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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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  • 1800 MAGNOLIA AVE, WINTER PARK, FL 32789

    $995,000101 Days on yellowkey   MLS ID: NS1087637

    REDUCED by $5,000 (0.5%) on 06/12/2026

    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: $6,429 (change assumption)
    Mortgage ($5,452) + Taxes in 2025 ($978)


    Taxes:$11,730

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 1751 GLENCOE RD, WINTER PARK, FL 32789

    $3,390,000233 Days on yellowkey   MLS ID: O6339739

    REDUCED by $100,000 (2.9%) on 06/06/2026

    For Sale O6339739 - 1751 GLENCOE RD, WINTER PARK, FL 32789 45 photos

    Bed: 5   Bath: 6.0   Gar: 2
    Liv Area Sq Ft: 4520
       Built: 2025   Tax: $12,895 (2024)
    Community: Forest Hills
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $19,649 (change assumption)
    Mortgage ($18,575) + Taxes in 2024 ($1,075)


    Taxes:$12,895

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Audubon Park K-8


  • 3463 ARNEL DR, WINTER PARK, FL 32792

    $424,900100 Days on yellowkey   MLS ID: O6390301

    REDUCED by $5,000 (1.2%) on 06/25/2026

    For Sale O6390301 - 3463 ARNEL DR, WINTER PARK, FL 32792 36 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1770
       Built: 1967   Tax: $4,648 (2024)
    Community: Eastbrook Sub Unit 11
    Single Family


    Estimated Monthly Payment: $2,715 (change assumption)
    Mortgage ($2,328) + Taxes in 2024 ($387)


    Taxes:$4,648

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 2500 LEE RD #104, WINTER PARK, FL 32789

    $259,99915 Days on yellowkey   MLS ID: TB8517242

    For Sale TB8517242 - 2500 LEE RD #104, WINTER PARK, FL 32789 24 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 956
       Built: 1969
    Monthly Fee: $431
       Tax: $2,327 (2025)
    Community: Lakeside Manor Apts Condo
    Spa: No

    Condo


    Estimated Monthly Payment: $2,050 (change assumption)
    Mortgage ($1,425) + Fees ($431) + Taxes in 2025 ($194)


    Taxes:$2,327

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2923 ANTIQUE OAKS CIR #34, WINTER PARK, FL 32792

    $190,00035 Days on yellowkey   MLS ID: S5150301

    For Sale S5150301 - 2923 ANTIQUE OAKS CIR #34, WINTER PARK, FL 32792 22 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1105
       Built: 1984
    Monthly Fee: $441
       Tax: $725 (2025)
    Community: Parkview Village
    Condo


    Estimated Monthly Payment: $1,542 (change assumption)
    Mortgage ($1,041) + Fees ($441) + Taxes in 2025 ($60)


    Taxes:$725

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1411 MILLER AVE, WINTER PARK, FL 32789

    $899,0009 Days on yellowkey   MLS ID: O6416926

    For Sale O6416926 - 1411 MILLER AVE, WINTER PARK, FL 32789 36 photos

    Bed: 3   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 1824
       Built: 2023
    Monthly Fee: $200
       Tax: $8,005 (2025)
    Community: H Vanwies Sub
    Townhouse


    Estimated Monthly Payment: $5,793 (change assumption)
    Mortgage ($4,926) + Fees ($200) + Taxes in 2025 ($667)


    Taxes:$8,005

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park Middle


  • 1473 BERKSHIRE AVE, WINTER PARK, FL 32789

    $1,429,00015 Days on yellowkey   MLS ID: O6415098

    For Sale O6415098 - 1473 BERKSHIRE AVE, WINTER PARK, FL 32789 38 photos

    Bed: 5   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 2351
       Built: 2025   Tax: $5,773 (2025)
    Community: Orwin Manor Westminster Sec
    Single Family


    Estimated Monthly Payment: $8,311 (change assumption)
    Mortgage ($7,830) + Taxes in 2025 ($481)


    Taxes:$5,773

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park Middle


  • 2430 CHANTILLY AVE, WINTER PARK, FL 32789

    $1,665,00042 Days on yellowkey   MLS ID: O6401352

    For Sale O6401352 - 2430 CHANTILLY AVE, WINTER PARK, FL 32789 49 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 2916
       Built: 2026   Tax: $4,730 (2025)
    Community: Winter Park Village
    Spa: No

    Single Family


    Estimated Monthly Payment: $9,517 (change assumption)
    Mortgage ($9,123) + Taxes in 2025 ($394)


    Taxes:$4,730

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 785 N PHELPS AVE, WINTER PARK, FL 32789

    $1,900,00092 Days on yellowkey   MLS ID: O6393117

    REDUCED by $89,000 (4.5%) on 06/05/2026

    For Sale O6393117 - 785 N PHELPS AVE, WINTER PARK, FL 32789 41 photos

    Bed: 5   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2964
       Built: 2026   Tax: $9,172 (2025)
    Community: Comstock Park
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $11,175 (change assumption)
    Mortgage ($10,411) + Taxes in 2025 ($764)


    Taxes:$9,172

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 426 WORTHINGTON DR, WINTER PARK, FL 32789

    $2,499,0001 Day on yellowkey   MLS ID: O6418049

    For Sale O6418049 - 426 WORTHINGTON DR, WINTER PARK, FL 32789 46 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3520
       Built: 2026   Tax: $9,459 (2025)
    Community: Kenilworth Shores Sec 01
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $14,481 (change assumption)
    Mortgage ($13,693) + Taxes in 2025 ($788)


    Taxes:$9,459

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 5340 N LAKE BURKETT LN, WINTER PARK, FL 32792

    $489,90020 Days on yellowkey   MLS ID: O6413717

    REDUCED by $5,100 (1.0%) on 06/21/2026

    For Sale O6413717 - 5340 N LAKE BURKETT LN, WINTER PARK, FL 32792 39 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1746
       Built: 1994
    Monthly Fee: $76
       Tax: $1,591 (2025)
    Community: Trinity Bay Ph 2
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,893 (change assumption)
    Mortgage ($2,684) + Fees ($76) + Taxes in 2025 ($133)


    Taxes:$1,591

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 4053 COOL WATER CT, WINTER PARK, FL 32792

    $549,000Listed 06/25/2026 7:16AM   MLS ID: O6419831

    For Sale O6419831 - 4053 COOL WATER CT, WINTER PARK, FL 32792 41 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1930
       Built: 1979
    Monthly Fee: $28
       Tax: $6,373 (2025)
    Community: Lake Waunatta Woods
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,567 (change assumption)
    Mortgage ($3,008) + Fees ($28) + Taxes in 2025 ($531)


    Taxes:$6,373

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 2249 MINNESOTA AVE, WINTER PARK, FL 32789

    $429,900Listed 06/24/2026 9:47PM   MLS ID: O6419820

    For Sale O6419820 - 2249 MINNESOTA AVE, WINTER PARK, FL 32789 81 photos

    Bed: 4   Bath: 2.0
    Liv Area Sq Ft: 1536
       Built: 1955   Tax: $5,223 (2025)
    Community: Olympia Heights Annex
    Single Family


    Estimated Monthly Payment: $2,791 (change assumption)
    Mortgage ($2,356) + Taxes in 2025 ($435)


    Taxes:$5,223

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park Middle


  • 2500 LEE RD #222, WINTER PARK, FL 32789

    $184,900Listed 06/24/2026 5:56PM   MLS ID: O6419663

    For Sale O6419663 - 2500 LEE RD #222, WINTER PARK, FL 32789 22 photos

    Bed: 1   Bath: 1.0
    Liv Area Sq Ft: 645
       Built: 1969
    Monthly Fee: $225
       Tax: $926 (2024)
    Community: Lakeside Manor
    Condo


    Estimated Monthly Payment: $1,315 (change assumption)
    Mortgage ($1,013) + Fees ($225) + Taxes in 2024 ($77)


    Taxes:$926

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • WINTER PARK, FL 32792

    $229,900Listed 06/24/2026 3:50PM   MLS ID: O6419422

    For Sale O6419422 - WINTER PARK, FL 32792 34 photos

    Bed: 2   Bath: 1.5
    Liv Area Sq Ft: 1219
       Built: 1970   Tax: $1,675 (2025)
    Community: Four Seasons Condo
    Condo


    Estimated Monthly Payment: $1,399 (change assumption)
    Mortgage ($1,260) + Taxes in 2025 ($140)


    Taxes:$1,675

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 2521 GALLIANO CIR, WINTER PARK, FL 32792

    $360,000Listed 06/24/2026 2:53PM   MLS ID: O6419329

    For Sale O6419329 - 2521 GALLIANO CIR, WINTER PARK, FL 32792 27 photos

    Bed: 3   Bath: 3.5   Gar: 1
    Liv Area Sq Ft: 1682
       Built: 2003
    Monthly Fee: $175
       Tax: $4,532 (2025)
    Community: Vistas At Lake Howell
    Townhouse


    Estimated Monthly Payment: $2,525 (change assumption)
    Mortgage ($1,973) + Fees ($175) + Taxes in 2025 ($378)


    Taxes:$4,532

    Elementary School: Sterling Park Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 1320 GLADIOLAS DR, WINTER PARK, FL 32792

    $475,00027 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


  • 2015 SUMMERFIELD RD, WINTER PARK, FL 32792

    $1,275,0007 Days on yellowkey   MLS ID: O6418198

    For Sale O6418198 - 2015 SUMMERFIELD RD, WINTER PARK, FL 32792 31 photos

    Bed: 4   Bath: 4.0   Gar: 1
    Liv Area Sq Ft: 3024
       Built: 1957   Tax: $7,243 (2025)
    Community: Kenilworth Shores Sec 07
    Single Family


    Estimated Monthly Payment: $7,590 (change assumption)
    Mortgage ($6,986) + Taxes in 2025 ($604)


    Taxes:$7,243

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 607 ELLEN DR, WINTER PARK, FL 32789

    $1,449,900247 Days on yellowkey   MLS ID: O6354269

    REDUCED by $50,000 (3.3%) on 05/23/2026

    For Sale O6354269 - 607 ELLEN DR, WINTER PARK, FL 32789 34 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 2812
       Built: 2025
    Monthly Fee: $76
       Tax: $4,224 (2024)
    Community: Lake Killarney Shores
    Spa: No

    Single Family


    Estimated Monthly Payment: $8,372 (change assumption)
    Mortgage ($7,944) + Fees ($76) + Taxes in 2024 ($352)


    Taxes:$4,224

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2024

    Middle School: College Park Middle


  • 2052 LEANNE CT, WINTER PARK, FL 32792

    $440,000142 Days on yellowkey   MLS ID: O6379323

    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




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.