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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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  • 1565 FOREST AVE, WINTER PARK, FL 32789

    $1,495,00091 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


  • 1200 VIA SALERNO, WINTER PARK, FL 32789

    $5,995,000151 Days on yellowkey   MLS ID: O6381761

    REDUCED by $205,000 (3.3%) on 05/07/2026

    For Sale O6381761 - 1200 VIA SALERNO, WINTER PARK, FL 32789 47 photos

    Bed: 5   Bath: 5.5   Gar: 3
    Liv Area Sq Ft: 5476
       Built: 2001   Tax: $40,087 (2024)
    Community: Cloister Grove Sub
    Spa: No

    Single Family


    Estimated Monthly Payment: $36,189 (change assumption)
    Mortgage ($32,848) + Taxes in 2024 ($3,341)


    Taxes:$40,087

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Maitland Middle


  • 2361 MULBRY DR, WINTER PARK, FL 32789

    $2,249,00089 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


  • 525 OLOLU DR, WINTER PARK, FL 32789

    $495,90075 Days on yellowkey   MLS ID: S5148431

    REDUCED by $19,100 (3.7%) on 07/02/2026

    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: $2,905 (change assumption)
    Mortgage ($2,717) + Taxes in 2025 ($187)


    Taxes:$2,249

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1841 LAKE SPIER DRIVE, WINTER PARK, FL 32789

    $1,595,00048 Days on yellowkey   MLS ID: O6407841

    REDUCED by $55,000 (3.3%) on 07/02/2026

    For Sale O6407841 - 1841 LAKE SPIER DRIVE, WINTER PARK, FL 32789 32 photos

    Bed: 3   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 2467
       Built: 1964   Tax: $4,844 (2025)
    Community: South Lakemont Shores
    Spa: No

    Single Family


    Estimated Monthly Payment: $9,143 (change assumption)
    Mortgage ($8,740) + Taxes in 2025 ($404)


    Taxes:$4,844

    Elementary School: Baldwin Park Elementary

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 1232 VALLEY CREEK RUN, WINTER PARK, FL 32792

    $535,00026 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

    $429,90020 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

    $598,00081 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


  • 2372 SUN VALLEY CIR #2372, WINTER PARK, FL 32792

    $285,00013 Days on yellowkey   MLS ID: O6421135

    For Sale O6421135 - 2372 SUN VALLEY CIR #2372, WINTER PARK, FL 32792 42 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1495
       Built: 1984   Tax: $1,918 (2025)
    Community: Cedarwood Village 1
    Condo


    Estimated Monthly Payment: $1,721 (change assumption)
    Mortgage ($1,562) + Taxes in 2025 ($160)


    Taxes:$1,918

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 7488 WHISPERWOOD DR #28, WINTER PARK, FL 32792

    $230,00021 Days on yellowkey   MLS ID: O6419151

    For Sale O6419151 - 7488 WHISPERWOOD DR #28, WINTER PARK, FL 32792 64 photos

    Bed: 2   Bath: 2.5
    Liv Area Sq Ft: 1578
       Built: 1974
    Monthly Fee: $575
       Tax: $3,078 (2025)
    Community: Whisperwood Condo
    Condo


    Estimated Monthly Payment: $2,092 (change assumption)
    Mortgage ($1,260) + Fees ($575) + Taxes in 2025 ($257)


    Taxes:$3,078

    Elementary School: Cheney Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 1600 S PENNSYLVANIA AVE, WINTER PARK, FL 32789

    $1,200,00064 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


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

    $180,00054 Days on yellowkey   MLS ID: S5150301

    REDUCED by $10,000 (5.3%) on 07/01/2026

    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: $1,488 (change assumption)
    Mortgage ($986) + Fees ($441) + Taxes in 2025 ($60)


    Taxes:$725

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


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

    $157,50084 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

    $1,449,999188 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


  • 2412 CHANTILLY AVE, WINTER PARK, FL 32789

    $2,394,500153 Days on yellowkey   MLS ID: O6381552

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

    REDUCED by $500 (0.0%) on 04/20/2026

    For Sale O6381552 - 2412 CHANTILLY AVE, WINTER PARK, FL 32789 61 photos

    Bed: 5   Bath: 6.5   Gar: 3
    Liv Area Sq Ft: 4506
       Built: 2026   Tax: $4,779 (2025)
    Community: Winter Park Village
    Single Family


    Estimated Monthly Payment: $13,518 (change assumption)
    Mortgage ($13,120) + Taxes in 2025 ($398)


    Taxes:$4,779

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 1404 BORDER DR, WINTER PARK, FL 32789

    $1,150,00046 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


  • 3009 NICHOLSON DR, WINTER PARK, FL 32792

    $449,90019 Days on yellowkey   MLS ID: O6419862

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

    For Sale O6419862 - 3009 NICHOLSON DR, WINTER PARK, FL 32792 39 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1645
       Built: 1980   Tax: $1,274 (2025)
    Community: Wrenwood Unit 3 3Rd Add
    Single Family


    Estimated Monthly Payment: $2,571 (change assumption)
    Mortgage ($2,465) + Taxes in 2025 ($106)


    Taxes:$1,274

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 2501 LAFAYETTE AVE, WINTER PARK, FL 32789

    $1,795,00027 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

    $1,900,000111 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

    $229,90020 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




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.