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Winter Park Homes For Sale & Real Estate - 436 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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  • 2500 LEE RD #104, WINTER PARK, FL 32789

    $259,9998 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


  • 7327 FOREST HILL CT #223, WINTER PARK, FL 32792

    $180,00045 Days on yellowkey   MLS ID: O6403841

    REDUCED by $5,000 (2.7%) on 06/11/2026

    For Sale O6403841 - 7327 FOREST HILL CT #223, WINTER PARK, FL 32792 18 photos

    Bed: 2   Bath: 2.5
    Liv Area Sq Ft: 1031
       Built: 1984
    Monthly Fee: $450
       Tax: $2,597 (2025)
    Community: Hidden Oaks Condo Ph 12
    Condo


    Estimated Monthly Payment: $1,653 (change assumption)
    Mortgage ($986) + Fees ($450) + Taxes in 2025 ($216)


    Taxes:$2,597

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2923 ANTIQUE OAKS CIR #37, WINTER PARK, FL 32792

    $178,900554 Days on yellowkey   MLS ID: A4632112

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

    REDUCED by $3,500 (1.9%) on 06/04/2026

    For Sale A4632112 - 2923 ANTIQUE OAKS CIR #37, WINTER PARK, FL 32792 7 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1105
       Built: 1984
    Monthly Fee: $442
       Tax: $2,648 (2023)
    Community: Parkview Village
    Condo


    Estimated Monthly Payment: $1,643 (change assumption)
    Mortgage ($980) + Fees ($442) + Taxes in 2023 ($221)


    Taxes:$2,648

    Elementary School: Aloma Elem

    High School: Winter Park High

    Tax Year: 2023

    Middle School: Glenridge Middle


  • 2889 ROUEN AVE, WINTER PARK, FL 32789

    $375,00058 Days on yellowkey   MLS ID: L4961275

    REDUCED by $24,500 (6.1%) on 06/01/2026

    For Sale L4961275 - 2889 ROUEN AVE, WINTER PARK, FL 32789 10 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1144
       Built: 1959   Tax: $5,061 (2025)
    Community: Winter Park Manor
    Single Family


    Estimated Monthly Payment: $2,477 (change assumption)
    Mortgage ($2,055) + Taxes in 2025 ($422)


    Taxes:$5,061

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 525 OLOLU DR, WINTER PARK, FL 32789

    $515,00049 Days on yellowkey   MLS ID: S5148431

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

    For Sale S5148431 - 525 OLOLU DR, WINTER PARK, FL 32789 42 photos

    Bed: 3   Bath: 3.0
    Liv Area Sq Ft: 1786
       Built: 1966   Tax: $2,249 (2025)
    Community: Killarney Circle
    Single Family


    Estimated Monthly Payment: $3,009 (change assumption)
    Mortgage ($2,822) + Taxes in 2025 ($187)


    Taxes:$2,249

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2408 LAFAYETTE AVE, WINTER PARK, FL 32789

    $1,495,00069 Days on yellowkey   MLS ID: O6397694

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

    For Sale O6397694 - 2408 LAFAYETTE AVE, WINTER PARK, FL 32789 31 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2838
       Built: 2024   Tax: $3,770 (2024)
    Community: Winter Park Village
    Spa: No

    Single Family


    Estimated Monthly Payment: $8,506 (change assumption)
    Mortgage ($8,192) + Taxes in 2024 ($314)


    Taxes:$3,770

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Maitland Middle


  • 2401 SUN VALLEY CIR #2401, WINTER PARK, FL 32792

    $265,00085 Days on yellowkey   MLS ID: S5146437

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

    REDUCED by $20,000 (7.0%) on 04/21/2026

    For Sale S5146437 - 2401 SUN VALLEY CIR #2401, WINTER PARK, FL 32792 26 photos

    Bed: 2   Bath: 2.5
    Liv Area Sq Ft: 1495
       Built: 1984   Tax: $3,702 (2024)
    Community: Cedarwood Village 1
    Condo


    Estimated Monthly Payment: $1,761 (change assumption)
    Mortgage ($1,452) + Taxes in 2024 ($308)


    Taxes:$3,702

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 2220 FAIRGLENN WAY, WINTER PARK, FL 32792

    $629,90062 Days on yellowkey   MLS ID: O6399993

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

    REDUCED by $20,000 (3.1%) on 06/08/2026

    For Sale O6399993 - 2220 FAIRGLENN WAY, WINTER PARK, FL 32792 53 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2636
       Built: 1986
    Monthly Fee: $53
       Tax: $3,357 (2025)
    Community: Quail Run
    Single Family


    Estimated Monthly Payment: $3,784 (change assumption)
    Mortgage ($3,451) + Fees ($53) + Taxes in 2025 ($280)


    Taxes:$3,357

    Elementary School: Red Bug Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 738 S PENNSYLVANIA AVE, WINTER PARK, FL 32789

    $735,00010 Days on yellowkey   MLS ID: S5151458

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

    For Sale S5151458 - 738 S PENNSYLVANIA AVE, WINTER PARK, FL 32789 55 photos

    Bed: 3   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1739
       Built: 1925   Tax: $2,730 (2025)
    Community: Winter Park
    Single Family


    Estimated Monthly Payment: $4,255 (change assumption)
    Mortgage ($4,027) + Taxes in 2025 ($228)


    Taxes:$2,730

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 1660 WALNUT AVE, WINTER PARK, FL 32789

    $1,569,00052 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


  • 2715 PRINCE JOHN RD, WINTER PARK, FL 32792

    $519,90010 Days on yellowkey   MLS ID: O6415084

    For Sale O6415084 - 2715 PRINCE JOHN RD, WINTER PARK, FL 32792 29 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1565
       Built: 1963   Tax: $7,101 (2025)
    Community: Winter Park Pines Rep
    Single Family


    Estimated Monthly Payment: $3,440 (change assumption)
    Mortgage ($2,849) + Taxes in 2025 ($592)


    Taxes:$7,101

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 3440 ALLSTON LN, WINTER PARK, FL 32792

    $405,00053 Days on yellowkey   MLS ID: O6401731

    REDUCED by $15,000 (3.6%) on 05/26/2026

    For Sale O6401731 - 3440 ALLSTON LN, WINTER PARK, FL 32792 36 photos

    Bed: 3   Bath: 2.5   Gar: 1
    Liv Area Sq Ft: 1533
       Built: 1993
    Monthly Fee: $65
       Tax: $1,364 (2024)
    Community: Villas Of Casselberry Ph 4
    Single Family


    Estimated Monthly Payment: $2,398 (change assumption)
    Mortgage ($2,219) + Fees ($65) + Taxes in 2024 ($114)


    Taxes:$1,364

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 1871 CASSELWOOD ST, WINTER PARK, FL 32792

    $419,90047 Days on yellowkey   MLS ID: O6404306

    0 Days Off yellowkey (back on 5/26/2026)

    REDUCED by $5,000 (1.2%) on 05/12/2026

    For Sale O6404306 - 1871 CASSELWOOD ST, WINTER PARK, FL 32792 37 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1616
       Built: 1988
    Monthly Fee: $39
       Tax: $1,223 (2024)
    Community: Villas Of Casselberry Ph 2
    Townhouse


    Estimated Monthly Payment: $2,442 (change assumption)
    Mortgage ($2,301) + Fees ($39) + Taxes in 2024 ($102)


    Taxes:$1,223

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 1695 LEE RD #E116, WINTER PARK, FL 32789

    $110,00045 Days on yellowkey   MLS ID: O6399346

    0 Days Off yellowkey (back on 6/9/2026)

    REDUCED by $15,000 (12.0%) on 06/02/2026

    For Sale O6399346 - 1695 LEE RD #E116, WINTER PARK, FL 32789 29 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1149
       Built: 1966
    Monthly Fee: $624
       Tax: $2,263 (2025)
    Community: Waterfall Cove/Winter Park
    Condo


    Estimated Monthly Payment: $1,415 (change assumption)
    Mortgage ($603) + Fees ($624) + Taxes in 2025 ($189)


    Taxes:$2,263

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 230 E ROCKWOOD WAY, WINTER PARK, FL 32789

    $2,189,00014 Days on yellowkey   MLS ID: O6412857

    0 Days Off yellowkey (back on 6/9/2026)

    For Sale O6412857 - 230 E ROCKWOOD WAY, WINTER PARK, FL 32789 59 photos

    Bed: 5   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 3374
       Built: 2017   Tax: $19,191 (2025)
    Community: Charmont
    Single Family


    Estimated Monthly Payment: $13,593 (change assumption)
    Mortgage ($11,994) + Taxes in 2025 ($1,599)


    Taxes:$19,191

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 1500 HARRIS CIR, WINTER PARK, FL 32789

    $1,195,000127 Days on yellowkey   MLS ID: O6379012

    REDUCED by $100,000 (7.7%) on 05/26/2026

    For Sale O6379012 - 1500 HARRIS CIR, WINTER PARK, FL 32789 27 photos

    Bed: 2   Bath: 3.0
    Liv Area Sq Ft: 2096
       Built: 1994   Tax: $11,846 (2024)
    Community: Sylvan Lake Shores
    Single Family


    Estimated Monthly Payment: $7,535 (change assumption)
    Mortgage ($6,548) + Taxes in 2024 ($987)


    Taxes:$11,846

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Glenridge Middle


  • 2454 BROOKSHIRE AVE, WINTER PARK, FL 32792

    $1,399,000112 Days on yellowkey   MLS ID: O6384924

    For Sale O6384924 - 2454 BROOKSHIRE AVE, WINTER PARK, FL 32792 34 photos

    Bed: 4   Bath: 3.5   Gar: 1
    Liv Area Sq Ft: 2509
       Built: 2023   Tax: $11,586 (2024)
    Community: Brookshire Heights 1St Add
    Single Family


    Estimated Monthly Payment: $8,631 (change assumption)
    Mortgage ($7,666) + Taxes in 2024 ($966)


    Taxes:$11,586

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Glenridge Middle


  • 1354 TIERRA CIR, WINTER PARK, FL 32792

    $425,000521 Days on yellowkey   MLS ID: O6271121

    0 Days Off yellowkey (back on 6/9/2026)

    For Sale O6271121 - 1354 TIERRA CIR, WINTER PARK, FL 32792 31 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1827
       Built: 1969
    Monthly Fee: $2
       Tax: $3,812 (2023)
    Community: Casa Aloma
    Single Family


    Estimated Monthly Payment: $2,648 (change assumption)
    Mortgage ($2,329) + Fees ($2) + Taxes in 2023 ($318)


    Taxes:$3,812

    Elementary School: English Estates Elementary

    High School: Lake Howell High

    Tax Year: 2023

    Middle School: Tuskawilla Middle


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

    $189,500179 Days on yellowkey   MLS ID: O6368580

    For Sale O6368580 - 2500 LEE RD. #222, WINTER PARK, FL 32789 26 photos

    Bed: 1   Bath: 1.0
    Liv Area Sq Ft: 645
       Built: 1969
    Monthly Fee: $245
       Tax: $926 (2024)
    Community: Lakeside Manor Apts Condo
    Condo


    Estimated Monthly Payment: $1,360 (change assumption)
    Mortgage ($1,038) + Fees ($245) + Taxes in 2024 ($77)


    Taxes:$926

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 2054 EASTBROOK BLVD, WINTER PARK, FL 32792

    $500,00016 Days on yellowkey   MLS ID: V4949389

    For Sale V4949389 - 2054 EASTBROOK BLVD, WINTER PARK, FL 32792 4 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2031
       Built: 1966   Tax: $5,054 (2025)
    Community: Eastbrook Sub Unit 8
    Single Family


    Estimated Monthly Payment: $3,161 (change assumption)
    Mortgage ($2,740) + Taxes in 2025 ($421)


    Taxes:$5,054

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla 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.