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Winter Park Homes For Sale & Real Estate - 416 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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  • 1310 FAIRVIEW AVE, WINTER PARK, FL 32789

    $925,00015 Days on yellowkey   MLS ID: O6424108

    For Sale O6424108 - 1310 FAIRVIEW AVE, WINTER PARK, FL 32789 14 photos

    Bed: 4   Bath: 2.5   Gar: 1
    Liv Area Sq Ft: 2552
       Built: 1947   Tax: $8,558 (2025)
    Community: Killarney Estates
    Single Family


    Estimated Monthly Payment: $5,782 (change assumption)
    Mortgage ($5,068) + Taxes in 2025 ($713)


    Taxes:$8,558

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 250 KILLARNEY, WINTER PARK, FL 32789

    $1,600,00015 Days on yellowkey   MLS ID: O6419382

    For Sale O6419382 - 250 KILLARNEY, WINTER PARK, FL 32789 10 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2568
       Built: 1997   Tax: $16,554 (2025)
    Community: Killarney Estates
    Single Family


    Estimated Monthly Payment: $10,146 (change assumption)
    Mortgage ($8,767) + Taxes in 2025 ($1,380)


    Taxes:$16,554

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park Middle


  • 2228 AZALEA PL, WINTER PARK, FL 32789

    $5,600,00032 Days on yellowkey   MLS ID: O6416342

    For Sale O6416342 - 2228 AZALEA PL, WINTER PARK, FL 32789 72 photos

    Bed: 5   Bath: 5.5   Gar: 3
    Liv Area Sq Ft: 5152
       Built: 2008   Tax: $26,904 (2025)
    Community: Maitland Shores First Add
    Spa: No

    Single Family


    Estimated Monthly Payment: $32,926 (change assumption)
    Mortgage ($30,684) + Taxes in 2025 ($2,242)


    Taxes:$26,904

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 1564 LAWNDALE CIR, WINTER PARK, FL 32792

    $450,00036 Days on yellowkey   MLS ID: O6418817

    For Sale O6418817 - 1564 LAWNDALE CIR, WINTER PARK, FL 32792 45 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1980
       Built: 1985
    Monthly Fee: $46
       Tax: $3,124 (2025)
    Community: Country Lane
    Single Family


    Estimated Monthly Payment: $2,772 (change assumption)
    Mortgage ($2,466) + Fees ($46) + Taxes in 2025 ($260)


    Taxes:$3,124

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 462 W LYMAN AVE, WINTER PARK, FL 32789

    $1,595,00016 Days on yellowkey   MLS ID: O6423842

    For Sale O6423842 - 462 W LYMAN AVE, WINTER PARK, FL 32789 25 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1944
       Built: 2022   Tax: $9,244 (2025)
    Community: Winter Park
    Single Family


    Estimated Monthly Payment: $9,510 (change assumption)
    Mortgage ($8,740) + Taxes in 2025 ($770)


    Taxes:$9,244

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 3037 ANTIQUE OAKS CIR #156, WINTER PARK, FL 32792

    $154,90034 Days on yellowkey   MLS ID: O6420008

    0 Days Off yellowkey (back on 7/14/2026)

    For Sale O6420008 - 3037 ANTIQUE OAKS CIR #156, WINTER PARK, FL 32792 21 photos

    Bed: 1   Bath: 1.0
    Liv Area Sq Ft: 749
       Built: 1984   Tax: $2,058 (2025)
    Community: Parkview Village
    Condo


    Estimated Monthly Payment: $1,020 (change assumption)
    Mortgage ($849) + Taxes in 2025 ($172)


    Taxes:$2,058

    Elementary School: Aloma Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 3054 BLUEBROOK DR, WINTER PARK, FL 32792

    $389,500108 Days on yellowkey   MLS ID: O6398450

    1 Days Off yellowkey (back on 7/14/2026)

    REDUCED by $20,500 (5.0%) on 06/30/2026

    For Sale O6398450 - 3054 BLUEBROOK DR, WINTER PARK, FL 32792 44 photos

    Bed: 3   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1939
       Built: 1973   Tax: $6,422 (2025)
    Community: Laurel Spgs
    Single Family


    Estimated Monthly Payment: $2,669 (change assumption)
    Mortgage ($2,134) + Taxes in 2025 ($535)


    Taxes:$6,422

    Elementary School: Aloma Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 1660 WALNUT AVE, WINTER PARK, FL 32789

    $1,569,00093 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


  • 229 ALEXANDER PL, WINTER PARK, FL 32789

    $4,250,00054 Days on yellowkey   MLS ID: O6412911

    For Sale O6412911 - 229 ALEXANDER PL, WINTER PARK, FL 32789 53 photos

    Bed: 4   Bath: 5.0   Gar: 3
    Liv Area Sq Ft: 4431
       Built: 2011   Tax: $36,713 (2025)
    Community: Alexander Place
    Spa: No

    Single Family


    Estimated Monthly Payment: $26,347 (change assumption)
    Mortgage ($23,287) + Taxes in 2025 ($3,059)


    Taxes:$36,713

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 4887 N MAGNOLIA AVE, WINTER PARK, FL 32792

    $495,00030 Days on yellowkey   MLS ID: O6420961

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

    For Sale O6420961 - 4887 N MAGNOLIA AVE, WINTER PARK, FL 32792 52 photos

    Bed: 4   Bath: 3.0
    Liv Area Sq Ft: 1955
       Built: 1964   Tax: $5,197 (2025)
    Community: Suburban Homes
    Single Family


    Estimated Monthly Payment: $3,145 (change assumption)
    Mortgage ($2,712) + Taxes in 2025 ($433)


    Taxes:$5,197

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 405 LAKE FAIR LN, WINTER PARK, FL 32789

    $444,900126 Days on yellowkey   MLS ID: O6393594

    REDUCED by $5,000 (1.1%) on 07/13/2026

    For Sale O6393594 - 405 LAKE FAIR LN, WINTER PARK, FL 32789 45 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1491
       Built: 1957   Tax: $1,355 (2025)
    Community: Fairbanks Shores 5Th Add
    Single Family


    Estimated Monthly Payment: $2,551 (change assumption)
    Mortgage ($2,438) + Taxes in 2025 ($113)


    Taxes:$1,355

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1981 BLUE RIDGE RD, WINTER PARK, FL 32789

    $1,150,00089 Days on yellowkey   MLS ID: O6402961

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

    For Sale O6402961 - 1981 BLUE RIDGE RD, WINTER PARK, FL 32789 52 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2750
       Built: 1963   Tax: $11,270 (2025)
    Community: Timberlane Shores
    Single Family


    Estimated Monthly Payment: $7,240 (change assumption)
    Mortgage ($6,301) + Taxes in 2025 ($939)


    Taxes:$11,270

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: None


  • 2905 PARKLAND DR, WINTER PARK, FL 32789

    $3,395,00021 Days on yellowkey   MLS ID: O6422550

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

    For Sale O6422550 - 2905 PARKLAND DR, WINTER PARK, FL 32789 98 photos

    Bed: 6   Bath: 7.0   Gar: 3
    Liv Area Sq Ft: 4850
       Built: 2026   Tax: $5,748 (2025)
    Community: Lake Forest Park
    Single Family


    Estimated Monthly Payment: $19,081 (change assumption)
    Mortgage ($18,602) + Taxes in 2025 ($479)


    Taxes:$5,748

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 5331 OAK CT, WINTER PARK, FL 32792

    $460,000378 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


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

    $138,00030 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

    $138,00030 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

    $138,00030 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


  • 439 N CAPEN AVE, WINTER PARK, FL 32789

    $849,00022 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


  • 1956 JAPONICA RD, WINTER PARK, FL 32792

    $549,00028 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

    $89,99922 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.