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Winter Park Homes For Sale & Real Estate - 447 homes

Winter Park homes for sale are located in Seminole 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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  • 3243 FOREST OAKS COURT #117, WINTER PARK, FL 32792

    $175,00021 Days on yellowkey   MLS ID: O6406448

    For Sale O6406448 - 3243 FOREST OAKS COURT #117, WINTER PARK, FL 32792 15 photos

    Bed: 2   Bath: 1.5
    Liv Area Sq Ft: 990
       Built: 1983   Tax: $2,723 (2025)
    Community: Hidden Oaks Condo Ph 7
    Spa: No

    Condo


    Estimated Monthly Payment: $1,186 (change assumption)
    Mortgage ($959) + Taxes in 2025 ($227)


    Taxes:$2,723

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2052 LEANNE CT, WINTER PARK, FL 32792

    $445,000116 Days on yellowkey   MLS ID: O6379323

    REDUCED by $5,000 (1.1%) on 05/28/2026

    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: $2,570 (change assumption)
    Mortgage ($2,438) + Taxes in 2024 ($132)


    Taxes:$1,581

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 2157 LAKE DR, WINTER PARK, FL 32789

    $759,000Listed 05/30/2026 6:32PM   MLS ID: O6412258

    For Sale O6412258 - 2157 LAKE DR, WINTER PARK, FL 32789 45 photos

    Bed: 3   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2633
       Built: 1962   Tax: $1,605 (2025)
    Community: Killarney Point
    Single Family


    Estimated Monthly Payment: $4,293 (change assumption)
    Mortgage ($4,159) + Taxes in 2025 ($134)


    Taxes:$1,605

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 151 N ORLANDO AVE ##115, WINTER PARK, FL 32789

    $298,000179 Days on yellowkey   MLS ID: O6362403

    For Sale O6362403 - 151 N ORLANDO AVE ##115, WINTER PARK, FL 32789 22 photos

    Bed: 2   Bath: 1.0
    Liv Area Sq Ft: 710
       Built: 1960   Tax: $2,965 (2025)
    Community: Lake Killarney Condo
    Spa: No

    Condo


    Estimated Monthly Payment: $1,880 (change assumption)
    Mortgage ($1,633) + Taxes in 2025 ($247)


    Taxes:$2,965

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park Middle


  • 338 BLUE HERON DR, WINTER PARK, FL 32789

    $865,000Listed 05/30/2026 6:12PM   MLS ID: O6410174

    For Sale O6410174 - 338 BLUE HERON DR, WINTER PARK, FL 32789 44 photos

    Bed: 3   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2017
       Built: 1960   Tax: $6,647 (2025)
    Community: Flamingo Shores
    Single Family


    Estimated Monthly Payment: $5,294 (change assumption)
    Mortgage ($4,740) + Taxes in 2025 ($554)


    Taxes:$6,647

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park Middle


  • 1822 YORKSHIRE DR, WINTER PARK, FL 32792

    $598,00036 Days on yellowkey   MLS ID: O6401364

    REDUCED by $26,000 (4.2%) on 05/20/2026

    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: $3,773 (change assumption)
    Mortgage ($3,277) + Taxes in 2025 ($497)


    Taxes:$5,959

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 1800 MAGNOLIA AVE, WINTER PARK, FL 32789

    $1,000,00075 Days on yellowkey   MLS ID: NS1087637

    REDUCED by $100,000 (9.1%) on 05/20/2026

    For Sale NS1087637 - 1800 MAGNOLIA AVE, WINTER PARK, FL 32789 65 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2431
       Built: 1996   Tax: $11,730 (2025)
    Community: Temple Terrace
    Spa: No

    Single Family


    Estimated Monthly Payment: $6,457 (change assumption)
    Mortgage ($5,479) + Taxes in 2025 ($978)


    Taxes:$11,730

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 1404 BORDER DR, WINTER PARK, FL 32789

    $1,200,000Listed 05/29/2026 10:05PM   MLS ID: O6412140

    For Sale O6412140 - 1404 BORDER DR, WINTER PARK, FL 32789 38 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 2469
       Built: 2023   Tax: $16,220 (2025)
    Community: Winter Park Village
    Single Family


    Estimated Monthly Payment: $7,927 (change assumption)
    Mortgage ($6,575) + Taxes in 2025 ($1,352)


    Taxes:$16,220

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 1320 GLADIOLAS DR, WINTER PARK, FL 32792

    $485,000Listed 05/29/2026 9:55PM   MLS ID: O6412139

    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: $2,772 (change assumption)
    Mortgage ($2,657) + Taxes in 2025 ($115)


    Taxes:$1,380

    Elementary School: Red Bug Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 2676 BARBADOS DR, WINTER PARK, FL 32792

    $340,0001 Day on yellowkey   MLS ID: O6411958

    For Sale O6411958 - 2676 BARBADOS DR, WINTER PARK, FL 32792 29 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1743
       Built: 1978
    Monthly Fee: $98
       Tax: $4,131 (2025)
    Community: Windward Square Sec 2
    Townhouse


    Estimated Monthly Payment: $2,305 (change assumption)
    Mortgage ($1,863) + Fees ($98) + Taxes in 2025 ($344)


    Taxes:$4,131

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 610 ELLENDALE DR, WINTER PARK, FL 32792

    $399,0001 Day on yellowkey   MLS ID: O6411325

    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


  • 1761 GLADIOLAS DR, WINTER PARK, FL 32792

    $375,0001 Day on yellowkey   MLS ID: O6411912

    For Sale O6411912 - 1761 GLADIOLAS DR, WINTER PARK, FL 32792 7 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1656
       Built: 1979   Tax: $1,453 (2025)
    Community: Garden Lake Estates Unit 1
    Single Family


    Estimated Monthly Payment: $2,176 (change assumption)
    Mortgage ($2,055) + Taxes in 2025 ($121)


    Taxes:$1,453

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2829 ALOMA, WINTER PARK, FL 32792

    $579,00029 Days on yellowkey   MLS ID: O6404107

    For Sale O6404107 - 2829 ALOMA, WINTER PARK, FL 32792 36 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1821
       Built: 1963   Tax: $4,277 (2025)
    Community: Winter Park Estates
    Single Family


    Estimated Monthly Payment: $3,529 (change assumption)
    Mortgage ($3,173) + Taxes in 2025 ($356)


    Taxes:$4,277

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1741 MIZELL AVE, WINTER PARK, FL 32789

    $1,095,0008 Days on yellowkey   MLS ID: O6410059

    For Sale O6410059 - 1741 MIZELL AVE, WINTER PARK, FL 32789 41 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2015
       Built: 1982   Tax: $11,682 (2025)
    Community: Lake Monte Sub
    Single Family


    Estimated Monthly Payment: $6,973 (change assumption)
    Mortgage ($6,000) + Taxes in 2025 ($974)


    Taxes:$11,682

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 333 CORNWALL RD, WINTER PARK, FL 32792

    $579,0008 Days on yellowkey   MLS ID: O6409379

    For Sale O6409379 - 333 CORNWALL RD, WINTER PARK, FL 32792 32 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1660
       Built: 1963
    Monthly Fee: $5
       Tax: $2,654 (2025)
    Community: Winter Park Pines
    Single Family


    Estimated Monthly Payment: $3,399 (change assumption)
    Mortgage ($3,173) + Fees ($5) + Taxes in 2025 ($221)


    Taxes:$2,654

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 1914 BONANZA CT, WINTER PARK, FL 32792

    $429,99915 Days on yellowkey   MLS ID: O6408461

    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


  • 1813 HARLAND PARK DR, WINTER PARK, FL 32789

    $1,875,00029 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


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

    $259,00040 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: 2.5
    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


  • 2702 PARKLAND DR, WINTER PARK, FL 32789

    $1,139,75050 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


  • 240 N PHELPS AVE, WINTER PARK, FL 32789

    $2,279,00082 Days on yellowkey   MLS ID: O6389035

    For Sale O6389035 - 240 N PHELPS AVE, WINTER PARK, FL 32789 68 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 2889
       Built: 2026   Tax: $6,605 (2025)
    Community: Sylvan Heights
    Spa: No

    Single Family


    Estimated Monthly Payment: $13,038 (change assumption)
    Mortgage ($12,487) + Taxes in 2025 ($550)


    Taxes:$6,605

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge 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.