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Winter Park Single Family Homes For Sale - 307 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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  • 1903 N PARK AVE, WINTER PARK, FL 32789

    $1,695,000148 Days on yellowkey   MLS ID: O6375766

    REDUCED by $100,000 (5.6%) on 05/14/2026

    For Sale O6375766 - 1903 N PARK AVE, WINTER PARK, FL 32789 42 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 2807
       Built: 2020   Tax: $17,232 (2025)
    Community: Twin Acres
    Single Family


    Estimated Monthly Payment: $10,723 (change assumption)
    Mortgage ($9,287) + Taxes in 2025 ($1,436)


    Taxes:$17,232

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 814 DENSMORE DR, WINTER PARK, FL 32792

    $425,00063 Days on yellowkey   MLS ID: O6399773

    2 Days Off yellowkey (back on 5/13/2026)

    For Sale O6399773 - 814 DENSMORE DR, WINTER PARK, FL 32792 24 photos

    Bed: 4   Bath: 2.0
    Liv Area Sq Ft: 1610
       Built: 1960   Tax: $5,402 (2025)
    Community: Winter Park Estates
    Single Family


    Estimated Monthly Payment: $2,779 (change assumption)
    Mortgage ($2,329) + Taxes in 2025 ($450)


    Taxes:$5,402

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 721 DUNBAR ST, WINTER PARK, FL 32789

    $399,99941 Days on yellowkey   MLS ID: O6405338

    1 Days Off yellowkey (back on 5/13/2026)

    For Sale O6405338 - 721 DUNBAR ST, WINTER PARK, FL 32789 36 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1018
       Built: 1950   Tax: $5,267 (2025)
    Community: Carver Town
    Single Family


    Estimated Monthly Payment: $2,631 (change assumption)
    Mortgage ($2,192) + Taxes in 2025 ($439)


    Taxes:$5,267

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 40 PALMER AVE, WINTER PARK, FL 32789

    $6,950,000129 Days on yellowkey   MLS ID: O6380444

    For Sale O6380444 - 40 PALMER AVE, WINTER PARK, FL 32789 17 photos

    Bed: 5   Bath: 5.5   Gar: 4
    Liv Area Sq Ft: 5905
       Built: 2026   Tax: $12,774 (2024)
    Community: Robert Dhu Macdonald Park
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $39,146 (change assumption)
    Mortgage ($38,081) + Taxes in 2024 ($1,065)


    Taxes:$12,774

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Maitland Middle


  • 541 W CANTON AVE, WINTER PARK, FL 32789

    $2,800,00089 Days on yellowkey   MLS ID: O6389829

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

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3553
       Built: 2024   Tax: $4,692 (2024)
    Community: Winter Park
    Single Family


    Estimated Monthly Payment: $15,733 (change assumption)
    Mortgage ($15,342) + Taxes in 2024 ($391)


    Taxes:$4,692

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Maitland Middle


  • 141 W LAKE SUE AVE, WINTER PARK, FL 32789

    $4,200,00041 Days on yellowkey   MLS ID: O6406437

    For Sale O6406437 - 141 W LAKE SUE AVE, WINTER PARK, FL 32789 5 photos

    Bed: 5   Bath: 6.0   Gar: 4
    Liv Area Sq Ft: 5500
       Built: 2027   Tax: $11,049 (2025)
    Community: Virginia Heights
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $23,934 (change assumption)
    Mortgage ($23,013) + Taxes in 2025 ($921)


    Taxes:$11,049

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1723 CHESTNUT AVE, WINTER PARK, FL 32789

    $1,125,00042 Days on yellowkey   MLS ID: O6402563

    0 Days Off yellowkey (back on 5/8/2026)

    For Sale O6402563 - 1723 CHESTNUT AVE, WINTER PARK, FL 32789 40 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2608
       Built: 1962   Tax: $4,880 (2025)
    Community: Conwill Estates
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $6,571 (change assumption)
    Mortgage ($6,164) + Taxes in 2025 ($407)


    Taxes:$4,880

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 1660 PALMER AVE, WINTER PARK, FL 32789

    $4,950,000483 Days on yellowkey   MLS ID: O6282425

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

    For Sale O6282425 - 1660 PALMER AVE, WINTER PARK, FL 32789 53 photos

    Bed: 5   Bath: 6.5   Gar: 3
    Liv Area Sq Ft: 6406
       Built: 2024   Tax: $6,144 (2024)
    Community: Comstock Park
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $27,635 (change assumption)
    Mortgage ($27,123) + Taxes in 2024 ($512)


    Taxes:$6,144

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Maitland Middle


  • 1636 ELIZABETHS WALK, WINTER PARK, FL 32789

    $2,195,00076 Days on yellowkey   MLS ID: O6395638

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

    For Sale O6395638 - 1636 ELIZABETHS WALK, WINTER PARK, FL 32789 31 photos

    Bed: 4   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3412
       Built: 2016
    Monthly Fee: $268
       Tax: $25,133 (2025)
    Community: Windsong Elizabeths Walk 43/81
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $14,389 (change assumption)
    Mortgage ($12,027) + Fees ($268) + Taxes in 2025 ($2,094)


    Taxes:$25,133

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 1630 LASBURY AVE, WINTER PARK, FL 32789

    $2,750,00047 Days on yellowkey   MLS ID: O6404300

    For Sale O6404300 - 1630 LASBURY AVE, WINTER PARK, FL 32789 37 photos

    Bed: 5   Bath: 4.0   Gar: 3
    Liv Area Sq Ft: 4917
       Built: 2003   Tax: $14,204 (2025)
    Community: Comstock Park
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $16,252 (change assumption)
    Mortgage ($15,068) + Taxes in 2025 ($1,184)


    Taxes:$14,204

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 770 W WEBSTER AVE, WINTER PARK, FL 32789

    $725,000350 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


  • 517 ROUGHBEARD RD, WINTER PARK, FL 32792

    $565,00065 Days on yellowkey   MLS ID: O6399029

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

    For Sale O6399029 - 517 ROUGHBEARD RD, WINTER PARK, FL 32792 53 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1873
       Built: 1971   Tax: $4,323 (2025)
    Community: Winter Park Pines Unit 17
    Single Family


    Estimated Monthly Payment: $3,456 (change assumption)
    Mortgage ($3,096) + Taxes in 2025 ($360)


    Taxes:$4,323

    Elementary School: Aloma Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • Lot #21 KAROLINA AVE, WINTER PARK, FL 32789

    $944,89097 Days on yellowkey   MLS ID: O6387812

    For Sale O6387812 - Lot #21 KAROLINA AVE, WINTER PARK, FL 32789 9 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2662
       Built: 2025   Tax: $2,207 (2024)
    Community: Karolina On Killarney
    Single Family


    Estimated Monthly Payment: $5,361 (change assumption)
    Mortgage ($5,177) + Taxes in 2024 ($184)


    Taxes:$2,207

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2024

    Middle School: Maitland Middle


  • 5331 OAK CT, WINTER PARK, FL 32792

    $460,000337 Days on yellowkey   MLS ID: S5130868

    For Sale S5130868 - 5331 OAK CT, WINTER PARK, FL 32792 41 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1263
       Built: 1976   Tax: $2,311 (2024)
    Community: Wrenwood Heights Unit 2
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,713 (change assumption)
    Mortgage ($2,520) + Taxes in 2024 ($193)


    Taxes:$2,311

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 1131 WILDMEADOW RUN, WINTER PARK, FL 32792

    $825,00086 Days on yellowkey   MLS ID: O6392218

    For Sale O6392218 - 1131 WILDMEADOW RUN, WINTER PARK, FL 32792 28 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2589
       Built: 2020
    Monthly Fee: $165
       Tax: $5,312 (2024)
    Community: Meadows At Hawks Crest
    Single Family


    Estimated Monthly Payment: $5,128 (change assumption)
    Mortgage ($4,520) + Fees ($165) + Taxes in 2024 ($443)


    Taxes:$5,312

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Sanford Middle


  • 1760 LEGION DR, WINTER PARK, FL 32789

    $2,295,000120 Days on yellowkey   MLS ID: O6383603

    For Sale O6383603 - 1760 LEGION DR, WINTER PARK, FL 32789 66 photos

    Bed: 4   Bath: 5.5   Gar: 2
    Liv Area Sq Ft: 4392
       Built: 1964   Tax: $13,622 (2025)
    Community: Green Oaks Rep
    Single Family


    Estimated Monthly Payment: $13,710 (change assumption)
    Mortgage ($12,575) + Taxes in 2025 ($1,135)


    Taxes:$13,622

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 2627 AMBERGATE RD, WINTER PARK, FL 32792

    $510,0001192 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


  • 150 DANA WAY, WINTER PARK, FL 32789

    $3,799,00083 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


  • 1354 INDIANA AVE, WINTER PARK, FL 32789

    $589,900105 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


  • 420 OHIO ST, WINTER PARK, FL 32789

    $1,360,00051 Days on yellowkey   MLS ID: O6399541

    For Sale O6399541 - 420 OHIO ST, WINTER PARK, FL 32789 8 photos

    Bed: 5   Bath: 5.5   Gar: 2
    Liv Area Sq Ft: 3735
       Built: 2026   Tax: $1,281 (2025)
    Community: Karolina On Killarney
    Single Family


    Estimated Monthly Payment: $7,559 (change assumption)
    Mortgage ($7,452) + Taxes in 2025 ($107)


    Taxes:$1,281

    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.