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 - 441 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:
  • 2715 PRINCE JOHN RD, WINTER PARK, FL 32792

    $498,90021 Days on yellowkey   MLS ID: O6415084

    REDUCED by $6,000 (1.2%) on 06/27/2026

    For Sale O6415084 - 2715 PRINCE JOHN RD, WINTER PARK, FL 32792 29 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1565
       Built: 1963   Tax: $7,101 (2025)
    Community: Winter Park Pines Rep
    Single Family


    Estimated Monthly Payment: $3,325 (change assumption)
    Mortgage ($2,734) + Taxes in 2025 ($592)


    Taxes:$7,101

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 1138 S PENNSYLVANIA AVE, WINTER PARK, FL 32789

    $1,050,0003 Days on yellowkey   MLS ID: O6420090

    For Sale O6420090 - 1138 S PENNSYLVANIA AVE, WINTER PARK, FL 32789 35 photos

    Bed: 3   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2434
       Built: 2005
    Monthly Fee: $500
       Tax: $10,213 (2025)
    Community: Virginia Heights Rep
    Townhouse


    Estimated Monthly Payment: $7,104 (change assumption)
    Mortgage ($5,753) + Fees ($500) + Taxes in 2025 ($851)


    Taxes:$10,213

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 1287 VERDANT GLADE PL, WINTER PARK, FL 32792

    $825,00066 Days on yellowkey   MLS ID: O6400331

    REDUCED by $22,000 (2.6%) on 06/19/2026

    For Sale O6400331 - 1287 VERDANT GLADE PL, WINTER PARK, FL 32792 50 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3020
       Built: 2020
    Monthly Fee: $413
       Tax: $6,133 (2025)
    Community: Meadows At Hawks Crest
    Single Family


    Estimated Monthly Payment: $5,444 (change assumption)
    Mortgage ($4,520) + Fees ($413) + Taxes in 2025 ($511)


    Taxes:$6,133

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 1900 WINTER PARK RD, WINTER PARK, FL 32789

    $799,00063 Days on yellowkey   MLS ID: O6402566

    REDUCED by $50,900 (6.0%) on 06/16/2026

    For Sale O6402566 - 1900 WINTER PARK RD, WINTER PARK, FL 32789 22 photos

    Bed: 4   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1511
       Built: 1947   Tax: $2,803 (2025)
    Community: Charmont
    Single Family


    Estimated Monthly Payment: $4,612 (change assumption)
    Mortgage ($4,378) + Taxes in 2025 ($234)


    Taxes:$2,803

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 3651 N GOLDENROD RD #D102, WINTER PARK, FL 32792

    $157,50069 Days on yellowkey   MLS ID: O6401114

    REDUCED by $400 (0.3%) on 06/27/2026

    For Sale O6401114 - 3651 N GOLDENROD RD #D102, WINTER PARK, FL 32792 16 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 840
       Built: 1990
    Monthly Fee: $370
       Tax: $2,461 (2025)
    Community: Lancelot/Winter Park
    Condo


    Estimated Monthly Payment: $1,438 (change assumption)
    Mortgage ($863) + Fees ($370) + Taxes in 2025 ($205)


    Taxes:$2,461

    Elementary School: Aloma Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


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

    $4,200,00052 Days on yellowkey   MLS ID: O6406437

    0 Days Off yellowkey (back on 6/27/2026)

    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


  • 981 ARAGON AVE, WINTER PARK, FL 32789

    $535,0003 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: Baldwin Park Elementary

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 3006 NORTHWOOD BLVD, WINTER PARK, FL 32789

    $1,300,0003 Days on yellowkey   MLS ID: O6419056

    For Sale O6419056 - 3006 NORTHWOOD BLVD, WINTER PARK, FL 32789 46 photos

    Bed: 4   Bath: 3.0   Gar: 1
    Liv Area Sq Ft: 2075
       Built: 1953   Tax: $4,188 (2025)
    Community: Northwood Terrace
    Spa: No

    Single Family


    Estimated Monthly Payment: $7,472 (change assumption)
    Mortgage ($7,123) + Taxes in 2025 ($349)


    Taxes:$4,188

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 731 BONGART ROAD, WINTER PARK, FL 32792

    $499,00053 Days on yellowkey   MLS ID: O6406004

    3 Days Off yellowkey (back on 6/27/2026)

    For Sale O6406004 - 731 BONGART ROAD, WINTER PARK, FL 32792 44 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 1526
       Built: 1961   Tax: $5,910 (2025)
    Community: Winter Park Estates
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,227 (change assumption)
    Mortgage ($2,734) + Taxes in 2025 ($493)


    Taxes:$5,910

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 333 CORNWALL RD, WINTER PARK, FL 32792

    $579,00038 Days on yellowkey   MLS ID: O6409379

    2 Days Off yellowkey (back on 6/26/2026)

    For Sale O6409379 - 333 CORNWALL RD, WINTER PARK, FL 32792 32 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1660
       Built: 1963
    Monthly Fee: $5
       Tax: $2,654 (2025)
    Community: Winter Park Pines
    Single Family


    Estimated Monthly Payment: $3,399 (change assumption)
    Mortgage ($3,173) + Fees ($5) + Taxes in 2025 ($221)


    Taxes:$2,654

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 938 ENCLAVE PL, WINTER PARK, FL 32792

    $2,099,00040 Days on yellowkey   MLS ID: O6408090

    For Sale O6408090 - 938 ENCLAVE PL, WINTER PARK, FL 32792 7 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3865
       Built: 2026
    Monthly Fee: $124
       Tax: $9,900 (2026)
    Community: The Enclave Winter Park
    Single Family


    Estimated Monthly Payment: $12,450 (change assumption)
    Mortgage ($11,501) + Fees ($124) + Taxes in 2026 ($825)


    Taxes:$9,900

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2026

    Middle School: Maitland Middle


  • 2831 MULFORD AVE, WINTER PARK, FL 32789

    $735,00022 Days on yellowkey   MLS ID: O6414319

    For Sale O6414319 - 2831 MULFORD AVE, WINTER PARK, FL 32789 28 photos

    Bed: 4   Bath: 2.5
    Liv Area Sq Ft: 1647
       Built: 1952   Tax: $3,192 (2025)
    Community: Orangewood Park
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,293 (change assumption)
    Mortgage ($4,027) + Taxes in 2025 ($266)


    Taxes:$3,192

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1695 LEE RD #E204, WINTER PARK, FL 32789

    $114,000201 Days on yellowkey   MLS ID: O6366205

    REDUCED by $1,000 (0.9%) on 06/01/2026

    For Sale O6366205 - 1695 LEE RD #E204, WINTER PARK, FL 32789 27 photos

    Bed: 2   Bath: 1.0
    Liv Area Sq Ft: 881
       Built: 1966
    Monthly Fee: $482
       Tax: $1,917 (2024)
    Community: Waterfall Cove
    Condo


    Estimated Monthly Payment: $1,266 (change assumption)
    Mortgage ($625) + Fees ($482) + Taxes in 2024 ($160)


    Taxes:$1,917

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 184 SANDLEWOOD TRL ##2, WINTER PARK, FL 32789

    $299,000142 Days on yellowkey   MLS ID: O6380753

    REDUCED by $13,000 (4.2%) on 06/18/2026

    For Sale O6380753 - 184 SANDLEWOOD TRL ##2, WINTER PARK, FL 32789 29 photos

    Bed: 2   Bath: 2.5
    Liv Area Sq Ft: 1133
       Built: 1985
    Monthly Fee: $310
       Tax: $2,915 (2025)
    Community: Sandlewood Creek Condo Ph 10
    Condo


    Estimated Monthly Payment: $2,191 (change assumption)
    Mortgage ($1,638) + Fees ($310) + Taxes in 2025 ($243)


    Taxes:$2,915

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 2923 ANTIQUE OAKS CIR #39, WINTER PARK, FL 32792

    $184,999494 Days on yellowkey   MLS ID: OM695642

    0 Days Off yellowkey (back on 6/26/2026)

    For Sale OM695642 - 2923 ANTIQUE OAKS CIR #39, WINTER PARK, FL 32792 22 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1105
       Built: 1984
    Monthly Fee: $442
       Tax: $2,702 (2024)
    Community: Parkview Village
    Condo


    Estimated Monthly Payment: $1,681 (change assumption)
    Mortgage ($1,014) + Fees ($442) + Taxes in 2024 ($225)


    Taxes:$2,702

    Elementary School: Aloma Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Glenridge Middle


  • 7471 CANFORD CT #19, WINTER PARK, FL 32792

    $199,000263 Days on yellowkey   MLS ID: G5103114

    For Sale G5103114 - 7471 CANFORD CT #19, WINTER PARK, FL 32792 15 photos

    Bed: 2   Bath: 1.5
    Liv Area Sq Ft: 1393
       Built: 1974   Tax: $2,750 (2024)
    Community: Whisperwood Condo
    Condo


    Estimated Monthly Payment: $1,320 (change assumption)
    Mortgage ($1,090) + Taxes in 2024 ($229)


    Taxes:$2,750

    Elementary School: Cheney Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Glenridge Middle


  • 2676 BARBADOS DR, WINTER PARK, FL 32792

    $340,00031 Days on yellowkey   MLS ID: O6411958

    2 Days Off yellowkey (back on 6/26/2026)

    For Sale O6411958 - 2676 BARBADOS DR, WINTER PARK, FL 32792 29 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1743
       Built: 1978
    Monthly Fee: $98
       Tax: $4,131 (2025)
    Community: Windward Square Sec 2
    Townhouse


    Estimated Monthly Payment: $2,305 (change assumption)
    Mortgage ($1,863) + Fees ($98) + Taxes in 2025 ($344)


    Taxes:$4,131

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 607 ELLEN DR, WINTER PARK, FL 32789

    $1,449,900251 Days on yellowkey   MLS ID: O6354269

    REDUCED by $50,000 (3.3%) on 05/23/2026

    For Sale O6354269 - 607 ELLEN DR, WINTER PARK, FL 32789 34 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 2812
       Built: 2025
    Monthly Fee: $76
       Tax: $4,224 (2024)
    Community: Lake Killarney Shores
    Spa: No

    Single Family


    Estimated Monthly Payment: $8,372 (change assumption)
    Mortgage ($7,944) + Fees ($76) + Taxes in 2024 ($352)


    Taxes:$4,224

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2024

    Middle School: College Park Middle


  • 2228 HOWARD DR, WINTER PARK, FL 32789

    $2,460,00047 Days on yellowkey   MLS ID: O6407733

    For Sale O6407733 - 2228 HOWARD DR, WINTER PARK, FL 32789 9 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3294
       Built: 2026   Tax: $3,647 (2025)
    Community: Lake Forest Park
    Single Family


    Estimated Monthly Payment: $13,783 (change assumption)
    Mortgage ($13,479) + Taxes in 2025 ($304)


    Taxes:$3,647

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 609 S PHELPS AVE, WINTER PARK, FL 32789

    $2,829,000105 Days on yellowkey   MLS ID: O6388598

    For Sale O6388598 - 609 S PHELPS AVE, WINTER PARK, FL 32789 23 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




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.