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Winter Park Homes For Sale & Real Estate - 367 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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  • 1618 INDIANA AVE, WINTER PARK, FL 32789

    $685,0005 Days on yellowkey   MLS ID: O6398673

    For Sale O6398673 - 1618 INDIANA AVE, WINTER PARK, FL 32789 31 photos

    Bed: 4   Bath: 0.0
    Liv Area Sq Ft: 1604
       Built: 1963   Tax: $5,477 (2025)
    Community: Lawndale
    Apartment


    Estimated Monthly Payment: $4,210 (change assumption)
    Mortgage ($3,753) + Taxes in 2025 ($456)


    Taxes:$5,477

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1589 VIBURNUM LN, WINTER PARK, FL 32792

    $365,0005 Days on yellowkey   MLS ID: O6398603

    For Sale O6398603 - 1589 VIBURNUM LN, WINTER PARK, FL 32792 10 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1356
       Built: 1961   Tax: $1,153 (2024)
    Community: Eastbrook Sub Unit 05
    Single Family


    Estimated Monthly Payment: $2,096 (change assumption)
    Mortgage ($2,000) + Taxes in 2024 ($96)


    Taxes:$1,153

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 1210 FAIRWAY DR, WINTER PARK, FL 32792

    $549,0005 Days on yellowkey   MLS ID: O6398533

    For Sale O6398533 - 1210 FAIRWAY DR, WINTER PARK, FL 32792 38 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1737
       Built: 1979   Tax: $7,265 (2025)
    Community: Golfside Sec 3
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,614 (change assumption)
    Mortgage ($3,008) + Taxes in 2025 ($605)


    Taxes:$7,265

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 841 W SWOOPE AVE, WINTER PARK, FL 32789

    $499,00079 Days on yellowkey   MLS ID: O6373287

    REDUCED by $241,000 (32.6%) on 04/13/2026

    For Sale O6373287 - 841 W SWOOPE AVE, WINTER PARK, FL 32789 31 photos

    Bed: 2   Bath: 1.0
    Liv Area Sq Ft: 1396
       Built: 1930   Tax: $3,824 (2024)
    Community: Capens Add
    Single Family


    Estimated Monthly Payment: $3,053 (change assumption)
    Mortgage ($2,734) + Taxes in 2024 ($319)


    Taxes:$3,824

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 1500 GAY RD #24B, WINTER PARK, FL 32789

    $261,500200 Days on yellowkey   MLS ID: O6348568

    REDUCED by $2,500 (0.9%) on 04/13/2026

    For Sale O6348568 - 1500 GAY RD #24B, WINTER PARK, FL 32789 21 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1026
       Built: 1972   Tax: $1,271 (2024)
    Community: Chateaux Du Lac
    Spa: No

    Condo


    Estimated Monthly Payment: $1,539 (change assumption)
    Mortgage ($1,433) + Taxes in 2024 ($106)


    Taxes:$1,271

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 640 N PARK AVE #5, WINTER PARK, FL 32789

    $450,000121 Days on yellowkey   MLS ID: O6367841

    0 Days Off yellowkey (back on 4/13/2026)

    For Sale O6367841 - 640 N PARK AVE #5, WINTER PARK, FL 32789 19 photos

    Bed: 1   Bath: 1.0
    Liv Area Sq Ft: 673
       Built: 1956
    Monthly Fee: $812
       Tax: $4,623 (2024)
    Community: Park Aire Condo
    Condo


    Estimated Monthly Payment: $3,663 (change assumption)
    Mortgage ($2,466) + Fees ($812) + Taxes in 2024 ($385)


    Taxes:$4,623

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Maitland Middle


  • 2823 WRIGHT AVE, WINTER PARK, FL 32789

    $929,90036 Days on yellowkey   MLS ID: O6390670

    For Sale O6390670 - 2823 WRIGHT AVE, WINTER PARK, FL 32789 19 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1536
       Built: 1958   Tax: $9,119 (2025)
    Community: Lake Forest Park
    Single Family


    Estimated Monthly Payment: $5,855 (change assumption)
    Mortgage ($5,095) + Taxes in 2025 ($760)


    Taxes:$9,119

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 1052 MANCHESTER CIR, WINTER PARK, FL 32792

    $470,00084 Days on yellowkey   MLS ID: O6376260

    REDUCED by $5,000 (1.1%) on 04/13/2026

    For Sale O6376260 - 1052 MANCHESTER CIR, WINTER PARK, FL 32792 41 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1703
       Built: 1983   Tax: $5,216 (2025)
    Community: Howell Estates 1St Add
    Single Family


    Estimated Monthly Payment: $3,010 (change assumption)
    Mortgage ($2,575) + Taxes in 2025 ($435)


    Taxes:$5,216

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 1367 TIERRA CIR, WINTER PARK, FL 32792

    $424,90088 Days on yellowkey   MLS ID: O6375221

    For Sale O6375221 - 1367 TIERRA CIR, WINTER PARK, FL 32792 62 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2083
       Built: 1969   Tax: $4,948 (2024)
    Community: Casa Aloma
    Single Family


    Estimated Monthly Payment: $2,740 (change assumption)
    Mortgage ($2,328) + Taxes in 2024 ($412)


    Taxes:$4,948

    Elementary School: English Estates Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 1695 LEE RD #E103, WINTER PARK, FL 32789

    $139,99022 Days on yellowkey   MLS ID: S5146352

    For Sale S5146352 - 1695 LEE RD #E103, WINTER PARK, FL 32789 23 photos

    Bed: 2   Bath: 1.0
    Liv Area Sq Ft: 881
       Built: 1966
    Monthly Fee: $482
       Tax: $2,041 (2025)
    Community: Waterfall Cove
    Condo


    Estimated Monthly Payment: $1,419 (change assumption)
    Mortgage ($767) + Fees ($482) + Taxes in 2025 ($170)


    Taxes:$2,041

    Elementary School: Hungerford Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park Middle


  • 1822 GREENWICH AVE, WINTER PARK, FL 32789

    $995,000176 Days on yellowkey   MLS ID: A4669605

    0 Days Off yellowkey (back on 4/13/2026)

    For Sale A4669605 - 1822 GREENWICH AVE, WINTER PARK, FL 32789 6 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1627
       Built: 1953   Tax: $2,519 (2024)
    Community: Golfview Heights
    Single Family


    Estimated Monthly Payment: $5,662 (change assumption)
    Mortgage ($5,452) + Taxes in 2024 ($210)


    Taxes:$2,519

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 2401 ANTILLES DR, WINTER PARK, FL 32792

    $320,000164 Days on yellowkey   MLS ID: O6357934

    For Sale O6357934 - 2401 ANTILLES DR, WINTER PARK, FL 32792 33 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1719
       Built: 1977
    Monthly Fee: $95

    Community: Windward Square Sec 1
    Townhouse


    Estimated Monthly Payment: $1,848 (change assumption)
    Mortgage ($1,753) + Fees ($95) + Taxes in 2024 ($0)


    Taxes:$0

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 106 S INTERLACHEN AVE #118, WINTER PARK, FL 32789

    $1,395,00071 Days on yellowkey   MLS ID: O6380506

    REDUCED by $55,000 (3.8%) on 04/13/2026

    For Sale O6380506 - 106 S INTERLACHEN AVE #118, WINTER PARK, FL 32789 55 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1834
       Built: 1971   Tax: $9,767 (2025)
    Community: Cloisters Condo
    Condo


    Estimated Monthly Payment: $8,458 (change assumption)
    Mortgage ($7,644) + Taxes in 2025 ($814)


    Taxes:$9,767

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 1636 ELIZABETHS WALK, WINTER PARK, FL 32789

    $2,195,00015 Days on yellowkey   MLS ID: O6395638

    For Sale O6395638 - 1636 ELIZABETHS WALK, WINTER PARK, FL 32789 31 photos

    Bed: 4   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3412
       Built: 2016
    Monthly Fee: $268
       Tax: $25,133 (2025)
    Community: Windsong Elizabeths Walk 43/81
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $14,389 (change assumption)
    Mortgage ($12,027) + Fees ($268) + Taxes in 2025 ($2,094)


    Taxes:$25,133

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 3711 VINSETTA CT, WINTER PARK, FL 32792

    $1,350,00085 Days on yellowkey   MLS ID: O6376139

    5 Days Off yellowkey (back on 4/13/2026)

    For Sale O6376139 - 3711 VINSETTA CT, WINTER PARK, FL 32792 66 photos

    Bed: 6   Bath: 4.0   Gar: 3
    Liv Area Sq Ft: 4214
       Built: 2015
    Monthly Fee: $178
       Tax: $7,488 (2025)
    Community: Lakeside Estates
    Single Family


    Estimated Monthly Payment: $8,199 (change assumption)
    Mortgage ($7,397) + Fees ($178) + Taxes in 2025 ($624)


    Taxes:$7,488

    Elementary School: Red Bug Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 350 CORNWALL RD, WINTER PARK, FL 32792

    $775,00020 Days on yellowkey   MLS ID: O6394524

    0 Days Off yellowkey (back on 4/12/2026)

    For Sale O6394524 - 350 CORNWALL RD, WINTER PARK, FL 32792 34 photos

    Bed: 4   Bath: 3.0
    Liv Area Sq Ft: 2038
       Built: 1963   Tax: $2,127 (2025)
    Community: Winter Park Pines Rep
    Single Family


    Estimated Monthly Payment: $4,424 (change assumption)
    Mortgage ($4,246) + Taxes in 2025 ($177)


    Taxes:$2,127

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 543 E LAKE SUE AVE, WINTER PARK, FL 32789

    $1,875,0009 Days on yellowkey   MLS ID: O6397480

    1 Days Off yellowkey (back on 4/13/2026)

    For Sale O6397480 - 543 E LAKE SUE AVE, WINTER PARK, FL 32789 47 photos

    Bed: 4   Bath: 4.5   Gar: 3
    Liv Area Sq Ft: 3657
       Built: 1986   Tax: $14,126 (2025)
    Community: Lake Virginia Pt Rep
    Spa: No

    Single Family


    Estimated Monthly Payment: $11,451 (change assumption)
    Mortgage ($10,274) + Taxes in 2025 ($1,177)


    Taxes:$14,126

    Elementary School: None

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 311 E MORSE BLVD #7-19, WINTER PARK, FL 32789

    $299,900110 Days on yellowkey   MLS ID: O6368912

    For Sale O6368912 - 311 E MORSE BLVD #7-19, WINTER PARK, FL 32789 34 photos

    Bed: 1   Bath: 1.0
    Liv Area Sq Ft: 482
       Built: 1960
    Monthly Fee: $870
       Tax: $3,161 (2024)
    Community: Whispering Waters
    Condo


    Estimated Monthly Payment: $2,777 (change assumption)
    Mortgage ($1,643) + Fees ($870) + Taxes in 2024 ($263)


    Taxes:$3,161

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Audubon Park K-8


  • 3054 BLUEBROOK DR, WINTER PARK, FL 32792

    $427,5006 Days on yellowkey   MLS ID: O6398450

    For Sale O6398450 - 3054 BLUEBROOK DR, WINTER PARK, FL 32792 27 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: $2,878 (change assumption)
    Mortgage ($2,342) + Taxes in 2025 ($535)


    Taxes:$6,422

    Elementary School: Aloma Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 2919 BOWER RD, WINTER PARK, FL 32792

    $779,00030 Days on yellowkey   MLS ID: O6391025

    3 Days Off yellowkey (back on 4/13/2026)

    For Sale O6391025 - 2919 BOWER RD, WINTER PARK, FL 32792 38 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2325
       Built: 1971   Tax: $9,857 (2025)
    Community: Winter Park Pines
    Single Family


    Estimated Monthly Payment: $5,090 (change assumption)
    Mortgage ($4,268) + Taxes in 2025 ($821)


    Taxes:$9,857

    Elementary School: None

    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.