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Winter Park Homes For Sale & Real Estate - 420 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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  • 120 BROADVIEW AVE, WINTER PARK, FL 32789

    $1,450,00068 Days on yellowkey   MLS ID: O6409860

    For Sale O6409860 - 120 BROADVIEW AVE, WINTER PARK, FL 32789 6 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1747
       Built: 1947   Tax: $2,693 (2025)
    Community: Killarney Estates
    Single Family


    Estimated Monthly Payment: $8,169 (change assumption)
    Mortgage ($7,945) + Taxes in 2025 ($224)


    Taxes:$2,693

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park Middle


  • 1695 LEE RD #B210, WINTER PARK, FL 32789

    $95,000188 Days on yellowkey   MLS ID: O6375872

    REDUCED by $3,000 (3.1%) on 07/03/2026

    For Sale O6375872 - 1695 LEE RD #B210, WINTER PARK, FL 32789 27 photos

    Bed: 1   Bath: 1.0
    Liv Area Sq Ft: 638
       Built: 1966   Tax: $1,493 (2024)
    Community: Waterfall Cove
    Spa: No

    Condo


    Estimated Monthly Payment: $645 (change assumption)
    Mortgage ($521) + Taxes in 2024 ($124)


    Taxes:$1,493

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 1751 GOODRICH AVE, WINTER PARK, FL 32789

    $1,380,000181 Days on yellowkey   MLS ID: O6377936

    REDUCED by $45,000 (3.2%) on 07/03/2026

    For Sale O6377936 - 1751 GOODRICH AVE, WINTER PARK, FL 32789 50 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2170
       Built: 2016   Tax: $9,263 (2024)
    Community: Sylvan Heights
    Single Family


    Estimated Monthly Payment: $8,333 (change assumption)
    Mortgage ($7,561) + Taxes in 2024 ($772)


    Taxes:$9,263

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Glenridge Middle


  • 1565 FOREST AVE, WINTER PARK, FL 32789

    $1,495,000106 Days on yellowkey   MLS ID: O6398694

    0 Days Off yellowkey (back on 7/2/2026)

    REDUCED by $155,000 (9.4%) on 06/15/2026

    For Sale O6398694 - 1565 FOREST AVE, WINTER PARK, FL 32789 37 photos

    Bed: 4   Bath: 2.0
    Liv Area Sq Ft: 2163
       Built: 1925   Tax: $2,803 (2025)
    Community: Ellno Willo
    Single Family


    Estimated Monthly Payment: $8,425 (change assumption)
    Mortgage ($8,192) + Taxes in 2025 ($234)


    Taxes:$2,803

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 2361 MULBRY DR, WINTER PARK, FL 32789

    $2,249,000104 Days on yellowkey   MLS ID: O6396840

    0 Days Off yellowkey (back on 7/2/2026)

    REDUCED by $40,000 (1.7%) on 06/10/2026

    For Sale O6396840 - 2361 MULBRY DR, WINTER PARK, FL 32789 76 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 3130
       Built: 2026   Tax: $6,436 (2025)
    Community: Lake Forest Park
    Single Family


    Estimated Monthly Payment: $12,859 (change assumption)
    Mortgage ($12,323) + Taxes in 2025 ($536)


    Taxes:$6,436

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 1232 VALLEY CREEK RUN, WINTER PARK, FL 32792

    $535,00041 Days on yellowkey   MLS ID: O6417190

    1 Days Off yellowkey (back on 7/2/2026)

    For Sale O6417190 - 1232 VALLEY CREEK RUN, WINTER PARK, FL 32792 48 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2071
       Built: 1994
    Monthly Fee: $22
       Tax: $2,283 (2025)
    Community: Lost Creek
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,144 (change assumption)
    Mortgage ($2,931) + Fees ($22) + Taxes in 2025 ($190)


    Taxes:$2,283

    Elementary School: Red Bug Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 2249 MINNESOTA AVE, WINTER PARK, FL 32789

    $429,90035 Days on yellowkey   MLS ID: O6419820

    1 Days Off yellowkey (back on 7/2/2026)

    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


  • 1822 YORKSHIRE DR, WINTER PARK, FL 32792

    $598,00096 Days on yellowkey   MLS ID: O6401364

    1 Days Off yellowkey (back on 7/2/2026)

    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


  • 1600 S PENNSYLVANIA AVE, WINTER PARK, FL 32789

    $1,200,00079 Days on yellowkey   MLS ID: NS1088189

    0 Days Off yellowkey (back on 7/1/2026)

    For Sale NS1088189 - 1600 S PENNSYLVANIA AVE, WINTER PARK, FL 32789 49 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2158
       Built: 1958   Tax: $5,218 (2025)
    Community: Banks Colonial Estates
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $7,010 (change assumption)
    Mortgage ($6,575) + Taxes in 2025 ($435)


    Taxes:$5,218

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 3651 N GOLDENROD RD #D102, WINTER PARK, FL 32792

    $157,50099 Days on yellowkey   MLS ID: O6401114

    1 Days Off yellowkey (back on 7/1/2026)

    REDUCED by $400 (0.3%) on 06/27/2026

    For Sale O6401114 - 3651 N GOLDENROD RD #D102, WINTER PARK, FL 32792 16 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 840
       Built: 1990
    Monthly Fee: $370
       Tax: $2,461 (2025)
    Community: Lancelot/Winter Park
    Condo


    Estimated Monthly Payment: $1,438 (change assumption)
    Mortgage ($863) + Fees ($370) + Taxes in 2025 ($205)


    Taxes:$2,461

    Elementary School: Aloma Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 1523 MILLER AVE, WINTER PARK, FL 32789

    $1,449,999203 Days on yellowkey   MLS ID: O6371649

    REDUCED by $50,000 (3.3%) on 07/01/2026

    For Sale O6371649 - 1523 MILLER AVE, WINTER PARK, FL 32789 65 photos

    Bed: 5   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 3164
       Built: 2026   Tax: $3,620 (2025)
    Community: Lawndale
    Single Family


    Estimated Monthly Payment: $8,247 (change assumption)
    Mortgage ($7,945) + Taxes in 2025 ($302)


    Taxes:$3,620

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park Middle


  • 1404 BORDER DR, WINTER PARK, FL 32789

    $1,150,00061 Days on yellowkey   MLS ID: O6412140

    REDUCED by $25,000 (2.1%) on 07/01/2026

    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: $7,653 (change assumption)
    Mortgage ($6,301) + Taxes in 2025 ($1,352)


    Taxes:$16,220

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 2501 LAFAYETTE AVE, WINTER PARK, FL 32789

    $1,795,00042 Days on yellowkey   MLS ID: O6416565

    0 Days Off yellowkey (back on 7/1/2026)

    For Sale O6416565 - 2501 LAFAYETTE AVE, WINTER PARK, FL 32789 22 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 2819
       Built: 2026   Tax: $4,608 (2026)
    Community: Winter Park Village
    Single Family


    Estimated Monthly Payment: $10,219 (change assumption)
    Mortgage ($9,835) + Taxes in 2026 ($384)


    Taxes:$4,608

    Elementary School: None

    High School: None

    Tax Year: 2026

    Middle School: None


  • 785 N PHELPS AVE, WINTER PARK, FL 32789

    $1,900,000126 Days on yellowkey   MLS ID: O6393117

    0 Days Off yellowkey (back on 7/1/2026)

    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


  • WINTER PARK, FL 32792

    $229,90035 Days on yellowkey   MLS ID: O6419422

    1 Days Off yellowkey (back on 7/1/2026)

    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


  • 4053 COOL WATER CT, WINTER PARK, FL 32792

    $549,00034 Days on yellowkey   MLS ID: O6419831

    0 Days Off yellowkey (back on 6/30/2026)

    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


  • 1131 WILDMEADOW RUN, WINTER PARK, FL 32792

    $825,000127 Days on yellowkey   MLS ID: O6392218

    For Sale O6392218 - 1131 WILDMEADOW RUN, WINTER PARK, FL 32792 28 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2589
       Built: 2020
    Monthly Fee: $165
       Tax: $5,312 (2024)
    Community: Meadows At Hawks Crest
    Single Family


    Estimated Monthly Payment: $5,128 (change assumption)
    Mortgage ($4,520) + Fees ($165) + Taxes in 2024 ($443)


    Taxes:$5,312

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Sanford Middle


  • 2222 MARSH SEDGE LN, WINTER PARK, FL 32792

    $739,000357 Days on yellowkey   MLS ID: O6333145

    4 Days Off yellowkey (back on 6/29/2026)

    REDUCED by $25,900 (3.4%) on 06/13/2026

    For Sale O6333145 - 2222 MARSH SEDGE LN, WINTER PARK, FL 32792 60 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2192
       Built: 2019
    Monthly Fee: $243
       Tax: $7,847 (2024)
    Community: Preserve At Hawks Crest
    Single Family


    Estimated Monthly Payment: $4,946 (change assumption)
    Mortgage ($4,049) + Fees ($243) + Taxes in 2024 ($654)


    Taxes:$7,847

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


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

    $184,900220 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: $1,335 (change assumption)
    Mortgage ($1,013) + Fees ($245) + Taxes in 2024 ($77)


    Taxes:$926

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 1405 MILLER AVE, WINTER PARK, FL 32789

    $899,000149 Days on yellowkey   MLS ID: O6386405

    0 Days Off yellowkey (back on 5/8/2026)

    REDUCED by $51,000 (5.4%) on 04/22/2026

    For Sale O6386405 - 1405 MILLER AVE, WINTER PARK, FL 32789 46 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1884
       Built: 2023
    Monthly Fee: $200
       Tax: $8,200 (2025)
    Community: H Vanwies Sub
    Townhouse


    Estimated Monthly Payment: $5,809 (change assumption)
    Mortgage ($4,926) + Fees ($200) + Taxes in 2025 ($683)


    Taxes:$8,200

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park 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.