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Winter Park Single Family Homes For Sale - 205 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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  • 218 ORANGE TERRACE DR, WINTER PARK, FL 32789

    $600,00032 Days on yellowkey   MLS ID: O6388723

    0 Days Off yellowkey (back on 4/9/2026)

    For Sale O6388723 - 218 ORANGE TERRACE DR, WINTER PARK, FL 32789 28 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1618
       Built: 1955   Tax: $4,694 (2025)
    Community: Orange Terrace
    Single Family


    Estimated Monthly Payment: $3,679 (change assumption)
    Mortgage ($3,288) + Taxes in 2025 ($391)


    Taxes:$4,694

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park Middle


  • 1541 WESTCHESTER AVE, WINTER PARK, FL 32789

    $1,100,00081 Days on yellowkey   MLS ID: O6374409

    0 Days Off yellowkey (back on 4/9/2026)

    For Sale O6374409 - 1541 WESTCHESTER AVE, WINTER PARK, FL 32789 47 photos

    Bed: 3   Bath: 2.5
    Liv Area Sq Ft: 2578
       Built: 1935   Tax: $5,932 (2024)
    Community: Orwin Manor Westminster Sec
    Spa: No

    Single Family


    Estimated Monthly Payment: $6,522 (change assumption)
    Mortgage ($6,027) + Taxes in 2024 ($494)


    Taxes:$5,932

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2024

    Middle School: College Park Middle


  • 1651 WESTCHESTER AVE, WINTER PARK, FL 32789

    $1,449,0008 Days on yellowkey   MLS ID: O6384358

    0 Days Off yellowkey (back on 4/9/2026)

    For Sale O6384358 - 1651 WESTCHESTER AVE, WINTER PARK, FL 32789 49 photos

    Bed: 3   Bath: 2.5   Gar: 1
    Liv Area Sq Ft: 2426
       Built: 1938   Tax: $10,973 (2025)
    Community: Orwin Manor Westminster Sec
    Single Family


    Estimated Monthly Payment: $8,854 (change assumption)
    Mortgage ($7,940) + Taxes in 2025 ($914)


    Taxes:$10,973

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park Middle


  • 647 RANDY LN, WINTER PARK, FL 32789

    $1,795,00033 Days on yellowkey   MLS ID: O6387217

    For Sale O6387217 - 647 RANDY LN, WINTER PARK, FL 32789 64 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2851
       Built: 1957   Tax: $5,627 (2025)
    Community: Timberline
    Single Family


    Estimated Monthly Payment: $10,304 (change assumption)
    Mortgage ($9,835) + Taxes in 2025 ($469)


    Taxes:$5,627

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 2501 WINTER PARK RD, WINTER PARK, FL 32789

    $1,690,00038 Days on yellowkey   MLS ID: O6384756

    REDUCED by $105,000 (5.8%) on 04/08/2026

    For Sale O6384756 - 2501 WINTER PARK RD, WINTER PARK, FL 32789 61 photos

    Bed: 5   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3304
       Built: 2014   Tax: $10,938 (2024)
    Community: Parklando #3
    Single Family


    Estimated Monthly Payment: $10,172 (change assumption)
    Mortgage ($9,260) + Taxes in 2024 ($912)


    Taxes:$10,938

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2024

    Middle School: None


  • 1761 LEGION DR, WINTER PARK, FL 32789

    $3,295,000303 Days on yellowkey   MLS ID: O6302616

    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: $19,899 (change assumption)
    Mortgage ($18,054) + Taxes in 2024 ($1,845)


    Taxes:$22,139

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Maitland Middle


  • 1336 COLLEGE PT, WINTER PARK, FL 32789

    $4,595,000116 Days on yellowkey   MLS ID: O6367878

    3 Days Off yellowkey (back on 4/9/2026)

    For Sale O6367878 - 1336 COLLEGE PT, WINTER PARK, FL 32789 53 photos

    Bed: 4   Bath: 4.0
    Liv Area Sq Ft: 3181
       Built: 1926   Tax: $36,033 (2025)
    Community: Virginia Heights
    Spa: No

    Single Family


    Estimated Monthly Payment: $28,180 (change assumption)
    Mortgage ($25,177) + Taxes in 2025 ($3,003)


    Taxes:$36,033

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 119 OAK GROVE RD, WINTER PARK, FL 32789

    $285,0002 Days on yellowkey   MLS ID: O6397460

    For Sale O6397460 - 119 OAK GROVE RD, WINTER PARK, FL 32789 13 photos

    Bed: 3   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1134
       Built: 1994   Tax: $608 (2025)
    Community: Winter Park Oaks
    Single Family


    Estimated Monthly Payment: $1,612 (change assumption)
    Mortgage ($1,562) + Taxes in 2025 ($51)


    Taxes:$608

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 7393 GRAND AVE, WINTER PARK, FL 32792

    $200,0005 Days on yellowkey   MLS ID: S5147029

    SHORT SALE S5147029 - 7393 GRAND AVE, WINTER PARK, FL 32792 10 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1518
       Built: 1983   Tax: $4,367 (2024)
    Community: Oakcrest-516
    Single Family


    Estimated Monthly Payment: $1,460 (change assumption)
    Mortgage ($1,096) + Taxes in 2024 ($364)


    Taxes:$4,367

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • WINTER PARK, FL 32792

    $440,00030 Days on yellowkey   MLS ID: S5145631

    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: $2,825 (change assumption)
    Mortgage ($2,411) + Taxes in 2025 ($414)


    Taxes:$4,968

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1108 FAIRWAY DR, WINTER PARK, FL 32792

    $725,00043 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


  • 2052 LEANNE CT, WINTER PARK, FL 32792

    $456,00067 Days on yellowkey   MLS ID: O6379323

    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: $2,630 (change assumption)
    Mortgage ($2,499) + Taxes in 2024 ($132)


    Taxes:$1,581

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 1510 MILLER AVE, WINTER PARK, FL 32789

    $1,634,900186 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


  • 423 OLOLU DR, WINTER PARK, FL 32789

    $589,00093 Days on yellowkey   MLS ID: O6369976

    For Sale O6369976 - 423 OLOLU DR, WINTER PARK, FL 32789 51 photos

    Bed: 3   Bath: 3.0
    Liv Area Sq Ft: 1920
       Built: 1981   Tax: $4,030 (2024)
    Community: Killarney Circle
    Single Family


    Estimated Monthly Payment: $3,563 (change assumption)
    Mortgage ($3,227) + Taxes in 2024 ($336)


    Taxes:$4,030

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2024

    Middle School: College Park Middle


  • 1177 KENWOOD AVE, WINTER PARK, FL 32789

    $1,870,00029 Days on yellowkey   MLS ID: O6390592

    REDUCED by $100,000 (5.1%) on 04/01/2026

    For Sale O6390592 - 1177 KENWOOD AVE, WINTER PARK, FL 32789 57 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 4363
       Built: 2007   Tax: $16,206 (2025)
    Community: Dixie Terrace
    Spa: No

    Single Family


    Estimated Monthly Payment: $11,597 (change assumption)
    Mortgage ($10,246) + Taxes in 2025 ($1,351)


    Taxes:$16,206

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1840 BRYAN AVE, WINTER PARK, FL 32789

    $1,899,50022 Days on yellowkey   MLS ID: O6391922

    For Sale O6391922 - 1840 BRYAN AVE, WINTER PARK, FL 32789 46 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3727
       Built: 2014   Tax: $19,607 (2025)
    Community: Lakeview Terrace
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $12,042 (change assumption)
    Mortgage ($10,408) + Taxes in 2025 ($1,634)


    Taxes:$19,607

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 629 COUNTRY CLUB DR, WINTER PARK, FL 32789

    $1,695,00042 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


  • 4190 BEAR GULLY RD, WINTER PARK, FL 32792

    $524,90095 Days on yellowkey   MLS ID: O6371014

    For Sale O6371014 - 4190 BEAR GULLY RD, WINTER PARK, FL 32792 30 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2058
       Built: 2003
    Monthly Fee: $52
       Tax: $5,630 (2024)
    Community: Bear Gully Forest
    Single Family


    Estimated Monthly Payment: $3,397 (change assumption)
    Mortgage ($2,876) + Fees ($52) + Taxes in 2024 ($469)


    Taxes:$5,630

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 550 PALMER AVE, WINTER PARK, FL 32789

    $6,895,000171 Days on yellowkey   MLS ID: O6349188

    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: $38,638 (change assumption)
    Mortgage ($37,780) + Taxes in 2025 ($858)


    Taxes:$10,292

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 1174 WILDMEADOW RUN, WINTER PARK, FL 32792

    $669,90011 Days on yellowkey   MLS ID: O6394974

    For Sale O6394974 - 1174 WILDMEADOW RUN, WINTER PARK, FL 32792 55 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1770
       Built: 2021
    Monthly Fee: $150
       Tax: $6,672 (2025)
    Community: Hawks Crest
    Single Family


    Estimated Monthly Payment: $4,377 (change assumption)
    Mortgage ($3,671) + Fees ($150) + Taxes in 2025 ($556)


    Taxes:$6,672

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla 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.