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Winter Park Homes For Sale & Real Estate - 367 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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  • 1760 GREENWICH AVE, WINTER PARK, FL 32789

    $650,00031 Days on yellowkey   MLS ID: O6392001

    For Sale O6392001 - 1760 GREENWICH AVE, WINTER PARK, FL 32789 18 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1610
       Built: 1967   Tax: $2,779 (2025)
    Community: Golfview Heights
    Single Family


    Estimated Monthly Payment: $3,793 (change assumption)
    Mortgage ($3,562) + Taxes in 2025 ($232)


    Taxes:$2,779

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 1780 MONDRIAN CIR, WINTER PARK, FL 32789

    $1,395,00037 Days on yellowkey   MLS ID: O6389472

    For Sale O6389472 - 1780 MONDRIAN CIR, WINTER PARK, FL 32789 51 photos

    Bed: 3   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2310
       Built: 2023
    Monthly Fee: $395
       Tax: $10,448 (2024)
    Community: Mondrian/Winder Park Twnhms
    Spa: No

    Townhouse


    Estimated Monthly Payment: $8,909 (change assumption)
    Mortgage ($7,644) + Fees ($395) + Taxes in 2024 ($871)


    Taxes:$10,448

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2024

    Middle School: College Park Middle


  • 311 E MORSE BLVD #7-19, WINTER PARK, FL 32789

    $299,900111 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


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

    $209,999122 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


  • 2401 ANTILLES DR, WINTER PARK, FL 32792

    $320,000165 Days on yellowkey   MLS ID: O6357934

    For Sale O6357934 - 2401 ANTILLES DR, WINTER PARK, FL 32792 33 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1719
       Built: 1977
    Monthly Fee: $95

    Community: Windward Square Sec 1
    Townhouse


    Estimated Monthly Payment: $1,848 (change assumption)
    Mortgage ($1,753) + Fees ($95) + Taxes in 2024 ($0)


    Taxes:$0

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 1510 MILLER AVE, WINTER PARK, FL 32789

    $1,634,900194 Days on yellowkey   MLS ID: O6350503

    For Sale O6350503 - 1510 MILLER AVE, WINTER PARK, FL 32789 70 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3252
       Built: 2026   Tax: $3,573 (2025)
    Community: Lawndale
    Single Family


    Estimated Monthly Payment: $9,256 (change assumption)
    Mortgage ($8,958) + Taxes in 2025 ($298)


    Taxes:$3,573

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park Middle


  • 240 ORANGE TERRACE DR, WINTER PARK, FL 32789

    $484,000255 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


  • 521 FAIRFAX AVE, WINTER PARK, FL 32789

    $790,0003 Days on yellowkey   MLS ID: O6399909

    1 Days Off yellowkey (back on 4/19/2026)

    For Sale O6399909 - 521 FAIRFAX AVE, WINTER PARK, FL 32789 16 photos

    Bed: 4   Bath: 2.0
    Liv Area Sq Ft: 2112
       Built: 1955   Tax: $9,907 (2025)
    Community: Virginia Heights Rep
    Half Duplex


    Estimated Monthly Payment: $5,154 (change assumption)
    Mortgage ($4,329) + Taxes in 2025 ($826)


    Taxes:$9,907

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 4864 TANGERINE AVE, WINTER PARK, FL 32792

    $200,00061 Days on yellowkey   MLS ID: O6383320

    INCREASED by $1,000 (0.5%) on 04/09/2026

    For Sale O6383320 - 4864 TANGERINE AVE, WINTER PARK, FL 32792 25 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1059
       Built: 1973
    Monthly Fee: $441
       Tax: $2,828 (2025)
    Community: Wrenwood Condo
    Townhouse


    Estimated Monthly Payment: $1,773 (change assumption)
    Mortgage ($1,096) + Fees ($441) + Taxes in 2025 ($236)


    Taxes:$2,828

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1807 MAGNOLIA AVE, WINTER PARK, FL 32789

    $1,199,0003 Days on yellowkey   MLS ID: O6396616

    For Sale O6396616 - 1807 MAGNOLIA AVE, WINTER PARK, FL 32789 38 photos

    Bed: 5   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2618
       Built: 2026   Tax: $4,720 (2025)
    Community: Temple Terrace
    Spa: No

    Single Family


    Estimated Monthly Payment: $6,963 (change assumption)
    Mortgage ($6,570) + Taxes in 2025 ($393)


    Taxes:$4,720

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 1507 GOLFSIDE DR, WINTER PARK, FL 32792

    $975,00017 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


  • 1250 FORMOSA AVE, WINTER PARK, FL 32789

    $560,00013 Days on yellowkey   MLS ID: O6393725

    For Sale O6393725 - 1250 FORMOSA AVE, WINTER PARK, FL 32789 37 photos

    Bed: 3   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 1937
       Built: 2022
    Monthly Fee: $252
       Tax: $8,328 (2025)
    Community: Urban Green 12
    Townhouse


    Estimated Monthly Payment: $4,014 (change assumption)
    Mortgage ($3,068) + Fees ($252) + Taxes in 2025 ($694)


    Taxes:$8,328

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 785 N PHELPS AVE, WINTER PARK, FL 32789

    $2,049,00025 Days on yellowkey   MLS ID: O6393117

    For Sale O6393117 - 785 N PHELPS AVE, WINTER PARK, FL 32789 41 photos

    Bed: 5   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2964
       Built: 2026   Tax: $9,172 (2025)
    Community: Comstock Park
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $11,991 (change assumption)
    Mortgage ($11,227) + Taxes in 2025 ($764)


    Taxes:$9,172

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 3463 ARNEL DR, WINTER PARK, FL 32792

    $459,90033 Days on yellowkey   MLS ID: O6390301

    REDUCED by $20,000 (4.2%) on 04/12/2026

    For Sale O6390301 - 3463 ARNEL DR, WINTER PARK, FL 32792 58 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1770
       Built: 1967   Tax: $4,648 (2024)
    Community: Eastbrook Sub Unit 11
    Single Family


    Estimated Monthly Payment: $2,907 (change assumption)
    Mortgage ($2,520) + Taxes in 2024 ($387)


    Taxes:$4,648

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 3131 LOWNDES DR, WINTER PARK, FL 32792

    $529,95040 Days on yellowkey   MLS ID: O6388846

    REDUCED by $4,950 (0.9%) on 04/16/2026

    For Sale O6388846 - 3131 LOWNDES DR, WINTER PARK, FL 32792 56 photos

    Bed: 4   Bath: 2.0
    Liv Area Sq Ft: 2126
       Built: 1967   Tax: $1,559 (2024)
    Community: Georgetown Estates
    Single Family


    Estimated Monthly Payment: $3,034 (change assumption)
    Mortgage ($2,904) + Taxes in 2024 ($130)


    Taxes:$1,559

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Maitland Middle


  • 1926 NATALEN RD, WINTER PARK, FL 32792

    $649,90044 Days on yellowkey   MLS ID: O6388308

    For Sale O6388308 - 1926 NATALEN RD, WINTER PARK, FL 32792 44 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1469
       Built: 1957   Tax: $7,308 (2024)
    Community: Kenilworth Shores Sec 07
    Single Family


    Estimated Monthly Payment: $4,170 (change assumption)
    Mortgage ($3,561) + Taxes in 2024 ($609)


    Taxes:$7,308

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Glenridge Middle


  • 1515 WINTER GREEN BLVD, WINTER PARK, FL 32792

    $315,00045 Days on yellowkey   MLS ID: O6384755

    For Sale O6384755 - 1515 WINTER GREEN BLVD, WINTER PARK, FL 32792 26 photos

    Bed: 3   Bath: 3.5
    Liv Area Sq Ft: 1652
       Built: 1984
    Monthly Fee: $188
       Tax: $3,993 (2024)
    Community: Winter Green
    Townhouse


    Estimated Monthly Payment: $2,247 (change assumption)
    Mortgage ($1,726) + Fees ($188) + Taxes in 2024 ($333)


    Taxes:$3,993

    Elementary School: English Estates Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 330 ELKHORN CT, WINTER PARK, FL 32792

    $559,90084 Days on yellowkey   MLS ID: O6376757

    REDUCED by $10,000 (1.8%) on 04/16/2026

    For Sale O6376757 - 330 ELKHORN CT, WINTER PARK, FL 32792 41 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1570
       Built: 1965   Tax: $2,086 (2025)
    Community: Winter Park Pines Merrie Oaks
    Single Family


    Estimated Monthly Payment: $3,242 (change assumption)
    Mortgage ($3,068) + Taxes in 2025 ($174)


    Taxes:$2,086

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1905 BONANZA CT, WINTER PARK, FL 32789

    $490,0003 Days on yellowkey   MLS ID: O6398772

    For Sale O6398772 - 1905 BONANZA CT, WINTER PARK, FL 32789 35 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1774
       Built: 1968   Tax: $5,015 (2024)
    Community: Eastbrook Sub Unit 13
    Single Family


    Estimated Monthly Payment: $3,103 (change assumption)
    Mortgage ($2,685) + Taxes in 2024 ($418)


    Taxes:$5,015

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 802 HAMILTON PLACE CT, WINTER PARK, FL 32789

    $1,349,0002 Days on yellowkey   MLS ID: O6398373

    For Sale O6398373 - 802 HAMILTON PLACE CT, WINTER PARK, FL 32789 22 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2843
       Built: 2018
    Monthly Fee: $142
       Tax: $9,300 (2025)
    Community: Hamilton Place
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $8,309 (change assumption)
    Mortgage ($7,392) + Fees ($142) + Taxes in 2025 ($775)


    Taxes:$9,300

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    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.