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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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  • 240 ORANGE TERRACE DR, WINTER PARK, FL 32789

    $484,000254 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


  • 2052 LEANNE CT, WINTER PARK, FL 32792

    $450,00074 Days on yellowkey   MLS ID: O6379323

    REDUCED by $6,000 (1.3%) on 04/15/2026

    For Sale O6379323 - 2052 LEANNE CT, WINTER PARK, FL 32792 30 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2264
       Built: 1969   Tax: $1,581 (2024)
    Community: Eastbrook Sub Unit 15
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,597 (change assumption)
    Mortgage ($2,466) + Taxes in 2024 ($132)


    Taxes:$1,581

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 102 BELL PL, WINTER PARK, FL 32792

    $1,399,0004 Days on yellowkey   MLS ID: O6398118

    For Sale O6398118 - 102 BELL PL, WINTER PARK, FL 32792 46 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2459
       Built: 2025   Tax: $4,224 (2025)
    Community: Eastgate Sub
    Single Family


    Estimated Monthly Payment: $8,018 (change assumption)
    Mortgage ($7,666) + Taxes in 2025 ($352)


    Taxes:$4,224

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 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


  • 2015 SUMMERFIELD RD, WINTER PARK, FL 32792

    $1,375,000163 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


  • 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


  • 1369 BLUE STEM LN, WINTER PARK, FL 32792

    $825,00011 Days on yellowkey   MLS ID: O6396971

    For Sale O6396971 - 1369 BLUE STEM LN, WINTER PARK, FL 32792 46 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2589
       Built: 2021
    Monthly Fee: $413
       Tax: $6,074 (2024)
    Community: Landings At Hawks Crest
    Single Family


    Estimated Monthly Payment: $5,440 (change assumption)
    Mortgage ($4,520) + Fees ($413) + Taxes in 2024 ($506)


    Taxes:$6,074

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 1300 MAYFIELD AVE, WINTER PARK, FL 32789

    $2,850,00022 Days on yellowkey   MLS ID: O6393777

    For Sale O6393777 - 1300 MAYFIELD AVE, WINTER PARK, FL 32789 56 photos

    Bed: 5   Bath: 5.5   Gar: 4
    Liv Area Sq Ft: 4389
       Built: 1958   Tax: $26,658 (2025)
    Community: Temple Heights
    Spa: No

    Single Family


    Estimated Monthly Payment: $17,838 (change assumption)
    Mortgage ($15,616) + Taxes in 2025 ($2,221)


    Taxes:$26,658

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 418 GILBERT RD, WINTER PARK, FL 32792

    $740,00023 Days on yellowkey   MLS ID: O6385950

    For Sale O6385950 - 418 GILBERT RD, WINTER PARK, FL 32792 30 photos

    Bed: 3   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 1680
       Built: 1964   Tax: $9,094 (2025)
    Community: Winter Park Pines Ut 5
    Single Family


    Estimated Monthly Payment: $4,813 (change assumption)
    Mortgage ($4,055) + Taxes in 2025 ($758)


    Taxes:$9,094

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 629 COUNTRY CLUB DR, WINTER PARK, FL 32789

    $1,695,00049 Days on yellowkey   MLS ID: O6386610

    For Sale O6386610 - 629 COUNTRY CLUB DR, WINTER PARK, FL 32789 46 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3031
       Built: 2026   Tax: $2,028 (2025)
    Community: Lords Sub
    Spa: No

    Single Family


    Estimated Monthly Payment: $9,456 (change assumption)
    Mortgage ($9,287) + Taxes in 2025 ($169)


    Taxes:$2,028

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 151 OAKWOOD WAY, WINTER PARK, FL 32789

    $2,950,00072 Days on yellowkey   MLS ID: O6380037

    REDUCED by $105,000 (3.4%) on 04/01/2026

    For Sale O6380037 - 151 OAKWOOD WAY, WINTER PARK, FL 32789 68 photos

    Bed: 4   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 4129
       Built: 2023   Tax: $34,218 (2025)
    Community: Charmont
    Spa: No

    Single Family


    Estimated Monthly Payment: $19,015 (change assumption)
    Mortgage ($16,164) + Taxes in 2025 ($2,852)


    Taxes:$34,218

    Elementary School: None

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 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


  • 1510 MILLER AVE, WINTER PARK, FL 32789

    $1,634,900193 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


  • 1807 MAGNOLIA AVE, WINTER PARK, FL 32789

    $1,199,0002 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


  • 2681 FITZHUGH RD, WINTER PARK, FL 32792

    $750,00058 Days on yellowkey   MLS ID: O6383699

    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


  • 2361 MULBRY DR, WINTER PARK, FL 32789

    $2,395,0002 Days on yellowkey   MLS ID: O6396840

    For Sale O6396840 - 2361 MULBRY DR, WINTER PARK, FL 32789 87 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 3111
       Built: 2026   Tax: $6,436 (2025)
    Community: Lake Forest Park
    Single Family


    Estimated Monthly Payment: $13,659 (change assumption)
    Mortgage ($13,123) + Taxes in 2025 ($536)


    Taxes:$6,436

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 2702 PARKLAND DR, WINTER PARK, FL 32789

    $1,175,0008 Days on yellowkey   MLS ID: O6397997

    For Sale O6397997 - 2702 PARKLAND DR, WINTER PARK, FL 32789 48 photos

    Bed: 5   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2656
       Built: 1949   Tax: $5,269 (2025)
    Community: Parklando
    Single Family


    Estimated Monthly Payment: $6,877 (change assumption)
    Mortgage ($6,438) + Taxes in 2025 ($439)


    Taxes:$5,269

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 1090 WILDMEADOW RUN, WINTER PARK, FL 32792

    $845,00022 Days on yellowkey   MLS ID: O6394208

    For Sale O6394208 - 1090 WILDMEADOW RUN, WINTER PARK, FL 32792 35 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2589
       Built: 2021
    Monthly Fee: $243
       Tax: $6,258 (2024)
    Community: Hawks Crest
    Single Family


    Estimated Monthly Payment: $5,394 (change assumption)
    Mortgage ($4,630) + Fees ($243) + Taxes in 2024 ($521)


    Taxes:$6,258

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 1570 PALMER AVE, WINTER PARK, FL 32789

    $1,640,00025 Days on yellowkey   MLS ID: O6383529

    REDUCED by $50,000 (3.0%) on 04/13/2026

    For Sale O6383529 - 1570 PALMER AVE, WINTER PARK, FL 32789 39 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3048
       Built: 2007   Tax: $10,527 (2024)
    Community: Comstock Park
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $9,863 (change assumption)
    Mortgage ($8,986) + Taxes in 2024 ($877)


    Taxes:$10,527

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 1782 PINE AVE, WINTER PARK, FL 32789

    $4,197,00037 Days on yellowkey   MLS ID: O6389039

    For Sale O6389039 - 1782 PINE AVE, WINTER PARK, FL 32789 66 photos

    Bed: 5   Bath: 6.5   Gar: 4
    Liv Area Sq Ft: 4782
       Built: 2026   Tax: $4,880 (2025)
    Community: Conwill Estates
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $23,403 (change assumption)
    Mortgage ($22,997) + Taxes in 2025 ($407)


    Taxes:$4,880

    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.