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Winter Park Homes For Sale & Real Estate - 444 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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  • 1809 HAMMERLIN AVE, WINTER PARK, FL 32789

    $549,000136 Days on yellowkey   MLS ID: O6373616

    REDUCED by $36,000 (6.2%) on 05/06/2026

    For Sale O6373616 - 1809 HAMMERLIN AVE, WINTER PARK, FL 32789 44 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1818
       Built: 2006   Tax: $5,826 (2024)
    Community: Terazzo Del Sol Condo Assn Inc
    Condo


    Estimated Monthly Payment: $3,494 (change assumption)
    Mortgage ($3,008) + Taxes in 2024 ($486)


    Taxes:$5,826

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Audubon Park K-8


  • 7444 WOODBURN CT #29, WINTER PARK, FL 32792

    $165,000293 Days on yellowkey   MLS ID: S5131940

    0 Days Off yellowkey (back on 4/10/2026)

    For Sale S5131940 - 7444 WOODBURN CT #29, WINTER PARK, FL 32792 9 photos

    Bed: 2   Bath: 2.5
    Liv Area Sq Ft: 1031
       Built: 1983   Tax: $2,549 (2024)
    Community: Hidden Oaks Condo Ph 02
    Townhouse


    Estimated Monthly Payment: $1,117 (change assumption)
    Mortgage ($904) + Taxes in 2024 ($212)


    Taxes:$2,549

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 1000 S SEMORAN BLVD #805, WINTER PARK, FL 32792

    $174,70070 Days on yellowkey   MLS ID: O6392099

    0 Days Off yellowkey (back on 5/6/2026)

    REDUCED by $5,000 (2.8%) on 04/13/2026

    For Sale O6392099 - 1000 S SEMORAN BLVD #805, WINTER PARK, FL 32792 19 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1003
       Built: 1969
    Monthly Fee: $355
       Tax: $1,111 (2025)
    Community: Golfside Villas Condo
    Condo


    Estimated Monthly Payment: $1,405 (change assumption)
    Mortgage ($957) + Fees ($355) + Taxes in 2025 ($93)


    Taxes:$1,111

    Elementary School: None

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 1630 LASBURY AVE, WINTER PARK, FL 32789

    $2,750,00028 Days on yellowkey   MLS ID: O6404300

    For Sale O6404300 - 1630 LASBURY AVE, WINTER PARK, FL 32789 37 photos

    Bed: 5   Bath: 4.0   Gar: 3
    Liv Area Sq Ft: 4917
       Built: 2003   Tax: $14,204 (2025)
    Community: Comstock Park
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $16,252 (change assumption)
    Mortgage ($15,068) + Taxes in 2025 ($1,184)


    Taxes:$14,204

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 770 W WEBSTER AVE, WINTER PARK, FL 32789

    $725,000331 Days on yellowkey   MLS ID: O6323574

    1 Days Off yellowkey (back on 4/11/2026)

    For Sale O6323574 - 770 W WEBSTER AVE, WINTER PARK, FL 32789 34 photos

    Bed: 4   Bath: 2.0
    Liv Area Sq Ft: 1008
       Built: 1967   Tax: $4,856 (2024)
    Community: Capens Add
    Single Family


    Estimated Monthly Payment: $4,377 (change assumption)
    Mortgage ($3,973) + Taxes in 2024 ($405)


    Taxes:$4,856

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Maitland Middle


  • 517 ROUGHBEARD RD, WINTER PARK, FL 32792

    $565,00046 Days on yellowkey   MLS ID: O6399029

    1 Days Off yellowkey (back on 5/2/2026)

    For Sale O6399029 - 517 ROUGHBEARD RD, WINTER PARK, FL 32792 53 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1873
       Built: 1971   Tax: $4,323 (2025)
    Community: Winter Park Pines Unit 17
    Single Family


    Estimated Monthly Payment: $3,456 (change assumption)
    Mortgage ($3,096) + Taxes in 2025 ($360)


    Taxes:$4,323

    Elementary School: Aloma Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • Lot #21 KAROLINA AVE, WINTER PARK, FL 32789

    $944,89078 Days on yellowkey   MLS ID: O6387812

    For Sale O6387812 - Lot #21 KAROLINA AVE, WINTER PARK, FL 32789 9 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2662
       Built: 2025   Tax: $2,207 (2024)
    Community: Karolina On Killarney
    Single Family


    Estimated Monthly Payment: $5,361 (change assumption)
    Mortgage ($5,177) + Taxes in 2024 ($184)


    Taxes:$2,207

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2024

    Middle School: Maitland Middle


  • 2774 BRIGHT BIRD LN, WINTER PARK, FL 32792

    $465,000526 Days on yellowkey   MLS ID: O6266098

    For Sale O6266098 - 2774 BRIGHT BIRD LN, WINTER PARK, FL 32792 26 photos

    Bed: 3   Bath: 2.5   Gar: 1
    Liv Area Sq Ft: 1907
       Built: 2024
    Monthly Fee: $375
       Tax: $1,009 (2023)
    Community: Grayson Square
    Townhouse


    Estimated Monthly Payment: $3,007 (change assumption)
    Mortgage ($2,548) + Fees ($375) + Taxes in 2023 ($84)


    Taxes:$1,009

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2023

    Middle School: Tuskawilla Middle


  • 688 BRECHIN DR, WINTER PARK, FL 32792

    $724,90030 Days on yellowkey   MLS ID: O6403080

    2 Days Off yellowkey (back on 5/5/2026)

    For Sale O6403080 - 688 BRECHIN DR, WINTER PARK, FL 32792 31 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1599
       Built: 1961   Tax: $6,760 (2025)
    Community: Kenilworth Shores Sec 04
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,535 (change assumption)
    Mortgage ($3,972) + Taxes in 2025 ($563)


    Taxes:$6,760

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 5331 OAK CT, WINTER PARK, FL 32792

    $460,000318 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


  • 150 KILLARNEY BAY CT #5, WINTER PARK, FL 32789

    $325,000316 Days on yellowkey   MLS ID: O6328063

    For Sale O6328063 - 150 KILLARNEY BAY CT #5, WINTER PARK, FL 32789 26 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1140
       Built: 1986
    Monthly Fee: $460
       Tax: $2,100 (2024)
    Community: Killarney Bay Condo
    Condo


    Estimated Monthly Payment: $2,416 (change assumption)
    Mortgage ($1,781) + Fees ($460) + Taxes in 2024 ($175)


    Taxes:$2,100

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2024

    Middle School: College Park Middle


  • 1489 ASTER CT, WINTER PARK, FL 32792

    $650,000170 Days on yellowkey   MLS ID: O6364069

    1 Days Off yellowkey (back on 5/5/2026)

    For Sale O6364069 - 1489 ASTER CT, WINTER PARK, FL 32792 64 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2227
       Built: 1983   Tax: $1,791 (2024)
    Community: Garden Lake Estates Unit 3
    Single Family


    Estimated Monthly Payment: $3,711 (change assumption)
    Mortgage ($3,562) + Taxes in 2024 ($149)


    Taxes:$1,791

    Elementary School: Red Bug Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 1695 LEE RD #E116, WINTER PARK, FL 32789

    $125,00026 Days on yellowkey   MLS ID: O6399346

    For Sale O6399346 - 1695 LEE RD #E116, WINTER PARK, FL 32789 29 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1149
       Built: 1966
    Monthly Fee: $624
       Tax: $2,263 (2025)
    Community: Waterfall Cove/Winter Park
    Condo


    Estimated Monthly Payment: $1,497 (change assumption)
    Mortgage ($685) + Fees ($624) + Taxes in 2025 ($189)


    Taxes:$2,263

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1018 BRADFORD DR, WINTER PARK, FL 32792

    $549,00030 Days on yellowkey   MLS ID: O6403259

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

    For Sale O6403259 - 1018 BRADFORD DR, WINTER PARK, FL 32792 65 photos

    Bed: 5   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2513
       Built: 1974   Tax: $2,229 (2024)
    Community: Howell Estates Rep
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,194 (change assumption)
    Mortgage ($3,008) + Taxes in 2024 ($186)


    Taxes:$2,229

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 3651 N GOLDENROD RD #D101, WINTER PARK, FL 32792

    $179,00073 Days on yellowkey   MLS ID: O6391256

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

    REDUCED by $6,000 (3.2%) on 04/24/2026

    For Sale O6391256 - 3651 N GOLDENROD RD #D101, WINTER PARK, FL 32792 39 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 840
       Built: 1990
    Monthly Fee: $370
       Tax: $2,000 (2025)
    Community: Lancelot/Winter Park
    Condo


    Estimated Monthly Payment: $1,517 (change assumption)
    Mortgage ($981) + Fees ($370) + Taxes in 2025 ($167)


    Taxes:$2,000

    Elementary School: Aloma Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 446 MELROSE AVE, WINTER PARK, FL 32789

    $1,695,00033 Days on yellowkey   MLS ID: O6402113

    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: $10,972 (change assumption)
    Mortgage ($9,287) + 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


  • 2111 MALLARD CIR, WINTER PARK, FL 32789

    $1,295,00037 Days on yellowkey   MLS ID: O6401350

    REDUCED by $55,000 (4.1%) on 05/04/2026

    For Sale O6401350 - 2111 MALLARD CIR, WINTER PARK, FL 32789 24 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2667
       Built: 1973   Tax: $7,352 (2025)
    Community: Quail Hollow
    Spa: No

    Single Family


    Estimated Monthly Payment: $7,708 (change assumption)
    Mortgage ($7,096) + Taxes in 2025 ($613)


    Taxes:$7,352

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 1117 KENWOOD AVE, WINTER PARK, FL 32789

    $3,978,90071 Days on yellowkey   MLS ID: O6389970

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

    For Sale O6389970 - 1117 KENWOOD AVE, WINTER PARK, FL 32789 67 photos

    Bed: 4   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 4353
       Built: 2024   Tax: $13,467 (2024)
    Community: Dixie Terrace
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $22,924 (change assumption)
    Mortgage ($21,802) + Taxes in 2024 ($1,122)


    Taxes:$13,467

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Maitland Middle


  • 1741 WESTCHESTER AVE, WINTER PARK, FL 32789

    $595,00044 Days on yellowkey   MLS ID: O6399014

    REDUCED by $14,900 (2.4%) on 05/04/2026

    For Sale O6399014 - 1741 WESTCHESTER AVE, WINTER PARK, FL 32789 24 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1434
       Built: 1964   Tax: $8,945 (2025)
    Community: Orwin Manor Westminster Sec
    Single Family


    Estimated Monthly Payment: $4,006 (change assumption)
    Mortgage ($3,260) + Taxes in 2025 ($745)


    Taxes:$8,945

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park Middle


  • 1131 WILDMEADOW RUN, WINTER PARK, FL 32792

    $825,00067 Days on yellowkey   MLS ID: O6392218

    For Sale O6392218 - 1131 WILDMEADOW RUN, WINTER PARK, FL 32792 28 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2589
       Built: 2020
    Monthly Fee: $165
       Tax: $5,312 (2024)
    Community: Meadows At Hawks Crest
    Single Family


    Estimated Monthly Payment: $5,128 (change assumption)
    Mortgage ($4,520) + Fees ($165) + Taxes in 2024 ($443)


    Taxes:$5,312

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Sanford 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.