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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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  • 2614 PARKLAND DR, WINTER PARK, FL 32789

    $1,924,450407 Days on yellowkey   MLS ID: O6301489

    REDUCED by $24,550 (1.3%) on 05/29/2026

    For Sale O6301489 - 2614 PARKLAND DR, WINTER PARK, FL 32789 54 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3307
       Built: 2007   Tax: $12,712 (2024)
    Community: Parklando 03
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $11,604 (change assumption)
    Mortgage ($10,545) + Taxes in 2024 ($1,059)


    Taxes:$12,712

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Audubon Park K-8


  • 151 OAKWOOD WAY, WINTER PARK, FL 32789

    $2,850,000116 Days on yellowkey   MLS ID: O6380037

    0 Days Off yellowkey (back on 5/29/2026)

    REDUCED by $100,000 (3.4%) on 05/26/2026

    For Sale O6380037 - 151 OAKWOOD WAY, WINTER PARK, FL 32789 68 photos

    Bed: 4   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 4129
       Built: 2023   Tax: $34,218 (2025)
    Community: Charmont
    Spa: No

    Single Family


    Estimated Monthly Payment: $18,468 (change assumption)
    Mortgage ($15,616) + Taxes in 2025 ($2,852)


    Taxes:$34,218

    Elementary School: None

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 1750 CAROLLEE LANE, WINTER PARK, FL 32789

    $1,820,00073 Days on yellowkey   MLS ID: O6391179

    REDUCED by $70,000 (3.7%) on 05/26/2026

    For Sale O6391179 - 1750 CAROLLEE LANE, WINTER PARK, FL 32789 46 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3249
       Built: 2012   Tax: $24,658 (2025)
    Community: Green Terrace V/140 Lot 3 Blk B
    Single Family


    Estimated Monthly Payment: $12,027 (change assumption)
    Mortgage ($9,972) + Taxes in 2025 ($2,055)


    Taxes:$24,658

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 1161 VALENCIA AVE, WINTER PARK, FL 32789

    $3,995,000284 Days on yellowkey   MLS ID: O6330736

    REDUCED by $80,000 (2.0%) on 05/29/2026

    For Sale O6330736 - 1161 VALENCIA AVE, WINTER PARK, FL 32789 65 photos

    Bed: 4   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 4181
       Built: 2021   Tax: $30,421 (2024)
    Community: Valencia Terrace
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $24,425 (change assumption)
    Mortgage ($21,890) + Taxes in 2024 ($2,535)


    Taxes:$30,421

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Maitland Middle


  • 2779 SANBINA ST, WINTER PARK, FL 32789

    $429,00080 Days on yellowkey   MLS ID: O6388746

    REDUCED by $10,000 (2.3%) on 05/29/2026

    For Sale O6388746 - 2779 SANBINA ST, WINTER PARK, FL 32789 29 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1405
       Built: 1960   Tax: $5,629 (2024)
    Community: Howell Heights
    Single Family


    Estimated Monthly Payment: $2,820 (change assumption)
    Mortgage ($2,351) + Taxes in 2024 ($469)


    Taxes:$5,629

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Maitland Middle


  • 1433 ASTER CT, WINTER PARK, FL 32792

    $389,00018 Days on yellowkey   MLS ID: O6407873

    0 Days Off yellowkey (back on 5/29/2026)

    REDUCED by $10,000 (2.5%) on 05/21/2026

    For Sale O6407873 - 1433 ASTER CT, WINTER PARK, FL 32792 30 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1363
       Built: 1984   Tax: $1,057 (2025)
    Community: Garden Lake Estates Unit 3
    Single Family


    Estimated Monthly Payment: $2,220 (change assumption)
    Mortgage ($2,131) + Taxes in 2025 ($88)


    Taxes:$1,057

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 234 DETMAR DR, WINTER PARK, FL 32789

    $1,599,000111 Days on yellowkey   MLS ID: O6379927

    2 Days Off yellowkey (back on 5/29/2026)

    REDUCED by $46,000 (2.8%) on 04/29/2026

    For Sale O6379927 - 234 DETMAR DR, WINTER PARK, FL 32789 49 photos

    Bed: 4   Bath: 5.5   Gar: 1
    Liv Area Sq Ft: 3609
       Built: 1935   Tax: $13,664 (2025)
    Community: Osceola Shores Sec 1
    Spa: No

    Single Family


    Estimated Monthly Payment: $9,900 (change assumption)
    Mortgage ($8,761) + Taxes in 2025 ($1,139)


    Taxes:$13,664

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 7120 BROOKSIDE TRL, WINTER PARK, FL 32792

    $510,00039 Days on yellowkey   MLS ID: O6398534

    0 Days Off yellowkey (back on 4/30/2026)

    For Sale O6398534 - 7120 BROOKSIDE TRL, WINTER PARK, FL 32792 35 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1753
       Built: 1976   Tax: $3,098 (2025)
    Community: Replat Of Lts 1 2 & 3 Brookside Sub
    Single Family


    Estimated Monthly Payment: $3,053 (change assumption)
    Mortgage ($2,794) + Taxes in 2025 ($258)


    Taxes:$3,098

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 4190 BEAR GULLY RD, WINTER PARK, FL 32792

    $499,900146 Days on yellowkey   MLS ID: O6371014

    REDUCED by $25,000 (4.8%) on 05/29/2026

    For Sale O6371014 - 4190 BEAR GULLY RD, WINTER PARK, FL 32792 30 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2058
       Built: 2003
    Monthly Fee: $52
       Tax: $5,630 (2024)
    Community: Bear Gully Forest
    Single Family


    Estimated Monthly Payment: $3,260 (change assumption)
    Mortgage ($2,739) + Fees ($52) + Taxes in 2024 ($469)


    Taxes:$5,630

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 1340 PLACE PICARDY, WINTER PARK, FL 32789

    $1,599,000109 Days on yellowkey   MLS ID: O6382113

    3 Days Off yellowkey (back on 3/30/2026)

    For Sale O6382113 - 1340 PLACE PICARDY, WINTER PARK, FL 32789 34 photos

    Bed: 3   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3459
       Built: 1997   Tax: $7,515 (2025)
    Community: Fontainebleau
    Single Family


    Estimated Monthly Payment: $9,388 (change assumption)
    Mortgage ($8,761) + Taxes in 2025 ($626)


    Taxes:$7,515

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 1052 MANCHESTER CIR, WINTER PARK, FL 32792

    $460,000128 Days on yellowkey   MLS ID: O6376260

    REDUCED by $10,000 (2.1%) on 05/28/2026

    For Sale O6376260 - 1052 MANCHESTER CIR, WINTER PARK, FL 32792 41 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1703
       Built: 1983   Tax: $5,216 (2025)
    Community: Howell Estates 1St Add
    Single Family


    Estimated Monthly Payment: $2,955 (change assumption)
    Mortgage ($2,520) + Taxes in 2025 ($435)


    Taxes:$5,216

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 1077 MINNESOTA AVE, WINTER PARK, FL 32789

    $1,395,0004 Days 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

    $2,099,00012 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

    $2,125,0004 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

    $2,175,0004 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


  • 942 ENCLAVE PL, WINTER PARK, FL 32792

    $2,195,0004 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


  • 1760 GREENWICH AVE, WINTER PARK, FL 32789

    $625,00074 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


  • 2418 EUSTON RD, WINTER PARK, FL 32789

    $789,0005 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

    $405,00036 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

    $649,000220 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




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.