REFINE SEARCH
Status
Keywords
Price
 
Bedrooms
Bathrooms
Garages
Liv Area Sq Ft
Min Year
Max Year
Property Types
No Image
Age Restricted
Foreclosure
Short Sale
Pets Allowed
Furnished
Pool
Spa
Reduced Price
Back on yellowkey
Possible Short Term Rental
Carports
Max Association Fee (monthly)
Max Monthly Payment
Search

Winter Park Homes For Sale & Real Estate - 443 homes

Winter Park homes for sale are located in Orange County, Florida. Find homes in Winter Park for sale with data from the Multiple Listing Service (MLS). Our REALTORS® can assist you in your real estate search for Winter Park houses.

Location: Winter Park

Sort:
  • 721 DUNBAR ST, WINTER PARK, FL 32789

    $399,99943 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


  • 311 SCOTTSDALE SQ #311, WINTER PARK, FL 32792

    $109,900238 Days on yellowkey   MLS ID: O6355536

    For Sale O6355536 - 311 SCOTTSDALE SQ #311, WINTER PARK, FL 32792 8 photos

    Bed: 1   Bath: 1.0
    Liv Area Sq Ft: 785
       Built: 1974
    Monthly Fee: $2,097
       Tax: $1,271 (2024)
    Community: Winter Park Woods Condo
    Condo


    Estimated Monthly Payment: $2,805 (change assumption)
    Mortgage ($602) + Fees ($2,097) + Taxes in 2024 ($106)


    Taxes:$1,271

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 432 W SWOOPE AVE, WINTER PARK, FL 32789

    $695,000150 Days on yellowkey   MLS ID: O6375719

    For Sale O6375719 - 432 W SWOOPE AVE, WINTER PARK, FL 32789 20 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2317
       Built: 2014
    Monthly Fee: $463
       Tax: $9,138 (2025)
    Community: Swoope Park
    Townhouse


    Estimated Monthly Payment: $5,033 (change assumption)
    Mortgage ($3,808) + Fees ($463) + Taxes in 2025 ($761)


    Taxes:$9,138

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 40 PALMER AVE, WINTER PARK, FL 32789

    $6,950,000131 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


  • 1745 INDIANA AVE #J, WINTER PARK, FL 32789

    $524,00047 Days on yellowkey   MLS ID: O6402920

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

    For Sale O6402920 - 1745 INDIANA AVE #J, WINTER PARK, FL 32789 22 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1616
       Built: 2008
    Monthly Fee: $464
       Tax: $6,444 (2025)
    Community: La Casas De Indiana
    Condo


    Estimated Monthly Payment: $3,872 (change assumption)
    Mortgage ($2,871) + Fees ($464) + Taxes in 2025 ($537)


    Taxes:$6,444

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park Middle


  • 541 W CANTON AVE, WINTER PARK, FL 32789

    $2,800,00091 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

    $4,200,00043 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


  • 408 HOLT AVE, WINTER PARK, FL 32789

    $745,00043 Days on yellowkey   MLS ID: O6405857

    For Sale O6405857 - 408 HOLT AVE, WINTER PARK, FL 32789 34 photos

    Bed: 2   Bath: 0.0
    Liv Area Sq Ft: 1440
       Built: 1942   Tax: $5,765 (2025)
    Community: Trotters Rep
    Spa: No

    Apartment


    Estimated Monthly Payment: $4,562 (change assumption)
    Mortgage ($4,082) + Taxes in 2025 ($480)


    Taxes:$5,765

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 1405 MILLER AVE, WINTER PARK, FL 32789

    $899,000110 Days on yellowkey   MLS ID: O6386405

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

    REDUCED by $51,000 (5.4%) on 04/22/2026

    For Sale O6386405 - 1405 MILLER AVE, WINTER PARK, FL 32789 46 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1884
       Built: 2023
    Monthly Fee: $200
       Tax: $8,200 (2025)
    Community: H Vanwies Sub
    Townhouse


    Estimated Monthly Payment: $5,809 (change assumption)
    Mortgage ($4,926) + Fees ($200) + Taxes in 2025 ($683)


    Taxes:$8,200

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park Middle


  • 5454 BRACKEN COURT, WINTER PARK, FL 32792

    $199,00044 Days on yellowkey   MLS ID: O6401099

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

    For Sale O6401099 - 5454 BRACKEN COURT, WINTER PARK, FL 32792 1 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1332
       Built: 1984
    Monthly Fee: $110
       Tax: $728 (2024)
    Community: Fernbrook Trails
    Townhouse


    Estimated Monthly Payment: $1,261 (change assumption)
    Mortgage ($1,090) + Fees ($110) + Taxes in 2024 ($61)


    Taxes:$728

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 1660 PALMER AVE, WINTER PARK, FL 32789

    $4,950,000485 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


  • 2500 LEE RD #202, WINTER PARK, FL 32789

    $224,999499 Days on yellowkey   MLS ID: O6277579

    REDUCED by $10,000 (4.3%) on 04/28/2026

    For Sale O6277579 - 2500 LEE RD #202, WINTER PARK, FL 32789 52 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 956
       Built: 1969
    Monthly Fee: $432
       Tax: $2,327 (2025)
    Community: Lakeside Manor Condominium Association, Inc.
    Condo


    Estimated Monthly Payment: $1,859 (change assumption)
    Mortgage ($1,233) + Fees ($432) + Taxes in 2025 ($194)


    Taxes:$2,327

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park Middle


  • 1809 HAMMERLIN AVE, WINTER PARK, FL 32789

    $549,000157 Days on yellowkey   MLS ID: O6373616

    REDUCED by $36,000 (6.2%) on 05/06/2026

    For Sale O6373616 - 1809 HAMMERLIN AVE, WINTER PARK, FL 32789 44 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1818
       Built: 2006   Tax: $5,826 (2024)
    Community: Terazzo Del Sol Condo Assn Inc
    Condo


    Estimated Monthly Payment: $3,494 (change assumption)
    Mortgage ($3,008) + Taxes in 2024 ($486)


    Taxes:$5,826

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Audubon Park K-8


  • 1630 LASBURY AVE, WINTER PARK, FL 32789

    $2,750,00049 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

    $725,000352 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

    $565,00067 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

    $944,89099 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


  • 2774 BRIGHT BIRD LN, WINTER PARK, FL 32792

    $465,000547 Days on yellowkey   MLS ID: O6266098

    For Sale O6266098 - 2774 BRIGHT BIRD LN, WINTER PARK, FL 32792 26 photos

    Bed: 3   Bath: 2.5   Gar: 1
    Liv Area Sq Ft: 1907
       Built: 2024
    Monthly Fee: $375
       Tax: $1,009 (2023)
    Community: Grayson Square
    Townhouse


    Estimated Monthly Payment: $3,007 (change assumption)
    Mortgage ($2,548) + Fees ($375) + Taxes in 2023 ($84)


    Taxes:$1,009

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2023

    Middle School: Tuskawilla Middle


  • 5331 OAK CT, WINTER PARK, FL 32792

    $460,000339 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

    $825,00088 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




Why Bother Searching Elsewhere for Winter Park Homes for Sale and Other Real Estate?

Winter Park home, townhome, condo, villa, and other listing sales 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 houses for sale in Winter Park . You can use our website to view Multiple Listing Service (MLS) data on Winter Park Real Estate. 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 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.