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Winter Park Single Family Homes For Sale - 312 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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  • 318 VITORIA AVE, WINTER PARK, FL 32789

    $1,980,00068 Days on yellowkey   MLS ID: O6388489

    REDUCED by $220,000 (10.0%) on 06/02/2026

    For Sale O6388489 - 318 VITORIA AVE, WINTER PARK, FL 32789 66 photos

    Bed: 3   Bath: 2.5
    Liv Area Sq Ft: 2433
       Built: 1922   Tax: $2,960 (2024)
    Community: College Quarter
    Spa: No

    Single Family


    Estimated Monthly Payment: $11,096 (change assumption)
    Mortgage ($10,849) + Taxes in 2024 ($247)


    Taxes:$2,960

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Glenridge Middle


  • 1864 GRINNELL TER, WINTER PARK, FL 32789

    $1,599,00033 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


  • 1082 WILDMEADOW RUN, WINTER PARK, FL 32792

    $650,00013 Days on yellowkey   MLS ID: O6408825

    For Sale O6408825 - 1082 WILDMEADOW RUN, WINTER PARK, FL 32792 40 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1770
       Built: 2021
    Monthly Fee: $170
       Tax: $5,154 (2025)
    Community: Meadows At Hawks Crest
    Single Family


    Estimated Monthly Payment: $4,161 (change assumption)
    Mortgage ($3,562) + Fees ($170) + Taxes in 2025 ($430)


    Taxes:$5,154

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 7577 DOCKSIDE ST, WINTER PARK, FL 32792

    $370,000Listed 06/02/2026 3:34PM   MLS ID: O6412514

    For Sale O6412514 - 7577 DOCKSIDE ST, WINTER PARK, FL 32792 30 photos

    Bed: 3   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1245
       Built: 1977   Tax: $3,722 (2025)
    Community: Woodcrest Unit 6
    Single Family


    Estimated Monthly Payment: $2,338 (change assumption)
    Mortgage ($2,027) + Taxes in 2025 ($310)


    Taxes:$3,722

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 1741 WESTCHESTER AVE, WINTER PARK, FL 32789

    $595,00048 Days on yellowkey   MLS ID: O6399014

    REDUCED by $14,900 (2.4%) on 05/04/2026

    For Sale O6399014 - 1741 WESTCHESTER AVE, WINTER PARK, FL 32789 24 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1434
       Built: 1964   Tax: $8,945 (2025)
    Community: Orwin Manor Westminster Sec
    Single Family


    Estimated Monthly Payment: $4,006 (change assumption)
    Mortgage ($3,260) + Taxes in 2025 ($745)


    Taxes:$8,945

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park Middle


  • 622 PENN PL, WINTER PARK, FL 32789

    $1,895,00013 Days on yellowkey   MLS ID: TB8511228

    For Sale TB8511228 - 622 PENN PL, WINTER PARK, FL 32789 26 photos

    Bed: 3   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2767
       Built: 2001
    Monthly Fee: $222
       Tax: $12,624 (2025)
    Community: Pennsylvania Place Rep
    Single Family


    Estimated Monthly Payment: $11,657 (change assumption)
    Mortgage ($10,383) + Fees ($222) + Taxes in 2025 ($1,052)


    Taxes:$12,624

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1090 WILDMEADOW RUN, WINTER PARK, FL 32792

    $835,00068 Days on yellowkey   MLS ID: O6394208

    REDUCED by $10,000 (1.2%) on 06/02/2026

    For Sale O6394208 - 1090 WILDMEADOW RUN, WINTER PARK, FL 32792 37 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: $5,340 (change assumption)
    Mortgage ($4,575) + 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


  • 1850 ASTER DR, WINTER PARK, FL 32792

    $500,000Listed 06/02/2026 8:55AM   MLS ID: TB8513990

    For Sale TB8513990 - 1850 ASTER DR, WINTER PARK, FL 32792 50 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1656
       Built: 1978   Tax: $1,584 (2025)
    Community: Garden Lake Estates Unit 1
    Single Family


    Estimated Monthly Payment: $2,872 (change assumption)
    Mortgage ($2,740) + Taxes in 2025 ($132)


    Taxes:$1,584

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1130 PARK NORTH PLACE, WINTER PARK, FL 32789

    $2,495,00069 Days on yellowkey   MLS ID: O6392394

    REDUCED by $155,000 (5.8%) on 04/22/2026

    For Sale O6392394 - 1130 PARK NORTH PLACE, WINTER PARK, FL 32789 41 photos

    Bed: 5   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 4011
       Built: 1968   Tax: $9,744 (2025)
    Community: Park North
    Single Family


    Estimated Monthly Payment: $14,483 (change assumption)
    Mortgage ($13,671) + Taxes in 2025 ($812)


    Taxes:$9,744

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 610 ELLENDALE DR, WINTER PARK, FL 32792

    $399,0005 Days on yellowkey   MLS ID: O6411325

    1 Days Off yellowkey (back on 6/2/2026)

    For Sale O6411325 - 610 ELLENDALE DR, WINTER PARK, FL 32792 29 photos

    Bed: 4   Bath: 3.0
    Liv Area Sq Ft: 1359
       Built: 1957   Tax: $2,321 (2025)
    Community: Winter Park Estates
    Single Family


    Estimated Monthly Payment: $2,380 (change assumption)
    Mortgage ($2,186) + Taxes in 2025 ($193)


    Taxes:$2,321

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 2054 EASTBROOK BLVD, WINTER PARK, FL 32792

    $500,000Listed 06/02/2026 11:16AM   MLS ID: V4949389

    For Sale V4949389 - 2054 EASTBROOK BLVD, WINTER PARK, FL 32792 2 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2031
       Built: 1966   Tax: $5,054 (2025)
    Community: Eastbrook Sub Unit 8
    Single Family


    Estimated Monthly Payment: $3,161 (change assumption)
    Mortgage ($2,740) + Taxes in 2025 ($421)


    Taxes:$5,054

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 1611 CHESTNUT AVE, WINTER PARK, FL 32789

    $1,100,00034 Days on yellowkey   MLS ID: O6402502

    For Sale O6402502 - 1611 CHESTNUT AVE, WINTER PARK, FL 32789 45 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 2916
       Built: 1973   Tax: $3,590 (2025)
    Community: Lake Knowles Terrace
    Single Family


    Estimated Monthly Payment: $6,326 (change assumption)
    Mortgage ($6,027) + Taxes in 2025 ($299)


    Taxes:$3,590

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 508 DUNRAVEN DR, WINTER PARK, FL 32792

    $595,000Listed 06/02/2026 10:15AM   MLS ID: O6412363

    For Sale O6412363 - 508 DUNRAVEN DR, WINTER PARK, FL 32792 34 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1370
       Built: 1958   Tax: $2,281 (2025)
    Community: Kenilworth Shores Sec 03
    Single Family


    Estimated Monthly Payment: $3,450 (change assumption)
    Mortgage ($3,260) + Taxes in 2025 ($190)


    Taxes:$2,281

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 1914 BONANZA CT, WINTER PARK, FL 32792

    $429,99919 Days on yellowkey   MLS ID: O6408461

    0 Days Off yellowkey (back on 6/2/2026)

    For Sale O6408461 - 1914 BONANZA CT, WINTER PARK, FL 32792 30 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1727
       Built: 1968   Tax: $4,497 (2025)
    Community: Eastbrook Sub Unit 13
    Single Family


    Estimated Monthly Payment: $2,731 (change assumption)
    Mortgage ($2,356) + Taxes in 2025 ($375)


    Taxes:$4,497

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 2006 CORNELL AVE, WINTER PARK, FL 32789

    $338,000Listed 06/02/2026 7:07AM   MLS ID: O6412789

    For Sale O6412789 - 2006 CORNELL AVE, WINTER PARK, FL 32789 28 photos

    Bed: 2   Bath: 1.0
    Liv Area Sq Ft: 797
       Built: 1940   Tax: $4,795 (2025)
    Community: Stansbury Estates
    Single Family


    Estimated Monthly Payment: $2,252 (change assumption)
    Mortgage ($1,852) + Taxes in 2025 ($400)


    Taxes:$4,795

    Elementary School: Princeton Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park Middle


  • 2261 MULBRY DRIVE, WINTER PARK, FL 32789

    $1,995,0005 Days on yellowkey   MLS ID: O6410979

    For Sale O6410979 - 2261 MULBRY DRIVE, WINTER PARK, FL 32789 77 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 3696
       Built: 2020   Tax: $11,789 (2025)
    Community: Lake Forest Park
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $11,914 (change assumption)
    Mortgage ($10,931) + Taxes in 2025 ($982)


    Taxes:$11,789

    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

    $1,139,75054 Days on yellowkey   MLS ID: O6397997

    REDUCED by $35,250 (3.0%) on 05/18/2026

    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: $6,684 (change assumption)
    Mortgage ($6,245) + 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


  • 1077 MINNESOTA AVE, WINTER PARK, FL 32789

    $1,395,0006 Days on yellowkey   MLS ID: O6411722

    For Sale O6411722 - 1077 MINNESOTA AVE, WINTER PARK, FL 32789 45 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 3046
       Built: 2025   Tax: $1,383 (2025)
    Community: Na
    Single Family


    Estimated Monthly Payment: $7,759 (change assumption)
    Mortgage ($7,644) + Taxes in 2025 ($115)


    Taxes:$1,383

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1813 HARLAND PARK DR, WINTER PARK, FL 32789

    $1,875,00033 Days on yellowkey   MLS ID: O6403483

    REDUCED by $120,000 (6.0%) on 05/28/2026

    For Sale O6403483 - 1813 HARLAND PARK DR, WINTER PARK, FL 32789 59 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3551
       Built: 2013
    Monthly Fee: $268
       Tax: $23,539 (2025)
    Community: Windsong - Knowles Place
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $12,503 (change assumption)
    Mortgage ($10,274) + Fees ($268) + Taxes in 2025 ($1,962)


    Taxes:$23,539

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 7001 JACKMAN BLVD, WINTER PARK, FL 32792

    $450,00019 Days on yellowkey   MLS ID: O6408371

    5 Days Off yellowkey (back on 6/2/2026)

    For Sale O6408371 - 7001 JACKMAN BLVD, WINTER PARK, FL 32792 33 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1482
       Built: 1977   Tax: $4,421 (2025)
    Community: Howell Branch Woods
    Single Family


    Estimated Monthly Payment: $2,834 (change assumption)
    Mortgage ($2,466) + Taxes in 2025 ($368)


    Taxes:$4,421

    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.