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Winter Park Single Family Homes For Sale in Winter Park - 51 homes

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

Location: Winter Park, Winter Park

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  • 2501 LAFAYETTE AVE, WINTER PARK, FL 32789

    $1,795,0002 Days on yellowkey   MLS ID: O6416565

    For Sale O6416565 - 2501 LAFAYETTE AVE, WINTER PARK, FL 32789 22 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 2819
       Built: 2026   Tax: $4,608 (2026)
    Community: Winter Park Village
    Single Family


    Estimated Monthly Payment: $10,219 (change assumption)
    Mortgage ($9,835) + Taxes in 2026 ($384)


    Taxes:$4,608

    Elementary School: None

    High School: None

    Tax Year: 2026

    Middle School: None


  • 528 SAINT DUNSTAN WAY, WINTER PARK, FL 32792

    $535,0009 Days on yellowkey   MLS ID: O6414677

    0 Days Off yellowkey (back on 6/16/2026)

    For Sale O6414677 - 528 SAINT DUNSTAN WAY, WINTER PARK, FL 32792 35 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1656
       Built: 1964   Tax: $6,000 (2025)
    Community: Winter Park Pines
    Single Family


    Estimated Monthly Payment: $3,431 (change assumption)
    Mortgage ($2,931) + Taxes in 2025 ($500)


    Taxes:$6,000

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 1404 BORDER DR, WINTER PARK, FL 32789

    $1,175,00021 Days on yellowkey   MLS ID: O6412140

    REDUCED by $25,000 (2.1%) on 06/16/2026

    For Sale O6412140 - 1404 BORDER DR, WINTER PARK, FL 32789 38 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 2469
       Built: 2023   Tax: $16,220 (2025)
    Community: Winter Park Village
    Single Family


    Estimated Monthly Payment: $7,790 (change assumption)
    Mortgage ($6,438) + Taxes in 2025 ($1,352)


    Taxes:$16,220

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 2708 LION HEART RD, WINTER PARK, FL 32792

    $617,500107 Days on yellowkey   MLS ID: O6387685

    REDUCED by $2,400 (0.4%) on 06/15/2026

    For Sale O6387685 - 2708 LION HEART RD, WINTER PARK, FL 32792 47 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1785
       Built: 1963   Tax: $7,007 (2024)
    Community: Winter Park Pines Rep
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,967 (change assumption)
    Mortgage ($3,383) + Taxes in 2024 ($584)


    Taxes:$7,007

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Glenridge Middle


  • 2803 BANCHORY RD, WINTER PARK, FL 32792

    $495,00021 Days on yellowkey   MLS ID: O6404011

    For Sale O6404011 - 2803 BANCHORY RD, WINTER PARK, FL 32792 31 photos

    Bed: 4   Bath: 2.0
    Liv Area Sq Ft: 1596
       Built: 1965
    Monthly Fee: $5
       Tax: $2,458 (2025)
    Community: Winter Park Pines
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,922 (change assumption)
    Mortgage ($2,712) + Fees ($5) + Taxes in 2025 ($205)


    Taxes:$2,458

    Elementary School: Aloma Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 731 BONGART ROAD, WINTER PARK, FL 32792

    $499,00043 Days on yellowkey   MLS ID: O6406004

    For Sale O6406004 - 731 BONGART ROAD, WINTER PARK, FL 32792 44 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 1526
       Built: 1961   Tax: $5,910 (2025)
    Community: Winter Park Estates
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,227 (change assumption)
    Mortgage ($2,734) + Taxes in 2025 ($493)


    Taxes:$5,910

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 641 W LYMAN AVE, WINTER PARK, FL 32789

    $509,00017 Days on yellowkey   MLS ID: O6408078

    For Sale O6408078 - 641 W LYMAN AVE, WINTER PARK, FL 32789 36 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1120
       Built: 2003   Tax: $6,342 (2025)
    Community: Town/Winter Park
    Single Family


    Estimated Monthly Payment: $3,317 (change assumption)
    Mortgage ($2,789) + Taxes in 2025 ($529)


    Taxes:$6,342

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 350 CORNWALL RD, WINTER PARK, FL 32792

    $765,00082 Days on yellowkey   MLS ID: O6394524

    REDUCED by $10,000 (1.3%) on 05/28/2026

    For Sale O6394524 - 350 CORNWALL RD, WINTER PARK, FL 32792 36 photos

    Bed: 4   Bath: 3.0
    Liv Area Sq Ft: 2038
       Built: 1963   Tax: $2,127 (2025)
    Community: Winter Park Pines Rep
    Single Family


    Estimated Monthly Payment: $4,369 (change assumption)
    Mortgage ($4,192) + Taxes in 2025 ($177)


    Taxes:$2,127

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 910 ENCLAVE PL, WINTER PARK, FL 32792

    $1,899,00036 Days on yellowkey   MLS ID: O6406803

    For Sale O6406803 - 910 ENCLAVE PL, WINTER PARK, FL 32792 1 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3620
       Built: 2027
    Monthly Fee: $124
       Tax: $9,900 (2026)
    Community: The Enclave Winter Park
    Single Family


    Estimated Monthly Payment: $11,354 (change assumption)
    Mortgage ($10,405) + 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


  • 2408 LAFAYETTE AVE, WINTER PARK, FL 32789

    $1,495,00070 Days on yellowkey   MLS ID: O6397694

    1 Days Off yellowkey (back on 6/10/2026)

    For Sale O6397694 - 2408 LAFAYETTE AVE, WINTER PARK, FL 32789 31 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2838
       Built: 2024   Tax: $3,770 (2024)
    Community: Winter Park Village
    Spa: No

    Single Family


    Estimated Monthly Payment: $8,506 (change assumption)
    Mortgage ($8,192) + Taxes in 2024 ($314)


    Taxes:$3,770

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Maitland Middle


  • 738 S PENNSYLVANIA AVE, WINTER PARK, FL 32789

    $735,00011 Days on yellowkey   MLS ID: S5151458

    0 Days Off yellowkey (back on 6/10/2026)

    For Sale S5151458 - 738 S PENNSYLVANIA AVE, WINTER PARK, FL 32789 55 photos

    Bed: 3   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1739
       Built: 1925   Tax: $2,730 (2025)
    Community: Winter Park
    Single Family


    Estimated Monthly Payment: $4,255 (change assumption)
    Mortgage ($4,027) + Taxes in 2025 ($228)


    Taxes:$2,730

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 505 CORNWALL RD, WINTER PARK, FL 32792

    $675,00030 Days on yellowkey   MLS ID: O6408759

    1 Days Off yellowkey (back on 6/9/2026)

    For Sale O6408759 - 505 CORNWALL RD, WINTER PARK, FL 32792 42 photos

    Bed: 4   Bath: 2.0
    Liv Area Sq Ft: 1813
       Built: 1965   Tax: $7,194 (2025)
    Community: Winter Park Pines
    Single Family


    Estimated Monthly Payment: $4,298 (change assumption)
    Mortgage ($3,699) + Taxes in 2025 ($600)


    Taxes:$7,194

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 650 DOUGLAS AVE, WINTER PARK, FL 32789

    $550,00011 Days on yellowkey   MLS ID: O6414807

    0 Days Off yellowkey (back on 6/8/2026)

    For Sale O6414807 - 650 DOUGLAS AVE, WINTER PARK, FL 32789 2 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1280
       Built: 2003   Tax: $7,799 (2025)
    Community: Winter Park
    Single Family


    Estimated Monthly Payment: $3,664 (change assumption)
    Mortgage ($3,014) + Taxes in 2025 ($650)


    Taxes:$7,799

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 418 GILBERT RD, WINTER PARK, FL 32792

    $710,00085 Days on yellowkey   MLS ID: O6385950

    REDUCED by $9,000 (1.3%) on 06/02/2026

    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: $4,648 (change assumption)
    Mortgage ($3,890) + Taxes in 2025 ($758)


    Taxes:$9,094

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 1319 BESSMOR RD, WINTER PARK, FL 32789

    $589,00059 Days on yellowkey   MLS ID: O6400395

    REDUCED by $6,000 (1.0%) on 06/08/2026

    For Sale O6400395 - 1319 BESSMOR RD, WINTER PARK, FL 32789 13 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1126
       Built: 1956   Tax: $5,626 (2025)
    Community: Winter Park Village
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,696 (change assumption)
    Mortgage ($3,227) + Taxes in 2025 ($469)


    Taxes:$5,626

    Elementary School: Dream Lake Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 2756 SHERIFF WAY, WINTER PARK, FL 32792

    $595,00052 Days on yellowkey   MLS ID: O6402570

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

    REDUCED by $30,000 (4.8%) on 06/05/2026

    For Sale O6402570 - 2756 SHERIFF WAY, WINTER PARK, FL 32792 48 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1812
       Built: 1965   Tax: $5,547 (2025)
    Community: Winter Park Pines
    Single Family


    Estimated Monthly Payment: $3,722 (change assumption)
    Mortgage ($3,260) + Taxes in 2025 ($462)


    Taxes:$5,547

    Elementary School: Aloma Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 2829 ALOMA, WINTER PARK, FL 32792

    $579,00049 Days on yellowkey   MLS ID: O6404107

    2 Days Off yellowkey (back on 6/5/2026)

    For Sale O6404107 - 2829 ALOMA, WINTER PARK, FL 32792 36 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1821
       Built: 1963   Tax: $4,277 (2025)
    Community: Winter Park Estates
    Single Family


    Estimated Monthly Payment: $3,529 (change assumption)
    Mortgage ($3,173) + Taxes in 2025 ($356)


    Taxes:$4,277

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 715 S RANGER BLVD, WINTER PARK, FL 32792

    $695,00024 Days on yellowkey   MLS ID: O6410899

    For Sale O6410899 - 715 S RANGER BLVD, WINTER PARK, FL 32792 48 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2312
       Built: 1967
    Monthly Fee: $4
       Tax: $2,773 (2025)
    Community: Winter Park Pines
    Single Family


    Estimated Monthly Payment: $4,043 (change assumption)
    Mortgage ($3,808) + Fees ($4) + Taxes in 2025 ($231)


    Taxes:$2,773

    Elementary School: Aloma Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 330 ELKHORN CT, WINTER PARK, FL 32792

    $549,900145 Days on yellowkey   MLS ID: O6376757

    REDUCED by $5,000 (0.9%) on 06/04/2026

    For Sale O6376757 - 330 ELKHORN CT, WINTER PARK, FL 32792 41 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1570
       Built: 1965   Tax: $2,086 (2025)
    Community: Winter Park Pines Merrie Oaks
    Single Family


    Estimated Monthly Payment: $3,187 (change assumption)
    Mortgage ($3,013) + Taxes in 2025 ($174)


    Taxes:$2,086

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 610 ELLENDALE DR, WINTER PARK, FL 32792

    $399,00021 Days on yellowkey   MLS ID: O6411325

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

    For Sale O6411325 - 610 ELLENDALE DR, WINTER PARK, FL 32792 29 photos

    Bed: 4   Bath: 3.0
    Liv Area Sq Ft: 1359
       Built: 1957   Tax: $2,321 (2025)
    Community: Winter Park Estates
    Single Family


    Estimated Monthly Payment: $2,380 (change assumption)
    Mortgage ($2,186) + Taxes in 2025 ($193)


    Taxes:$2,321

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


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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.