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Winter Park Homes For Sale & Real Estate - 417 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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  • 7488 WHISPERWOOD DR #28, WINTER PARK, FL 32792

    $220,00036 Days on yellowkey   MLS ID: O6419151

    REDUCED by $10,000 (4.3%) on 07/17/2026

    For Sale O6419151 - 7488 WHISPERWOOD DR #28, WINTER PARK, FL 32792 36 photos

    Bed: 2   Bath: 2.5
    Liv Area Sq Ft: 1578
       Built: 1974
    Monthly Fee: $575
       Tax: $3,078 (2025)
    Community: Whisperwood Condo
    Condo


    Estimated Monthly Payment: $2,037 (change assumption)
    Mortgage ($1,205) + Fees ($575) + Taxes in 2025 ($257)


    Taxes:$3,078

    Elementary School: Cheney Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 1871 BARKER DR, WINTER PARK, FL 32789

    $779,00013 Days on yellowkey   MLS ID: O6425831

    0 Days Off yellowkey (back on 7/24/2026)

    For Sale O6425831 - 1871 BARKER DR, WINTER PARK, FL 32789 36 photos

    Bed: 3   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 2231
       Built: 1957   Tax: $8,858 (2025)
    Community: South Lakemont Shores
    Spa: No

    Single Family


    Estimated Monthly Payment: $5,007 (change assumption)
    Mortgage ($4,268) + Taxes in 2025 ($738)


    Taxes:$8,858

    Elementary School: Baldwin Park Elementary

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 1369 BLUE STEM LN, WINTER PARK, FL 32792

    $799,000113 Days on yellowkey   MLS ID: O6396971

    REDUCED by $20,000 (2.4%) on 07/24/2026

    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: $5,297 (change assumption)
    Mortgage ($4,378) + Fees ($413) + Taxes in 2024 ($506)


    Taxes:$6,074

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 7426 BLUE JACKET PL E, WINTER PARK, FL 32792

    $324,9006 Days on yellowkey   MLS ID: O6427029

    For Sale O6427029 - 7426 BLUE JACKET PL E, WINTER PARK, FL 32792 28 photos

    Bed: 3   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1150
       Built: 1971   Tax: $753 (2025)
    Community: Woodcrest Unit 03
    Single Family


    Estimated Monthly Payment: $1,843 (change assumption)
    Mortgage ($1,780) + Taxes in 2025 ($63)


    Taxes:$753

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 1456 E BROOKSHIRE CT, WINTER PARK, FL 32792

    $449,00012 Days on yellowkey   MLS ID: O6425661

    2 Days Off yellowkey (back on 7/24/2026)

    For Sale O6425661 - 1456 E BROOKSHIRE CT, WINTER PARK, FL 32792 57 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1673
       Built: 1987
    Monthly Fee: $33
       Tax: $4,650 (2025)
    Community: Hyde Park
    Single Family


    Estimated Monthly Payment: $2,881 (change assumption)
    Mortgage ($2,460) + Fees ($33) + Taxes in 2025 ($388)


    Taxes:$4,650

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 885 CARNATION DR, WINTER PARK, FL 32792

    $385,00017 Days on yellowkey   MLS ID: S5153456

    INCREASED by $10,000 (2.7%) on 07/24/2026

    For Sale S5153456 - 885 CARNATION DR, WINTER PARK, FL 32792 38 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1240
       Built: 1959   Tax: $5,196 (2025)
    Community: Eastbrook Sub
    Single Family


    Estimated Monthly Payment: $2,543 (change assumption)
    Mortgage ($2,110) + Taxes in 2025 ($433)


    Taxes:$5,196

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2703 TIERRA CIR, WINTER PARK, FL 32792

    $469,0006 Days on yellowkey   MLS ID: O6427460

    For Sale O6427460 - 2703 TIERRA CIR, WINTER PARK, FL 32792 54 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1737
       Built: 1970   Tax: $1,360 (2025)
    Community: Casa Aloma
    Single Family


    Estimated Monthly Payment: $2,683 (change assumption)
    Mortgage ($2,570) + Taxes in 2025 ($113)


    Taxes:$1,360

    Elementary School: English Estates Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 2500 LEE RD #232, WINTER PARK, FL 32789

    $149,00084 Days on yellowkey   MLS ID: O6404916

    REDUCED by $15,900 (9.6%) on 06/27/2026

    For Sale O6404916 - 2500 LEE RD #232, WINTER PARK, FL 32789 26 photos

    Bed: 1   Bath: 1.0
    Liv Area Sq Ft: 645
       Built: 1969
    Monthly Fee: $292
       Tax: $2,216 (2025)
    Community: Lakeside Manor Apts Condo
    Condo


    Estimated Monthly Payment: $1,293 (change assumption)
    Mortgage ($816) + Fees ($292) + Taxes in 2025 ($185)


    Taxes:$2,216

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 616 BRECHIN DR, WINTER PARK, FL 32792

    $999,00068 Days on yellowkey   MLS ID: O6409911

    REDUCED by $46,000 (4.4%) on 07/24/2026

    For Sale O6409911 - 616 BRECHIN DR, WINTER PARK, FL 32792 44 photos

    Bed: 4   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 2638
       Built: 1961   Tax: $4,251 (2025)
    Community: Kenilworth Shores Sec 04
    Single Family


    Estimated Monthly Payment: $5,828 (change assumption)
    Mortgage ($5,474) + Taxes in 2025 ($354)


    Taxes:$4,251

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 200 SAINT ANDREWS BLVD #2904, WINTER PARK, FL 32792

    $230,0006 Days on yellowkey   MLS ID: O6427536

    For Sale O6427536 - 200 SAINT ANDREWS BLVD #2904, WINTER PARK, FL 32792 21 photos

    Bed: 2   Bath: 1.5
    Liv Area Sq Ft: 1219
       Built: 1970
    Monthly Fee: $430
       Tax: $3,519 (2025)
    Community: Four Seasons Condo
    Condo


    Estimated Monthly Payment: $1,983 (change assumption)
    Mortgage ($1,260) + Fees ($430) + Taxes in 2025 ($293)


    Taxes:$3,519

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 1130 PARK NORTH PLACE, WINTER PARK, FL 32789

    $2,200,000125 Days on yellowkey   MLS ID: O6392394

    0 Days Off yellowkey (back on 7/24/2026)

    REDUCED by $295,000 (11.8%) on 06/29/2026

    For Sale O6392394 - 1130 PARK NORTH PLACE, WINTER PARK, FL 32789 39 photos

    Bed: 5   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 4011
       Built: 1968   Tax: $9,744 (2025)
    Community: Park North
    Single Family


    Estimated Monthly Payment: $12,866 (change assumption)
    Mortgage ($12,054) + Taxes in 2025 ($812)


    Taxes:$9,744

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 708 BALMORAL RD, WINTER PARK, FL 32789

    $1,690,00020 Days on yellowkey   MLS ID: O6423883

    For Sale O6423883 - 708 BALMORAL RD, WINTER PARK, FL 32789 1 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2786
       Built: 1960   Tax: $6,459 (2025)
    Community: Kenilworth Shores Sec 06
    Spa: No

    Single Family


    Estimated Monthly Payment: $9,798 (change assumption)
    Mortgage ($9,260) + Taxes in 2025 ($538)


    Taxes:$6,459

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 2914 REEF KNOT PL, WINTER PARK, FL 32792

    $1,725,00041 Days on yellowkey   MLS ID: O6418185

    For Sale O6418185 - 2914 REEF KNOT PL, WINTER PARK, FL 32792 64 photos

    Bed: 6   Bath: 5.0   Gar: 3
    Liv Area Sq Ft: 4173
       Built: 2019
    Monthly Fee: $186
       Tax: $17,688 (2025)
    Community: Lake Florence Preserve
    Spa: No

    Single Family


    Estimated Monthly Payment: $11,112 (change assumption)
    Mortgage ($9,452) + Fees ($186) + Taxes in 2025 ($1,474)


    Taxes:$17,688

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 216 BLOSSOM LN, WINTER PARK, FL 32789

    $624,9009 Days on yellowkey   MLS ID: O6426403

    0 Days Off yellowkey (back on 7/23/2026)

    For Sale O6426403 - 216 BLOSSOM LN, WINTER PARK, FL 32789 63 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1933
       Built: 1955   Tax: $5,912 (2025)
    Community: Shores Lake Killarney
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,917 (change assumption)
    Mortgage ($3,424) + Taxes in 2025 ($493)


    Taxes:$5,912

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park Middle


  • 2708 LION HEART RD, WINTER PARK, FL 32792

    $614,500147 Days on yellowkey   MLS ID: O6387685

    REDUCED by $500 (0.1%) on 07/23/2026

    For Sale O6387685 - 2708 LION HEART RD, WINTER PARK, FL 32792 47 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1785
       Built: 1963   Tax: $7,007 (2024)
    Community: Winter Park Pines Rep
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,951 (change assumption)
    Mortgage ($3,367) + Taxes in 2024 ($584)


    Taxes:$7,007

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Glenridge Middle


  • 1037 N VIRGINIA AVE, WINTER PARK, FL 32789

    $649,00034 Days on yellowkey   MLS ID: O6419694

    0 Days Off yellowkey (back on 7/23/2026)

    For Sale O6419694 - 1037 N VIRGINIA AVE, WINTER PARK, FL 32789 35 photos

    Bed: 3   Bath: 1.0   Gar: 1
    Liv Area Sq Ft: 1101
       Built: 1960   Tax: $7,186 (2024)
    Community: Tantum Add
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,155 (change assumption)
    Mortgage ($3,556) + Taxes in 2024 ($599)


    Taxes:$7,186

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Maitland Middle


  • 2504 FORFARSHIRE DR, WINTER PARK, FL 32792

    $630,00013 Days on yellowkey   MLS ID: O6424656

    0 Days Off yellowkey (back on 7/22/2026)

    For Sale O6424656 - 2504 FORFARSHIRE DR, WINTER PARK, FL 32792 45 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1915
       Built: 1962   Tax: $2,733 (2025)
    Community: Brookshire Heights 2Nd Add
    Single Family


    Estimated Monthly Payment: $3,680 (change assumption)
    Mortgage ($3,452) + Taxes in 2025 ($228)


    Taxes:$2,733

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 1271 PALMER AVE, WINTER PARK, FL 32789

    $2,275,0009 Days on yellowkey   MLS ID: O6426530

    For Sale O6426530 - 1271 PALMER AVE, WINTER PARK, FL 32789 50 photos

    Bed: 4   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 2835
       Built: 1948   Tax: $23,515 (2025)
    Community: J Kronenberger Sub
    Spa: No

    Single Family


    Estimated Monthly Payment: $14,425 (change assumption)
    Mortgage ($12,465) + Taxes in 2025 ($1,960)


    Taxes:$23,515

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 2336 SUN VALLEY CIR #BLDG 20, WINTER PARK, FL 32792

    $285,000300 Days on yellowkey   MLS ID: O6342993

    For Sale O6342993 - 2336 SUN VALLEY CIR #BLDG 20, WINTER PARK, FL 32792 12 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1669
       Built: 1986
    Monthly Fee: $511
       Tax: $3,477 (2024)
    Community: Cedarwood Village
    Spa: No

    Condo


    Estimated Monthly Payment: $2,362 (change assumption)
    Mortgage ($1,562) + Fees ($511) + Taxes in 2024 ($290)


    Taxes:$3,477

    Elementary School: English Estates Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 1660 PALMER AVE, WINTER PARK, FL 32789

    $4,950,000524 Days on yellowkey   MLS ID: O6282425

    3 Days Off yellowkey (back on 5/7/2026)

    For Sale O6282425 - 1660 PALMER AVE, WINTER PARK, FL 32789 53 photos

    Bed: 5   Bath: 6.5   Gar: 3
    Liv Area Sq Ft: 6406
       Built: 2024   Tax: $6,144 (2024)
    Community: Comstock Park
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $27,635 (change assumption)
    Mortgage ($27,123) + Taxes in 2024 ($512)


    Taxes:$6,144

    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.