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Winter Park Homes For Sale & Real Estate - 379 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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  • 1510 MILLER AVE, WINTER PARK, FL 32789

    $1,634,900199 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


  • 2361 MULBRY DR, WINTER PARK, FL 32789

    $2,395,0008 Days on yellowkey   MLS ID: O6396840

    For Sale O6396840 - 2361 MULBRY DR, WINTER PARK, FL 32789 82 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


  • 3651 N GOLDENROD RD #D101, WINTER PARK, FL 32792

    $179,00037 Days on yellowkey   MLS ID: O6391256

    REDUCED by $6,000 (3.2%) on 04/24/2026

    For Sale O6391256 - 3651 N GOLDENROD RD #D101, WINTER PARK, FL 32792 39 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 840
       Built: 1990
    Monthly Fee: $370
       Tax: $2,000 (2025)
    Community: Lancelot/Winter Park
    Condo


    Estimated Monthly Payment: $1,517 (change assumption)
    Mortgage ($981) + Fees ($370) + Taxes in 2025 ($167)


    Taxes:$2,000

    Elementary School: Aloma Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 501 LAKEVIEW AVE, WINTER PARK, FL 32789

    $1,390,000280 Days on yellowkey   MLS ID: O6325192

    For Sale O6325192 - 501 LAKEVIEW AVE, WINTER PARK, FL 32789 59 photos

    Bed: 4   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3253
       Built: 2026   Tax: $2,820 (2024)
    Community: Killarney Estates
    Single Family


    Estimated Monthly Payment: $7,851 (change assumption)
    Mortgage ($7,616) + Taxes in 2024 ($235)


    Taxes:$2,820

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2024

    Middle School: College Park Middle


  • 1660 PALMER AVE, WINTER PARK, FL 32789

    $4,950,000428 Days on yellowkey   MLS ID: O6282425

    For Sale O6282425 - 1660 PALMER AVE, WINTER PARK, FL 32789 53 photos

    Bed: 5   Bath: 6.5   Gar: 3
    Liv Area Sq Ft: 6406
       Built: 2024   Tax: $6,144 (2024)
    Community: Comstock Park
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $27,635 (change assumption)
    Mortgage ($27,123) + Taxes in 2024 ($512)


    Taxes:$6,144

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Maitland Middle


  • 291 LEWFIELD CIR #291, WINTER PARK, FL 32792

    $144,00067 Days on yellowkey   MLS ID: O6382547

    For Sale O6382547 - 291 LEWFIELD CIR #291, WINTER PARK, FL 32792 32 photos

    Bed: 1   Bath: 1.0
    Liv Area Sq Ft: 678
       Built: 1973
    Monthly Fee: $350
       Tax: $1,942 (2025)
    Community: Stratford Winter Park
    Condo


    Estimated Monthly Payment: $1,301 (change assumption)
    Mortgage ($789) + Fees ($350) + Taxes in 2025 ($162)


    Taxes:$1,942

    Elementary School: English Estates Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 1036 ARAGON AVE, WINTER PARK, FL 32789

    $510,00070 Days on yellowkey   MLS ID: O6382491

    REDUCED by $15,000 (2.9%) on 04/11/2026

    For Sale O6382491 - 1036 ARAGON AVE, WINTER PARK, FL 32789 41 photos

    Bed: 2   Bath: 1.0
    Liv Area Sq Ft: 1073
       Built: 1957   Tax: $5,764 (2024)
    Community: Seville Park
    Single Family


    Estimated Monthly Payment: $3,275 (change assumption)
    Mortgage ($2,794) + Taxes in 2024 ($480)


    Taxes:$5,764

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Audubon Park K-8


  • 1287 VERDANT GLADE PL, WINTER PARK, FL 32792

    $850,000Listed 04/24/2026 2:35PM   MLS ID: O6400331

    For Sale O6400331 - 1287 VERDANT GLADE PL, WINTER PARK, FL 32792 50 photos

    Bed: 5   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3020
       Built: 2020
    Monthly Fee: $413
       Tax: $6,133 (2025)
    Community: Meadows At Hawks Crest
    Single Family


    Estimated Monthly Payment: $5,581 (change assumption)
    Mortgage ($4,657) + Fees ($413) + Taxes in 2025 ($511)


    Taxes:$6,133

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


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

    $241,9007 Days on yellowkey   MLS ID: O6397587

    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: $1,840 (change assumption)
    Mortgage ($1,325) + 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


  • 7761 FOX KNOLL PL, WINTER PARK, FL 32792

    $425,0001 Day on yellowkey   MLS ID: O6401159

    For Sale O6401159 - 7761 FOX KNOLL PL, WINTER PARK, FL 32792 34 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1485
       Built: 1989
    Monthly Fee: $20
       Tax: $4,308 (2024)
    Community: Bridgewater
    Single Family


    Estimated Monthly Payment: $2,708 (change assumption)
    Mortgage ($2,329) + Fees ($20) + Taxes in 2024 ($359)


    Taxes:$4,308

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 1822 YORKSHIRE DR, WINTER PARK, FL 32792

    $624,000Listed 04/24/2026 8:49AM   MLS ID: O6401364

    For Sale O6401364 - 1822 YORKSHIRE DR, WINTER PARK, FL 32792 42 photos

    Bed: 3   Bath: 3.0
    Liv Area Sq Ft: 1620
       Built: 1957   Tax: $5,959 (2025)
    Community: Park Manor
    Single Family


    Estimated Monthly Payment: $3,916 (change assumption)
    Mortgage ($3,419) + Taxes in 2025 ($497)


    Taxes:$5,959

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 1468 AUBURN GREEN LOOP, WINTER PARK, FL 32792

    $480,0004 Days on yellowkey   MLS ID: O6399199

    For Sale O6399199 - 1468 AUBURN GREEN LOOP, WINTER PARK, FL 32792 43 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1676
       Built: 1984
    Monthly Fee: $49
       Tax: $6,243 (2024)
    Community: Country Lane
    Single Family


    Estimated Monthly Payment: $3,199 (change assumption)
    Mortgage ($2,630) + Fees ($49) + Taxes in 2024 ($520)


    Taxes:$6,243

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 250 CORTLAND AVE, WINTER PARK, FL 32789

    $950,00021 Days on yellowkey   MLS ID: O6395137

    For Sale O6395137 - 250 CORTLAND AVE, WINTER PARK, FL 32789 46 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2114
       Built: 1981   Tax: $4,370 (2024)
    Community: Cortland Park
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $5,569 (change assumption)
    Mortgage ($5,205) + Taxes in 2024 ($364)


    Taxes:$4,370

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Glenridge Middle


  • 1830 EDWIN BLVD, WINTER PARK, FL 32789

    $679,8008 Days on yellowkey   MLS ID: O6400055

    For Sale O6400055 - 1830 EDWIN BLVD, WINTER PARK, FL 32789 52 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1287
       Built: 1957   Tax: $3,955 (2025)
    Community: Campo Bello
    Single Family


    Estimated Monthly Payment: $4,054 (change assumption)
    Mortgage ($3,725) + Taxes in 2025 ($330)


    Taxes:$3,955

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 2020 COCOS CT, WINTER PARK, FL 32792

    $458,99042 Days on yellowkey   MLS ID: O6389901

    1 Days Off yellowkey (back on 4/24/2026)

    REDUCED by $1,000 (0.2%) on 04/17/2026

    For Sale O6389901 - 2020 COCOS CT, WINTER PARK, FL 32792 22 photos

    Bed: 3   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1715
       Built: 1966   Tax: $1,410 (2024)
    Community: Eastbrook Sub Unit 8
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,632 (change assumption)
    Mortgage ($2,515) + Taxes in 2024 ($117)


    Taxes:$1,410

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 633 LANDER RD, WINTER PARK, FL 32792

    $424,90042 Days on yellowkey   MLS ID: O6390096

    0 Days Off yellowkey (back on 3/19/2026)

    For Sale O6390096 - 633 LANDER RD, WINTER PARK, FL 32792 38 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1400
       Built: 1956   Tax: $1,562 (2025)
    Community: Eastgate Sub
    Single Family


    Estimated Monthly Payment: $2,458 (change assumption)
    Mortgage ($2,328) + Taxes in 2025 ($130)


    Taxes:$1,562

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1923 LINDEN RD, WINTER PARK, FL 32792

    $475,00025 Days on yellowkey   MLS ID: O6393643

    REDUCED by $24,999 (5.0%) on 04/17/2026

    For Sale O6393643 - 1923 LINDEN RD, WINTER PARK, FL 32792 33 photos

    Bed: 4   Bath: 3.0
    Liv Area Sq Ft: 2117
       Built: 1955   Tax: $340 (2024)
    Community: Tanglewood Sec 4
    Single Family


    Estimated Monthly Payment: $2,631 (change assumption)
    Mortgage ($2,603) + Taxes in 2024 ($28)


    Taxes:$340

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 1807 HAMMERLIN AVE #G, WINTER PARK, FL 32789

    $580,00038 Days on yellowkey   MLS ID: O6391277

    For Sale O6391277 - 1807 HAMMERLIN AVE #G, WINTER PARK, FL 32789 25 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1818
       Built: 2006   Tax: $6,197 (2025)
    Community: Terrazo Del Sol
    Condo


    Estimated Monthly Payment: $3,694 (change assumption)
    Mortgage ($3,178) + Taxes in 2025 ($516)


    Taxes:$6,197

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 2838 WRIGHT AVE, WINTER PARK, FL 32789

    $2,399,0002 Days on yellowkey   MLS ID: O6399931

    For Sale O6399931 - 2838 WRIGHT AVE, WINTER PARK, FL 32789 10 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3479
       Built: 2026   Tax: $6,037 (2025)
    Community: Lake Forest Park
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $13,648 (change assumption)
    Mortgage ($13,145) + Taxes in 2025 ($503)


    Taxes:$6,037

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 1319 BESSMOR RD, WINTER PARK, FL 32789

    $595,0003 Days on yellowkey   MLS ID: O6400395

    1 Days Off yellowkey (back on 4/24/2026)

    For Sale O6400395 - 1319 BESSMOR RD, WINTER PARK, FL 32789 13 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1126
       Built: 1956   Tax: $5,626 (2025)
    Community: Winter Park Village
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,729 (change assumption)
    Mortgage ($3,260) + Taxes in 2025 ($469)


    Taxes:$5,626

    Elementary School: Dream Lake Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle




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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.