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Winter Park Single Family Homes For Sale in Winter Park - 19 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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  • 2412 CHANTILLY AVE, WINTER PARK, FL 32789

    $2,395,00054 Days on yellowkey   MLS ID: O6381552

    For Sale O6381552 - 2412 CHANTILLY AVE, WINTER PARK, FL 32789 61 photos

    Bed: 5   Bath: 6.5   Gar: 3
    Liv Area Sq Ft: 4506
       Built: 2026   Tax: $4,779 (2025)
    Community: Winter Park Village
    Single Family


    Estimated Monthly Payment: $13,521 (change assumption)
    Mortgage ($13,123) + Taxes in 2025 ($398)


    Taxes:$4,779

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 781 NORTHWOOD CIR, WINTER PARK, FL 32789

    $775,0005 Days on yellowkey   MLS ID: O6394119

    0 Days Off yellowkey (back on 4/5/2026)

    For Sale O6394119 - 781 NORTHWOOD CIR, WINTER PARK, FL 32789 33 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1566
       Built: 1971   Tax: $6,931 (2025)
    Community: Winter Park Oasis
    Single Family


    Estimated Monthly Payment: $4,824 (change assumption)
    Mortgage ($4,246) + Taxes in 2025 ($578)


    Taxes:$6,931

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 639 FRIAR RD, WINTER PARK, FL 32792

    $795,0004 Days on yellowkey   MLS ID: O6395715

    For Sale O6395715 - 639 FRIAR RD, WINTER PARK, FL 32792 50 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 1950
       Built: 1967   Tax: $3,415 (2025)
    Community: Winter Park Pines
    Single Family


    Estimated Monthly Payment: $4,641 (change assumption)
    Mortgage ($4,356) + Taxes in 2025 ($285)


    Taxes:$3,415

    Elementary School: Aloma Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 731 BONGART RD, WINTER PARK, FL 32792

    $499,99994 Days on yellowkey   MLS ID: S5140952

    For Sale S5140952 - 731 BONGART RD, WINTER PARK, FL 32792 29 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 1826
       Built: 1961   Tax: $5,910 (2025)
    Community: Winter Park Estates
    Single Family


    Estimated Monthly Payment: $3,232 (change assumption)
    Mortgage ($2,740) + Taxes in 2025 ($493)


    Taxes:$5,910

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 330 ELKHORN CT, WINTER PARK, FL 32792

    $569,90071 Days on yellowkey   MLS ID: O6376757

    REDUCED by $5,099 (0.9%) on 04/03/2026

    For Sale O6376757 - 330 ELKHORN CT, WINTER PARK, FL 32792 34 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: $3,297 (change assumption)
    Mortgage ($3,123) + Taxes in 2025 ($174)


    Taxes:$2,086

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2708 LION HEART RD, WINTER PARK, FL 32792

    $629,50033 Days on yellowkey   MLS ID: O6387685

    REDUCED by $5,000 (0.8%) on 04/02/2026

    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
    Single Family


    Estimated Monthly Payment: $4,033 (change assumption)
    Mortgage ($3,449) + Taxes in 2024 ($584)


    Taxes:$7,007

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Glenridge Middle


  • 837 APPALACHEE AVE, WINTER PARK, FL 32792

    $439,00010 Days on yellowkey   MLS ID: O6393151

    1 Days Off yellowkey (back on 4/1/2026)

    For Sale O6393151 - 837 APPALACHEE AVE, WINTER PARK, FL 32792 33 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1771
       Built: 1968   Tax: $6,834 (2025)
    Community: Winter Park Forest
    Single Family


    Estimated Monthly Payment: $2,975 (change assumption)
    Mortgage ($2,405) + Taxes in 2025 ($570)


    Taxes:$6,834

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 350 CORNWALL RD, WINTER PARK, FL 32792

    $775,0008 Days on yellowkey   MLS ID: O6394524

    For Sale O6394524 - 350 CORNWALL RD, WINTER PARK, FL 32792 35 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: $4,424 (change assumption)
    Mortgage ($4,246) + Taxes in 2025 ($177)


    Taxes:$2,127

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 621 HUNTINGTON AVE, WINTER PARK, FL 32789

    $1,795,0006 Days on yellowkey   MLS ID: O6394464

    For Sale O6394464 - 621 HUNTINGTON AVE, WINTER PARK, FL 32789 38 photos

    Bed: 3   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2399
       Built: 2008   Tax: $12,854 (2025)
    Community: Winter Park Rev
    Single Family


    Estimated Monthly Payment: $10,907 (change assumption)
    Mortgage ($9,835) + Taxes in 2025 ($1,071)


    Taxes:$12,854

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 2652 ABBEY RD, WINTER PARK, FL 32792

    $450,0008 Days on yellowkey   MLS ID: O6394577

    0 Days Off yellowkey (back on 3/31/2026)

    For Sale O6394577 - 2652 ABBEY RD, WINTER PARK, FL 32792 19 photos

    Bed: 5   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1938
       Built: 1967   Tax: $7,337 (2025)
    Community: Winter Park Pines Merrie Oaks
    Single Family


    Estimated Monthly Payment: $3,077 (change assumption)
    Mortgage ($2,466) + Taxes in 2025 ($611)


    Taxes:$7,337

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 744 CORNWALL RD, WINTER PARK, FL 32792

    $715,000248 Days on yellowkey   MLS ID: O6332168

    For Sale O6332168 - 744 CORNWALL RD, WINTER PARK, FL 32792 59 photos

    Bed: 4   Bath: 2.0
    Liv Area Sq Ft: 1968
       Built: 1968   Tax: $5,359 (2024)
    Community: Winter Park Pines
    Single Family


    Estimated Monthly Payment: $4,364 (change assumption)
    Mortgage ($3,918) + Taxes in 2024 ($447)


    Taxes:$5,359

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Glenridge Middle


  • 914 ENCLAVE PL, WINTER PARK, FL 32792

    $1,895,00017 Days on yellowkey   MLS ID: O6391825

    For Sale O6391825 - 914 ENCLAVE PL, WINTER PARK, FL 32792 3 photos

    Bed: 5   Bath: 4.5
    Liv Area Sq Ft: 3617
       Built: 2026
    Monthly Fee: $372
       Tax: $10,000 (2025)
    Community: The Enclave Winter Park
    Single Family


    Estimated Monthly Payment: $11,589 (change assumption)
    Mortgage ($10,383) + Fees ($372) + Taxes in 2025 ($833)


    Taxes:$10,000

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 906 ENCLAVE PL, WINTER PARK, FL 32792

    $1,925,00017 Days on yellowkey   MLS ID: O6383092

    For Sale O6383092 - 906 ENCLAVE PL, WINTER PARK, FL 32792 5 photos

    Bed: 5   Bath: 4.5
    Liv Area Sq Ft: 3618
       Built: 2026
    Monthly Fee: $372
       Tax: $9,900 (2026)
    Community: The Enclave Winter Park
    Single Family


    Estimated Monthly Payment: $11,745 (change assumption)
    Mortgage ($10,548) + Fees ($372) + Taxes in 2026 ($825)


    Taxes:$9,900

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2026

    Middle School: Maitland Middle


  • 2919 BOWER RD, WINTER PARK, FL 32792

    $779,00018 Days on yellowkey   MLS ID: O6391025

    For Sale O6391025 - 2919 BOWER RD, WINTER PARK, FL 32792 38 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 2325
       Built: 1971   Tax: $9,857 (2025)
    Community: Winter Park Pines
    Single Family


    Estimated Monthly Payment: $5,090 (change assumption)
    Mortgage ($4,268) + Taxes in 2025 ($821)


    Taxes:$9,857

    Elementary School: None

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 418 GILBERT RD, WINTER PARK, FL 32792

    $740,00011 Days on yellowkey   MLS ID: O6385950

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

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


    Estimated Monthly Payment: $4,813 (change assumption)
    Mortgage ($4,055) + Taxes in 2025 ($758)


    Taxes:$9,094

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 457 E NEW ENGLAND AVE, WINTER PARK, FL 32789

    $3,100,000192 Days on yellowkey   MLS ID: O6345511

    4 Days Off yellowkey (back on 3/26/2026)

    For Sale O6345511 - 457 E NEW ENGLAND AVE, WINTER PARK, FL 32789 30 photos

    Bed: 5   Bath: 4.5
    Liv Area Sq Ft: 3896
       Built: 1920
    Community: Winter Park
    Single Family


    Estimated Monthly Payment: $16,986 (change assumption)
    Mortgage ($16,986)


    Taxes:

    Elementary School: None

    High School: None

    Tax Year:

    Middle School: None


  • 541 W CANTON AVE, WINTER PARK, FL 32789

    $2,800,00016 Days on yellowkey   MLS ID: O6389829

    For Sale O6389829 - 541 W CANTON AVE, WINTER PARK, FL 32789 51 photos

    Bed: 4   Bath: 3.5
    Liv Area Sq Ft: 3553
       Built: 2024
    Community: Winter Park
    Single Family


    Estimated Monthly Payment: $15,342 (change assumption)
    Mortgage ($15,342)


    Taxes:

    Elementary School: None

    High School: None

    Tax Year:

    Middle School: None


  • WINTER PARK, FL 32792

    $440,00025 Days on yellowkey   MLS ID: S5145631

    For Sale S5145631 - WINTER PARK, FL 32792 11 photos

    Bed: 4   Bath: 2.0
    Liv Area Sq Ft: 1296
       Built: 1958
    Community: Winter Park Estates
    Single Family


    Estimated Monthly Payment: $2,411 (change assumption)
    Mortgage ($2,411)


    Taxes:

    Elementary School: None

    High School: None

    Tax Year:

    Middle School: None


  • 2814 SHERIFF WAY, WINTER PARK, FL 32792

    $574,900   MLS ID: O6383098

    For Sale O6383098 - 2814 SHERIFF WAY, WINTER PARK, FL 32792 55 photos

    Bed: 4   Bath: 2.0
    Liv Area Sq Ft: 1948
       Built: 1965
    Community: Winter Park Pines
    Single Family


    Estimated Monthly Payment: $3,150 (change assumption)
    Mortgage ($3,150)


    Taxes:

    Elementary School: None

    High School: None

    Tax Year:

    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.