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Winter Park Homes For Sale & Real Estate - 447 homes

Winter Park homes for sale are located in Orange County, Florida. Find homes in Winter Park for sale with data from the Multiple Listing Service (MLS). Our REALTORS® can assist you in your real estate search for Winter Park houses.

Location: Winter Park

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  • 649 N PARK AVE, WINTER PARK, FL 32789

    $3,500,000Listed 06/02/2026 10:18AM   MLS ID: O6411141

    For Sale O6411141 - 649 N PARK AVE, WINTER PARK, FL 32789 44 photos

    Bed: 3   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 3180
       Built: 2019
    Monthly Fee: $948
       Tax: $22,599 (2025)
    Community: Park Hill
    Townhouse


    Estimated Monthly Payment: $22,009 (change assumption)
    Mortgage ($19,178) + Fees ($948) + Taxes in 2025 ($1,883)


    Taxes:$22,599

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 1611 CHESTNUT AVE, WINTER PARK, FL 32789

    $1,100,00033 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


  • 7117 SWALLOW RUN #G1, WINTER PARK, FL 32792

    $236,80096 Days on yellowkey   MLS ID: O6385942

    REDUCED by $13,000 (5.2%) on 04/23/2026

    For Sale O6385942 - 7117 SWALLOW RUN #G1, WINTER PARK, FL 32792 22 photos

    Bed: 3   Bath: 2.5   Gar: 1
    Liv Area Sq Ft: 1565
       Built: 2011
    Monthly Fee: $385
       Tax: $3,776 (2024)
    Community: Village/Whisperwood
    Condo


    Estimated Monthly Payment: $1,997 (change assumption)
    Mortgage ($1,298) + Fees ($385) + Taxes in 2024 ($315)


    Taxes:$3,776

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 1914 BONANZA CT, WINTER PARK, FL 32792

    $429,99918 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


  • 2383 SUN VALLEY CIR #2383, WINTER PARK, FL 32792

    $259,00043 Days on yellowkey   MLS ID: O6400674

    REDUCED by $10,000 (3.7%) on 05/24/2026

    For Sale O6400674 - 2383 SUN VALLEY CIR #2383, WINTER PARK, FL 32792 32 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1295
       Built: 1985
    Monthly Fee: $499
       Tax: $2,560 (2024)
    Community: Cedarwood Village 1
    Condo


    Estimated Monthly Payment: $2,131 (change assumption)
    Mortgage ($1,419) + Fees ($499) + Taxes in 2024 ($213)


    Taxes:$2,560

    Elementary School: English Estates Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 126 SCOTTSDALE SQ #126, WINTER PARK, FL 32792

    $150,000165 Days on yellowkey   MLS ID: S5140472

    For Sale S5140472 - 126 SCOTTSDALE SQ #126, WINTER PARK, FL 32792 25 photos

    Bed: 2   Bath: 1.5
    Liv Area Sq Ft: 1085
       Built: 1974
    Monthly Fee: $950
       Tax: $1,660 (2024)
    Community: Winter Park Woods Condo
    Condo


    Estimated Monthly Payment: $1,910 (change assumption)
    Mortgage ($822) + Fees ($950) + Taxes in 2024 ($138)


    Taxes:$1,660

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 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


  • 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


  • 2503 TAHOE CIR #2503, WINTER PARK, FL 32792

    $250,00061 Days on yellowkey   MLS ID: O6395130

    For Sale O6395130 - 2503 TAHOE CIR #2503, WINTER PARK, FL 32792 20 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1173
       Built: 1981   Tax: $506 (2025)
    Community: Cedarwood Village 1
    Condo


    Estimated Monthly Payment: $1,412 (change assumption)
    Mortgage ($1,370) + Taxes in 2025 ($42)


    Taxes:$506

    Elementary School: English Estates Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 2261 MULBRY DRIVE, WINTER PARK, FL 32789

    $1,995,0004 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


  • 7794 COUNTRY PL #2, WINTER PARK, FL 32792

    $232,00046 Days on yellowkey   MLS ID: O6397587

    REDUCED by $5,000 (2.1%) on 06/02/2026

    For Sale O6397587 - 7794 COUNTRY PL #2, WINTER PARK, FL 32792 17 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1068
       Built: 1988
    Monthly Fee: $296
       Tax: $2,620 (2024)
    Community: Goldenrod Villas Condo
    Spa: No

    Condo


    Estimated Monthly Payment: $1,786 (change assumption)
    Mortgage ($1,271) + Fees ($296) + Taxes in 2024 ($218)


    Taxes:$2,620

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 2702 PARKLAND DR, WINTER PARK, FL 32789

    $1,139,75053 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

    $1,395,0005 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


  • 2808 BRIGHT BIRD LN, WINTER PARK, FL 32792

    $399,0003 Days on yellowkey   MLS ID: O6410294

    For Sale O6410294 - 2808 BRIGHT BIRD LN, WINTER PARK, FL 32792 35 photos

    Bed: 3   Bath: 2.5   Gar: 1
    Liv Area Sq Ft: 1907
       Built: 2024
    Monthly Fee: $375
       Tax: $6,126 (2025)
    Community: Grayson Square
    Townhouse


    Estimated Monthly Payment: $3,072 (change assumption)
    Mortgage ($2,186) + Fees ($375) + Taxes in 2025 ($511)


    Taxes:$6,126

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 1813 HARLAND PARK DR, WINTER PARK, FL 32789

    $1,875,00032 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


  • 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


  • 7001 JACKMAN BLVD, WINTER PARK, FL 32792

    $450,00018 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


  • 7517 LAUREL SPRINGS DR, WINTER PARK, FL 32792

    $399,9905 Days on yellowkey   MLS ID: O6411247

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

    For Sale O6411247 - 7517 LAUREL SPRINGS DR, WINTER PARK, FL 32792 53 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1678
       Built: 1972   Tax: $6,116 (2025)
    Community: Laurel Springs
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $2,701 (change assumption)
    Mortgage ($2,192) + Taxes in 2025 ($510)


    Taxes:$6,116

    Elementary School: Aloma Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 1448 LAKE FLORENCE WAY, WINTER PARK, FL 32792

    $1,199,0006 Days on yellowkey   MLS ID: O6411164

    For Sale O6411164 - 1448 LAKE FLORENCE WAY, WINTER PARK, FL 32792 51 photos

    Bed: 5   Bath: 4.5   Gar: 3
    Liv Area Sq Ft: 3652
       Built: 2018
    Monthly Fee: $186
       Tax: $7,277 (2025)
    Community: Lake Florence Preserve
    Spa: No

    Single Family


    Estimated Monthly Payment: $7,362 (change assumption)
    Mortgage ($6,570) + Fees ($186) + Taxes in 2025 ($606)


    Taxes:$7,277

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle




Why Bother Searching Elsewhere for Winter Park Homes for Sale and Other Real Estate?

Winter Park home, townhome, condo, villa, and other listing sales 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 houses for sale in Winter Park . You can use our website to view Multiple Listing Service (MLS) data on Winter Park Real Estate. 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 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.