REFINE SEARCH
Status
Keywords
Price
 
Bedrooms
Bathrooms
Garages
Liv Area Sq Ft
Min Year
Max Year
Property Types
No Image
Age Restricted
Foreclosure
Short Sale
Pets Allowed
Furnished
Pool
Spa
Reduced Price
Back on yellowkey
Possible Short Term Rental
Carports
Max Association Fee (monthly)
Max Monthly Payment
Search

Winter Park Homes For Sale & Real Estate - 449 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

Sort:
  • 311 E MORSE BLVD #1-3, WINTER PARK, FL 32789

    $1,925,00039 Days on yellowkey   MLS ID: O6406368

    REDUCED by $70,000 (3.5%) on 06/12/2026

    For Sale O6406368 - 311 E MORSE BLVD #1-3, WINTER PARK, FL 32789 28 photos

    Bed: 2   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2304
       Built: 1960
    Monthly Fee: $2,471
       Tax: $16,493 (2025)
    Community: Whispering Waters/Phillips Circle Rep
    Condo


    Estimated Monthly Payment: $14,393 (change assumption)
    Mortgage ($10,548) + Fees ($2,471) + Taxes in 2025 ($1,374)


    Taxes:$16,493

    Elementary School: None

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 1441 CARDINAL CT, WINTER PARK, FL 32789

    $4,285,00062 Days on yellowkey   MLS ID: O6399395

    For Sale O6399395 - 1441 CARDINAL CT, WINTER PARK, FL 32789 85 photos

    Bed: 4   Bath: 5.5   Gar: 2
    Liv Area Sq Ft: 4066
       Built: 2022   Tax: $47,740 (2025)
    Community: Winflor Court
    Spa: No

    Single Family


    Estimated Monthly Payment: $27,457 (change assumption)
    Mortgage ($23,479) + Taxes in 2025 ($3,978)


    Taxes:$47,740

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 4469 OLD BEAR RUN, WINTER PARK, FL 32792

    $1,799,999127 Days on yellowkey   MLS ID: O6375415

    REDUCED by $50,001 (2.7%) on 05/22/2026

    For Sale O6375415 - 4469 OLD BEAR RUN, WINTER PARK, FL 32792 77 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 4288
       Built: 1978   Tax: $10,710 (2024)
    Community: Pervis Survey For R E
    Spa: No

    Single Family


    Estimated Monthly Payment: $10,755 (change assumption)
    Mortgage ($9,863) + Taxes in 2024 ($893)


    Taxes:$10,710

    Elementary School: Red Bug Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 649 N PARK AVE, WINTER PARK, FL 32789

    $3,500,00014 Days on yellowkey   MLS ID: O6411141

    For Sale O6411141 - 649 N PARK AVE, WINTER PARK, FL 32789 44 photos

    Bed: 3   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 3180
       Built: 2019
    Monthly Fee: $948
       Tax: $22,599 (2025)
    Community: Park Hill
    Townhouse


    Estimated Monthly Payment: $22,009 (change assumption)
    Mortgage ($19,178) + Fees ($948) + Taxes in 2025 ($1,883)


    Taxes:$22,599

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 269 E CANTON AVE #269, WINTER PARK, FL 32789

    $989,50026 Days on yellowkey   MLS ID: O6404706

    For Sale O6404706 - 269 E CANTON AVE #269, WINTER PARK, FL 32789 44 photos

    Bed: 1   Bath: 1.5
    Liv Area Sq Ft: 1109
       Built: 1971
    Monthly Fee: $1,039
       Tax: $3,470 (2025)
    Community: Village Winterset Inc
    Condo


    Estimated Monthly Payment: $6,750 (change assumption)
    Mortgage ($5,422) + Fees ($1,039) + Taxes in 2025 ($289)


    Taxes:$3,470

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2430 CHANTILLY AVE, WINTER PARK, FL 32789

    $1,665,00033 Days on yellowkey   MLS ID: O6401352

    For Sale O6401352 - 2430 CHANTILLY AVE, WINTER PARK, FL 32789 49 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 2916
       Built: 2026   Tax: $4,730 (2025)
    Community: Winter Park Village
    Spa: No

    Single Family


    Estimated Monthly Payment: $9,517 (change assumption)
    Mortgage ($9,123) + Taxes in 2025 ($394)


    Taxes:$4,730

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 1438 TIERRA CIR, WINTER PARK, FL 32792

    $519,90045 Days on yellowkey   MLS ID: O6403855

    REDUCED by $5,100 (1.0%) on 06/04/2026

    For Sale O6403855 - 1438 TIERRA CIR, WINTER PARK, FL 32792 36 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1627
       Built: 1968   Tax: $1,630 (2024)
    Community: Casa Aloma
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,985 (change assumption)
    Mortgage ($2,849) + Taxes in 2024 ($136)


    Taxes:$1,630

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 1611 CHESTNUT AVE, WINTER PARK, FL 32789

    $1,070,00047 Days on yellowkey   MLS ID: O6402502

    REDUCED by $30,000 (2.7%) on 06/10/2026

    For Sale O6402502 - 1611 CHESTNUT AVE, WINTER PARK, FL 32789 45 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 2916
       Built: 1973   Tax: $3,590 (2025)
    Community: Lake Knowles Terrace
    Single Family


    Estimated Monthly Payment: $6,162 (change assumption)
    Mortgage ($5,863) + Taxes in 2025 ($299)


    Taxes:$3,590

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 350 CORNWALL RD, WINTER PARK, FL 32792

    $765,00079 Days on yellowkey   MLS ID: O6394524

    REDUCED by $10,000 (1.3%) on 05/28/2026

    For Sale O6394524 - 350 CORNWALL RD, WINTER PARK, FL 32792 36 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: $4,369 (change assumption)
    Mortgage ($4,192) + Taxes in 2025 ($177)


    Taxes:$2,127

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 700 MELROSE AVE #K25, WINTER PARK, FL 32789

    $245,0007 Days on yellowkey   MLS ID: O6414821

    0 Days Off yellowkey (back on 6/13/2026)

    For Sale O6414821 - 700 MELROSE AVE #K25, WINTER PARK, FL 32789 30 photos

    Bed: 1   Bath: 1.0
    Liv Area Sq Ft: 787
       Built: 1964   Tax: $3,196 (2025)
    Community: Winter Park Gardens Condo
    Condo


    Estimated Monthly Payment: $1,609 (change assumption)
    Mortgage ($1,342) + Taxes in 2025 ($266)


    Taxes:$3,196

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 700 MELROSE AVE #J24, WINTER PARK, FL 32789

    $390,00025 Days on yellowkey   MLS ID: R4911307

    For Sale R4911307 - 700 MELROSE AVE #J24, WINTER PARK, FL 32789 28 photos

    Bed: 2   Bath: 1.0
    Liv Area Sq Ft: 987
       Built: 1964   Tax: $3,874 (2025)
    Community: Winter Park Gardens Condo
    Condo


    Estimated Monthly Payment: $2,460 (change assumption)
    Mortgage ($2,137) + Taxes in 2025 ($323)


    Taxes:$3,874

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1760 PERUVIAN LN, WINTER PARK, FL 32792

    $324,000101 Days on yellowkey   MLS ID: A4685217

    REDUCED by $15,000 (4.4%) on 06/09/2026

    For Sale A4685217 - 1760 PERUVIAN LN, WINTER PARK, FL 32792 21 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1160
       Built: 1960   Tax: $3,470 (2025)
    Community: Eastbrook Sub Unit 06
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,064 (change assumption)
    Mortgage ($1,775) + Taxes in 2025 ($289)


    Taxes:$3,470

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 946 ENCLAVE PL, WINTER PARK, FL 32792

    $2,175,00019 Days on yellowkey   MLS ID: O6411633

    For Sale O6411633 - 946 ENCLAVE PL, WINTER PARK, FL 32792 3 photos

    Bed: 5   Bath: 5.5   Gar: 2
    Liv Area Sq Ft: 3989
       Built: 2026
    Monthly Fee: $375
       Tax: $9,900 (2026)
    Community: The Enclave Winter Park
    Single Family


    Estimated Monthly Payment: $13,118 (change assumption)
    Mortgage ($11,918) + Fees ($375) + Taxes in 2026 ($825)


    Taxes:$9,900

    Elementary School: None

    High School: None

    Tax Year: 2026

    Middle School: None


  • 950 ENCLAVE PL, WINTER PARK, FL 32792

    $2,125,00019 Days on yellowkey   MLS ID: O6410963

    For Sale O6410963 - 950 ENCLAVE PL, WINTER PARK, FL 32792 3 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3797
       Built: 2027
    Monthly Fee: $124
       Tax: $9,900 (2026)
    Community: The Enclave Winter Park
    Single Family


    Estimated Monthly Payment: $12,593 (change assumption)
    Mortgage ($11,644) + Fees ($124) + Taxes in 2026 ($825)


    Taxes:$9,900

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2026

    Middle School: Maitland Middle


  • 942 ENCLAVE PL, WINTER PARK, FL 32792

    $2,195,00019 Days on yellowkey   MLS ID: O6411550

    For Sale O6411550 - 942 ENCLAVE PL, WINTER PARK, FL 32792 3 photos

    Bed: 5   Bath: 5.0   Gar: 2
    Liv Area Sq Ft: 3831
       Built: 2026
    Monthly Fee: $372
       Tax: $9,900 (2026)
    Community: The Enclave Winter Park
    Single Family


    Estimated Monthly Payment: $13,224 (change assumption)
    Mortgage ($12,027) + Fees ($372) + Taxes in 2026 ($825)


    Taxes:$9,900

    Elementary School: None

    High School: None

    Tax Year: 2026

    Middle School: None


  • 938 ENCLAVE PL, WINTER PARK, FL 32792

    $2,099,00027 Days on yellowkey   MLS ID: O6408090

    For Sale O6408090 - 938 ENCLAVE PL, WINTER PARK, FL 32792 4 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3865
       Built: 2026
    Monthly Fee: $124
       Tax: $9,900 (2026)
    Community: The Enclave Winter Park
    Single Family


    Estimated Monthly Payment: $12,450 (change assumption)
    Mortgage ($11,501) + Fees ($124) + Taxes in 2026 ($825)


    Taxes:$9,900

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2026

    Middle School: Maitland Middle


  • 910 ENCLAVE PL, WINTER PARK, FL 32792

    $1,899,00033 Days on yellowkey   MLS ID: O6406803

    For Sale O6406803 - 910 ENCLAVE PL, WINTER PARK, FL 32792 1 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3620
       Built: 2027
    Monthly Fee: $124
       Tax: $9,900 (2026)
    Community: The Enclave Winter Park
    Single Family


    Estimated Monthly Payment: $11,354 (change assumption)
    Mortgage ($10,405) + Fees ($124) + Taxes in 2026 ($825)


    Taxes:$9,900

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2026

    Middle School: Maitland Middle


  • 930 ENCLAVE PL, WINTER PARK, FL 32792

    $2,050,00033 Days on yellowkey   MLS ID: O6403032

    For Sale O6403032 - 930 ENCLAVE PL, WINTER PARK, FL 32792 4 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3813
       Built: 2026
    Monthly Fee: $124
       Tax: $9,900 (2026)
    Community: The Enclave Winter Park
    Single Family


    Estimated Monthly Payment: $12,182 (change assumption)
    Mortgage ($11,233) + Fees ($124) + Taxes in 2026 ($825)


    Taxes:$9,900

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2026

    Middle School: Maitland Middle


  • 901 ENCLAVE PL, WINTER PARK, FL 32792

    $1,495,00088 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

    $1,495,00088 Days on yellowkey   MLS ID: O6383679

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

    Bed: 3   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




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.