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Winter Park Homes For Sale & Real Estate - 442 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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  • 1870 WALKER AVE, WINTER PARK, FL 32789

    $1,299,000107 Days on yellowkey   MLS ID: O6390504

    REDUCED by $100,000 (7.1%) on 05/29/2026

    For Sale O6390504 - 1870 WALKER AVE, WINTER PARK, FL 32789 32 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2046
       Built: 2026   Tax: $3,981 (2025)
    Community: Osceola Heights
    Single Family


    Estimated Monthly Payment: $7,449 (change assumption)
    Mortgage ($7,118) + Taxes in 2025 ($332)


    Taxes:$3,981

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 1150 VIA SALERNO, WINTER PARK, FL 32789

    $4,195,000365 Days on yellowkey   MLS ID: O6321143

    REDUCED by $555,000 (11.7%) on 04/25/2026

    For Sale O6321143 - 1150 VIA SALERNO, WINTER PARK, FL 32789 62 photos

    Bed: 4   Bath: 5.5   Gar: 2
    Liv Area Sq Ft: 3850
       Built: 2025   Tax: $10,158 (2024)
    Community: Cloister Grove Sub
    Spa: No

    Single Family


    Estimated Monthly Payment: $23,832 (change assumption)
    Mortgage ($22,986) + Taxes in 2024 ($847)


    Taxes:$10,158

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Maitland Middle


  • 2831 MULFORD AVE, WINTER PARK, FL 32789

    $735,00021 Days on yellowkey   MLS ID: O6414319

    For Sale O6414319 - 2831 MULFORD AVE, WINTER PARK, FL 32789 28 photos

    Bed: 4   Bath: 2.5
    Liv Area Sq Ft: 1647
       Built: 1952   Tax: $3,192 (2025)
    Community: Orangewood Park
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,293 (change assumption)
    Mortgage ($4,027) + Taxes in 2025 ($266)


    Taxes:$3,192

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1695 LEE RD #E204, WINTER PARK, FL 32789

    $114,000200 Days on yellowkey   MLS ID: O6366205

    REDUCED by $1,000 (0.9%) on 06/01/2026

    For Sale O6366205 - 1695 LEE RD #E204, WINTER PARK, FL 32789 27 photos

    Bed: 2   Bath: 1.0
    Liv Area Sq Ft: 881
       Built: 1966
    Monthly Fee: $482
       Tax: $1,917 (2024)
    Community: Waterfall Cove
    Condo


    Estimated Monthly Payment: $1,266 (change assumption)
    Mortgage ($625) + Fees ($482) + Taxes in 2024 ($160)


    Taxes:$1,917

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 3463 ARNEL DR, WINTER PARK, FL 32792

    $419,900103 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: $2,688 (change assumption)
    Mortgage ($2,301) + Taxes in 2024 ($387)


    Taxes:$4,648

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 184 SANDLEWOOD TRL ##2, WINTER PARK, FL 32789

    $299,000141 Days on yellowkey   MLS ID: O6380753

    REDUCED by $13,000 (4.2%) on 06/18/2026

    For Sale O6380753 - 184 SANDLEWOOD TRL ##2, WINTER PARK, FL 32789 29 photos

    Bed: 2   Bath: 2.5
    Liv Area Sq Ft: 1133
       Built: 1985
    Monthly Fee: $310
       Tax: $2,915 (2025)
    Community: Sandlewood Creek Condo Ph 10
    Condo


    Estimated Monthly Payment: $2,191 (change assumption)
    Mortgage ($1,638) + Fees ($310) + Taxes in 2025 ($243)


    Taxes:$2,915

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 2923 ANTIQUE OAKS CIR #39, WINTER PARK, FL 32792

    $184,999493 Days on yellowkey   MLS ID: OM695642

    0 Days Off yellowkey (back on 6/26/2026)

    For Sale OM695642 - 2923 ANTIQUE OAKS CIR #39, WINTER PARK, FL 32792 22 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1105
       Built: 1984
    Monthly Fee: $442
       Tax: $2,702 (2024)
    Community: Parkview Village
    Condo


    Estimated Monthly Payment: $1,681 (change assumption)
    Mortgage ($1,014) + Fees ($442) + Taxes in 2024 ($225)


    Taxes:$2,702

    Elementary School: Aloma Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Glenridge Middle


  • 7471 CANFORD CT #19, WINTER PARK, FL 32792

    $199,000262 Days on yellowkey   MLS ID: G5103114

    For Sale G5103114 - 7471 CANFORD CT #19, WINTER PARK, FL 32792 15 photos

    Bed: 2   Bath: 1.5
    Liv Area Sq Ft: 1393
       Built: 1974   Tax: $2,750 (2024)
    Community: Whisperwood Condo
    Condo


    Estimated Monthly Payment: $1,320 (change assumption)
    Mortgage ($1,090) + Taxes in 2024 ($229)


    Taxes:$2,750

    Elementary School: Cheney Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Glenridge Middle


  • 2676 BARBADOS DR, WINTER PARK, FL 32792

    $340,00030 Days on yellowkey   MLS ID: O6411958

    2 Days Off yellowkey (back on 6/26/2026)

    For Sale O6411958 - 2676 BARBADOS DR, WINTER PARK, FL 32792 29 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1743
       Built: 1978
    Monthly Fee: $98
       Tax: $4,131 (2025)
    Community: Windward Square Sec 2
    Townhouse


    Estimated Monthly Payment: $2,305 (change assumption)
    Mortgage ($1,863) + Fees ($98) + Taxes in 2025 ($344)


    Taxes:$4,131

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 3006 NORTHWOOD BLVD, WINTER PARK, FL 32789

    $1,300,0002 Days on yellowkey   MLS ID: O6419056

    For Sale O6419056 - 3006 NORTHWOOD BLVD, WINTER PARK, FL 32789 0 photos

    Bed: 4   Bath: 3.0   Gar: 1
    Liv Area Sq Ft: 2075
       Built: 1953   Tax: $4,188 (2025)
    Community: Northwood Terrace
    Spa: No

    Single Family


    Estimated Monthly Payment: $7,472 (change assumption)
    Mortgage ($7,123) + Taxes in 2025 ($349)


    Taxes:$4,188

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 259 ORANGE TERRACE DRIVE, WINTER PARK, FL 32789

    $465,5002 Days on yellowkey   MLS ID: O6419225

    For Sale O6419225 - 259 ORANGE TERRACE DRIVE, WINTER PARK, FL 32789 26 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1248
       Built: 1953   Tax: $5,488 (2025)
    Community: Orange Terrace
    Single Family


    Estimated Monthly Payment: $3,008 (change assumption)
    Mortgage ($2,551) + Taxes in 2025 ($457)


    Taxes:$5,488

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park Middle


  • 607 ELLEN DR, WINTER PARK, FL 32789

    $1,449,900250 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


  • 2228 HOWARD DR, WINTER PARK, FL 32789

    $2,460,00046 Days on yellowkey   MLS ID: O6407733

    For Sale O6407733 - 2228 HOWARD DR, WINTER PARK, FL 32789 9 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3294
       Built: 2026   Tax: $3,647 (2025)
    Community: Lake Forest Park
    Single Family


    Estimated Monthly Payment: $13,783 (change assumption)
    Mortgage ($13,479) + Taxes in 2025 ($304)


    Taxes:$3,647

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 609 S PHELPS AVE, WINTER PARK, FL 32789

    $2,829,000104 Days on yellowkey   MLS ID: O6388598

    For Sale O6388598 - 609 S PHELPS AVE, WINTER PARK, FL 32789 23 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 4018
       Built: 2026   Tax: $8,522 (2024)
    Community: Kenilworth Shores Sec 06
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $16,211 (change assumption)
    Mortgage ($15,501) + Taxes in 2024 ($710)


    Taxes:$8,522

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Glenridge Middle


  • 2249 MINNESOTA AVE, WINTER PARK, FL 32789

    $429,9004 Days on yellowkey   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


  • 3641 OAK VISTA LN, WINTER PARK, FL 32792

    $475,00020 Days on yellowkey   MLS ID: O6412855

    0 Days Off yellowkey (back on 6/26/2026)

    For Sale O6412855 - 3641 OAK VISTA LN, WINTER PARK, FL 32792 46 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1645
       Built: 1981   Tax: $1,562 (2025)
    Community: Garden Lake Estates Unit 2
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,733 (change assumption)
    Mortgage ($2,603) + Taxes in 2025 ($130)


    Taxes:$1,562

    Elementary School: Red Bug Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 3381 CEDAR SPRINGS PL #151, WINTER PARK, FL 32792

    $179,9003 Days on yellowkey   MLS ID: O6419959

    For Sale O6419959 - 3381 CEDAR SPRINGS PL #151, WINTER PARK, FL 32792 32 photos

    Bed: 2   Bath: 2.5
    Liv Area Sq Ft: 1031
       Built: 1984   Tax: $197 (2025)
    Community: Hidden. Oaks
    Spa: No

    Condo


    Estimated Monthly Payment: $1,002 (change assumption)
    Mortgage ($986) + Taxes in 2025 ($16)


    Taxes:$197

    Elementary School: Aloma Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 1741 MIZELL AVE, WINTER PARK, FL 32789

    $1,050,00037 Days on yellowkey   MLS ID: O6410059

    REDUCED by $45,000 (4.1%) on 06/26/2026

    For Sale O6410059 - 1741 MIZELL AVE, WINTER PARK, FL 32789 41 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2015
       Built: 1982   Tax: $11,682 (2025)
    Community: Lake Monte Sub
    Single Family


    Estimated Monthly Payment: $6,727 (change assumption)
    Mortgage ($5,753) + Taxes in 2025 ($974)


    Taxes:$11,682

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 3009 NICHOLSON DR, WINTER PARK, FL 32792

    $449,9003 Days on yellowkey   MLS ID: O6419862

    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


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

    $230,0005 Days on yellowkey   MLS ID: O6419151

    For Sale O6419151 - 7488 WHISPERWOOD DR #28, WINTER PARK, FL 32792 63 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




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.