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Winter Park Homes For Sale & Real Estate - 336 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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  • 1210 FAIRWAY DR, WINTER PARK, FL 32792

    $549,000Listed 04/13/2026 11:42AM   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


  • 2020 COCOS CT, WINTER PARK, FL 32792

    $459,99031 Days on yellowkey   MLS ID: O6389901

    REDUCED by $4,910 (1.1%) on 04/06/2026

    For Sale O6389901 - 2020 COCOS CT, WINTER PARK, FL 32792 22 photos

    Bed: 3   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1715
       Built: 1966   Tax: $1,410 (2024)
    Community: Eastbrook Sub Unit 8
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,638 (change assumption)
    Mortgage ($2,520) + Taxes in 2024 ($117)


    Taxes:$1,410

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 1473 BERKSHIRE AVE, WINTER PARK, FL 32789

    $1,499,000295 Days on yellowkey   MLS ID: O6320741

    For Sale O6320741 - 1473 BERKSHIRE AVE, WINTER PARK, FL 32789 53 photos

    Bed: 5   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 2895
       Built: 2025   Tax: $5,730 (2024)
    Community: Orwin Manor Westminster Sec
    Single Family


    Estimated Monthly Payment: $8,691 (change assumption)
    Mortgage ($8,213) + Taxes in 2024 ($478)


    Taxes:$5,730

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2024

    Middle School: College Park Middle


  • 240 N PHELPS AVE, WINTER PARK, FL 32789

    $2,279,00035 Days on yellowkey   MLS ID: O6389035

    For Sale O6389035 - 240 N PHELPS AVE, WINTER PARK, FL 32789 68 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 2889
       Built: 2026   Tax: $6,605 (2025)
    Community: Sylvan Heights
    Spa: No

    Single Family


    Estimated Monthly Payment: $13,038 (change assumption)
    Mortgage ($12,487) + Taxes in 2025 ($550)


    Taxes:$6,605

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 7796 FERNBROOK WAY, WINTER PARK, FL 32792

    $290,00024 Days on yellowkey   MLS ID: O6392180

    REDUCED by $10,000 (3.3%) on 04/13/2026

    For Sale O6392180 - 7796 FERNBROOK WAY, WINTER PARK, FL 32792 45 photos

    Bed: 3   Bath: 1.5
    Liv Area Sq Ft: 1332
       Built: 1985
    Monthly Fee: $110
       Tax: $3,296 (2024)
    Community: Fernbrook Trails Ph 3
    Townhouse


    Estimated Monthly Payment: $1,974 (change assumption)
    Mortgage ($1,589) + Fees ($110) + Taxes in 2024 ($275)


    Taxes:$3,296

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 350 CORNWALL RD, WINTER PARK, FL 32792

    $775,00015 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

    $1,875,0004 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

    $299,900105 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

    $427,500Listed 04/12/2026 11:09PM   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


  • 1367 TIERRA CIR, WINTER PARK, FL 32792

    $424,90083 Days on yellowkey   MLS ID: O6375221

    For Sale O6375221 - 1367 TIERRA CIR, WINTER PARK, FL 32792 54 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


  • 1540 MILLER AVE, WINTER PARK, FL 32789

    $1,399,900Listed 04/13/2026 10:28AM   MLS ID: O6398421

    For Sale O6398421 - 1540 MILLER AVE, WINTER PARK, FL 32789 55 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2984
       Built: 2026   Tax: $3,573 (2025)
    Community: Lawndale
    Spa: No

    Single Family


    Estimated Monthly Payment: $7,968 (change assumption)
    Mortgage ($7,670) + Taxes in 2025 ($298)


    Taxes:$3,573

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park Middle


  • 1951 STAUNTON AVE, WINTER PARK, FL 32789

    $599,00067 Days on yellowkey   MLS ID: O6379543

    For Sale O6379543 - 1951 STAUNTON AVE, WINTER PARK, FL 32789 31 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2556
       Built: 1984   Tax: $2,501 (2024)
    Community: Karolina On Killarney
    Single Family


    Estimated Monthly Payment: $3,491 (change assumption)
    Mortgage ($3,282) + Taxes in 2024 ($208)


    Taxes:$2,501

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2024

    Middle School: College Park Middle


  • 2919 BOWER RD, WINTER PARK, FL 32792

    $779,00025 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


  • 647 RANDY LN, WINTER PARK, FL 32789

    $1,795,00035 Days on yellowkey   MLS ID: O6387217

    For Sale O6387217 - 647 RANDY LN, WINTER PARK, FL 32789 64 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2851
       Built: 1957   Tax: $5,627 (2025)
    Community: Timberlane
    Single Family


    Estimated Monthly Payment: $10,304 (change assumption)
    Mortgage ($9,835) + Taxes in 2025 ($469)


    Taxes:$5,627

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 850 JUANITA RAEL, WINTER PARK, FL 32789

    $1,425,00096 Days on yellowkey   MLS ID: O6370568

    1 Days Off yellowkey (back on 1/12/2026)

    For Sale O6370568 - 850 JUANITA RAEL, WINTER PARK, FL 32789 50 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2306
       Built: 1966   Tax: $6,218 (2024)
    Community: Green Oaks Rep 03
    Spa: No

    Single Family


    Estimated Monthly Payment: $8,326 (change assumption)
    Mortgage ($7,808) + Taxes in 2024 ($518)


    Taxes:$6,218

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Maitland Middle


  • 3312 HEARTWOOD AVE, WINTER PARK, FL 32792

    $465,000177 Days on yellowkey   MLS ID: O6352582

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

    REDUCED by $19,000 (3.9%) on 04/08/2026

    For Sale O6352582 - 3312 HEARTWOOD AVE, WINTER PARK, FL 32792 36 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2878
       Built: 1983   Tax: $2,183 (2025)
    Community: Bel-Aire Pines
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,730 (change assumption)
    Mortgage ($2,548) + Taxes in 2025 ($182)


    Taxes:$2,183

    Elementary School: Aloma Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 3021 AARON BURR AVE #3, WINTER PARK, FL 32792

    $140,000Listed 04/12/2026 11:07PM   MLS ID: S5147382

    For Sale S5147382 - 3021 AARON BURR AVE #3, WINTER PARK, FL 32792 21 photos

    Bed: 2   Bath: 2.5
    Liv Area Sq Ft: 1090
       Built: 1974
    Monthly Fee: $479
       Tax: $1,992 (2025)
    Community: Colonies
    Condo


    Estimated Monthly Payment: $1,412 (change assumption)
    Mortgage ($767) + Fees ($479) + Taxes in 2025 ($166)


    Taxes:$1,992

    Elementary School: Cheney Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 1453 VIA SANGRO PL, WINTER PARK, FL 32792

    $995,0004 Days on yellowkey   MLS ID: O6397250

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

    For Sale O6397250 - 1453 VIA SANGRO PL, WINTER PARK, FL 32792 59 photos

    Bed: 4   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 3057
       Built: 2015
    Monthly Fee: $188
       Tax: $5,858 (2024)
    Community: Lakeside Estates
    Spa: No

    Single Family


    Estimated Monthly Payment: $6,128 (change assumption)
    Mortgage ($5,452) + Fees ($188) + Taxes in 2024 ($488)


    Taxes:$5,858

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 851 MILES AVE #13, WINTER PARK, FL 32789

    $209,999116 Days on yellowkey   MLS ID: O6368234

    For Sale O6368234 - 851 MILES AVE #13, WINTER PARK, FL 32789 24 photos

    Bed: 2   Bath: 1.0
    Liv Area Sq Ft: 808
       Built: 1984   Tax: $2,694 (2025)
    Community: Aragon Condo
    Condo


    Estimated Monthly Payment: $1,375 (change assumption)
    Mortgage ($1,151) + Taxes in 2025 ($224)


    Taxes:$2,694

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 1507 GOLFSIDE DR, WINTER PARK, FL 32792

    $975,00011 Days on yellowkey   MLS ID: O6395355

    For Sale O6395355 - 1507 GOLFSIDE DR, WINTER PARK, FL 32792 44 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2003
       Built: 1981   Tax: $2,783 (2025)
    Community: Greenview At Winter Pines
    Single Family


    Estimated Monthly Payment: $5,574 (change assumption)
    Mortgage ($5,342) + Taxes in 2025 ($232)


    Taxes:$2,783

    Elementary School: Brookshire Elem

    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.