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Winter Park Homes For Sale & Real Estate - 358 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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  • 2211 AZALEA PL, WINTER PARK, FL 32789

    $5,250,000298 Days on yellowkey   MLS ID: O6319674

    For Sale O6319674 - 2211 AZALEA PL, WINTER PARK, FL 32789 99 photos

    Bed: 5   Bath: 6.5   Gar: 5
    Liv Area Sq Ft: 7278
       Built: 2008   Tax: $36,209 (2024)
    Community: Maitland Shores
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $31,784 (change assumption)
    Mortgage ($28,766) + Taxes in 2024 ($3,017)


    Taxes:$36,209

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Maitland Middle


  • 2454 BROOKSHIRE AVE, WINTER PARK, FL 32792

    $1,399,00050 Days on yellowkey   MLS ID: O6384924

    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


  • 1000 S SEMORAN BLVD #512, WINTER PARK, FL 32792

    $128,50073 Days on yellowkey   MLS ID: O6379459

    0 Days Off yellowkey (back on 3/16/2026)

    For Sale O6379459 - 1000 S SEMORAN BLVD #512, WINTER PARK, FL 32792 11 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1072
       Built: 1969
    Monthly Fee: $350
       Tax: $1,766 (2024)
    Community: Golfside Villas Condo
    Condo


    Estimated Monthly Payment: $1,201 (change assumption)
    Mortgage ($704) + Fees ($350) + Taxes in 2024 ($147)


    Taxes:$1,766

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 2600 EUSTON RD, WINTER PARK, FL 32789

    $630,0007 Days on yellowkey   MLS ID: O6397890

    For Sale O6397890 - 2600 EUSTON RD, WINTER PARK, FL 32789 36 photos

    Bed: 6   Bath: 3.0
    Liv Area Sq Ft: 3145
       Built: 1951   Tax: $7,446 (2024)
    Community: Glencoe Sub
    Single Family


    Estimated Monthly Payment: $4,072 (change assumption)
    Mortgage ($3,452) + Taxes in 2024 ($620)


    Taxes:$7,446

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 240 ORANGE TERRACE DR, WINTER PARK, FL 32789

    $484,000253 Days on yellowkey   MLS ID: O6330690

    REDUCED by $1,000 (0.2%) on 04/15/2026

    For Sale O6330690 - 240 ORANGE TERRACE DR, WINTER PARK, FL 32789 30 photos

    Bed: 4   Bath: 2.0
    Liv Area Sq Ft: 1718
       Built: 1955   Tax: $6,210 (2024)
    Community: Orange Terrace
    Single Family


    Estimated Monthly Payment: $3,169 (change assumption)
    Mortgage ($2,652) + Taxes in 2024 ($518)


    Taxes:$6,210

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2024

    Middle School: Robinswood Middle


  • 501 HERITAGE BLVD, WINTER PARK, FL 32792

    $489,99035 Days on yellowkey   MLS ID: S5145746

    REDUCED by $10,000 (2.0%) on 04/15/2026

    For Sale S5145746 - 501 HERITAGE BLVD, WINTER PARK, FL 32792 17 photos

    Bed: 4   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1376
       Built: 1966   Tax: $10,434 (2025)
    Community: Georgetown Estates
    Single Family


    Estimated Monthly Payment: $3,554 (change assumption)
    Mortgage ($2,685) + Taxes in 2025 ($870)


    Taxes:$10,434

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 2015 SUMMERFIELD RD, WINTER PARK, FL 32792

    $1,375,000162 Days on yellowkey   MLS ID: O6357615

    For Sale O6357615 - 2015 SUMMERFIELD RD, WINTER PARK, FL 32792 50 photos

    Bed: 4   Bath: 4.0   Gar: 1
    Liv Area Sq Ft: 3024
       Built: 1957   Tax: $7,243 (2025)
    Community: Kenilworth Shores Sec 07
    Spa: No

    Single Family


    Estimated Monthly Payment: $8,138 (change assumption)
    Mortgage ($7,534) + Taxes in 2025 ($604)


    Taxes:$7,243

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 1036 MANCHESTER CIR, WINTER PARK, FL 32792

    $400,00015 Days on yellowkey   MLS ID: O6395138

    3 Days Off yellowkey (back on 4/15/2026)

    For Sale O6395138 - 1036 MANCHESTER CIR, WINTER PARK, FL 32792 26 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1574
       Built: 1974   Tax: $4,126 (2024)
    Community: Howell Estates Rep
    Single Family


    Estimated Monthly Payment: $2,536 (change assumption)
    Mortgage ($2,192) + Taxes in 2024 ($344)


    Taxes:$4,126

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 5130 LAZY OAKS DR #5130, WINTER PARK, FL 32792

    $230,00045 Days on yellowkey   MLS ID: O6386224

    0 Days Off yellowkey (back on 4/15/2026)

    For Sale O6386224 - 5130 LAZY OAKS DR #5130, WINTER PARK, FL 32792 31 photos

    Bed: 2   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1008
       Built: 1982
    Monthly Fee: $277
       Tax: $749 (2024)
    Community: Lazy Oaks Condo
    Condo


    Estimated Monthly Payment: $1,600 (change assumption)
    Mortgage ($1,260) + Fees ($277) + Taxes in 2024 ($62)


    Taxes:$749

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


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

    $580,00031 Days on yellowkey   MLS ID: O6391277

    For Sale O6391277 - 1807 HAMMERLIN AVE #G, WINTER PARK, FL 32789 25 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: $3,694 (change assumption)
    Mortgage ($3,178) + 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


  • 1565 FOREST AVE, WINTER PARK, FL 32789

    $1,750,0003 Days on yellowkey   MLS ID: O6398694

    For Sale O6398694 - 1565 FOREST AVE, WINTER PARK, FL 32789 37 photos

    Bed: 4   Bath: 2.0
    Liv Area Sq Ft: 2163
       Built: 1925   Tax: $2,803 (2025)
    Community: Ellno Willo
    Single Family


    Estimated Monthly Payment: $9,822 (change assumption)
    Mortgage ($9,589) + Taxes in 2025 ($234)


    Taxes:$2,803

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 744 CORNWALL RD, WINTER PARK, FL 32792

    $695,000259 Days on yellowkey   MLS ID: O6332168

    REDUCED by $20,000 (2.8%) on 04/15/2026

    For Sale O6332168 - 744 CORNWALL RD, WINTER PARK, FL 32792 59 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1968
       Built: 1968   Tax: $5,359 (2024)
    Community: Winter Park Pines
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,255 (change assumption)
    Mortgage ($3,808) + Taxes in 2024 ($447)


    Taxes:$5,359

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Glenridge Middle


  • 2400 DOMINICA RUN, WINTER PARK, FL 32792

    $225,00021 Days on yellowkey   MLS ID: O6394406

    For Sale O6394406 - 2400 DOMINICA RUN, WINTER PARK, FL 32792 29 photos

    Bed: 2   Bath: 1.0
    Liv Area Sq Ft: 854
       Built: 1979
    Monthly Fee: $99
       Tax: $433 (2025)
    Community: Windward Square Sec 3
    Townhouse


    Estimated Monthly Payment: $1,368 (change assumption)
    Mortgage ($1,233) + Fees ($99) + Taxes in 2025 ($36)


    Taxes:$433

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 352 CAMBRIDGE BLVD, WINTER PARK, FL 32789

    $650,00080 Days on yellowkey   MLS ID: O6377540

    2 Days Off yellowkey (back on 3/11/2026)

    For Sale O6377540 - 352 CAMBRIDGE BLVD, WINTER PARK, FL 32789 37 photos

    Bed: 5   Bath: 0.0
    Liv Area Sq Ft: 1917
       Built: 1920   Tax: $9,806 (2024)
    Community: Glencoe Sub
    Apartment


    Estimated Monthly Payment: $4,379 (change assumption)
    Mortgage ($3,562) + Taxes in 2024 ($817)


    Taxes:$9,806

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 352 CAMBRIDGE BLVD, WINTER PARK, FL 32789

    $650,00085 Days on yellowkey   MLS ID: O6375545

    2 Days Off yellowkey (back on 3/11/2026)

    For Sale O6375545 - 352 CAMBRIDGE BLVD, WINTER PARK, FL 32789 37 photos

    Bed: 5   Bath: 3.0
    Liv Area Sq Ft: 1917
       Built: 1920   Tax: $9,806 (2024)
    Community: Glencoe Sub
    Single Family


    Estimated Monthly Payment: $4,379 (change assumption)
    Mortgage ($3,562) + Taxes in 2024 ($817)


    Taxes:$9,806

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 3207 LOWNDES DR, WINTER PARK, FL 32792

    $495,00077 Days on yellowkey   MLS ID: O6362285

    For Sale O6362285 - 3207 LOWNDES DR, WINTER PARK, FL 32792 31 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 2028
       Built: 1967   Tax: $4,172 (2024)
    Community: Georgetown Estates
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,060 (change assumption)
    Mortgage ($2,712) + Taxes in 2024 ($348)


    Taxes:$4,172

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Maitland Middle


  • 2713 EASTERN PKWY, WINTER PARK, FL 32789

    $670,0007 Days on yellowkey   MLS ID: O6398076

    For Sale O6398076 - 2713 EASTERN PKWY, WINTER PARK, FL 32789 44 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1304
       Built: 1988   Tax: $2,713 (2025)
    Community: Parklando
    Single Family


    Estimated Monthly Payment: $3,897 (change assumption)
    Mortgage ($3,671) + Taxes in 2025 ($226)


    Taxes:$2,713

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 7529 VILLAGE GREEN DR, WINTER PARK, FL 32792

    $325,0008 Days on yellowkey   MLS ID: O6396985

    1 Days Off yellowkey (back on 4/14/2026)

    For Sale O6396985 - 7529 VILLAGE GREEN DR, WINTER PARK, FL 32792 30 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1575
       Built: 1972   Tax: $1,320 (2024)
    Community: Village Green
    Single Family


    Estimated Monthly Payment: $1,891 (change assumption)
    Mortgage ($1,781) + Taxes in 2024 ($110)


    Taxes:$1,320

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 200 SAINT ANDREWS BLVD #705, WINTER PARK, FL 32792

    $180,00049 Days on yellowkey   MLS ID: O6386469

    1 Days Off yellowkey (back on 4/14/2026)

    For Sale O6386469 - 200 SAINT ANDREWS BLVD #705, WINTER PARK, FL 32792 52 photos

    Bed: 1   Bath: 1.0
    Liv Area Sq Ft: 727
       Built: 1970   Tax: $2,018 (2024)
    Community: Four Seasons Condo
    Condo


    Estimated Monthly Payment: $1,154 (change assumption)
    Mortgage ($986) + Taxes in 2024 ($168)


    Taxes:$2,018

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Glenridge Middle


  • 2015 N PARK AVE, WINTER PARK, FL 32789

    $2,295,00074 Days on yellowkey   MLS ID: O6372603

    For Sale O6372603 - 2015 N PARK AVE, WINTER PARK, FL 32789 64 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3963
       Built: 2023   Tax: $27,508 (2024)
    Community: Twin Acres
    Spa: No

    Single Family


    Estimated Monthly Payment: $14,867 (change assumption)
    Mortgage ($12,575) + Taxes in 2024 ($2,292)


    Taxes:$27,508

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Maitland 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.