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Winter Park Single Family Homes For Sale - 308 homes

Winter Park Single Family Homes for Sale are located in Orange County, Florida. Find single family homes for sale in Winter Park with data from the Multiple Listing Service (MLS). Our REALTORS® can assist you in your real estate search for Winter Park single family houses.

Location: Winter Park

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  • 1870 WALKER AVE, WINTER PARK, FL 32789

    $1,299,00078 Days on yellowkey   MLS ID: O6390504

    REDUCED by $100,000 (7.1%) on 05/29/2026

    For Sale O6390504 - 1870 WALKER AVE, WINTER PARK, FL 32789 32 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2046
       Built: 2026   Tax: $3,981 (2025)
    Community: Osceola Heights
    Single Family


    Estimated Monthly Payment: $7,449 (change assumption)
    Mortgage ($7,118) + Taxes in 2025 ($332)


    Taxes:$3,981

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 418 GILBERT RD, WINTER PARK, FL 32792

    $719,00065 Days on yellowkey   MLS ID: O6385950

    REDUCED by $10,000 (1.4%) on 05/19/2026

    For Sale O6385950 - 418 GILBERT RD, WINTER PARK, FL 32792 30 photos

    Bed: 3   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 1680
       Built: 1964   Tax: $9,094 (2025)
    Community: Winter Park Pines Ut 5
    Single Family


    Estimated Monthly Payment: $4,697 (change assumption)
    Mortgage ($3,940) + Taxes in 2025 ($758)


    Taxes:$9,094

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 1420 MAGNOLIA AVE, WINTER PARK, FL 32789

    $1,750,00024 Days on yellowkey   MLS ID: O6404564

    For Sale O6404564 - 1420 MAGNOLIA AVE, WINTER PARK, FL 32789 67 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3174
       Built: 2015   Tax: $21,173 (2025)
    Community: Lake Knowles Terrace Add 02
    Spa: No

    Single Family


    Estimated Monthly Payment: $11,353 (change assumption)
    Mortgage ($9,589) + Taxes in 2025 ($1,764)


    Taxes:$21,173

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 1077 MINNESOTA AVE, WINTER PARK, FL 32789

    $1,395,0001 Day on yellowkey   MLS ID: O6411722

    For Sale O6411722 - 1077 MINNESOTA AVE, WINTER PARK, FL 32789 45 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 3046
       Built: 2025   Tax: $1,383 (2025)
    Community: Na
    Single Family


    Estimated Monthly Payment: $7,759 (change assumption)
    Mortgage ($7,644) + Taxes in 2025 ($115)


    Taxes:$1,383

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 938 ENCLAVE PL, WINTER PARK, FL 32792

    $2,099,00010 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

    $2,125,0001 Day 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

    $2,175,0001 Day 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


  • 942 ENCLAVE PL, WINTER PARK, FL 32792

    $2,195,0001 Day 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


  • 7517 LAUREL SPRINGS DR, WINTER PARK, FL 32792

    $399,9902 Days on yellowkey   MLS ID: O6411247

    For Sale O6411247 - 7517 LAUREL SPRINGS DR, WINTER PARK, FL 32792 53 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1678
       Built: 1972   Tax: $6,116 (2025)
    Community: Laurel Springs
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $2,701 (change assumption)
    Mortgage ($2,192) + Taxes in 2025 ($510)


    Taxes:$6,116

    Elementary School: Aloma Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 723 SYMONDS AVE, WINTER PARK, FL 32789

    $2,000,0002 Days on yellowkey   MLS ID: O6406823

    For Sale O6406823 - 723 SYMONDS AVE, WINTER PARK, FL 32789 50 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 3065
       Built: 2023   Tax: $15,884 (2025)
    Community: Horton Aaron
    Single Family


    Estimated Monthly Payment: $12,282 (change assumption)
    Mortgage ($10,959) + Taxes in 2025 ($1,324)


    Taxes:$15,884

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 2361 MULBRY DR, WINTER PARK, FL 32789

    $2,289,00044 Days on yellowkey   MLS ID: O6396840

    REDUCED by $36,000 (1.5%) on 05/28/2026

    For Sale O6396840 - 2361 MULBRY DR, WINTER PARK, FL 32789 80 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 3111
       Built: 2026   Tax: $6,436 (2025)
    Community: Lake Forest Park
    Single Family


    Estimated Monthly Payment: $13,079 (change assumption)
    Mortgage ($12,542) + Taxes in 2025 ($536)


    Taxes:$6,436

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 1760 GREENWICH AVE, WINTER PARK, FL 32789

    $625,00072 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


  • 5117 CYPRESS CT, WINTER PARK, FL 32792

    $449,99016 Days on yellowkey   MLS ID: O6407713

    For Sale O6407713 - 5117 CYPRESS CT, WINTER PARK, FL 32792 26 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1534
       Built: 1972   Tax: $3,877 (2025)
    Community: Wrenwood Heights
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,789 (change assumption)
    Mortgage ($2,466) + Taxes in 2025 ($323)


    Taxes:$3,877

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1032 MANCHESTER CIR, WINTER PARK, FL 32792

    $470,000101 Days on yellowkey   MLS ID: O6383113

    For Sale O6383113 - 1032 MANCHESTER CIR, WINTER PARK, FL 32792 27 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1787
       Built: 1976   Tax: $1,535 (2025)
    Community: Howell Estates Rep
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,703 (change assumption)
    Mortgage ($2,575) + Taxes in 2025 ($128)


    Taxes:$1,535

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 1150 VIA SALERNO, WINTER PARK, FL 32789

    $4,195,000336 Days on yellowkey   MLS ID: O6321143

    REDUCED by $555,000 (11.7%) on 04/25/2026

    For Sale O6321143 - 1150 VIA SALERNO, WINTER PARK, FL 32789 62 photos

    Bed: 4   Bath: 5.5   Gar: 2
    Liv Area Sq Ft: 3850
       Built: 2025   Tax: $10,158 (2024)
    Community: Cloister Grove Sub
    Spa: No

    Single Family


    Estimated Monthly Payment: $23,832 (change assumption)
    Mortgage ($22,986) + Taxes in 2024 ($847)


    Taxes:$10,158

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Maitland Middle


  • 2418 EUSTON RD, WINTER PARK, FL 32789

    $789,0003 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

    $405,00034 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


  • 3018 NORTHWOOD BLVD, WINTER PARK, FL 32789

    $649,000218 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


  • 7740 LAKE DAWN DR, WINTER PARK, FL 32792

    $729,0005 Days on yellowkey   MLS ID: O6410689

    For Sale O6410689 - 7740 LAKE DAWN DR, WINTER PARK, FL 32792 68 photos

    Bed: 5   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2495
       Built: 1959   Tax: $5,157 (2025)
    Community: Na
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,424 (change assumption)
    Mortgage ($3,994) + Taxes in 2025 ($430)


    Taxes:$5,157

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 3720 JONQUIL LN, WINTER PARK, FL 32792

    $445,00045 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 Single Family Homes for Sale?

Winter Park home, townhome, and condo, villa, and other listing sale 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 single family homes for sale in Winter Park. You can use our website to view Multiple Listing Service (MLS) data on Winter Park single family homes. 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 single family home 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.