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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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  • 1540 MILLER AVE, WINTER PARK, FL 32789

    $1,399,90094 Days on yellowkey   MLS ID: O6398421

    For Sale O6398421 - 1540 MILLER AVE, WINTER PARK, FL 32789 55 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2984
       Built: 2026   Tax: $3,573 (2025)
    Community: Lawndale
    Spa: No

    Single Family


    Estimated Monthly Payment: $7,968 (change assumption)
    Mortgage ($7,670) + Taxes in 2025 ($298)


    Taxes:$3,573

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park Middle


  • 1420 MAGNOLIA AVE, WINTER PARK, FL 32789

    $1,695,00071 Days on yellowkey   MLS ID: O6404564

    REDUCED by $55,000 (3.1%) on 07/14/2026

    For Sale O6404564 - 1420 MAGNOLIA AVE, WINTER PARK, FL 32789 67 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3174
       Built: 2015   Tax: $21,173 (2025)
    Community: Lake Knowles Terrace Add 02
    Spa: No

    Single Family


    Estimated Monthly Payment: $11,052 (change assumption)
    Mortgage ($9,287) + Taxes in 2025 ($1,764)


    Taxes:$21,173

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 8433 COMMANDER CV, WINTER PARK, FL 32792

    $440,00033 Days on yellowkey   MLS ID: O6416635

    REDUCED by $5,000 (1.1%) on 07/15/2026

    For Sale O6416635 - 8433 COMMANDER CV, WINTER PARK, FL 32792 59 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1903
       Built: 1986
    Monthly Fee: $76
       Tax: $3,556 (2025)
    Community: Trinity Bay
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,783 (change assumption)
    Mortgage ($2,411) + Fees ($76) + Taxes in 2025 ($296)


    Taxes:$3,556

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 1622 ARBOR PARK DR, WINTER PARK, FL 32789

    $695,00015 Days on yellowkey   MLS ID: O6420928

    0 Days Off yellowkey (back on 7/15/2026)

    For Sale O6420928 - 1622 ARBOR PARK DR, WINTER PARK, FL 32789 10 photos

    Bed: 3   Bath: 1.5
    Liv Area Sq Ft: 1351
       Built: 1957   Tax: $6,562 (2025)
    Community: Conwill Estates
    Single Family


    Estimated Monthly Payment: $4,355 (change assumption)
    Mortgage ($3,808) + Taxes in 2025 ($547)


    Taxes:$6,562

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 2052 LEANNE CT, WINTER PARK, FL 32792

    $440,000163 Days on yellowkey   MLS ID: O6379323

    0 Days Off yellowkey (back on 7/13/2026)

    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


  • 5225 ALBERT DR, WINTER PARK, FL 32792

    $435,0003 Days on yellowkey   MLS ID: O6424623

    0 Days Off yellowkey (back on 7/15/2026)

    For Sale O6424623 - 5225 ALBERT DR, WINTER PARK, FL 32792 51 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1716
       Built: 1979   Tax: $4,476 (2025)
    Community: Wrenwood Unit 3 3Rd Add
    Single Family


    Estimated Monthly Payment: $2,757 (change assumption)
    Mortgage ($2,384) + Taxes in 2025 ($373)


    Taxes:$4,476

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 3641 HAWTHORNE LN, WINTER PARK, FL 32792

    $475,00022 Days on yellowkey   MLS ID: TB8519391

    For Sale TB8519391 - 3641 HAWTHORNE LN, WINTER PARK, FL 32792 43 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1622
       Built: 1979   Tax: $4,051 (2025)
    Community: Garden Lake Estates Unit 1
    Single Family


    Estimated Monthly Payment: $2,940 (change assumption)
    Mortgage ($2,603) + Taxes in 2025 ($338)


    Taxes:$4,051

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1581 MAGNOLIA AVE, WINTER PARK, FL 32789

    $1,465,00079 Days on yellowkey   MLS ID: O6396118

    REDUCED by $30,000 (2.0%) on 07/15/2026

    For Sale O6396118 - 1581 MAGNOLIA AVE, WINTER PARK, FL 32789 75 photos

    Bed: 4   Bath: 4.0
    Liv Area Sq Ft: 2756
       Built: 2005   Tax: $14,857 (2025)
    Community: Lake Knowles Terrace Add 02
    Spa: No

    Single Family


    Estimated Monthly Payment: $9,265 (change assumption)
    Mortgage ($8,027) + Taxes in 2025 ($1,238)


    Taxes:$14,857

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 1741 MIZELL AVE, WINTER PARK, FL 32789

    $1,050,00055 Days on yellowkey   MLS ID: O6410059

    REDUCED by $45,000 (4.1%) on 06/26/2026

    For Sale O6410059 - 1741 MIZELL AVE, WINTER PARK, FL 32789 41 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2015
       Built: 1982   Tax: $11,682 (2025)
    Community: Lake Monte Sub
    Single Family


    Estimated Monthly Payment: $6,727 (change assumption)
    Mortgage ($5,753) + Taxes in 2025 ($974)


    Taxes:$11,682

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 4965 ORANGE AVE, WINTER PARK, FL 32792

    $379,9007 Days on yellowkey   MLS ID: O6423739

    For Sale O6423739 - 4965 ORANGE AVE, WINTER PARK, FL 32792 29 photos

    Bed: 4   Bath: 2.0
    Liv Area Sq Ft: 1444
       Built: 1959   Tax: $2,909 (2025)
    Community: Suburban Homes First Add
    Single Family


    Estimated Monthly Payment: $2,324 (change assumption)
    Mortgage ($2,082) + Taxes in 2025 ($242)


    Taxes:$2,909

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 3463 ARNEL DR, WINTER PARK, FL 32792

    $409,900121 Days on yellowkey   MLS ID: O6390301

    REDUCED by $5,000 (1.2%) on 07/15/2026

    For Sale O6390301 - 3463 ARNEL DR, WINTER PARK, FL 32792 35 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1770
       Built: 1967   Tax: $4,648 (2024)
    Community: Eastbrook Sub Unit 11
    Single Family


    Estimated Monthly Payment: $2,633 (change assumption)
    Mortgage ($2,246) + Taxes in 2024 ($387)


    Taxes:$4,648

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 922 N PENNSYLVANIA AVE, WINTER PARK, FL 32789

    $1,995,0002 Days on yellowkey   MLS ID: O6424685

    For Sale O6424685 - 922 N PENNSYLVANIA AVE, WINTER PARK, FL 32789 30 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 3440
       Built: 2001   Tax: $10,684 (2025)
    Community: Tantum Add
    Single Family


    Estimated Monthly Payment: $11,822 (change assumption)
    Mortgage ($10,931) + Taxes in 2025 ($890)


    Taxes:$10,684

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 1760 PERUVIAN LN, WINTER PARK, FL 32792

    $324,000131 Days on yellowkey   MLS ID: A4685217

    5 Days Off yellowkey (back on 7/15/2026)

    REDUCED by $15,000 (4.4%) on 06/09/2026

    For Sale A4685217 - 1760 PERUVIAN LN, WINTER PARK, FL 32792 21 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1160
       Built: 1960   Tax: $3,470 (2025)
    Community: Eastbrook Sub Unit 06
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,064 (change assumption)
    Mortgage ($1,775) + Taxes in 2025 ($289)


    Taxes:$3,470

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2361 ROXBURY RD, WINTER PARK, FL 32789

    $599,00016 Days on yellowkey   MLS ID: O6418164

    For Sale O6418164 - 2361 ROXBURY RD, WINTER PARK, FL 32789 34 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1723
       Built: 1951   Tax: $2,184 (2025)
    Community: Glencoe Subdivision
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,464 (change assumption)
    Mortgage ($3,282) + Taxes in 2025 ($182)


    Taxes:$2,184

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park Middle


  • 501 LAKEVIEW AVE, WINTER PARK, FL 32789

    $1,390,000363 Days on yellowkey   MLS ID: O6325192

    For Sale O6325192 - 501 LAKEVIEW AVE, WINTER PARK, FL 32789 59 photos

    Bed: 4   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3253
       Built: 2026   Tax: $2,820 (2024)
    Community: Killarney Estates
    Single Family


    Estimated Monthly Payment: $7,851 (change assumption)
    Mortgage ($7,616) + Taxes in 2024 ($235)


    Taxes:$2,820

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2024

    Middle School: College Park Middle


  • 275 N RANGER BLVD, WINTER PARK, FL 32792

    $775,00036 Days on yellowkey   MLS ID: O6415904

    For Sale O6415904 - 275 N RANGER BLVD, WINTER PARK, FL 32792 32 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 1950
       Built: 1965   Tax: $6,817 (2025)
    Community: Winter Park Pines
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,815 (change assumption)
    Mortgage ($4,246) + Taxes in 2025 ($568)


    Taxes:$6,817

    Elementary School: Aloma Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 840 W CANTON AVE, WINTER PARK, FL 32789

    $675,00045 Days on yellowkey   MLS ID: O6412754

    For Sale O6412754 - 840 W CANTON AVE, WINTER PARK, FL 32789 63 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1370
       Built: 1952   Tax: $5,722 (2025)
    Community: N/A
    Single Family


    Estimated Monthly Payment: $4,175 (change assumption)
    Mortgage ($3,699) + Taxes in 2025 ($477)


    Taxes:$5,722

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 1946 STRATHAVEN RD, WINTER PARK, FL 32792

    $625,00050 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


  • 723 SYMONDS AVE, WINTER PARK, FL 32789

    $1,800,00049 Days on yellowkey   MLS ID: O6406823

    For Sale O6406823 - 723 SYMONDS AVE, WINTER PARK, FL 32789 50 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 3065
       Built: 2023   Tax: $15,884 (2025)
    Community: Horton Aaron
    Single Family


    Estimated Monthly Payment: $11,186 (change assumption)
    Mortgage ($9,863) + Taxes in 2025 ($1,324)


    Taxes:$15,884

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 3135 HEARTLEAF PL, WINTER PARK, FL 32792

    $649,00055 Days on yellowkey   MLS ID: O6410276

    5 Days Off yellowkey (back on 6/28/2026)

    REDUCED by $10,900 (1.7%) on 06/17/2026

    For Sale O6410276 - 3135 HEARTLEAF PL, WINTER PARK, FL 32792 36 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2749
       Built: 1994
    Monthly Fee: $20
       Tax: $2,825 (2025)
    Community: Lost Creek
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,812 (change assumption)
    Mortgage ($3,556) + Fees ($20) + Taxes in 2025 ($235)


    Taxes:$2,825

    Elementary School: Red Bug Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla 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.