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Winter Park Homes For Sale & Real Estate - 438 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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  • 1130 PARK NORTH PLACE, WINTER PARK, FL 32789

    $2,200,000110 Days on yellowkey   MLS ID: O6392394

    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


  • 901 ENCLAVE PL, WINTER PARK, FL 32792

    $1,495,000116 Days on yellowkey   MLS ID: O6383602

    For Sale O6383602 - 901 ENCLAVE PL, WINTER PARK, FL 32792 2 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2738
       Built: 2026
    Monthly Fee: $247
       Tax: $9,900 (2026)
    Community: The Enclave Winter Park
    Townhouse


    Estimated Monthly Payment: $9,264 (change assumption)
    Mortgage ($8,192) + Fees ($247) + Taxes in 2026 ($825)


    Taxes:$9,900

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2026

    Middle School: Maitland Middle


  • 905 ENCLAVE PL, WINTER PARK, FL 32792

    $1,495,000116 Days on yellowkey   MLS ID: O6383679

    For Sale O6383679 - 905 ENCLAVE PL, WINTER PARK, FL 32792 2 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2756
       Built: 2026
    Monthly Fee: $247
       Tax: $9,900 (2026)
    Community: The Enclave Winter Park
    Townhouse


    Estimated Monthly Payment: $9,264 (change assumption)
    Mortgage ($8,192) + Fees ($247) + Taxes in 2026 ($825)


    Taxes:$9,900

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2026

    Middle School: Maitland Middle


  • 914 ENCLAVE PL, WINTER PARK, FL 32792

    $1,895,000116 Days on yellowkey   MLS ID: O6391825

    For Sale O6391825 - 914 ENCLAVE PL, WINTER PARK, FL 32792 3 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3617
       Built: 2026
    Monthly Fee: $372
       Tax: $10,000 (2025)
    Community: The Enclave Winter Park
    Single Family


    Estimated Monthly Payment: $11,589 (change assumption)
    Mortgage ($10,383) + Fees ($372) + Taxes in 2025 ($833)


    Taxes:$10,000

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 1751 GLENCOE RD, WINTER PARK, FL 32789

    $3,390,000252 Days on yellowkey   MLS ID: O6339739

    REDUCED by $100,000 (2.9%) on 06/06/2026

    For Sale O6339739 - 1751 GLENCOE RD, WINTER PARK, FL 32789 45 photos

    Bed: 5   Bath: 6.0   Gar: 2
    Liv Area Sq Ft: 4520
       Built: 2025   Tax: $12,895 (2024)
    Community: Forest Hills
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $19,649 (change assumption)
    Mortgage ($18,575) + Taxes in 2024 ($1,075)


    Taxes:$12,895

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Audubon Park K-8


  • 1298 BEACHVIEW AVE, WINTER PARK, FL 32789

    $1,375,0004 Days on yellowkey   MLS ID: O6417337

    0 Days Off yellowkey (back on 7/10/2026)

    For Sale O6417337 - 1298 BEACHVIEW AVE, WINTER PARK, FL 32789 23 photos

    Bed: 1   Bath: 1.0
    Liv Area Sq Ft: 1665
       Built: 1941   Tax: $7,634 (2025)
    Community: Killarney Estates
    Single Family


    Estimated Monthly Payment: $8,170 (change assumption)
    Mortgage ($7,534) + Taxes in 2025 ($636)


    Taxes:$7,634

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park Middle


  • 275 N RANGER BLVD, WINTER PARK, FL 32792

    $775,00034 Days on yellowkey   MLS ID: O6415904

    For Sale O6415904 - 275 N RANGER BLVD, WINTER PARK, FL 32792 32 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 1950
       Built: 1965   Tax: $6,817 (2025)
    Community: Winter Park Pines Merrie Oaks
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,815 (change assumption)
    Mortgage ($4,246) + Taxes in 2025 ($568)


    Taxes:$6,817

    Elementary School: Aloma Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 1037 N VIRGINIA AVE, WINTER PARK, FL 32789

    $649,00019 Days on yellowkey   MLS ID: O6419694

    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


  • 8433 COMMANDER CV, WINTER PARK, FL 32792

    $445,00031 Days on yellowkey   MLS ID: O6416635

    REDUCED by $10,000 (2.2%) on 07/11/2026

    For Sale O6416635 - 8433 COMMANDER CV, WINTER PARK, FL 32792 59 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1903
       Built: 1986
    Monthly Fee: $76
       Tax: $3,556 (2025)
    Community: Trinity Bay
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,811 (change assumption)
    Mortgage ($2,438) + Fees ($76) + Taxes in 2025 ($296)


    Taxes:$3,556

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 2831 MULFORD AVE, WINTER PARK, FL 32789

    $715,00037 Days on yellowkey   MLS ID: O6414319

    REDUCED by $20,000 (2.7%) on 07/11/2026

    For Sale O6414319 - 2831 MULFORD AVE, WINTER PARK, FL 32789 28 photos

    Bed: 4   Bath: 2.5
    Liv Area Sq Ft: 1647
       Built: 1952   Tax: $3,192 (2025)
    Community: Orangewood Park
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,184 (change assumption)
    Mortgage ($3,918) + Taxes in 2025 ($266)


    Taxes:$3,192

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1369 BLUE STEM LN, WINTER PARK, FL 32792

    $819,00098 Days on yellowkey   MLS ID: O6396971

    REDUCED by $6,000 (0.7%) on 07/11/2026

    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: $5,407 (change assumption)
    Mortgage ($4,488) + Fees ($413) + Taxes in 2024 ($506)


    Taxes:$6,074

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 770 W WEBSTER AVE, WINTER PARK, FL 32789

    $725,000376 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


  • 1180 VIA LUGANO, WINTER PARK, FL 32789

    $4,900,00015 Days on yellowkey   MLS ID: O6413198

    For Sale O6413198 - 1180 VIA LUGANO, WINTER PARK, FL 32789 67 photos

    Bed: 5   Bath: 5.5   Gar: 3
    Liv Area Sq Ft: 4961
       Built: 2006   Tax: $43,400 (2025)
    Community: Woodmere Terrace Rep
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $30,465 (change assumption)
    Mortgage ($26,849) + Taxes in 2025 ($3,617)


    Taxes:$43,400

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 1908 CYRIL CT, WINTER PARK, FL 32792

    $639,0005 Days on yellowkey   MLS ID: O6422937

    For Sale O6422937 - 1908 CYRIL CT, WINTER PARK, FL 32792 29 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2471
       Built: 1990
    Monthly Fee: $41
       Tax: $7,674 (2025)
    Community: Kawilla Crest
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,182 (change assumption)
    Mortgage ($3,501) + Fees ($41) + Taxes in 2025 ($640)


    Taxes:$7,674

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 303 SCOTTSDALE SQ #303, WINTER PARK, FL 32792

    $80,0004 Days on yellowkey   MLS ID: O6424296

    For Sale O6424296 - 303 SCOTTSDALE SQ #303, WINTER PARK, FL 32792 3 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1020
       Built: 1974   Tax: $1,392 (2025)
    Community: Winter Park Woods Condo
    Condo


    Estimated Monthly Payment: $554 (change assumption)
    Mortgage ($438) + Taxes in 2025 ($116)


    Taxes:$1,392

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 2450 GRAND TETON CIR #2450, WINTER PARK, FL 32792

    $255,0004 Days on yellowkey   MLS ID: O6418973

    For Sale O6418973 - 2450 GRAND TETON CIR #2450, WINTER PARK, FL 32792 37 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1311
       Built: 1981   Tax: $889 (2025)
    Community: Cedarwood Village 1
    Spa: No

    Condo


    Estimated Monthly Payment: $1,471 (change assumption)
    Mortgage ($1,397) + Taxes in 2025 ($74)


    Taxes:$889

    Elementary School: English Estates Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 2010 SUMMERFIELD RD, WINTER PARK, FL 32792

    $594,5004 Days on yellowkey   MLS ID: O6420140

    For Sale O6420140 - 2010 SUMMERFIELD RD, WINTER PARK, FL 32792 40 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1889
       Built: 1957   Tax: $7,917 (2025)
    Community: Kenilworth Shores Sec 07
    Single Family


    Estimated Monthly Payment: $3,917 (change assumption)
    Mortgage ($3,257) + Taxes in 2025 ($660)


    Taxes:$7,917

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 2189 SUSSEX RD, WINTER PARK, FL 32792

    $375,0005 Days on yellowkey   MLS ID: O6423782

    FORECLOSURE O6423782 - 2189 SUSSEX RD, WINTER PARK, FL 32792 29 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1776
       Built: 1968
    Monthly Fee: $2
       Tax: $4,646 (2025)
    Community: Winter Woods Unit 01
    Single Family


    Estimated Monthly Payment: $2,444 (change assumption)
    Mortgage ($2,055) + Fees ($2) + Taxes in 2025 ($387)


    Taxes:$4,646

    Elementary School: English Estates Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 3019 ANTIQUE OAKS CIR #124, WINTER PARK, FL 32792

    $142,500326 Days on yellowkey   MLS ID: O6337083

    REDUCED by $2,000 (1.4%) on 07/10/2026

    For Sale O6337083 - 3019 ANTIQUE OAKS CIR #124, WINTER PARK, FL 32792 26 photos

    Bed: 1   Bath: 1.0
    Liv Area Sq Ft: 749
       Built: 1984
    Monthly Fee: $300
       Tax: $2,050 (2024)
    Community: Parkview Village
    Spa: No

    Condo


    Estimated Monthly Payment: $1,252 (change assumption)
    Mortgage ($781) + Fees ($300) + Taxes in 2024 ($171)


    Taxes:$2,050

    Elementary School: Aloma Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Glenridge Middle


  • 1920 HEATHWOOD DR, WINTER PARK, FL 32792

    $370,000111 Days on yellowkey   MLS ID: O6393303

    4 Days Off yellowkey (back on 7/10/2026)

    For Sale O6393303 - 1920 HEATHWOOD DR, WINTER PARK, FL 32792 37 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1978
       Built: 1980   Tax: $4,895 (2025)
    Community: Cedar Ridge Unit 1
    Single Family


    Estimated Monthly Payment: $2,435 (change assumption)
    Mortgage ($2,027) + Taxes in 2025 ($408)


    Taxes:$4,895

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None




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.