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Winter Park Single Family Homes For Sale - 277 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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  • 1473 BERKSHIRE AVE, WINTER PARK, FL 32789

    $1,499,000316 Days on yellowkey   MLS ID: O6320741

    For Sale O6320741 - 1473 BERKSHIRE AVE, WINTER PARK, FL 32789 53 photos

    Bed: 5   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 2895
       Built: 2025   Tax: $5,730 (2024)
    Community: Orwin Manor Westminster Sec
    Single Family


    Estimated Monthly Payment: $8,691 (change assumption)
    Mortgage ($8,213) + Taxes in 2024 ($478)


    Taxes:$5,730

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2024

    Middle School: College Park Middle


  • 688 BRECHIN DR, WINTER PARK, FL 32792

    $724,9004 Days on yellowkey   MLS ID: O6403080

    For Sale O6403080 - 688 BRECHIN DR, WINTER PARK, FL 32792 31 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1599
       Built: 1961   Tax: $6,760 (2025)
    Community: Kenilworth Shores Sec 04
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,535 (change assumption)
    Mortgage ($3,972) + Taxes in 2025 ($563)


    Taxes:$6,760

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 1981 BLUE RIDGE RD, WINTER PARK, FL 32789

    $1,150,0003 Days on yellowkey   MLS ID: O6402961

    For Sale O6402961 - 1981 BLUE RIDGE RD, WINTER PARK, FL 32789 52 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2750
       Built: 1963   Tax: $11,270 (2025)
    Community: Timberlane Shores
    Single Family


    Estimated Monthly Payment: $7,240 (change assumption)
    Mortgage ($6,301) + Taxes in 2025 ($939)


    Taxes:$11,270

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: None


  • 2648 GALLIANO CIR, WINTER PARK, FL 32792

    $355,00069 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


  • 1018 BRADFORD DR, WINTER PARK, FL 32792

    $549,0004 Days on yellowkey   MLS ID: O6403259

    For Sale O6403259 - 1018 BRADFORD DR, WINTER PARK, FL 32792 65 photos

    Bed: 5   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2513
       Built: 1974   Tax: $2,229 (2024)
    Community: Howell Estates Rep
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,194 (change assumption)
    Mortgage ($3,008) + Taxes in 2024 ($186)


    Taxes:$2,229

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 3627 SEAGRAPE DR, WINTER PARK, FL 32792

    $339,0001 Day on yellowkey   MLS ID: O6403218

    For Sale O6403218 - 3627 SEAGRAPE DR, WINTER PARK, FL 32792 22 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1233
       Built: 1965   Tax: $3,401 (2024)
    Community: Eastbrook Sub Unit 03
    Single Family


    Estimated Monthly Payment: $2,141 (change assumption)
    Mortgage ($1,857) + Taxes in 2024 ($283)


    Taxes:$3,401

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 418 GILBERT RD, WINTER PARK, FL 32792

    $729,00039 Days on yellowkey   MLS ID: O6385950

    REDUCED by $11,000 (1.5%) on 05/01/2026

    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: $4,752 (change assumption)
    Mortgage ($3,994) + Taxes in 2025 ($758)


    Taxes:$9,094

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 2922 REEF KNOT PL, WINTER PARK, FL 32792

    $1,149,000330 Days on yellowkey   MLS ID: O6316445

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

    For Sale O6316445 - 2922 REEF KNOT PL, WINTER PARK, FL 32792 49 photos

    Bed: 4   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 3153
       Built: 2019
    Monthly Fee: $186
       Tax: $10,521 (2024)
    Community: Lake Florence Preserve
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $7,358 (change assumption)
    Mortgage ($6,296) + Fees ($186) + Taxes in 2024 ($877)


    Taxes:$10,521

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 2627 AMBERGATE RD, WINTER PARK, FL 32792

    $510,0001147 Days on yellowkey   MLS ID: O6093816

    For Sale O6093816 - 2627 AMBERGATE RD, WINTER PARK, FL 32792 19 photos

    Bed: 4   Bath: 3.0   Gar: 1
    Liv Area Sq Ft: 1805
       Built: 1959   Tax: $4,750 (2022)
    Community: Winter Park Estates
    Single Family


    Estimated Monthly Payment: $3,190 (change assumption)
    Mortgage ($2,794) + Taxes in 2022 ($396)


    Taxes:$4,750

    Elementary School: None

    High School: None

    Tax Year: 2022

    Middle School: None


  • 1351 MAGNOLIA AVE, WINTER PARK, FL 32789

    $3,100,0003 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


  • 2237 WOODCREST DR, WINTER PARK, FL 32792

    $490,0003 Days on yellowkey   MLS ID: O6404115

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

    For Sale O6404115 - 2237 WOODCREST DR, WINTER PARK, FL 32792 1 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1492
       Built: 1959   Tax: $1,919 (2025)
    Community: Kenilworth Estates 1St Add
    Single Family


    Estimated Monthly Payment: $2,845 (change assumption)
    Mortgage ($2,685) + Taxes in 2025 ($160)


    Taxes:$1,919

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 4571 KAWILLA CREST PL, WINTER PARK, FL 32792

    $899,9993 Days on yellowkey   MLS ID: O6400672

    For Sale O6400672 - 4571 KAWILLA CREST PL, WINTER PARK, FL 32792 35 photos

    Bed: 6   Bath: 5.0   Gar: 2
    Liv Area Sq Ft: 3715
       Built: 1989
    Monthly Fee: $40
       Tax: $9,671 (2024)
    Community: Kawilla Crest
    Single Family


    Estimated Monthly Payment: $5,777 (change assumption)
    Mortgage ($4,931) + Fees ($40) + Taxes in 2024 ($806)


    Taxes:$9,671

    Elementary School: Red Bug Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 1836 GRINNELL TER, WINTER PARK, FL 32789

    $1,050,00087 Days on yellowkey   MLS ID: O6380457

    For Sale O6380457 - 1836 GRINNELL TER, WINTER PARK, FL 32789 24 photos

    Bed: 3   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1907
       Built: 1995   Tax: $11,979 (2025)
    Community: Lake Virginia
    Single Family


    Estimated Monthly Payment: $6,752 (change assumption)
    Mortgage ($5,753) + Taxes in 2025 ($998)


    Taxes:$11,979

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 3440 ALLSTON LN, WINTER PARK, FL 32792

    $420,0008 Days on yellowkey   MLS ID: O6401731

    For Sale O6401731 - 3440 ALLSTON LN, WINTER PARK, FL 32792 37 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: $2,480 (change assumption)
    Mortgage ($2,301) + 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


  • 150 DANA WAY, WINTER PARK, FL 32789

    $3,799,00038 Days on yellowkey   MLS ID: O6394012

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

    For Sale O6394012 - 150 DANA WAY, WINTER PARK, FL 32789 81 photos

    Bed: 5   Bath: 5.0   Gar: 2
    Liv Area Sq Ft: 4451
       Built: 2026   Tax: $14,010 (2025)
    Community: Charmont
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $21,983 (change assumption)
    Mortgage ($20,816) + Taxes in 2025 ($1,168)


    Taxes:$14,010

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 2299 VIA TUSCANY, WINTER PARK, FL 32789

    $2,200,000181 Days on yellowkey   MLS ID: O6355858

    For Sale O6355858 - 2299 VIA TUSCANY, WINTER PARK, FL 32789 60 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3986
       Built: 1953   Tax: $13,185 (2025)
    Community: Maitland Shores
    Single Family


    Estimated Monthly Payment: $13,153 (change assumption)
    Mortgage ($12,054) + Taxes in 2025 ($1,099)


    Taxes:$13,185

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • WINTER PARK, FL 32792

    $430,00053 Days on yellowkey   MLS ID: S5145631

    REDUCED by $10,000 (2.3%) on 04/15/2026

    For Sale S5145631 - WINTER PARK, FL 32792 11 photos

    Bed: 4   Bath: 2.0
    Liv Area Sq Ft: 1296
       Built: 1958   Tax: $4,968 (2025)
    Community: Winter Park Estates
    Single Family


    Estimated Monthly Payment: $2,770 (change assumption)
    Mortgage ($2,356) + Taxes in 2025 ($414)


    Taxes:$4,968

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1354 INDIANA AVE, WINTER PARK, FL 32789

    $589,90060 Days on yellowkey   MLS ID: O6387500

    For Sale O6387500 - 1354 INDIANA AVE, WINTER PARK, FL 32789 39 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1269
       Built: 1947   Tax: $5,352 (2024)
    Community: Metzingers Add
    Single Family


    Estimated Monthly Payment: $3,678 (change assumption)
    Mortgage ($3,232) + Taxes in 2024 ($446)


    Taxes:$5,352

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 950 HANOVER AVE, WINTER PARK, FL 32789

    $470,00023 Days on yellowkey   MLS ID: O6398273

    For Sale O6398273 - 950 HANOVER AVE, WINTER PARK, FL 32789 28 photos

    Bed: 3   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1606
       Built: 1956   Tax: $3,525 (2025)
    Community: Albert Lee Ridge 1St Add
    Single Family


    Estimated Monthly Payment: $2,869 (change assumption)
    Mortgage ($2,575) + Taxes in 2025 ($294)


    Taxes:$3,525

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 7761 FOX KNOLL PL, WINTER PARK, FL 32792

    $425,00011 Days on yellowkey   MLS ID: O6401159

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

    For Sale O6401159 - 7761 FOX KNOLL PL, WINTER PARK, FL 32792 34 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1485
       Built: 1989
    Monthly Fee: $20
       Tax: $4,308 (2024)
    Community: Bridgewater
    Single Family


    Estimated Monthly Payment: $2,708 (change assumption)
    Mortgage ($2,329) + Fees ($20) + Taxes in 2024 ($359)


    Taxes:$4,308

    Elementary School: None

    High School: None

    Tax Year: 2024

    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.