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Winter Park Single Family Homes For Sale - 311 homes

Winter Park Single Family Homes for Sale are located in Seminole 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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  • 2220 FAIRGLENN WAY, WINTER PARK, FL 32792

    $649,90048 Days on yellowkey   MLS ID: O6399993

    REDUCED by $25,000 (3.7%) on 04/30/2026

    For Sale O6399993 - 2220 FAIRGLENN WAY, WINTER PARK, FL 32792 53 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2636
       Built: 1986
    Monthly Fee: $53
       Tax: $3,357 (2025)
    Community: Quail Run
    Single Family


    Estimated Monthly Payment: $3,894 (change assumption)
    Mortgage ($3,561) + Fees ($53) + Taxes in 2025 ($280)


    Taxes:$3,357

    Elementary School: Red Bug Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 2052 LEANNE CT, WINTER PARK, FL 32792

    $445,000121 Days on yellowkey   MLS ID: O6379323

    REDUCED by $5,000 (1.1%) on 05/28/2026

    For Sale O6379323 - 2052 LEANNE CT, WINTER PARK, FL 32792 30 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2264
       Built: 1969   Tax: $1,581 (2024)
    Community: Eastbrook Sub Unit 15
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,570 (change assumption)
    Mortgage ($2,438) + Taxes in 2024 ($132)


    Taxes:$1,581

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 1161 VALENCIA AVE, WINTER PARK, FL 32789

    $3,995,000287 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


  • 1529 HOLTS GROVE CIR, WINTER PARK, FL 32789

    $2,699,00064 Days on yellowkey   MLS ID: O6395062

    REDUCED by $96,000 (3.4%) on 05/20/2026

    For Sale O6395062 - 1529 HOLTS GROVE CIR, WINTER PARK, FL 32789 86 photos

    Bed: 4   Bath: 5.0   Gar: 3
    Liv Area Sq Ft: 4356
       Built: 2005
    Monthly Fee: $262
       Tax: $21,342 (2025)
    Community: Windsong Lakeside Sec 02 43/71
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $16,829 (change assumption)
    Mortgage ($14,789) + Fees ($262) + Taxes in 2025 ($1,779)


    Taxes:$21,342

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 609 S PHELPS AVE, WINTER PARK, FL 32789

    $2,829,00080 Days on yellowkey   MLS ID: O6388598

    For Sale O6388598 - 609 S PHELPS AVE, WINTER PARK, FL 32789 24 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 4018
       Built: 2026   Tax: $8,522 (2024)
    Community: Kenilworth Shores Sec 06
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $16,211 (change assumption)
    Mortgage ($15,501) + Taxes in 2024 ($710)


    Taxes:$8,522

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Glenridge Middle


  • 1651 WESTCHESTER AVE, WINTER PARK, FL 32789

    $1,175,00062 Days on yellowkey   MLS ID: O6384358

    REDUCED by $100,000 (7.8%) on 06/01/2026

    For Sale O6384358 - 1651 WESTCHESTER AVE, WINTER PARK, FL 32789 47 photos

    Bed: 3   Bath: 2.5   Gar: 1
    Liv Area Sq Ft: 2426
       Built: 1938   Tax: $10,973 (2025)
    Community: Orwin Manor Westminster Sec
    Single Family


    Estimated Monthly Payment: $7,353 (change assumption)
    Mortgage ($6,438) + Taxes in 2025 ($914)


    Taxes:$10,973

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park Middle


  • 450 LAKEWOOD DR, WINTER PARK, FL 32789

    $2,500,00034 Days on yellowkey   MLS ID: O6403490

    For Sale O6403490 - 450 LAKEWOOD DR, WINTER PARK, FL 32789 78 photos

    Bed: 5   Bath: 5.0   Gar: 3
    Liv Area Sq Ft: 4572
       Built: 2000   Tax: $11,393 (2025)
    Community: Osceola Shores Sec 03
    Single Family


    Estimated Monthly Payment: $14,648 (change assumption)
    Mortgage ($13,698) + Taxes in 2025 ($949)


    Taxes:$11,393

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 1565 FOREST AVE, WINTER PARK, FL 32789

    $1,650,00051 Days on yellowkey   MLS ID: O6398694

    REDUCED by $100,000 (5.7%) on 05/11/2026

    For Sale O6398694 - 1565 FOREST AVE, WINTER PARK, FL 32789 37 photos

    Bed: 4   Bath: 2.0
    Liv Area Sq Ft: 2163
       Built: 1925   Tax: $2,803 (2025)
    Community: Ellno Willo
    Single Family


    Estimated Monthly Payment: $9,274 (change assumption)
    Mortgage ($9,041) + Taxes in 2025 ($234)


    Taxes:$2,803

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 1611 CHESTNUT AVE, WINTER PARK, FL 32789

    $1,100,00035 Days on yellowkey   MLS ID: O6402502

    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: $6,326 (change assumption)
    Mortgage ($6,027) + Taxes in 2025 ($299)


    Taxes:$3,590

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 926 ENCLAVE PL, WINTER PARK, FL 32792

    $2,235,00015 Days on yellowkey   MLS ID: O6408030

    For Sale O6408030 - 926 ENCLAVE PL, WINTER PARK, FL 32792 3 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 4150
       Built: 2026
    Monthly Fee: $124
       Tax: $9,900 (2026)
    Community: The Enclave Winter Park
    Single Family


    Estimated Monthly Payment: $13,195 (change assumption)
    Mortgage ($12,246) + 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

    $2,125,0007 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


  • 938 ENCLAVE PL, WINTER PARK, FL 32792

    $2,099,00015 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


  • 1287 VERDANT GLADE PL, WINTER PARK, FL 32792

    $847,00041 Days on yellowkey   MLS ID: O6400331

    REDUCED by $3,000 (0.4%) on 06/03/2026

    For Sale O6400331 - 1287 VERDANT GLADE PL, WINTER PARK, FL 32792 50 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3020
       Built: 2020
    Monthly Fee: $413
       Tax: $6,133 (2025)
    Community: Meadows At Hawks Crest
    Single Family


    Estimated Monthly Payment: $5,565 (change assumption)
    Mortgage ($4,641) + Fees ($413) + Taxes in 2025 ($511)


    Taxes:$6,133

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 2361 MULBRY DR, WINTER PARK, FL 32789

    $2,289,00049 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 77 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 3130
       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


  • 1813 HARLAND PARK DR, WINTER PARK, FL 32789

    $1,875,00034 Days on yellowkey   MLS ID: O6403483

    REDUCED by $120,000 (6.0%) on 05/28/2026

    For Sale O6403483 - 1813 HARLAND PARK DR, WINTER PARK, FL 32789 59 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3551
       Built: 2013
    Monthly Fee: $268
       Tax: $23,539 (2025)
    Community: Windsong - Knowles Place
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $12,503 (change assumption)
    Mortgage ($10,274) + Fees ($268) + Taxes in 2025 ($1,962)


    Taxes:$23,539

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 5275 PINE LILY CIR, WINTER PARK, FL 32792

    $665,000125 Days on yellowkey   MLS ID: O6377988

    0 Days Off yellowkey (back on 4/27/2026)

    For Sale O6377988 - 5275 PINE LILY CIR, WINTER PARK, FL 32792 34 photos

    Bed: 5   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 3152
       Built: 2014
    Monthly Fee: $182
       Tax: $7,425 (2024)
    Community: Sanctuary At Aloma
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $4,444 (change assumption)
    Mortgage ($3,644) + Fees ($182) + Taxes in 2024 ($619)


    Taxes:$7,425

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 2823 WRIGHT AVE, WINTER PARK, FL 32789

    $899,90083 Days on yellowkey   MLS ID: O6390670

    0 Days Off yellowkey (back on 6/3/2026)

    REDUCED by $30,000 (3.2%) on 05/07/2026

    For Sale O6390670 - 2823 WRIGHT AVE, WINTER PARK, FL 32789 19 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1536
       Built: 1958   Tax: $9,119 (2025)
    Community: Lake Forest Park
    Single Family


    Estimated Monthly Payment: $5,691 (change assumption)
    Mortgage ($4,931) + Taxes in 2025 ($760)


    Taxes:$9,119

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 1920 HEATHWOOD DR, WINTER PARK, FL 32792

    $370,00071 Days on yellowkey   MLS ID: O6393303

    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


  • 2648 GALLIANO CIR, WINTER PARK, FL 32792

    $355,000100 Days on yellowkey   MLS ID: S5144547

    For Sale S5144547 - 2648 GALLIANO CIR, WINTER PARK, FL 32792 39 photos

    Bed: 2   Bath: 2.5   Gar: 1
    Liv Area Sq Ft: 1550
       Built: 2004
    Monthly Fee: $175
       Tax: $4,736 (2024)
    Community: Vistas At Lake Howell
    Single Family


    Estimated Monthly Payment: $2,515 (change assumption)
    Mortgage ($1,945) + Fees ($175) + Taxes in 2024 ($395)


    Taxes:$4,736

    Elementary School: Sterling Park Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 1351 MAGNOLIA AVE, WINTER PARK, FL 32789

    $3,100,00034 Days on yellowkey   MLS ID: O6404105

    0 Days Off yellowkey (back on 5/1/2026)

    For Sale O6404105 - 1351 MAGNOLIA AVE, WINTER PARK, FL 32789 1 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3460
       Built: 2026   Tax: $9,720 (2025)
    Community: Lake Knowles Terrace Add 02
    Single Family


    Estimated Monthly Payment: $17,796 (change assumption)
    Mortgage ($16,986) + Taxes in 2025 ($810)


    Taxes:$9,720

    Elementary School: None

    High School: None

    Tax Year: 2025

    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.