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Winter Park Homes For Sale & Real Estate - 438 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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  • 259 ORANGE TERRACE DRIVE, WINTER PARK, FL 32789

    $465,50018 Days on yellowkey   MLS ID: O6419225

    For Sale O6419225 - 259 ORANGE TERRACE DRIVE, WINTER PARK, FL 32789 26 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1248
       Built: 1953   Tax: $5,488 (2025)
    Community: Orange Terrace
    Single Family


    Estimated Monthly Payment: $3,008 (change assumption)
    Mortgage ($2,551) + Taxes in 2025 ($457)


    Taxes:$5,488

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park Middle


  • 1600 LEGION DR, WINTER PARK, FL 32789

    $3,795,00031 Days on yellowkey   MLS ID: O6415591

    REDUCED by $200,000 (5.0%) on 07/13/2026

    For Sale O6415591 - 1600 LEGION DR, WINTER PARK, FL 32789 70 photos

    Bed: 5   Bath: 5.5   Gar: 3
    Liv Area Sq Ft: 4483
       Built: 2008   Tax: $20,740 (2025)
    Community: Green Oaks Rep
    Spa: No

    Single Family


    Estimated Monthly Payment: $22,522 (change assumption)
    Mortgage ($20,794) + Taxes in 2025 ($1,728)


    Taxes:$20,740

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 1660 WALNUT AVE, WINTER PARK, FL 32789

    $1,569,00078 Days on yellowkey   MLS ID: O6395277

    1 Days Off yellowkey (back on 6/10/2026)

    REDUCED by $81,000 (4.9%) on 05/30/2026

    For Sale O6395277 - 1660 WALNUT AVE, WINTER PARK, FL 32789 43 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2249
       Built: 2026   Tax: $6,297 (2025)
    Community: Lake Knowles Terrace
    Spa: No

    Single Family


    Estimated Monthly Payment: $9,122 (change assumption)
    Mortgage ($8,597) + Taxes in 2025 ($525)


    Taxes:$6,297

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 1320 GLADIOLAS DR, WINTER PARK, FL 32792

    $475,00046 Days on yellowkey   MLS ID: O6412139

    REDUCED by $5,000 (1.0%) on 06/15/2026

    For Sale O6412139 - 1320 GLADIOLAS DR, WINTER PARK, FL 32792 43 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1624
       Built: 1983   Tax: $1,380 (2025)
    Community: Garden Lake Estates Unit 3
    Single Family


    Estimated Monthly Payment: $2,718 (change assumption)
    Mortgage ($2,603) + Taxes in 2025 ($115)


    Taxes:$1,380

    Elementary School: Red Bug Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 885 CARNATION DR, WINTER PARK, FL 32792

    $375,0002 Days on yellowkey   MLS ID: S5153456

    For Sale S5153456 - 885 CARNATION DR, WINTER PARK, FL 32792 19 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1240
       Built: 1959   Tax: $5,196 (2025)
    Community: Eastbrook Sub
    Single Family


    Estimated Monthly Payment: $2,488 (change assumption)
    Mortgage ($2,055) + Taxes in 2025 ($433)


    Taxes:$5,196

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2223 CONIFER AVE, WINTER PARK, FL 32792

    $435,0001 Day on yellowkey   MLS ID: O6424677

    For Sale O6424677 - 2223 CONIFER AVE, WINTER PARK, FL 32792 26 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1620
       Built: 1970   Tax: $2,253 (2025)
    Community: Eastbrook Sub Unit 16
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,571 (change assumption)
    Mortgage ($2,384) + Taxes in 2025 ($188)


    Taxes:$2,253

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 263 SCOTTSDALE SQ #263, WINTER PARK, FL 32792

    $80,0001 Day on yellowkey   MLS ID: O6424619

    For Sale O6424619 - 263 SCOTTSDALE SQ #263, WINTER PARK, FL 32792 3 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1020
       Built: 1974   Tax: $1,392 (2025)
    Community: Winter Park Woods Condo
    Condo


    Estimated Monthly Payment: $554 (change assumption)
    Mortgage ($438) + Taxes in 2025 ($116)


    Taxes:$1,392

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 4437 GLENMOOR CT, WINTER PARK, FL 32792

    $539,0001 Day on yellowkey   MLS ID: O6424511

    For Sale O6424511 - 4437 GLENMOOR CT, WINTER PARK, FL 32792 39 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2633
       Built: 1986   Tax: $8,163 (2025)
    Community: Glenmoor
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,634 (change assumption)
    Mortgage ($2,953) + Taxes in 2025 ($680)


    Taxes:$8,163

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 462 W LYMAN AVE, WINTER PARK, FL 32789

    $1,595,0001 Day on yellowkey   MLS ID: O6423842

    For Sale O6423842 - 462 W LYMAN AVE, WINTER PARK, FL 32789 25 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1944
       Built: 2022   Tax: $9,244 (2025)
    Community: Winter Park
    Single Family


    Estimated Monthly Payment: $9,510 (change assumption)
    Mortgage ($8,740) + Taxes in 2025 ($770)


    Taxes:$9,244

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 1778 MONDRIAN CIR, WINTER PARK, FL 32789

    $1,339,000Listed 07/13/2026 5:15PM   MLS ID: O6422941

    For Sale O6422941 - 1778 MONDRIAN CIR, WINTER PARK, FL 32789 52 photos

    Bed: 3   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2377
       Built: 2023
    Monthly Fee: $395
       Tax: $12,451 (2025)
    Community: Mondrian/Winter Park Twnhms
    Spa: No

    Townhouse


    Estimated Monthly Payment: $8,769 (change assumption)
    Mortgage ($7,337) + Fees ($395) + Taxes in 2025 ($1,038)


    Taxes:$12,451

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park Middle


  • 730 W SWOOPE AVE, WINTER PARK, FL 32789

    $839,0008 Days on yellowkey   MLS ID: S5152493

    INCREASED by $69,000 (9.0%) on 07/13/2026

    For Sale S5152493 - 730 W SWOOPE AVE, WINTER PARK, FL 32789 35 photos

    Bed: 5   Bath: 3.0
    Liv Area Sq Ft: 2132
       Built: 1950   Tax: $6,026 (2025)
    Community: Carver Town First Add
    Spa: No

    Single Family


    Estimated Monthly Payment: $5,099 (change assumption)
    Mortgage ($4,597) + Taxes in 2025 ($502)


    Taxes:$6,026

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 229 ALEXANDER PL, WINTER PARK, FL 32789

    $4,250,00039 Days on yellowkey   MLS ID: O6412911

    For Sale O6412911 - 229 ALEXANDER PL, WINTER PARK, FL 32789 53 photos

    Bed: 4   Bath: 5.0   Gar: 3
    Liv Area Sq Ft: 4431
       Built: 2011   Tax: $36,713 (2025)
    Community: Alexander Place
    Spa: No

    Single Family


    Estimated Monthly Payment: $26,347 (change assumption)
    Mortgage ($23,287) + Taxes in 2025 ($3,059)


    Taxes:$36,713

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 4887 N MAGNOLIA AVE, WINTER PARK, FL 32792

    $495,00015 Days on yellowkey   MLS ID: O6420961

    0 Days Off yellowkey (back on 7/13/2026)

    For Sale O6420961 - 4887 N MAGNOLIA AVE, WINTER PARK, FL 32792 52 photos

    Bed: 4   Bath: 3.0
    Liv Area Sq Ft: 1955
       Built: 1964   Tax: $5,197 (2025)
    Community: Suburban Homes
    Single Family


    Estimated Monthly Payment: $3,145 (change assumption)
    Mortgage ($2,712) + Taxes in 2025 ($433)


    Taxes:$5,197

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 2087 LAURELWOOD WAY, WINTER PARK, FL 32792

    $625,00033 Days on yellowkey   MLS ID: O6415387

    For Sale O6415387 - 2087 LAURELWOOD WAY, WINTER PARK, FL 32792 48 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1920
       Built: 2019
    Monthly Fee: $244
       Tax: $4,970 (2025)
    Community: Hawks Crest
    Single Family


    Estimated Monthly Payment: $4,083 (change assumption)
    Mortgage ($3,425) + Fees ($244) + Taxes in 2025 ($414)


    Taxes:$4,970

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 405 LAKE FAIR LN, WINTER PARK, FL 32789

    $444,900111 Days on yellowkey   MLS ID: O6393594

    REDUCED by $5,000 (1.1%) on 07/13/2026

    For Sale O6393594 - 405 LAKE FAIR LN, WINTER PARK, FL 32789 45 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1491
       Built: 1957   Tax: $1,355 (2025)
    Community: Fairbanks Shores 5Th Add
    Single Family


    Estimated Monthly Payment: $2,551 (change assumption)
    Mortgage ($2,438) + Taxes in 2025 ($113)


    Taxes:$1,355

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1840 ASTER DR, WINTER PARK, FL 32792

    $419,90043 Days on yellowkey   MLS ID: O6412364

    REDUCED by $10,090 (2.3%) on 07/09/2026

    For Sale O6412364 - 1840 ASTER DR, WINTER PARK, FL 32792 20 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1667
       Built: 1978   Tax: $864 (2025)
    Community: Garden Lake Estates Unit 1
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,373 (change assumption)
    Mortgage ($2,301) + Taxes in 2025 ($72)


    Taxes:$864

    Elementary School: Red Bug Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 1960 BISCAYNE DR, WINTER PARK, FL 32789

    $300,00014 Days on yellowkey   MLS ID: O6421199

    For Sale O6421199 - 1960 BISCAYNE DR, WINTER PARK, FL 32789 19 photos

    Bed: 2   Bath: 1.0
    Liv Area Sq Ft: 1272
       Built: 1935   Tax: $4,157 (2025)
    Community: Karolina On Killarney
    Single Family


    Estimated Monthly Payment: $1,990 (change assumption)
    Mortgage ($1,644) + Taxes in 2025 ($346)


    Taxes:$4,157

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park Middle


  • 1981 BLUE RIDGE RD, WINTER PARK, FL 32789

    $1,150,00074 Days on yellowkey   MLS ID: O6402961

    0 Days Off yellowkey (back on 7/13/2026)

    For Sale O6402961 - 1981 BLUE RIDGE RD, WINTER PARK, FL 32789 52 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2750
       Built: 1963   Tax: $11,270 (2025)
    Community: Timberlane Shores
    Single Family


    Estimated Monthly Payment: $7,240 (change assumption)
    Mortgage ($6,301) + Taxes in 2025 ($939)


    Taxes:$11,270

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: None


  • 2905 PARKLAND DR, WINTER PARK, FL 32789

    $3,395,0006 Days on yellowkey   MLS ID: O6422550

    0 Days Off yellowkey (back on 7/13/2026)

    For Sale O6422550 - 2905 PARKLAND DR, WINTER PARK, FL 32789 98 photos

    Bed: 6   Bath: 7.0   Gar: 3
    Liv Area Sq Ft: 4850
       Built: 2026   Tax: $5,748 (2025)
    Community: Lake Forest Park
    Single Family


    Estimated Monthly Payment: $19,081 (change assumption)
    Mortgage ($18,602) + Taxes in 2025 ($479)


    Taxes:$5,748

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 2052 LEANNE CT, WINTER PARK, FL 32792

    $440,000161 Days on yellowkey   MLS ID: O6379323

    0 Days Off yellowkey (back on 7/13/2026)

    REDUCED by $5,000 (1.1%) on 06/17/2026

    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: $2,543 (change assumption)
    Mortgage ($2,411) + Taxes in 2024 ($132)


    Taxes:$1,581

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None




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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.