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Winter Park Single Family Homes For Sale - 243 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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  • 2015 SUMMERFIELD RD, WINTER PARK, FL 32792

    $1,375,000165 Days on yellowkey   MLS ID: O6357615

    For Sale O6357615 - 2015 SUMMERFIELD RD, WINTER PARK, FL 32792 50 photos

    Bed: 4   Bath: 4.0   Gar: 1
    Liv Area Sq Ft: 3024
       Built: 1957   Tax: $7,243 (2025)
    Community: Kenilworth Shores Sec 07
    Spa: No

    Single Family


    Estimated Monthly Payment: $8,138 (change assumption)
    Mortgage ($7,534) + Taxes in 2025 ($604)


    Taxes:$7,243

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 607 ELLEN DR, WINTER PARK, FL 32789

    $1,499,900181 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


  • 744 CORNWALL RD, WINTER PARK, FL 32792

    $695,000262 Days on yellowkey   MLS ID: O6332168

    REDUCED by $20,000 (2.8%) on 04/15/2026

    For Sale O6332168 - 744 CORNWALL RD, WINTER PARK, FL 32792 59 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1968
       Built: 1968   Tax: $5,359 (2024)
    Community: Winter Park Pines
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,255 (change assumption)
    Mortgage ($3,808) + Taxes in 2024 ($447)


    Taxes:$5,359

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Glenridge Middle


  • 1761 LEGION DR, WINTER PARK, FL 32789

    $3,270,000312 Days on yellowkey   MLS ID: O6302616

    REDUCED by $25,000 (0.8%) on 04/15/2026

    For Sale O6302616 - 1761 LEGION DR, WINTER PARK, FL 32789 54 photos

    Bed: 5   Bath: 5.5   Gar: 3
    Liv Area Sq Ft: 4955
       Built: 2017   Tax: $22,139 (2024)
    Community: Green Oaks Rep 02
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $19,762 (change assumption)
    Mortgage ($17,917) + Taxes in 2024 ($1,845)


    Taxes:$22,139

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Maitland Middle


  • 2408 LAFAYETTE AVE, WINTER PARK, FL 32789

    $1,495,00010 Days on yellowkey   MLS ID: O6397694

    For Sale O6397694 - 2408 LAFAYETTE AVE, WINTER PARK, FL 32789 31 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2838
       Built: 2024   Tax: $3,770 (2024)
    Community: Winter Park Village
    Spa: No

    Single Family


    Estimated Monthly Payment: $8,506 (change assumption)
    Mortgage ($8,192) + Taxes in 2024 ($314)


    Taxes:$3,770

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Maitland Middle


  • 150 DANA WAY, WINTER PARK, FL 32789

    $3,799,00024 Days on yellowkey   MLS ID: O6394012

    For Sale O6394012 - 150 DANA WAY, WINTER PARK, FL 32789 81 photos

    Bed: 5   Bath: 5.0   Gar: 2
    Liv Area Sq Ft: 4451
       Built: 2026   Tax: $14,010 (2025)
    Community: Charmont
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $21,983 (change assumption)
    Mortgage ($20,816) + Taxes in 2025 ($1,168)


    Taxes:$14,010

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 405 LAKE FAIR LN, WINTER PARK, FL 32789

    $459,99926 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


  • 1760 GREENWICH AVE, WINTER PARK, FL 32789

    $650,00032 Days on yellowkey   MLS ID: O6392001

    For Sale O6392001 - 1760 GREENWICH AVE, WINTER PARK, FL 32789 18 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1610
       Built: 1967   Tax: $2,779 (2025)
    Community: Golfview Heights
    Single Family


    Estimated Monthly Payment: $3,793 (change assumption)
    Mortgage ($3,562) + Taxes in 2025 ($232)


    Taxes:$2,779

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 1510 MILLER AVE, WINTER PARK, FL 32789

    $1,634,900195 Days on yellowkey   MLS ID: O6350503

    For Sale O6350503 - 1510 MILLER AVE, WINTER PARK, FL 32789 70 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3252
       Built: 2026   Tax: $3,573 (2025)
    Community: Lawndale
    Single Family


    Estimated Monthly Payment: $9,256 (change assumption)
    Mortgage ($8,958) + Taxes in 2025 ($298)


    Taxes:$3,573

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park Middle


  • 240 ORANGE TERRACE DR, WINTER PARK, FL 32789

    $484,000256 Days on yellowkey   MLS ID: O6330690

    REDUCED by $1,000 (0.2%) on 04/15/2026

    For Sale O6330690 - 240 ORANGE TERRACE DR, WINTER PARK, FL 32789 30 photos

    Bed: 4   Bath: 2.0
    Liv Area Sq Ft: 1718
       Built: 1955   Tax: $6,210 (2024)
    Community: Orange Terrace
    Single Family


    Estimated Monthly Payment: $3,169 (change assumption)
    Mortgage ($2,652) + Taxes in 2024 ($518)


    Taxes:$6,210

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2024

    Middle School: Robinswood Middle


  • 1807 MAGNOLIA AVE, WINTER PARK, FL 32789

    $1,199,0004 Days on yellowkey   MLS ID: O6396616

    For Sale O6396616 - 1807 MAGNOLIA AVE, WINTER PARK, FL 32789 38 photos

    Bed: 5   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2618
       Built: 2026   Tax: $4,720 (2025)
    Community: Temple Terrace
    Spa: No

    Single Family


    Estimated Monthly Payment: $6,963 (change assumption)
    Mortgage ($6,570) + Taxes in 2025 ($393)


    Taxes:$4,720

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 785 N PHELPS AVE, WINTER PARK, FL 32789

    $2,049,00026 Days on yellowkey   MLS ID: O6393117

    For Sale O6393117 - 785 N PHELPS AVE, WINTER PARK, FL 32789 41 photos

    Bed: 5   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2964
       Built: 2026   Tax: $9,172 (2025)
    Community: Comstock Park
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $11,991 (change assumption)
    Mortgage ($11,227) + Taxes in 2025 ($764)


    Taxes:$9,172

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 3463 ARNEL DR, WINTER PARK, FL 32792

    $459,90034 Days on yellowkey   MLS ID: O6390301

    REDUCED by $20,000 (4.2%) on 04/12/2026

    For Sale O6390301 - 3463 ARNEL DR, WINTER PARK, FL 32792 58 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1770
       Built: 1967   Tax: $4,648 (2024)
    Community: Eastbrook Sub Unit 11
    Single Family


    Estimated Monthly Payment: $2,907 (change assumption)
    Mortgage ($2,520) + Taxes in 2024 ($387)


    Taxes:$4,648

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 3131 LOWNDES DR, WINTER PARK, FL 32792

    $529,95041 Days on yellowkey   MLS ID: O6388846

    REDUCED by $4,950 (0.9%) on 04/16/2026

    For Sale O6388846 - 3131 LOWNDES DR, WINTER PARK, FL 32792 56 photos

    Bed: 4   Bath: 2.0
    Liv Area Sq Ft: 2126
       Built: 1967   Tax: $1,559 (2024)
    Community: Georgetown Estates
    Single Family


    Estimated Monthly Payment: $3,034 (change assumption)
    Mortgage ($2,904) + Taxes in 2024 ($130)


    Taxes:$1,559

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Maitland Middle


  • 1926 NATALEN RD, WINTER PARK, FL 32792

    $649,90045 Days on yellowkey   MLS ID: O6388308

    For Sale O6388308 - 1926 NATALEN RD, WINTER PARK, FL 32792 44 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1469
       Built: 1957   Tax: $7,308 (2024)
    Community: Kenilworth Shores Sec 07
    Single Family


    Estimated Monthly Payment: $4,170 (change assumption)
    Mortgage ($3,561) + Taxes in 2024 ($609)


    Taxes:$7,308

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Glenridge Middle


  • 330 ELKHORN CT, WINTER PARK, FL 32792

    $559,90085 Days on yellowkey   MLS ID: O6376757

    REDUCED by $10,000 (1.8%) on 04/16/2026

    For Sale O6376757 - 330 ELKHORN CT, WINTER PARK, FL 32792 41 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1570
       Built: 1965   Tax: $2,086 (2025)
    Community: Winter Park Pines Merrie Oaks
    Single Family


    Estimated Monthly Payment: $3,242 (change assumption)
    Mortgage ($3,068) + Taxes in 2025 ($174)


    Taxes:$2,086

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1905 BONANZA CT, WINTER PARK, FL 32789

    $490,0004 Days on yellowkey   MLS ID: O6398772

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


  • 2220 FAIRGLENN WAY, WINTER PARK, FL 32792

    $674,9003 Days on yellowkey   MLS ID: O6399993

    For Sale O6399993 - 2220 FAIRGLENN WAY, WINTER PARK, FL 32792 54 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2636
       Built: 1986
    Monthly Fee: $53
       Tax: $3,357 (2025)
    Community: Quail Run
    Single Family


    Estimated Monthly Payment: $4,031 (change assumption)
    Mortgage ($3,698) + Fees ($53) + Taxes in 2025 ($280)


    Taxes:$3,357

    Elementary School: Red Bug Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 638 BLAIRSHIRE CIR, WINTER PARK, FL 32792

    $639,0002 Days on yellowkey   MLS ID: C7524884

    0 Days Off yellowkey (back on 4/18/2026)

    For Sale C7524884 - 638 BLAIRSHIRE CIR, WINTER PARK, FL 32792 51 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1701
       Built: 1964   Tax: $2,816 (2025)
    Community: Brookshire Heights 4Th Add
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $3,736 (change assumption)
    Mortgage ($3,501) + Taxes in 2025 ($235)


    Taxes:$2,816

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1870 WALKER AVE, WINTER PARK, FL 32789

    $1,399,00038 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




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.