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Winter Park Homes For Sale & Real Estate - 420 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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  • 3641 HAWTHORNE LN, WINTER PARK, FL 32792

    $475,00035 Days on yellowkey   MLS ID: TB8519391

    For Sale TB8519391 - 3641 HAWTHORNE LN, WINTER PARK, FL 32792 43 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1622
       Built: 1979   Tax: $4,051 (2025)
    Community: Garden Lake Estates Unit 1
    Single Family


    Estimated Monthly Payment: $2,940 (change assumption)
    Mortgage ($2,603) + Taxes in 2025 ($338)


    Taxes:$4,051

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2015 SUMMERFIELD RD, WINTER PARK, FL 32792

    $1,262,50041 Days on yellowkey   MLS ID: O6418198

    REDUCED by $12,500 (1.0%) on 07/23/2026

    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: $7,521 (change assumption)
    Mortgage ($6,918) + Taxes in 2025 ($604)


    Taxes:$7,243

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 1421 CHAPMAN CIR, WINTER PARK, FL 32789

    $1,450,00047 Days on yellowkey   MLS ID: O6415941

    REDUCED by $100,000 (6.5%) on 07/11/2026

    For Sale O6415941 - 1421 CHAPMAN CIR, WINTER PARK, FL 32789 49 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3578
       Built: 2005
    Monthly Fee: $268
       Tax: $10,592 (2025)
    Community: Windsong Elizabeths Walk 43/81
    Single Family


    Estimated Monthly Payment: $9,096 (change assumption)
    Mortgage ($7,945) + Fees ($268) + Taxes in 2025 ($883)


    Taxes:$10,592

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 1707 HARMON AVE, WINTER PARK, FL 32789

    $639,00071 Days on yellowkey   MLS ID: O6409180

    REDUCED by $10,000 (1.5%) on 07/19/2026

    For Sale O6409180 - 1707 HARMON AVE, WINTER PARK, FL 32789 37 photos

    Bed: 3   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1669
       Built: 1927   Tax: $4,658 (2025)
    Community: Lawndale
    Single Family


    Estimated Monthly Payment: $3,889 (change assumption)
    Mortgage ($3,501) + Taxes in 2025 ($388)


    Taxes:$4,658

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park Middle


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

    $245,000100 Days on yellowkey   MLS ID: O6400674

    REDUCED by $5,000 (2.0%) on 07/11/2026

    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: $2,055 (change assumption)
    Mortgage ($1,342) + 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


  • 950 HANOVER AVE, WINTER PARK, FL 32789

    $460,000109 Days on yellowkey   MLS ID: O6398273

    REDUCED by $10,000 (2.1%) on 06/01/2026

    For Sale O6398273 - 950 HANOVER AVE, WINTER PARK, FL 32789 25 photos

    Bed: 3   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1606
       Built: 1956   Tax: $3,525 (2025)
    Community: Albert Lee Ridge 1St Add
    Single Family


    Estimated Monthly Payment: $2,814 (change assumption)
    Mortgage ($2,520) + Taxes in 2025 ($294)


    Taxes:$3,525

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2305 SUN VALLEY CIR, WINTER PARK, FL 32792, WINTER PARK, FL 32792

    $279,90027 Days on yellowkey   MLS ID: O6421422

    For Sale O6421422 - 2305 SUN VALLEY CIR, WINTER PARK, FL 32792, WINTER PARK, FL 32792 42 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1295
       Built: 1985
    Monthly Fee: $499

    Community: Cedarwood Village
    Condo


    Estimated Monthly Payment: $2,033 (change assumption)
    Mortgage ($1,534) + Fees ($499) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1540 FLORENTINO LN, WINTER PARK, FL 32792

    $315,00067 Days on yellowkey   MLS ID: O6408841

    REDUCED by $20,000 (6.0%) on 07/12/2026

    For Sale O6408841 - 1540 FLORENTINO LN, WINTER PARK, FL 32792 20 photos

    Bed: 3   Bath: 2.5   Gar: 1
    Liv Area Sq Ft: 1682
       Built: 2004
    Monthly Fee: $175
       Tax: $5,340 (2025)
    Community: Vistas At Lake Howell
    Townhouse


    Estimated Monthly Payment: $2,346 (change assumption)
    Mortgage ($1,726) + Fees ($175) + Taxes in 2025 ($445)


    Taxes:$5,340

    Elementary School: Sterling Park Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 311 E MORSE BLVD #1-3, WINTER PARK, FL 32789

    $1,895,00082 Days on yellowkey   MLS ID: O6406368

    REDUCED by $30,000 (1.6%) on 07/13/2026

    For Sale O6406368 - 311 E MORSE BLVD #1-3, WINTER PARK, FL 32789 28 photos

    Bed: 2   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2304
       Built: 1960
    Monthly Fee: $2,471
       Tax: $16,493 (2025)
    Community: Whispering Waters/Phillips Circle Rep
    Condo


    Estimated Monthly Payment: $14,229 (change assumption)
    Mortgage ($10,383) + Fees ($2,471) + Taxes in 2025 ($1,374)


    Taxes:$16,493

    Elementary School: None

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 2702 PARKLAND DR, WINTER PARK, FL 32789

    $1,049,000110 Days on yellowkey   MLS ID: O6397997

    REDUCED by $50,000 (4.5%) on 07/21/2026

    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: $6,187 (change assumption)
    Mortgage ($5,748) + 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


  • 2833 PRINCE JOHN RD, WINTER PARK, FL 32792

    $684,0007 Days on yellowkey   MLS ID: O6427246

    For Sale O6427246 - 2833 PRINCE JOHN RD, WINTER PARK, FL 32792 31 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1605
       Built: 1963   Tax: $6,145 (2025)
    Community: Winter Park Pines Rep
    Single Family


    Estimated Monthly Payment: $4,260 (change assumption)
    Mortgage ($3,748) + Taxes in 2025 ($512)


    Taxes:$6,145

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2803 RIDDLE DR, WINTER PARK, FL 32789

    $569,00019 Days on yellowkey   MLS ID: O6423829

    REDUCED by $20,000 (3.4%) on 07/20/2026

    For Sale O6423829 - 2803 RIDDLE DR, WINTER PARK, FL 32789 28 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1709
       Built: 1955   Tax: $6,477 (2025)
    Community: Fairshores Place
    Single Family


    Estimated Monthly Payment: $3,657 (change assumption)
    Mortgage ($3,118) + Taxes in 2025 ($540)


    Taxes:$6,477

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park Middle


  • 1473 BERKSHIRE AVE, WINTER PARK, FL 32789

    $1,429,00049 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


  • 1250 FORMOSA AVE, WINTER PARK, FL 32789

    $560,00056 Days on yellowkey   MLS ID: O6412954

    For Sale O6412954 - 1250 FORMOSA AVE, WINTER PARK, FL 32789 37 photos

    Bed: 3   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 1937
       Built: 2022
    Monthly Fee: $252
       Tax: $8,328 (2025)
    Community: Urban Green 12
    Townhouse


    Estimated Monthly Payment: $4,014 (change assumption)
    Mortgage ($3,068) + Fees ($252) + Taxes in 2025 ($694)


    Taxes:$8,328

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2430 CHANTILLY AVE, WINTER PARK, FL 32789

    $1,599,00076 Days on yellowkey   MLS ID: O6401352

    REDUCED by $66,000 (4.0%) on 07/07/2026

    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: $9,156 (change assumption)
    Mortgage ($8,761) + Taxes in 2025 ($394)


    Taxes:$4,730

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 102 BELL PL, WINTER PARK, FL 32792

    $1,399,000106 Days on yellowkey   MLS ID: O6398118

    For Sale O6398118 - 102 BELL PL, WINTER PARK, FL 32792 46 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2459
       Built: 2025   Tax: $4,224 (2025)
    Community: Eastgate Sub
    Spa: No

    Single Family


    Estimated Monthly Payment: $8,018 (change assumption)
    Mortgage ($7,666) + Taxes in 2025 ($352)


    Taxes:$4,224

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1581 FOREST AVE, WINTER PARK, FL 32789

    $3,275,000139 Days on yellowkey   MLS ID: O6382377

    REDUCED by $118,000 (3.5%) on 07/20/2026

    For Sale O6382377 - 1581 FOREST AVE, WINTER PARK, FL 32789 57 photos

    Bed: 4   Bath: 5.0   Gar: 2
    Liv Area Sq Ft: 4683
       Built: 1954   Tax: $20,042 (2024)
    Community: Ellno Willo
    Spa: No

    Single Family


    Estimated Monthly Payment: $19,615 (change assumption)
    Mortgage ($17,945) + Taxes in 2024 ($1,670)


    Taxes:$20,042

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Audubon Park K-8


  • 607 ELLEN DR, WINTER PARK, FL 32789

    $1,399,500281 Days on yellowkey   MLS ID: O6354269

    REDUCED by $50,400 (3.5%) on 07/11/2026

    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: $8,096 (change assumption)
    Mortgage ($7,668) + 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


  • 1751 GLENCOE RD, WINTER PARK, FL 32789

    $3,390,000267 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


  • 240 N PHELPS AVE, WINTER PARK, FL 32789

    $2,250,00048 Days on yellowkey   MLS ID: O6415360

    For Sale O6415360 - 240 N PHELPS AVE, WINTER PARK, FL 32789 39 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 2889
       Built: 2026   Tax: $6,605 (2025)
    Community: Sylvan Heights
    Single Family


    Estimated Monthly Payment: $12,879 (change assumption)
    Mortgage ($12,328) + Taxes in 2025 ($550)


    Taxes:$6,605

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge 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.