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Winter Park Homes For Sale & Real Estate - 447 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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  • 643 N PARK AVE, WINTER PARK, FL 32789

    $4,295,00017 Days on yellowkey   MLS ID: O6403591

    For Sale O6403591 - 643 N PARK AVE, WINTER PARK, FL 32789 82 photos

    Bed: 3   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 4231
       Built: 2018
    Monthly Fee: $948
       Tax: $22,352 (2025)
    Community: Park Hill
    Townhouse


    Estimated Monthly Payment: $26,344 (change assumption)
    Mortgage ($23,534) + Fees ($948) + Taxes in 2025 ($1,863)


    Taxes:$22,352

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 938 ENCLAVE PL, WINTER PARK, FL 32792

    $2,099,00011 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: 3858
       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


  • 950 ENCLAVE PL, WINTER PARK, FL 32792

    $2,125,0003 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


  • 946 ENCLAVE PL, WINTER PARK, FL 32792

    $2,175,0003 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


  • 2529 WINDWARD WAY, WINTER PARK, FL 32792

    $299,0003 Days on yellowkey   MLS ID: S5150790

    For Sale S5150790 - 2529 WINDWARD WAY, WINTER PARK, FL 32792 20 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1105
       Built: 1977
    Monthly Fee: $99
       Tax: $332 (2025)
    Community: Windward Square Sec 1
    Townhouse


    Estimated Monthly Payment: $1,765 (change assumption)
    Mortgage ($1,638) + Fees ($99) + Taxes in 2025 ($28)


    Taxes:$332

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 942 ENCLAVE PL, WINTER PARK, FL 32792

    $2,195,0003 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: 4231
       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


  • 1695 LEE RD #B210, WINTER PARK, FL 32789

    $99,000129 Days on yellowkey   MLS ID: O6375872

    REDUCED by $5,000 (4.8%) on 05/28/2026

    For Sale O6375872 - 1695 LEE RD #B210, WINTER PARK, FL 32789 27 photos

    Bed: 1   Bath: 1.0
    Liv Area Sq Ft: 638
       Built: 1966   Tax: $1,493 (2024)
    Community: Waterfall Cove
    Spa: No

    Condo


    Estimated Monthly Payment: $667 (change assumption)
    Mortgage ($542) + Taxes in 2024 ($124)


    Taxes:$1,493

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 3651 N GOLDENROD RD #D102, WINTER PARK, FL 32792

    $159,00040 Days on yellowkey   MLS ID: O6401114

    REDUCED by $1,000 (0.6%) on 05/28/2026

    For Sale O6401114 - 3651 N GOLDENROD RD #D102, WINTER PARK, FL 32792 14 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 840
       Built: 1990
    Monthly Fee: $370
       Tax: $2,461 (2025)
    Community: Lancelot/Winter Park
    Condo


    Estimated Monthly Payment: $1,446 (change assumption)
    Mortgage ($871) + Fees ($370) + Taxes in 2025 ($205)


    Taxes:$2,461

    Elementary School: Aloma Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 1760 GREENWICH AVE, WINTER PARK, FL 32789

    $625,00073 Days on yellowkey   MLS ID: O6392001

    0 Days Off yellowkey (back on 5/28/2026)

    REDUCED by $25,000 (3.8%) on 05/05/2026

    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: $3,656 (change assumption)
    Mortgage ($3,425) + Taxes in 2025 ($232)


    Taxes:$2,779

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 3282 OAK LAKE PL #3282, WINTER PARK, FL 32792

    $159,00031 Days on yellowkey   MLS ID: O6403912

    REDUCED by $10,500 (6.2%) on 05/28/2026

    For Sale O6403912 - 3282 OAK LAKE PL #3282, WINTER PARK, FL 32792 27 photos

    Bed: 2   Bath: 1.5
    Liv Area Sq Ft: 990
       Built: 1984   Tax: $2,899 (2025)
    Community: Hidden Oaks Condominium Association, Inc
    Condo


    Estimated Monthly Payment: $1,113 (change assumption)
    Mortgage ($871) + Taxes in 2025 ($242)


    Taxes:$2,899

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2418 EUSTON RD, WINTER PARK, FL 32789

    $789,0004 Days on yellowkey   MLS ID: O6409323

    For Sale O6409323 - 2418 EUSTON RD, WINTER PARK, FL 32789 34 photos

    Bed: 3   Bath: 2.5   Gar: 1
    Liv Area Sq Ft: 2228
       Built: 1950   Tax: $7,927 (2025)
    Community: Glencoe Sub
    Single Family


    Estimated Monthly Payment: $4,984 (change assumption)
    Mortgage ($4,323) + Taxes in 2025 ($661)


    Taxes:$7,927

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park Middle


  • 3440 ALLSTON LN, WINTER PARK, FL 32792

    $405,00035 Days on yellowkey   MLS ID: O6401731

    REDUCED by $15,000 (3.6%) on 05/26/2026

    For Sale O6401731 - 3440 ALLSTON LN, WINTER PARK, FL 32792 36 photos

    Bed: 3   Bath: 2.5   Gar: 1
    Liv Area Sq Ft: 1533
       Built: 1993
    Monthly Fee: $65
       Tax: $1,364 (2024)
    Community: Villas Of Casselberry Ph 4
    Single Family


    Estimated Monthly Payment: $2,398 (change assumption)
    Mortgage ($2,219) + Fees ($65) + Taxes in 2024 ($114)


    Taxes:$1,364

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 3370 CEDAR SPRINGS PL #156, WINTER PARK, FL 32792

    $185,000323 Days on yellowkey   MLS ID: O6326460

    REDUCED by $4,000 (2.1%) on 05/11/2026

    For Sale O6326460 - 3370 CEDAR SPRINGS PL #156, WINTER PARK, FL 32792 26 photos

    Bed: 2   Bath: 2.5
    Liv Area Sq Ft: 1031
       Built: 1984
    Monthly Fee: $420
       Tax: $2,549 (2024)
    Community: Hidden Oaks Condo Ph 09
    Condo


    Estimated Monthly Payment: $1,646 (change assumption)
    Mortgage ($1,014) + Fees ($420) + Taxes in 2024 ($212)


    Taxes:$2,549

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 151 N ORLANDO AVE #259, WINTER PARK, FL 32789

    $239,00010 Days on yellowkey   MLS ID: O6409651

    For Sale O6409651 - 151 N ORLANDO AVE #259, WINTER PARK, FL 32789 31 photos

    Bed: 1   Bath: 1.0
    Liv Area Sq Ft: 582
       Built: 1960   Tax: $2,552 (2025)
    Community: Lake Killarney Condo
    Condo


    Estimated Monthly Payment: $1,522 (change assumption)
    Mortgage ($1,310) + Taxes in 2025 ($213)


    Taxes:$2,552

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park Middle


  • 2500 LEE RD. #222, WINTER PARK, FL 32789

    $189,500161 Days on yellowkey   MLS ID: O6368580

    For Sale O6368580 - 2500 LEE RD. #222, WINTER PARK, FL 32789 26 photos

    Bed: 1   Bath: 1.0
    Liv Area Sq Ft: 645
       Built: 1969
    Monthly Fee: $245
       Tax: $926 (2024)
    Community: Lakeside Manor Apts Condo
    Condo


    Estimated Monthly Payment: $1,360 (change assumption)
    Mortgage ($1,038) + Fees ($245) + Taxes in 2024 ($77)


    Taxes:$926

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


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

    $149,000282 Days on yellowkey   MLS ID: O6337083

    REDUCED by $5,000 (3.2%) on 04/17/2026

    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: $1,287 (change assumption)
    Mortgage ($816) + 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


  • 3018 NORTHWOOD BLVD, WINTER PARK, FL 32789

    $649,000219 Days on yellowkey   MLS ID: G5103499

    0 Days Off yellowkey (back on 5/28/2026)

    REDUCED by $10,000 (1.5%) on 05/22/2026

    For Sale G5103499 - 3018 NORTHWOOD BLVD, WINTER PARK, FL 32789 47 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1761
       Built: 1954   Tax: $6,623 (2024)
    Community: Northwood Terrace
    Single Family


    Estimated Monthly Payment: $4,108 (change assumption)
    Mortgage ($3,556) + Taxes in 2024 ($552)


    Taxes:$6,623

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Audubon Park K-8


  • 1995 CANNY CV, WINTER PARK, FL 32792

    $425,00014 Days on yellowkey   MLS ID: G5112476

    For Sale G5112476 - 1995 CANNY CV, WINTER PARK, FL 32792 26 photos

    Bed: 3   Bath: 2.5   Gar: 1
    Liv Area Sq Ft: 1907
       Built: 2023
    Monthly Fee: $375
       Tax: $5,957 (2025)
    Community: Grayson Square
    Townhouse


    Estimated Monthly Payment: $3,200 (change assumption)
    Mortgage ($2,329) + Fees ($375) + Taxes in 2025 ($496)


    Taxes:$5,957

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 5806 MARBLE CT, WINTER PARK, FL 32792

    $289,00027 Days on yellowkey   MLS ID: O6399228

    REDUCED by $6,000 (2.0%) on 05/28/2026

    For Sale O6399228 - 5806 MARBLE CT, WINTER PARK, FL 32792 20 photos

    Bed: 2   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1140
       Built: 1989
    Monthly Fee: $69
       Tax: $3,411 (2025)
    Community: Aloma Park
    Half Duplex


    Estimated Monthly Payment: $1,937 (change assumption)
    Mortgage ($1,584) + Fees ($69) + Taxes in 2025 ($284)


    Taxes:$3,411

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 3720 JONQUIL LN, WINTER PARK, FL 32792

    $445,00046 Days on yellowkey   MLS ID: O6399628

    0 Days Off yellowkey (back on 4/16/2026)

    For Sale O6399628 - 3720 JONQUIL LN, WINTER PARK, FL 32792 1 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1647
       Built: 1982   Tax: $1,835 (2024)
    Community: Garden Lake Estates Unit 2
    Single Family


    Estimated Monthly Payment: $2,591 (change assumption)
    Mortgage ($2,438) + Taxes in 2024 ($153)


    Taxes:$1,835

    Elementary School: None

    High School: None

    Tax Year: 2024

    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.