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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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  • 2418 EUSTON RD, WINTER PARK, FL 32789

    $668,99848 Days on yellowkey   MLS ID: O6409323

    REDUCED by $2,113 (0.3%) on 07/13/2026

    For Sale O6409323 - 2418 EUSTON RD, WINTER PARK, FL 32789 34 photos

    Bed: 3   Bath: 2.5   Gar: 1
    Liv Area Sq Ft: 2048
       Built: 1950   Tax: $7,927 (2025)
    Community: Glencoe Sub
    Single Family


    Estimated Monthly Payment: $4,326 (change assumption)
    Mortgage ($3,666) + Taxes in 2025 ($661)


    Taxes:$7,927

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park Middle


  • 5331 OAK CT, WINTER PARK, FL 32792

    $460,000363 Days on yellowkey   MLS ID: S5130868

    For Sale S5130868 - 5331 OAK CT, WINTER PARK, FL 32792 41 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1263
       Built: 1976   Tax: $2,311 (2024)
    Community: Wrenwood Heights Unit 2
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,713 (change assumption)
    Mortgage ($2,520) + Taxes in 2024 ($193)


    Taxes:$2,311

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 1800 MAGNOLIA AVE, WINTER PARK, FL 32789

    $994,000120 Days on yellowkey   MLS ID: NS1087637

    REDUCED by $1,000 (0.1%) on 07/13/2026

    For Sale NS1087637 - 1800 MAGNOLIA AVE, WINTER PARK, FL 32789 65 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2431
       Built: 1996   Tax: $11,730 (2025)
    Community: Temple Terrace
    Spa: No

    Single Family


    Estimated Monthly Payment: $6,424 (change assumption)
    Mortgage ($5,446) + Taxes in 2025 ($978)


    Taxes:$11,730

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 1000 S SEMORAN BLVD #408, WINTER PARK, FL 32792

    $138,00015 Days on yellowkey   MLS ID: R4911527

    REDUCED by $10,000 (6.8%) on 07/13/2026

    For Sale R4911527 - 1000 S SEMORAN BLVD #408, WINTER PARK, FL 32792 11 photos

    Bed: 1   Bath: 1.0
    Liv Area Sq Ft: 776
       Built: 1969   Tax: $1,937 (2025)
    Community: Golfside Villas Condo
    Condo


    Estimated Monthly Payment: $918 (change assumption)
    Mortgage ($756) + Taxes in 2025 ($161)


    Taxes:$1,937

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1000 S SEMORAN BLVD #404, WINTER PARK, FL 32792

    $138,00015 Days on yellowkey   MLS ID: R4911526

    REDUCED by $10,000 (6.8%) on 07/13/2026

    For Sale R4911526 - 1000 S SEMORAN BLVD #404, WINTER PARK, FL 32792 5 photos

    Bed: 1   Bath: 1.0
    Liv Area Sq Ft: 776
       Built: 1969   Tax: $1,937 (2025)
    Community: Golfside Villas Condo
    Condo


    Estimated Monthly Payment: $918 (change assumption)
    Mortgage ($756) + Taxes in 2025 ($161)


    Taxes:$1,937

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1000 S SEMORAN BLVD #306, WINTER PARK, FL 32792

    $138,00015 Days on yellowkey   MLS ID: R4911525

    REDUCED by $10,000 (6.8%) on 07/13/2026

    For Sale R4911525 - 1000 S SEMORAN BLVD #306, WINTER PARK, FL 32792 13 photos

    Bed: 1   Bath: 1.0
    Liv Area Sq Ft: 796
       Built: 1969   Tax: $1,987 (2025)
    Community: Golfside Villas Condo
    Condo


    Estimated Monthly Payment: $922 (change assumption)
    Mortgage ($756) + Taxes in 2025 ($166)


    Taxes:$1,987

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1438 TIERRA CIR, WINTER PARK, FL 32792

    $514,90073 Days on yellowkey   MLS ID: O6403855

    REDUCED by $5,000 (1.0%) on 06/24/2026

    For Sale O6403855 - 1438 TIERRA CIR, WINTER PARK, FL 32792 36 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1627
       Built: 1968   Tax: $1,630 (2024)
    Community: Casa Aloma
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,957 (change assumption)
    Mortgage ($2,821) + Taxes in 2024 ($136)


    Taxes:$1,630

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 2651 CAYMAN WAY, WINTER PARK, FL 32792

    $255,000175 Days on yellowkey   MLS ID: O6375086

    For Sale O6375086 - 2651 CAYMAN WAY, WINTER PARK, FL 32792 28 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1020
       Built: 1978
    Monthly Fee: $99
       Tax: $3,553 (2024)
    Community: Windward Square Sec 2
    Townhouse


    Estimated Monthly Payment: $1,792 (change assumption)
    Mortgage ($1,397) + Fees ($99) + Taxes in 2024 ($296)


    Taxes:$3,553

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


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

    $245,00085 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


  • 3360 ROYAL ST, WINTER PARK, FL 32792

    $179,9006 Days on yellowkey   MLS ID: O6423106

    0 Days Off yellowkey (back on 7/13/2026)

    For Sale O6423106 - 3360 ROYAL ST, WINTER PARK, FL 32792 2 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 981
       Built: 1983   Tax: $3,149 (2025)
    Community: Coronation Add
    Half Duplex


    Estimated Monthly Payment: $1,248 (change assumption)
    Mortgage ($986) + Taxes in 2025 ($262)


    Taxes:$3,149

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 3463 ARNEL DR, WINTER PARK, FL 32792

    $414,900119 Days on yellowkey   MLS ID: O6390301

    REDUCED by $5,000 (1.2%) on 07/02/2026

    For Sale O6390301 - 3463 ARNEL DR, WINTER PARK, FL 32792 35 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: $2,661 (change assumption)
    Mortgage ($2,273) + Taxes in 2024 ($387)


    Taxes:$4,648

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


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

    $1,895,00067 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


  • 1624 BARCELONA WAY, WINTER PARK, FL 32789

    $2,235,000236 Days on yellowkey   MLS ID: O6362124

    3 Days Off yellowkey (back on 6/22/2026)

    REDUCED by $15,000 (0.7%) on 05/30/2026

    For Sale O6362124 - 1624 BARCELONA WAY, WINTER PARK, FL 32789 62 photos

    Bed: 3   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 3818
       Built: 1972
    Monthly Fee: $87
       Tax: $12,501 (2024)
    Community: Sevilla
    Spa: No

    Single Family


    Estimated Monthly Payment: $13,375 (change assumption)
    Mortgage ($12,246) + Fees ($87) + Taxes in 2024 ($1,042)


    Taxes:$12,501

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Audubon Park K-8


  • 316 BECKETT CT, WINTER PARK, FL 32792

    $450,00048 Days on yellowkey   MLS ID: O6411108

    For Sale O6411108 - 316 BECKETT CT, WINTER PARK, FL 32792 33 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1651
       Built: 1966   Tax: $2,232 (2025)
    Community: Winter Park Pines Merrie Oaks
    Single Family


    Estimated Monthly Payment: $2,652 (change assumption)
    Mortgage ($2,466) + Taxes in 2025 ($186)


    Taxes:$2,232

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 439 N CAPEN AVE, WINTER PARK, FL 32789

    $849,0007 Days on yellowkey   MLS ID: O6422949

    3 Days Off yellowkey (back on 7/13/2026)

    For Sale O6422949 - 439 N CAPEN AVE, WINTER PARK, FL 32789 29 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1861
       Built: 2017
    Monthly Fee: $400
       Tax: $11,803 (2025)
    Community: Canton Ave Cottages 1
    Single Family


    Estimated Monthly Payment: $6,036 (change assumption)
    Mortgage ($4,652) + Fees ($400) + Taxes in 2025 ($984)


    Taxes:$11,803

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 141 W LAKE SUE AVE, WINTER PARK, FL 32789

    $4,200,00067 Days on yellowkey   MLS ID: O6406437

    For Sale O6406437 - 141 W LAKE SUE AVE, WINTER PARK, FL 32789 5 photos

    Bed: 5   Bath: 6.0   Gar: 4
    Liv Area Sq Ft: 5500
       Built: 2027   Tax: $11,049 (2025)
    Community: Virginia Heights
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $23,934 (change assumption)
    Mortgage ($23,013) + Taxes in 2025 ($921)


    Taxes:$11,049

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1850 ASTER DR, WINTER PARK, FL 32792

    $485,00042 Days on yellowkey   MLS ID: TB8513990

    REDUCED by $15,000 (3.0%) on 06/13/2026

    For Sale TB8513990 - 1850 ASTER DR, WINTER PARK, FL 32792 50 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1656
       Built: 1978   Tax: $1,584 (2025)
    Community: Garden Lake Estates Unit 1
    Single Family


    Estimated Monthly Payment: $2,789 (change assumption)
    Mortgage ($2,657) + Taxes in 2025 ($132)


    Taxes:$1,584

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1507 GOLFSIDE DR, WINTER PARK, FL 32792

    $850,000103 Days on yellowkey   MLS ID: O6395355

    REDUCED by $49,000 (5.5%) on 07/03/2026

    For Sale O6395355 - 1507 GOLFSIDE DR, WINTER PARK, FL 32792 44 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2003
       Built: 1981   Tax: $2,783 (2025)
    Community: Greenview At Winter Pines
    Single Family


    Estimated Monthly Payment: $4,889 (change assumption)
    Mortgage ($4,657) + Taxes in 2025 ($232)


    Taxes:$2,783

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 1956 JAPONICA RD, WINTER PARK, FL 32792

    $549,00013 Days on yellowkey   MLS ID: O6421731

    0 Days Off yellowkey (back on 7/13/2026)

    For Sale O6421731 - 1956 JAPONICA RD, WINTER PARK, FL 32792 21 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1923
       Built: 1972
    Monthly Fee: $2
       Tax: $4,849 (2025)
    Community: Winter Woods
    Single Family


    Estimated Monthly Payment: $3,414 (change assumption)
    Mortgage ($3,008) + Fees ($2) + Taxes in 2025 ($404)


    Taxes:$4,849

    Elementary School: English Estates Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 1695 LEE RD #B108, WINTER PARK, FL 32789

    $89,9997 Days on yellowkey   MLS ID: O6422568

    For Sale O6422568 - 1695 LEE RD #B108, WINTER PARK, FL 32789 15 photos

    Bed: 1   Bath: 1.0
    Liv Area Sq Ft: 638
       Built: 1966
    Monthly Fee: $347
       Tax: $1,781 (2025)
    Community: Waterfall Cove Of Winter Park
    Condo


    Estimated Monthly Payment: $989 (change assumption)
    Mortgage ($493) + Fees ($347) + Taxes in 2025 ($148)


    Taxes:$1,781

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None




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.