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Winter Park Single Family Homes For Sale - 242 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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  • 1540 MILLER AVE, WINTER PARK, FL 32789

    $1,399,9005 Days on yellowkey   MLS ID: O6398421

    For Sale O6398421 - 1540 MILLER AVE, WINTER PARK, FL 32789 55 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2984
       Built: 2026   Tax: $3,573 (2025)
    Community: Lawndale
    Spa: No

    Single Family


    Estimated Monthly Payment: $7,968 (change assumption)
    Mortgage ($7,670) + Taxes in 2025 ($298)


    Taxes:$3,573

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park Middle


  • 3110 HEARTLEAF PL, WINTER PARK, FL 32792

    $629,0008 Days on yellowkey   MLS ID: O6397396

    3 Days Off yellowkey (back on 4/16/2026)

    For Sale O6397396 - 3110 HEARTLEAF PL, WINTER PARK, FL 32792 43 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2704
       Built: 1998
    Monthly Fee: $21
       Tax: $7,231 (2025)
    Community: Lost Creek
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $4,070 (change assumption)
    Mortgage ($3,446) + Fees ($21) + Taxes in 2025 ($603)


    Taxes:$7,231

    Elementary School: Red Bug Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 1711 BARCELONA WAY, WINTER PARK, FL 32789

    $2,100,00094 Days on yellowkey   MLS ID: O6372739

    0 Days Off yellowkey (back on 4/16/2026)

    For Sale O6372739 - 1711 BARCELONA WAY, WINTER PARK, FL 32789 60 photos

    Bed: 5   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 3669
       Built: 1979
    Monthly Fee: $87
       Tax: $23,155 (2025)
    Community: Sevilla
    Spa: No

    Single Family


    Estimated Monthly Payment: $13,523 (change assumption)
    Mortgage ($11,507) + Fees ($87) + Taxes in 2025 ($1,930)


    Taxes:$23,155

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 1441 CARDINAL CT, WINTER PARK, FL 32789

    $4,285,0003 Days on yellowkey   MLS ID: O6399395

    For Sale O6399395 - 1441 CARDINAL CT, WINTER PARK, FL 32789 85 photos

    Bed: 4   Bath: 5.5   Gar: 2
    Liv Area Sq Ft: 4066
       Built: 2022   Tax: $47,740 (2025)
    Community: Winflor Court
    Spa: No

    Single Family


    Estimated Monthly Payment: $27,457 (change assumption)
    Mortgage ($23,479) + Taxes in 2025 ($3,978)


    Taxes:$47,740

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 1905 BONANZA CT, WINTER PARK, FL 32789

    $490,0002 Days on yellowkey   MLS ID: O6398772

    For Sale O6398772 - 1905 BONANZA CT, WINTER PARK, FL 32789 34 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


  • 405 LAKE FAIR LN, WINTER PARK, FL 32789

    $459,99924 Days on yellowkey   MLS ID: O6393594

    For Sale O6393594 - 405 LAKE FAIR LN, WINTER PARK, FL 32789 45 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1491
       Built: 1957   Tax: $1,355 (2025)
    Community: Fairbanks Shores 5Th Add
    Single Family


    Estimated Monthly Payment: $2,633 (change assumption)
    Mortgage ($2,520) + Taxes in 2025 ($113)


    Taxes:$1,355

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • WINTER PARK, FL 32792

    $430,00037 Days on yellowkey   MLS ID: S5145631

    REDUCED by $10,000 (2.3%) on 04/15/2026

    For Sale S5145631 - WINTER PARK, FL 32792 11 photos

    Bed: 4   Bath: 2.0
    Liv Area Sq Ft: 1296
       Built: 1958   Tax: $4,968 (2025)
    Community: Winter Park Estates
    Single Family


    Estimated Monthly Payment: $2,770 (change assumption)
    Mortgage ($2,356) + Taxes in 2025 ($414)


    Taxes:$4,968

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 640 ARJAY WAY, WINTER PARK, FL 32789

    $1,925,00088 Days on yellowkey   MLS ID: O6372947

    REDUCED by $49,900 (2.5%) on 04/15/2026

    For Sale O6372947 - 640 ARJAY WAY, WINTER PARK, FL 32789 46 photos

    Bed: 5   Bath: 4.0   Gar: 3
    Liv Area Sq Ft: 3953
       Built: 1958   Tax: $11,586 (2024)
    Community: Timberlane Shores
    Single Family


    Estimated Monthly Payment: $11,513 (change assumption)
    Mortgage ($10,548) + Taxes in 2024 ($965)


    Taxes:$11,586

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Audubon Park K-8


  • 250 CORTLAND AVE, WINTER PARK, FL 32789

    $950,00015 Days on yellowkey   MLS ID: O6395137

    For Sale O6395137 - 250 CORTLAND AVE, WINTER PARK, FL 32789 46 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2114
       Built: 1981   Tax: $4,370 (2024)
    Community: Cortland Park
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $5,569 (change assumption)
    Mortgage ($5,205) + Taxes in 2024 ($364)


    Taxes:$4,370

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 2330 COLDSTREAM DR, WINTER PARK, FL 32792

    $650,00026 Days on yellowkey   MLS ID: O6384436

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

    For Sale O6384436 - 2330 COLDSTREAM DR, WINTER PARK, FL 32792 20 photos

    Bed: 4   Bath: 2.0
    Liv Area Sq Ft: 1750
       Built: 1958   Tax: $6,951 (2024)
    Community: Brookshire Heights
    Single Family


    Estimated Monthly Payment: $4,141 (change assumption)
    Mortgage ($3,562) + Taxes in 2024 ($579)


    Taxes:$6,951

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Glenridge Middle


  • 2007 EDWIN BLVD, WINTER PARK, FL 32792

    $369,90012 Days on yellowkey   MLS ID: O6396498

    REDUCED by $5,100 (1.4%) on 04/15/2026

    For Sale O6396498 - 2007 EDWIN BLVD, WINTER PARK, FL 32792 16 photos

    Bed: 4   Bath: 1.5
    Liv Area Sq Ft: 1296
       Built: 1955   Tax: $3,535 (2025)
    Community: Eastgate Sub
    Single Family


    Estimated Monthly Payment: $2,321 (change assumption)
    Mortgage ($2,027) + Taxes in 2025 ($295)


    Taxes:$3,535

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 3312 HEARTWOOD AVE, WINTER PARK, FL 32792

    $465,000182 Days on yellowkey   MLS ID: O6352582

    1 Days Off yellowkey (back on 4/13/2026)

    REDUCED by $19,000 (3.9%) on 04/08/2026

    For Sale O6352582 - 3312 HEARTWOOD AVE, WINTER PARK, FL 32792 36 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2878
       Built: 1983   Tax: $2,183 (2025)
    Community: Bel-Aire Pines
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,730 (change assumption)
    Mortgage ($2,548) + Taxes in 2025 ($182)


    Taxes:$2,183

    Elementary School: Aloma Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 1885 TEMPLE DR, WINTER PARK, FL 32789

    $2,265,000157 Days on yellowkey   MLS ID: O6359471

    For Sale O6359471 - 1885 TEMPLE DR, WINTER PARK, FL 32789 53 photos

    Bed: 5   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3691
       Built: 1963   Tax: $6,073 (2025)
    Community: Lugano Terrace
    Spa: No

    Single Family


    Estimated Monthly Payment: $12,917 (change assumption)
    Mortgage ($12,411) + Taxes in 2025 ($506)


    Taxes:$6,073

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 1108 FAIRWAY DR, WINTER PARK, FL 32792

    $725,00050 Days on yellowkey   MLS ID: O6386266

    For Sale O6386266 - 1108 FAIRWAY DR, WINTER PARK, FL 32792 46 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1677
       Built: 1978   Tax: $6,713 (2024)
    Community: Golfside Sec 03
    Single Family


    Estimated Monthly Payment: $4,532 (change assumption)
    Mortgage ($3,973) + Taxes in 2024 ($559)


    Taxes:$6,713

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Glenridge Middle


  • 1340 BLUE STEM LN, WINTER PARK, FL 32792

    $724,900109 Days on yellowkey   MLS ID: O6365415

    REDUCED by $5,000 (0.7%) on 04/11/2026

    For Sale O6365415 - 1340 BLUE STEM LN, WINTER PARK, FL 32792 48 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2587
       Built: 2022
    Monthly Fee: $235
       Tax: $6,594 (2025)
    Community: Landings At Hawks Crest
    Single Family


    Estimated Monthly Payment: $4,756 (change assumption)
    Mortgage ($3,972) + Fees ($235) + Taxes in 2025 ($550)


    Taxes:$6,594

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 1110 ALABAMA DR, WINTER PARK, FL 32789

    $1,750,00016 Days on yellowkey   MLS ID: O6395692

    For Sale O6395692 - 1110 ALABAMA DR, WINTER PARK, FL 32789 53 photos

    Bed: 3   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2488
       Built: 1958   Tax: $12,858 (2025)
    Community: J Kronenberger Sub
    Spa: No

    Single Family


    Estimated Monthly Payment: $10,660 (change assumption)
    Mortgage ($9,589) + Taxes in 2025 ($1,072)


    Taxes:$12,858

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 1260 ALABAMA DR, WINTER PARK, FL 32789

    $6,900,00046 Days on yellowkey   MLS ID: O6387200

    For Sale O6387200 - 1260 ALABAMA DR, WINTER PARK, FL 32789 58 photos

    Bed: 6   Bath: 6.0   Gar: 3
    Liv Area Sq Ft: 6396
       Built: 1991   Tax: $59,749 (2025)
    Community: J Kronenberger Sub
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $42,786 (change assumption)
    Mortgage ($37,807) + Taxes in 2025 ($4,979)


    Taxes:$59,749

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 607 ELLEN DR, WINTER PARK, FL 32789

    $1,499,900179 Days on yellowkey   MLS ID: O6354269

    REDUCED by $50,100 (3.2%) on 04/15/2026

    For Sale O6354269 - 607 ELLEN DR, WINTER PARK, FL 32789 34 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 2812
       Built: 2025
    Monthly Fee: $76
       Tax: $4,224 (2024)
    Community: Lake Killarney Shores
    Spa: No

    Single Family


    Estimated Monthly Payment: $8,646 (change assumption)
    Mortgage ($8,218) + Fees ($76) + Taxes in 2024 ($352)


    Taxes:$4,224

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2024

    Middle School: College Park Middle


  • 1760 LEGION DR, WINTER PARK, FL 32789

    $2,295,00059 Days on yellowkey   MLS ID: O6383603

    For Sale O6383603 - 1760 LEGION DR, WINTER PARK, FL 32789 66 photos

    Bed: 4   Bath: 5.5   Gar: 2
    Liv Area Sq Ft: 4392
       Built: 1964   Tax: $13,622 (2025)
    Community: Green Oaks Rep
    Single Family


    Estimated Monthly Payment: $13,710 (change assumption)
    Mortgage ($12,575) + Taxes in 2025 ($1,135)


    Taxes:$13,622

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 989 EASTBROOK BLVD, WINTER PARK, FL 32792

    $349,00078 Days on yellowkey   MLS ID: O6376456

    REDUCED by $10,000 (2.8%) on 04/15/2026

    For Sale O6376456 - 989 EASTBROOK BLVD, WINTER PARK, FL 32792 27 photos

    Bed: 3   Bath: 1.5   Gar: 1
    Liv Area Sq Ft: 1140
       Built: 1959   Tax: $4,334 (2025)
    Community: Eastbrook
    Single Family


    Estimated Monthly Payment: $2,273 (change assumption)
    Mortgage ($1,912) + Taxes in 2025 ($361)


    Taxes:$4,334

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None




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.