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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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  • 1564 LAWNDALE CIR, WINTER PARK, FL 32792

    $450,000Listed 06/23/2026 1:02PM   MLS ID: O6418817

    For Sale O6418817 - 1564 LAWNDALE CIR, WINTER PARK, FL 32792 45 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1980
       Built: 1985
    Monthly Fee: $46
       Tax: $3,124 (2025)
    Community: Country Lane
    Single Family


    Estimated Monthly Payment: $2,772 (change assumption)
    Mortgage ($2,466) + Fees ($46) + Taxes in 2025 ($260)


    Taxes:$3,124

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 1565 FOREST AVE, WINTER PARK, FL 32789

    $1,495,00071 Days on yellowkey   MLS ID: O6398694

    REDUCED by $155,000 (9.4%) on 06/15/2026

    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: $8,425 (change assumption)
    Mortgage ($8,192) + 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


  • 240 ORANGE TERRACE DR, WINTER PARK, FL 32789

    $470,000321 Days on yellowkey   MLS ID: O6330690

    REDUCED by $9,900 (2.1%) on 06/23/2026

    For Sale O6330690 - 240 ORANGE TERRACE DR, WINTER PARK, FL 32789 32 photos

    Bed: 4   Bath: 2.0
    Liv Area Sq Ft: 1718
       Built: 1955   Tax: $6,210 (2024)
    Community: Orange Terrace
    Single Family


    Estimated Monthly Payment: $3,093 (change assumption)
    Mortgage ($2,575) + Taxes in 2024 ($518)


    Taxes:$6,210

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2024

    Middle School: Robinswood Middle


  • 2052 LEANNE CT, WINTER PARK, FL 32792

    $440,000141 Days on yellowkey   MLS ID: O6379323

    REDUCED by $5,000 (1.1%) on 06/17/2026

    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: $2,543 (change assumption)
    Mortgage ($2,411) + Taxes in 2024 ($132)


    Taxes:$1,581

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 1813 HARLAND PARK DR, WINTER PARK, FL 32789

    $1,875,00054 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


  • 1826 BANCHORY RD, WINTER PARK, FL 32789

    $779,000Listed 06/23/2026 5:37PM   MLS ID: O6419474

    0 Days Off yellowkey (back on 6/23/2026)

    For Sale O6419474 - 1826 BANCHORY RD, WINTER PARK, FL 32789 1 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2391
       Built: 1962   Tax: $7,662 (2025)
    Community: Kenilworth Shores Sec 06
    Single Family


    Estimated Monthly Payment: $4,907 (change assumption)
    Mortgage ($4,268) + Taxes in 2025 ($639)


    Taxes:$7,662

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1649 HARMON AVE, WINTER PARK, FL 32789

    $1,299,90096 Days on yellowkey   MLS ID: O6392216

    REDUCED by $50,000 (3.7%) on 06/12/2026

    For Sale O6392216 - 1649 HARMON AVE, WINTER PARK, FL 32789 57 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3223
       Built: 2018   Tax: $11,908 (2025)
    Community: Lawndale
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $8,115 (change assumption)
    Mortgage ($7,123) + Taxes in 2025 ($992)


    Taxes:$11,908

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park Middle


  • 926 ENCLAVE PL, WINTER PARK, FL 32792

    $2,235,00035 Days on yellowkey   MLS ID: O6408030

    For Sale O6408030 - 926 ENCLAVE PL, WINTER PARK, FL 32792 5 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


  • 1840 ASTER DR, WINTER PARK, FL 32792

    $439,90023 Days on yellowkey   MLS ID: O6412364

    REDUCED by $10,000 (2.2%) on 06/21/2026

    For Sale O6412364 - 1840 ASTER DR, WINTER PARK, FL 32792 20 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1667
       Built: 1978   Tax: $864 (2025)
    Community: Garden Lake Estates Unit 1
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,482 (change assumption)
    Mortgage ($2,410) + Taxes in 2025 ($72)


    Taxes:$864

    Elementary School: Red Bug Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 685 OVERSPIN DR, WINTER PARK, FL 32789

    $629,00014 Days on yellowkey   MLS ID: O6415537

    0 Days Off yellowkey (back on 6/23/2026)

    For Sale O6415537 - 685 OVERSPIN DR, WINTER PARK, FL 32789 26 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2112
       Built: 2003   Tax: $8,533 (2025)
    Community: Dubsdread Heights
    Single Family


    Estimated Monthly Payment: $4,158 (change assumption)
    Mortgage ($3,446) + Taxes in 2025 ($711)


    Taxes:$8,533

    Elementary School: Princeton Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park Middle


  • 2111 MALLARD CIR, WINTER PARK, FL 32789

    $1,245,00062 Days on yellowkey   MLS ID: O6401350

    REDUCED by $50,000 (3.9%) on 06/04/2026

    For Sale O6401350 - 2111 MALLARD CIR, WINTER PARK, FL 32789 28 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2667
       Built: 1973   Tax: $7,352 (2025)
    Community: Quail Hollow
    Spa: No

    Single Family


    Estimated Monthly Payment: $7,434 (change assumption)
    Mortgage ($6,822) + Taxes in 2025 ($613)


    Taxes:$7,352

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 1300 MAYFIELD AVE, WINTER PARK, FL 32789

    $2,490,00089 Days on yellowkey   MLS ID: O6393777

    0 Days Off yellowkey (back on 6/23/2026)

    REDUCED by $205,000 (7.6%) on 06/19/2026

    For Sale O6393777 - 1300 MAYFIELD AVE, WINTER PARK, FL 32789 50 photos

    Bed: 5   Bath: 5.5   Gar: 4
    Liv Area Sq Ft: 4389
       Built: 1958   Tax: $26,658 (2025)
    Community: Temple Heights
    Spa: No

    Single Family


    Estimated Monthly Payment: $15,865 (change assumption)
    Mortgage ($13,643) + Taxes in 2025 ($2,221)


    Taxes:$26,658

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 332 FLEET RD, WINTER PARK, FL 32792

    $595,0006 Days on yellowkey   MLS ID: O6414829

    2 Days Off yellowkey (back on 6/23/2026)

    For Sale O6414829 - 332 FLEET RD, WINTER PARK, FL 32792 35 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2355
       Built: 1966   Tax: $4,919 (2025)
    Community: Winter Park Pines Merrie Oaks
    Single Family


    Estimated Monthly Payment: $3,670 (change assumption)
    Mortgage ($3,260) + Taxes in 2025 ($410)


    Taxes:$4,919

    Elementary School: Aloma Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 437 N CAPEN AVE, WINTER PARK, FL 32789

    $849,0009 Days on yellowkey   MLS ID: O6414283

    For Sale O6414283 - 437 N CAPEN AVE, WINTER PARK, FL 32789 36 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1904
       Built: 2016
    Monthly Fee: $400
       Tax: $11,943 (2025)
    Community: Canton Ave Cottages 1
    Single Family


    Estimated Monthly Payment: $6,047 (change assumption)
    Mortgage ($4,652) + Fees ($400) + Taxes in 2025 ($995)


    Taxes:$11,943

    Elementary School: Killarney Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 948 POINCIANA LN, WINTER PARK, FL 32789

    $2,899,900163 Days on yellowkey   MLS ID: O6372165

    REDUCED by $274,100 (8.6%) on 06/13/2026

    For Sale O6372165 - 948 POINCIANA LN, WINTER PARK, FL 32789 57 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3676
       Built: 2001   Tax: $19,753 (2025)
    Community: Maitland Shores First Add
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $17,536 (change assumption)
    Mortgage ($15,889) + Taxes in 2025 ($1,646)


    Taxes:$19,753

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 102 BELL PL, WINTER PARK, FL 32792

    $1,399,00071 Days on yellowkey   MLS ID: O6398118

    For Sale O6398118 - 102 BELL PL, WINTER PARK, FL 32792 46 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2459
       Built: 2025   Tax: $4,224 (2025)
    Community: Eastgate Sub
    Spa: No

    Single Family


    Estimated Monthly Payment: $8,018 (change assumption)
    Mortgage ($7,666) + Taxes in 2025 ($352)


    Taxes:$4,224

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 240 N PHELPS AVE, WINTER PARK, FL 32789

    $2,250,00013 Days on yellowkey   MLS ID: O6415360

    For Sale O6415360 - 240 N PHELPS AVE, WINTER PARK, FL 32789 41 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 2889
       Built: 2026   Tax: $6,605 (2025)
    Community: Sylvan Heights
    Single Family


    Estimated Monthly Payment: $12,879 (change assumption)
    Mortgage ($12,328) + Taxes in 2025 ($550)


    Taxes:$6,605

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 1023 WORTHING CT, WINTER PARK, FL 32792

    $450,00012 Days on yellowkey   MLS ID: O6416552

    0 Days Off yellowkey (back on 6/23/2026)

    REDUCED by $10,000 (2.2%) on 06/15/2026

    For Sale O6416552 - 1023 WORTHING CT, WINTER PARK, FL 32792 28 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1184
       Built: 1983   Tax: $1,092 (2025)
    Community: Howell Estates 2Nd Add
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,557 (change assumption)
    Mortgage ($2,466) + Taxes in 2025 ($91)


    Taxes:$1,092

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 501 HERITAGE BLVD, WINTER PARK, FL 32792

    $474,900103 Days on yellowkey   MLS ID: S5145746

    REDUCED by $5,000 (1.0%) on 06/23/2026

    For Sale S5145746 - 501 HERITAGE BLVD, WINTER PARK, FL 32792 20 photos

    Bed: 4   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1376
       Built: 1966   Tax: $10,434 (2025)
    Community: Georgetown Estates
    Single Family


    Estimated Monthly Payment: $3,472 (change assumption)
    Mortgage ($2,602) + Taxes in 2025 ($870)


    Taxes:$10,434

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 234 DETMAR DR, WINTER PARK, FL 32789

    $1,599,000134 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




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.