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Winter Park Single Family Homes For Sale - 303 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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  • 770 W WEBSTER AVE, WINTER PARK, FL 32789

    $725,000376 Days on yellowkey   MLS ID: O6323574

    1 Days Off yellowkey (back on 4/11/2026)

    For Sale O6323574 - 770 W WEBSTER AVE, WINTER PARK, FL 32789 34 photos

    Bed: 4   Bath: 2.0
    Liv Area Sq Ft: 1008
       Built: 1967   Tax: $4,856 (2024)
    Community: Capens Add
    Single Family


    Estimated Monthly Payment: $4,377 (change assumption)
    Mortgage ($3,973) + Taxes in 2024 ($405)


    Taxes:$4,856

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Maitland Middle


  • 1180 VIA LUGANO, WINTER PARK, FL 32789

    $4,900,00015 Days on yellowkey   MLS ID: O6413198

    For Sale O6413198 - 1180 VIA LUGANO, WINTER PARK, FL 32789 67 photos

    Bed: 5   Bath: 5.5   Gar: 3
    Liv Area Sq Ft: 4961
       Built: 2006   Tax: $43,400 (2025)
    Community: Woodmere Terrace Rep
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $30,465 (change assumption)
    Mortgage ($26,849) + Taxes in 2025 ($3,617)


    Taxes:$43,400

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 1908 CYRIL CT, WINTER PARK, FL 32792

    $639,0005 Days on yellowkey   MLS ID: O6422937

    For Sale O6422937 - 1908 CYRIL CT, WINTER PARK, FL 32792 29 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2471
       Built: 1990
    Monthly Fee: $41
       Tax: $7,674 (2025)
    Community: Kawilla Crest
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,182 (change assumption)
    Mortgage ($3,501) + Fees ($41) + Taxes in 2025 ($640)


    Taxes:$7,674

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2010 SUMMERFIELD RD, WINTER PARK, FL 32792

    $594,5004 Days on yellowkey   MLS ID: O6420140

    For Sale O6420140 - 2010 SUMMERFIELD RD, WINTER PARK, FL 32792 40 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1889
       Built: 1957   Tax: $7,917 (2025)
    Community: Kenilworth Shores Sec 07
    Single Family


    Estimated Monthly Payment: $3,917 (change assumption)
    Mortgage ($3,257) + Taxes in 2025 ($660)


    Taxes:$7,917

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 2189 SUSSEX RD, WINTER PARK, FL 32792

    $375,0005 Days on yellowkey   MLS ID: O6423782

    FORECLOSURE O6423782 - 2189 SUSSEX RD, WINTER PARK, FL 32792 29 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1776
       Built: 1968
    Monthly Fee: $2
       Tax: $4,646 (2025)
    Community: Winter Woods Unit 01
    Single Family


    Estimated Monthly Payment: $2,444 (change assumption)
    Mortgage ($2,055) + Fees ($2) + Taxes in 2025 ($387)


    Taxes:$4,646

    Elementary School: English Estates Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 1920 HEATHWOOD DR, WINTER PARK, FL 32792

    $370,000111 Days on yellowkey   MLS ID: O6393303

    4 Days Off yellowkey (back on 7/10/2026)

    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


  • 1946 STRATHAVEN RD, WINTER PARK, FL 32792

    $625,00048 Days on yellowkey   MLS ID: O6411329

    REDUCED by $25,000 (3.8%) on 07/10/2026

    For Sale O6411329 - 1946 STRATHAVEN RD, WINTER PARK, FL 32792 37 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2102
       Built: 1960   Tax: $8,540 (2025)
    Community: Kenilworth Shores Sec 07
    Single Family


    Estimated Monthly Payment: $4,136 (change assumption)
    Mortgage ($3,425) + Taxes in 2025 ($712)


    Taxes:$8,540

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 1354 INDIANA AVE, WINTER PARK, FL 32789

    $574,900131 Days on yellowkey   MLS ID: O6387500

    REDUCED by $15,000 (2.5%) on 07/10/2026

    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: $3,596 (change assumption)
    Mortgage ($3,150) + Taxes in 2024 ($446)


    Taxes:$5,352

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 3621 HAWTHORNE LN, WINTER PARK, FL 32792

    $415,0008 Days on yellowkey   MLS ID: S5153086

    For Sale S5153086 - 3621 HAWTHORNE LN, WINTER PARK, FL 32792 34 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1525
       Built: 1979   Tax: $1,108 (2025)
    Community: Garden Lake Estates Unit 1
    Single Family


    Estimated Monthly Payment: $2,366 (change assumption)
    Mortgage ($2,274) + Taxes in 2025 ($92)


    Taxes:$1,108

    Elementary School: Evans Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 1610 GLADIOLAS DR, WINTER PARK, FL 32792

    $430,00017 Days on yellowkey   MLS ID: O6420292

    For Sale O6420292 - 1610 GLADIOLAS DR, WINTER PARK, FL 32792 42 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1808
       Built: 1979   Tax: $1,442 (2025)
    Community: Garden Lake Estates Unit 1
    Single Family


    Estimated Monthly Payment: $2,476 (change assumption)
    Mortgage ($2,356) + Taxes in 2025 ($120)


    Taxes:$1,442

    Elementary School: Red Bug Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 2700 CADY WAY, WINTER PARK, FL 32792

    $649,000287 Days on yellowkey   MLS ID: O6347690

    4 Days Off yellowkey (back on 7/10/2026)

    For Sale O6347690 - 2700 CADY WAY, WINTER PARK, FL 32792 49 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1876
       Built: 1965   Tax: $8,335 (2024)
    Community: Winter Park Pines Unit 4
    Single Family


    Estimated Monthly Payment: $4,251 (change assumption)
    Mortgage ($3,556) + Taxes in 2024 ($695)


    Taxes:$8,335

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Glenridge Middle


  • 1120 WISCONSIN AVE, WINTER PARK, FL 32789

    $1,095,00049 Days on yellowkey   MLS ID: O6406800

    0 Days Off yellowkey (back on 7/10/2026)

    For Sale O6406800 - 1120 WISCONSIN AVE, WINTER PARK, FL 32789 37 photos

    Bed: 3   Bath: 3.5   Gar: 1
    Liv Area Sq Ft: 2213
       Built: 2021   Tax: $10,451 (2025)
    Community: Henkel Add
    Single Family


    Estimated Monthly Payment: $6,871 (change assumption)
    Mortgage ($6,000) + Taxes in 2025 ($871)


    Taxes:$10,451

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park Middle


  • 981 ARAGON AVE, WINTER PARK, FL 32789

    $535,00018 Days on yellowkey   MLS ID: O6420093

    For Sale O6420093 - 981 ARAGON AVE, WINTER PARK, FL 32789 7 photos

    Bed: 2   Bath: 1.0   Gar: 1
    Liv Area Sq Ft: 857
       Built: 1956   Tax: $6,248 (2025)
    Community: Seville Park
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $3,452 (change assumption)
    Mortgage ($2,931) + Taxes in 2025 ($521)


    Taxes:$6,248

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 1830 EDWIN BLVD, WINTER PARK, FL 32789

    $625,00089 Days on yellowkey   MLS ID: O6400055

    0 Days Off yellowkey (back on 7/9/2026)

    REDUCED by $14,900 (2.3%) on 06/15/2026

    For Sale O6400055 - 1830 EDWIN BLVD, WINTER PARK, FL 32789 48 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1287
       Built: 1957   Tax: $3,955 (2025)
    Community: Campo Bello
    Single Family


    Estimated Monthly Payment: $3,754 (change assumption)
    Mortgage ($3,425) + Taxes in 2025 ($330)


    Taxes:$3,955

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 1662 TREMONT LN, WINTER PARK, FL 32792

    $384,90039 Days on yellowkey   MLS ID: O6414180

    REDUCED by $5,000 (1.3%) on 06/19/2026

    For Sale O6414180 - 1662 TREMONT LN, WINTER PARK, FL 32792 56 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1534
       Built: 1986
    Monthly Fee: $49
       Tax: $4,339 (2025)
    Community: Country Lane
    Single Family


    Estimated Monthly Payment: $2,520 (change assumption)
    Mortgage ($2,109) + Fees ($49) + Taxes in 2025 ($362)


    Taxes:$4,339

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 609 S PHELPS AVE, WINTER PARK, FL 32789

    $2,829,000120 Days on yellowkey   MLS ID: O6388598

    For Sale O6388598 - 609 S PHELPS AVE, WINTER PARK, FL 32789 20 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


  • 2041 JEWELL AVE, WINTER PARK, FL 32789

    $470,00015 Days on yellowkey   MLS ID: O6420660

    For Sale O6420660 - 2041 JEWELL AVE, WINTER PARK, FL 32789 30 photos

    Bed: 3   Bath: 1.0
    Liv Area Sq Ft: 1508
       Built: 1947   Tax: $999 (2025)
    Community: Pines
    Single Family


    Estimated Monthly Payment: $2,658 (change assumption)
    Mortgage ($2,575) + Taxes in 2025 ($83)


    Taxes:$999

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 440 CAMBRIDGE BLVD, WINTER PARK, FL 32789

    $380,00068 Days on yellowkey   MLS ID: O6403694

    For Sale O6403694 - 440 CAMBRIDGE BLVD, WINTER PARK, FL 32789 31 photos

    Bed: 2   Bath: 1.0   Gar: 1
    Liv Area Sq Ft: 988
       Built: 1950   Tax: $4,386 (2025)
    Community: Glencoe Sub
    Single Family


    Estimated Monthly Payment: $2,448 (change assumption)
    Mortgage ($2,082) + Taxes in 2025 ($366)


    Taxes:$4,386

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park Middle


  • 1448 LAKE FLORENCE WAY, WINTER PARK, FL 32792

    $1,149,90048 Days on yellowkey   MLS ID: O6411164

    REDUCED by $49,100 (4.1%) on 06/17/2026

    For Sale O6411164 - 1448 LAKE FLORENCE WAY, WINTER PARK, FL 32792 49 photos

    Bed: 5   Bath: 4.5   Gar: 3
    Liv Area Sq Ft: 3652
       Built: 2018
    Monthly Fee: $186
       Tax: $7,277 (2025)
    Community: Lake Florence Preserve
    Spa: No

    Single Family


    Estimated Monthly Payment: $7,093 (change assumption)
    Mortgage ($6,301) + Fees ($186) + Taxes in 2025 ($606)


    Taxes:$7,277

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 2889 ROUEN AVE, WINTER PARK, FL 32789

    $365,00084 Days on yellowkey   MLS ID: L4961275

    0 Days Off yellowkey (back on 6/24/2026)

    REDUCED by $10,000 (2.7%) on 06/23/2026

    For Sale L4961275 - 2889 ROUEN AVE, WINTER PARK, FL 32789 10 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1144
       Built: 1959   Tax: $5,061 (2025)
    Community: Winter Park Manor
    Single Family


    Estimated Monthly Payment: $2,422 (change assumption)
    Mortgage ($2,000) + Taxes in 2025 ($422)


    Taxes:$5,061

    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.