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Winter Park Single Family Homes For Sale - 284 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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  • 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


  • 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


  • 281 BREWER AVE, WINTER PARK, FL 32789

    $1,800,0009 Days on yellowkey   MLS ID: O6424364

    SHORT SALE O6424364 - 281 BREWER AVE, WINTER PARK, FL 32789 54 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 4029
       Built: 2022   Tax: $26,908 (2025)
    Community: Osceola Shores Sec 02
    Single Family


    Estimated Monthly Payment: $12,105 (change assumption)
    Mortgage ($9,863) + Taxes in 2025 ($2,242)


    Taxes:$26,908

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 501 LAKEVIEW AVE, WINTER PARK, FL 32789

    $1,390,000376 Days on yellowkey   MLS ID: O6325192

    0 Days Off yellowkey (back on 7/20/2026)

    For Sale O6325192 - 501 LAKEVIEW AVE, WINTER PARK, FL 32789 59 photos

    Bed: 4   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3253
       Built: 2026   Tax: $2,820 (2024)
    Community: Killarney Estates
    Single Family


    Estimated Monthly Payment: $7,851 (change assumption)
    Mortgage ($7,616) + Taxes in 2024 ($235)


    Taxes:$2,820

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2024

    Middle School: College Park Middle


  • Lot #21 KAROLINA AVE, WINTER PARK, FL 32789

    $918,000138 Days on yellowkey   MLS ID: O6387812

    REDUCED by $26,890 (2.8%) on 07/20/2026

    For Sale O6387812 - Lot #21 KAROLINA AVE, WINTER PARK, FL 32789 9 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2662
       Built: 2025   Tax: $2,207 (2024)
    Community: Karolina On Killarney
    Single Family


    Estimated Monthly Payment: $5,214 (change assumption)
    Mortgage ($5,030) + Taxes in 2024 ($184)


    Taxes:$2,207

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2024

    Middle School: Maitland Middle


  • 5340 N LAKE BURKETT LN, WINTER PARK, FL 32792

    $459,00054 Days on yellowkey   MLS ID: O6413717

    REDUCED by $10,900 (2.3%) on 07/20/2026

    For Sale O6413717 - 5340 N LAKE BURKETT LN, WINTER PARK, FL 32792 33 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1746
       Built: 1994
    Monthly Fee: $76
       Tax: $1,591 (2025)
    Community: Trinity Bay Ph 2
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,724 (change assumption)
    Mortgage ($2,515) + Fees ($76) + Taxes in 2025 ($133)


    Taxes:$1,591

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 1287 VERDANT GLADE PL, WINTER PARK, FL 32792

    $799,90096 Days on yellowkey   MLS ID: O6400331

    REDUCED by $25,100 (3.0%) on 07/20/2026

    For Sale O6400331 - 1287 VERDANT GLADE PL, WINTER PARK, FL 32792 50 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3020
       Built: 2020
    Monthly Fee: $413
       Tax: $6,133 (2025)
    Community: Meadows At Hawks Crest
    Single Family


    Estimated Monthly Payment: $5,307 (change assumption)
    Mortgage ($4,383) + Fees ($413) + Taxes in 2025 ($511)


    Taxes:$6,133

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 2189 SUSSEX RD, WINTER PARK, FL 32792

    $375,00020 Days on yellowkey   MLS ID: O6423782

    0 Days Off yellowkey (back on 7/20/2026)

    FORECLOSURE O6423782 - 2189 SUSSEX RD, WINTER PARK, FL 32792 29 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1776
       Built: 1968
    Monthly Fee: $2
       Tax: $4,646 (2025)
    Community: Winter Woods Unit 01
    Single Family


    Estimated Monthly Payment: $2,444 (change assumption)
    Mortgage ($2,055) + Fees ($2) + Taxes in 2025 ($387)


    Taxes:$4,646

    Elementary School: English Estates Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 2008 HOUNDSLAKE DR, WINTER PARK, FL 32792

    $490,00044 Days on yellowkey   MLS ID: O6414369

    REDUCED by $25,000 (4.9%) on 07/20/2026

    For Sale O6414369 - 2008 HOUNDSLAKE DR, WINTER PARK, FL 32792 33 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2250
       Built: 1980   Tax: $5,253 (2025)
    Community: Cedar Ridge
    Single Family


    Estimated Monthly Payment: $3,123 (change assumption)
    Mortgage ($2,685) + Taxes in 2025 ($438)


    Taxes:$5,253

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 316 BECKETT CT, WINTER PARK, FL 32792

    $450,00063 Days on yellowkey   MLS ID: O6411108

    For Sale O6411108 - 316 BECKETT CT, WINTER PARK, FL 32792 33 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1651
       Built: 1966   Tax: $2,232 (2025)
    Community: Winter Park Pines Merrie Oaks
    Single Family


    Estimated Monthly Payment: $2,652 (change assumption)
    Mortgage ($2,466) + Taxes in 2025 ($186)


    Taxes:$2,232

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 501 HERITAGE BLVD, WINTER PARK, FL 32792

    $458,000138 Days on yellowkey   MLS ID: S5145746

    REDUCED by $11,000 (2.3%) on 07/20/2026

    For Sale S5145746 - 501 HERITAGE BLVD, WINTER PARK, FL 32792 20 photos

    Bed: 4   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1376
       Built: 1966   Tax: $10,434 (2025)
    Community: Georgetown Estates
    Single Family


    Estimated Monthly Payment: $3,379 (change assumption)
    Mortgage ($2,510) + Taxes in 2025 ($870)


    Taxes:$10,434

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 1600 LEGION DR, WINTER PARK, FL 32789

    $3,795,00046 Days on yellowkey   MLS ID: O6415591

    REDUCED by $200,000 (5.0%) on 07/13/2026

    For Sale O6415591 - 1600 LEGION DR, WINTER PARK, FL 32789 70 photos

    Bed: 5   Bath: 5.5   Gar: 3
    Liv Area Sq Ft: 4483
       Built: 2008   Tax: $20,740 (2025)
    Community: Green Oaks Rep
    Spa: No

    Single Family


    Estimated Monthly Payment: $22,522 (change assumption)
    Mortgage ($20,794) + Taxes in 2025 ($1,728)


    Taxes:$20,740

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 1864 GRINNELL TER, WINTER PARK, FL 32789

    $1,599,00089 Days on yellowkey   MLS ID: O6403822

    For Sale O6403822 - 1864 GRINNELL TER, WINTER PARK, FL 32789 43 photos

    Bed: 5   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3028
       Built: 2006   Tax: $16,615 (2025)
    Community: Fremar
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $10,146 (change assumption)
    Mortgage ($8,761) + Taxes in 2025 ($1,385)


    Taxes:$16,615

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge 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.