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Winter Park Homes For Sale & Real Estate - 445 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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  • 1695 LEE RD #D211, WINTER PARK, FL 32789

    $114,00079 Days on yellowkey   MLS ID: O6396190

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

    For Sale O6396190 - 1695 LEE RD #D211, WINTER PARK, FL 32789 28 photos

    Bed: 2   Bath: 1.0
    Liv Area Sq Ft: 881
       Built: 1966   Tax: $2,051 (2025)
    Community: Waterfall Cove/Winter Park
    Condo


    Estimated Monthly Payment: $796 (change assumption)
    Mortgage ($625) + Taxes in 2025 ($171)


    Taxes:$2,051

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2454 BROOKSHIRE AVE, WINTER PARK, FL 32792

    $1,399,000120 Days on yellowkey   MLS ID: O6384924

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

    For Sale O6384924 - 2454 BROOKSHIRE AVE, WINTER PARK, FL 32792 34 photos

    Bed: 4   Bath: 3.5   Gar: 1
    Liv Area Sq Ft: 2509
       Built: 2023   Tax: $11,586 (2024)
    Community: Brookshire Heights 1St Add
    Single Family


    Estimated Monthly Payment: $8,631 (change assumption)
    Mortgage ($7,666) + Taxes in 2024 ($966)


    Taxes:$11,586

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Glenridge Middle


  • 101 S NEW YORK AVE #311, WINTER PARK, FL 32789

    $1,849,9009 Days on yellowkey   MLS ID: O6416927

    For Sale O6416927 - 101 S NEW YORK AVE #311, WINTER PARK, FL 32789 39 photos

    Bed: 3   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3112
       Built: 2008
    Monthly Fee: $1,303
       Tax: $20,039 (2025)
    Community: Winter Park Residential
    Condo


    Estimated Monthly Payment: $13,109 (change assumption)
    Mortgage ($10,136) + Fees ($1,303) + Taxes in 2025 ($1,670)


    Taxes:$20,039

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 5530 S LAKE BURKETT LN, WINTER PARK, FL 32792

    $450,00022 Days on yellowkey   MLS ID: O6409433

    REDUCED by $15,000 (3.2%) on 06/22/2026

    For Sale O6409433 - 5530 S LAKE BURKETT LN, WINTER PARK, FL 32792 36 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1669
       Built: 1985
    Monthly Fee: $69
       Tax: $3,871 (2025)
    Community: Trinity Bay
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,857 (change assumption)
    Mortgage ($2,466) + Fees ($69) + Taxes in 2025 ($323)


    Taxes:$3,871

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 340 KILLARNEY BAY CT #4-4, WINTER PARK, FL 32789

    $379,00042 Days on yellowkey   MLS ID: O6407259

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

    REDUCED by $16,000 (4.1%) on 06/16/2026

    For Sale O6407259 - 340 KILLARNEY BAY CT #4-4, WINTER PARK, FL 32789 37 photos

    Bed: 2   Bath: 2.5
    Liv Area Sq Ft: 1428
       Built: 1986   Tax: $1,080 (2025)
    Community: Killarney Bay Condo
    Condo


    Estimated Monthly Payment: $2,167 (change assumption)
    Mortgage ($2,077) + Taxes in 2025 ($90)


    Taxes:$1,080

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park Middle


  • 151 N ORLANDO AVE #259, WINTER PARK, FL 32789

    $229,90036 Days on yellowkey   MLS ID: O6409651

    0 Days Off yellowkey (back on 6/21/2026)

    REDUCED by $9,100 (3.8%) on 06/17/2026

    For Sale O6409651 - 151 N ORLANDO AVE #259, WINTER PARK, FL 32789 31 photos

    Bed: 1   Bath: 1.0
    Liv Area Sq Ft: 582
       Built: 1960   Tax: $2,552 (2025)
    Community: Lake Killarney Condo
    Condo


    Estimated Monthly Payment: $1,472 (change assumption)
    Mortgage ($1,260) + Taxes in 2025 ($213)


    Taxes:$2,552

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park Middle


  • 641 W LYMAN AVE, WINTER PARK, FL 32789

    $509,00024 Days on yellowkey   MLS ID: O6408078

    0 Days Off yellowkey (back on 6/21/2026)

    For Sale O6408078 - 641 W LYMAN AVE, WINTER PARK, FL 32789 36 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1120
       Built: 2003   Tax: $6,342 (2025)
    Community: Town/Winter Park
    Single Family


    Estimated Monthly Payment: $3,317 (change assumption)
    Mortgage ($2,789) + Taxes in 2025 ($529)


    Taxes:$6,342

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 333 CORNWALL RD, WINTER PARK, FL 32792

    $579,00035 Days on yellowkey   MLS ID: O6409379

    For Sale O6409379 - 333 CORNWALL RD, WINTER PARK, FL 32792 32 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1660
       Built: 1963
    Monthly Fee: $5
       Tax: $2,654 (2025)
    Community: Winter Park Pines
    Single Family


    Estimated Monthly Payment: $3,399 (change assumption)
    Mortgage ($3,173) + Fees ($5) + Taxes in 2025 ($221)


    Taxes:$2,654

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 446 MELROSE AVE, WINTER PARK, FL 32789

    $1,625,00060 Days on yellowkey   MLS ID: O6402113

    REDUCED by $70,000 (4.1%) on 06/18/2026

    For Sale O6402113 - 446 MELROSE AVE, WINTER PARK, FL 32789 39 photos

    Bed: 4   Bath: 2.0
    Liv Area Sq Ft: 2640
       Built: 1987   Tax: $20,217 (2025)
    Community: Virginia Heights Rep
    Spa: No

    Single Family


    Estimated Monthly Payment: $10,589 (change assumption)
    Mortgage ($8,904) + Taxes in 2025 ($1,685)


    Taxes:$20,217

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 1807 HAMMERLIN AVE #G, WINTER PARK, FL 32789

    $515,000101 Days on yellowkey   MLS ID: O6391277

    REDUCED by $10,000 (1.9%) on 06/15/2026

    For Sale O6391277 - 1807 HAMMERLIN AVE #G, WINTER PARK, FL 32789 29 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1818
       Built: 2006   Tax: $6,197 (2025)
    Community: Terrazo Del Sol
    Condo


    Estimated Monthly Payment: $3,338 (change assumption)
    Mortgage ($2,822) + Taxes in 2025 ($516)


    Taxes:$6,197

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 1836 GRINNELL TER, WINTER PARK, FL 32789

    $999,000140 Days on yellowkey   MLS ID: O6380457

    REDUCED by $51,000 (4.9%) on 05/06/2026

    For Sale O6380457 - 1836 GRINNELL TER, WINTER PARK, FL 32789 24 photos

    Bed: 3   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1907
       Built: 1995   Tax: $11,979 (2025)
    Community: Lake Virginia
    Single Family


    Estimated Monthly Payment: $6,472 (change assumption)
    Mortgage ($5,474) + Taxes in 2025 ($998)


    Taxes:$11,979

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 2974 CHANTILLY AVE, WINTER PARK, FL 32789

    $499,00020 Days on yellowkey   MLS ID: O6412851

    REDUCED by $51,000 (9.3%) on 06/15/2026

    For Sale O6412851 - 2974 CHANTILLY AVE, WINTER PARK, FL 32789 26 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1433
       Built: 1960   Tax: $1,178 (2025)
    Community: Winter Park Manor
    Single Family


    Estimated Monthly Payment: $2,832 (change assumption)
    Mortgage ($2,734) + Taxes in 2025 ($98)


    Taxes:$1,178

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 641 NORTHWOOD CIRCLE, WINTER PARK, FL 32789

    $1,795,00025 Days on yellowkey   MLS ID: O6412554

    For Sale O6412554 - 641 NORTHWOOD CIRCLE, WINTER PARK, FL 32789 41 photos

    Bed: 3   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 2756
       Built: 2023   Tax: $18,393 (2025)
    Community: Winter Park Oasis
    Single Family


    Estimated Monthly Payment: $11,368 (change assumption)
    Mortgage ($9,835) + Taxes in 2025 ($1,533)


    Taxes:$18,393

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 2032 KIMBRACE PL, WINTER PARK, FL 32792

    $2,188,88817 Days on yellowkey   MLS ID: O6414862

    For Sale O6414862 - 2032 KIMBRACE PL, WINTER PARK, FL 32792 84 photos

    Bed: 5   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 3382
       Built: 2021   Tax: $16,035 (2025)
    Community: Kenilworth Shores Sec 03
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $13,330 (change assumption)
    Mortgage ($11,994) + Taxes in 2025 ($1,336)


    Taxes:$16,035

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 2676 BARBADOS DR, WINTER PARK, FL 32792

    $340,00028 Days on yellowkey   MLS ID: O6411958

    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


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

    $157,90066 Days on yellowkey   MLS ID: O6401114

    REDUCED by $100 (0.1%) on 06/17/2026

    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: $1,440 (change assumption)
    Mortgage ($865) + 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


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

    $259,500269 Days on yellowkey   MLS ID: O6348568

    0 Days Off yellowkey (back on 6/21/2026)

    REDUCED by $2,000 (0.8%) on 05/15/2026

    For Sale O6348568 - 1500 GAY RD #24B, WINTER PARK, FL 32789 23 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: $1,528 (change assumption)
    Mortgage ($1,422) + Taxes in 2024 ($106)


    Taxes:$1,271

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 1369 BLUE STEM LN, WINTER PARK, FL 32792

    $825,00080 Days on yellowkey   MLS ID: O6396971

    For Sale O6396971 - 1369 BLUE STEM LN, WINTER PARK, FL 32792 46 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2589
       Built: 2021
    Monthly Fee: $413
       Tax: $6,074 (2024)
    Community: Landings At Hawks Crest
    Single Family


    Estimated Monthly Payment: $5,440 (change assumption)
    Mortgage ($4,520) + Fees ($413) + Taxes in 2024 ($506)


    Taxes:$6,074

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 2718 SANDWELL DR, WINTER PARK, FL 32792

    $525,0008 Days on yellowkey   MLS ID: O6410283

    0 Days Off yellowkey (back on 6/20/2026)

    For Sale O6410283 - 2718 SANDWELL DR, WINTER PARK, FL 32792 56 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1597
       Built: 1968
    Monthly Fee: $5
       Tax: $2,105 (2025)
    Community: Winter Park Pines
    Single Family


    Estimated Monthly Payment: $3,057 (change assumption)
    Mortgage ($2,877) + Fees ($5) + Taxes in 2025 ($175)


    Taxes:$2,105

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 338 BLUE HERON DR, WINTER PARK, FL 32789

    $865,00027 Days on yellowkey   MLS ID: O6410174

    For Sale O6410174 - 338 BLUE HERON DR, WINTER PARK, FL 32789 44 photos

    Bed: 3   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2017
       Built: 1960   Tax: $6,647 (2025)
    Community: Flamingo Shores
    Single Family


    Estimated Monthly Payment: $5,294 (change assumption)
    Mortgage ($4,740) + Taxes in 2025 ($554)


    Taxes:$6,647

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park 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.