unit 1
    Single Family


    Estimated Monthly Payment: $2,367 (change assumption)
    Mortgage ($2,247) + Taxes in 2025 ($120)


    Taxes:$1,442

    Elementary School: Red Bug Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 2006 CORNELL AVE, WINTER PARK, FL 32789

    $328,00057 Days on yellowkey   MLS ID: O6412789

    REDUCED by $10,000 (3.0%) on 07/21/2026

    For Sale O6412789 - 2006 CORNELL AVE, WINTER PARK, FL 32789 28 photos

    Bed: 2   Bath: 1.0
    Liv Area Sq Ft: 797
       Built: 1940   Tax: $4,795 (2025)
    Community: Stansbury Estates
    Single Family


    Estimated Monthly Payment: $2,197 (change assumption)
    Mortgage ($1,797) + Taxes in 2025 ($400)


    Taxes:$4,795

    Elementary School: Princeton Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park Middle


  • 241 W LAKE SUE AVE, WINTER PARK, FL 32789

    $995,00062 Days on yellowkey   MLS ID: O6411621

    REDUCED by $4,000 (0.4%) on 07/21/2026

    For Sale O6411621 - 241 W LAKE SUE AVE, WINTER PARK, FL 32789 58 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2304
       Built: 1950   Tax: $14,823 (2025)
    Community: Virginia Heights
    Single Family


    Estimated Monthly Payment: $6,687 (change assumption)
    Mortgage ($5,452) + Taxes in 2025 ($1,235)


    Taxes:$14,823

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 1841 LAKE SPIER DRIVE, WINTER PARK, FL 32789

    $1,595,00063 Days on yellowkey   MLS ID: O6407841

    REDUCED by $55,000 (3.3%) on 07/02/2026

    For Sale O6407841 - 1841 LAKE SPIER DRIVE, WINTER PARK, FL 32789 33 photos

    Bed: 3   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 2467
       Built: 1964   Tax: $4,844 (2025)
    Community: South Lakemont Shores
    Spa: No

    Single Family


    Estimated Monthly Payment: $9,143 (change assumption)
    Mortgage ($8,740) + Taxes in 2025 ($404)


    Taxes:$4,844

    Elementary School: Baldwin Park Elementary

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 1113 VIA DEL MAR, WINTER PARK, FL 32789

    $1,595,000175 Days on yellowkey   MLS ID: O6379697

    1 Days Off yellowkey (back on 7/21/2026)

    For Sale O6379697 - 1113 VIA DEL MAR, WINTER PARK, FL 32789 9 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2012
       Built: 1957   Tax: $13,924 (2024)
    Community: Tuscany Terrace
    Spa: No

    Single Family


    Estimated Monthly Payment: $9,900 (change assumption)
    Mortgage ($8,740) + Taxes in 2024 ($1,160)


    Taxes:$13,924

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Maitland Middle


  • 1823 SUNSET DR, WINTER PARK, FL 32789

    $2,549,00022 Days on yellowkey   MLS ID: O6421690

    For Sale O6421690 - 1823 SUNSET DR, WINTER PARK, FL 32789 14 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3479
       Built: 2026   Tax: $3,358 (2025)
    Community: Lake Knowles Terrace Add 02
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $14,247 (change assumption)
    Mortgage ($13,967) + Taxes in 2025 ($280)


    Taxes:$3,358

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 938 GOLFSIDE DR, WINTER PARK, FL 32792

    $820,00013 Days on yellowkey   MLS ID: O6425467

    0 Days Off yellowkey (back on 7/21/2026)

    For Sale O6425467 - 938 GOLFSIDE DR, WINTER PARK, FL 32792 48 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2366
       Built: 1968   Tax: $5,917 (2025)
    Community: Golfside Sec 2
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,986 (change assumption)
    Mortgage ($4,493) + Taxes in 2025 ($493)


    Taxes:$5,917

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 528 SAINT DUNSTAN WAY, WINTER PARK, FL 32792

    $524,99049 Days on yellowkey   MLS ID: O6414677

    0 Days Off yellowkey (back on 7/21/2026)

    REDUCED by $10,010 (1.9%) on 07/11/2026

    For Sale O6414677 - 528 SAINT DUNSTAN WAY, WINTER PARK, FL 32792 35 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1656
       Built: 1964   Tax: $6,000 (2025)
    Community: Winter Park Pines
    Single Family


    Estimated Monthly Payment: $3,377 (change assumption)
    Mortgage ($2,877) + Taxes in 2025 ($500)


    Taxes:$6,000

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 840 W CANTON AVE, WINTER PARK, FL 32789

    $649,90058 Days on yellowkey   MLS ID: O6412754

    REDUCED by $25,100 (3.7%) on 07/21/2026

    For Sale O6412754 - 840 W CANTON AVE, WINTER PARK, FL 32789 63 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1370
       Built: 1952   Tax: $5,722 (2025)
    Community: N/A
    Single Family


    Estimated Monthly Payment: $4,038 (change assumption)
    Mortgage ($3,561) + Taxes in 2025 ($477)


    Taxes:$5,722

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 5117 CYPRESS CT, WINTER PARK, FL 32792

    $449,99076 Days on yellowkey   MLS ID: O6407713

    1 Days Off yellowkey (back on 6/20/2026)

    For Sale O6407713 - 5117 CYPRESS CT, WINTER PARK, FL 32792 26 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1534
       Built: 1972   Tax: $3,877 (2025)
    Community: Wrenwood Heights
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,789 (change assumption)
    Mortgage ($2,466) + Taxes in 2025 ($323)


    Taxes:$3,877

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2240 VENETIAN WAY, WINTER PARK, FL 32789

    $3,500,00054 Days on yellowkey   MLS ID: O6413398

    For Sale O6413398 - 2240 VENETIAN WAY, WINTER PARK, FL 32789 25 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 4036
       Built: 2011   Tax: $26,300 (2025)
    Community: Maitland Shores 1St Add
    Spa: No

    Single Family


    Estimated Monthly Payment: $21,369 (change assumption)
    Mortgage ($19,178) + Taxes in 2025 ($2,192)


    Taxes:$26,300

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 2412 CHANTILLY AVE, WINTER PARK, FL 32789

    $2,394,500168 Days on yellowkey   MLS ID: O6381552

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

    REDUCED by $500 (0.0%) on 04/20/2026

    For Sale O6381552 - 2412 CHANTILLY AVE, WINTER PARK, FL 32789 61 photos

    Bed: 5   Bath: 6.5   Gar: 3
    Liv Area Sq Ft: 4506
       Built: 2026   Tax: $4,779 (2025)
    Community: Winter Park Village
    Single Family


    Estimated Monthly Payment: $13,518 (change assumption)
    Mortgage ($13,120) + Taxes in 2025 ($398)


    Taxes:$4,779

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 1870 WALKER AVE, WINTER PARK, FL 32789

    $1,225,000138 Days on yellowkey   MLS ID: O6390504

    REDUCED by $74,000 (5.7%) on 07/07/2026

    For Sale O6390504 - 1870 WALKER AVE, WINTER PARK, FL 32789 32 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: $7,044 (change assumption)
    Mortgage ($6,712) + Taxes in 2025 ($332)


    Taxes:$3,981

    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.