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 Seminole 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:
  • 3641 OAK VISTA LN, WINTER PARK, FL 32792

    $475,00021 Days on yellowkey   MLS ID: O6412855

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

    For Sale O6412855 - 3641 OAK VISTA LN, WINTER PARK, FL 32792 46 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1645
       Built: 1981   Tax: $1,562 (2025)
    Community: Garden Lake Estates Unit 2
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,733 (change assumption)
    Mortgage ($2,603) + Taxes in 2025 ($130)


    Taxes:$1,562

    Elementary School: Red Bug Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 3009 NICHOLSON DR, WINTER PARK, FL 32792

    $449,9004 Days on yellowkey   MLS ID: O6419862

    For Sale O6419862 - 3009 NICHOLSON DR, WINTER PARK, FL 32792 39 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1645
       Built: 1980   Tax: $1,274 (2025)
    Community: Wrenwood Unit 3 3Rd Add
    Single Family


    Estimated Monthly Payment: $2,571 (change assumption)
    Mortgage ($2,465) + Taxes in 2025 ($106)


    Taxes:$1,274

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 7488 WHISPERWOOD DR #28, WINTER PARK, FL 32792

    $230,0006 Days on yellowkey   MLS ID: O6419151

    For Sale O6419151 - 7488 WHISPERWOOD DR #28, WINTER PARK, FL 32792 63 photos

    Bed: 2   Bath: 2.5
    Liv Area Sq Ft: 1578
       Built: 1974
    Monthly Fee: $575
       Tax: $3,078 (2025)
    Community: Whisperwood Condo
    Condo


    Estimated Monthly Payment: $2,092 (change assumption)
    Mortgage ($1,260) + Fees ($575) + Taxes in 2025 ($257)


    Taxes:$3,078

    Elementary School: Cheney Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 7733 COUNTRY PL #G2, WINTER PARK, FL 32792

    $244,0007 Days on yellowkey   MLS ID: O6418682

    For Sale O6418682 - 7733 COUNTRY PL #G2, WINTER PARK, FL 32792 21 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1068
       Built: 1982   Tax: $371 (2025)
    Community: Goldenrod Villas Condo
    Condo


    Estimated Monthly Payment: $1,368 (change assumption)
    Mortgage ($1,337) + Taxes in 2025 ($31)


    Taxes:$371

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1421 CHAPMAN CIR, WINTER PARK, FL 32789

    $1,550,00017 Days on yellowkey   MLS ID: O6415941

    For Sale O6415941 - 1421 CHAPMAN CIR, WINTER PARK, FL 32789 49 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3578
       Built: 2005
    Monthly Fee: $268
       Tax: $10,592 (2025)
    Community: Windsong Elizabeths Walk 43/81
    Single Family


    Estimated Monthly Payment: $9,644 (change assumption)
    Mortgage ($8,493) + Fees ($268) + Taxes in 2025 ($883)


    Taxes:$10,592

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 1761 GLADIOLAS DR, WINTER PARK, FL 32792

    $375,00031 Days on yellowkey   MLS ID: O6411912

    1 Days Off yellowkey (back on 6/6/2026)

    For Sale O6411912 - 1761 GLADIOLAS DR, WINTER PARK, FL 32792 7 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1656
       Built: 1979   Tax: $1,453 (2025)
    Community: Garden Lake Estates Unit 1
    Single Family


    Estimated Monthly Payment: $2,176 (change assumption)
    Mortgage ($2,055) + Taxes in 2025 ($121)


    Taxes:$1,453

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1871 CASSELWOOD ST, WINTER PARK, FL 32792

    $419,90058 Days on yellowkey   MLS ID: O6404306

    0 Days Off yellowkey (back on 5/26/2026)

    REDUCED by $5,000 (1.2%) on 05/12/2026

    For Sale O6404306 - 1871 CASSELWOOD ST, WINTER PARK, FL 32792 37 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1616
       Built: 1988
    Monthly Fee: $39
       Tax: $1,223 (2024)
    Community: Villas Of Casselberry Ph 2
    Townhouse


    Estimated Monthly Payment: $2,442 (change assumption)
    Mortgage ($2,301) + Fees ($39) + Taxes in 2024 ($102)


    Taxes:$1,223

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 700 MELROSE AVE #F 21, WINTER PARK, FL 32789

    $235,90024 Days on yellowkey   MLS ID: O6413612

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

    For Sale O6413612 - 700 MELROSE AVE #F 21, WINTER PARK, FL 32789 27 photos

    Bed: 1   Bath: 1.0
    Liv Area Sq Ft: 787
       Built: 1964   Tax: $1,123 (2025)
    Community: Winter Park Gdns Condo
    Condo


    Estimated Monthly Payment: $1,386 (change assumption)
    Mortgage ($1,293) + Taxes in 2025 ($94)


    Taxes:$1,123

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 330 ELKHORN CT, WINTER PARK, FL 32792

    $544,900155 Days on yellowkey   MLS ID: O6376757

    REDUCED by $5,000 (0.9%) on 06/26/2026

    For Sale O6376757 - 330 ELKHORN CT, WINTER PARK, FL 32792 41 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1570
       Built: 1965   Tax: $2,086 (2025)
    Community: Winter Park Pines Merrie Oaks
    Single Family


    Estimated Monthly Payment: $3,160 (change assumption)
    Mortgage ($2,986) + Taxes in 2025 ($174)


    Taxes:$2,086

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 910 ENCLAVE PL, WINTER PARK, FL 32792

    $1,899,00046 Days on yellowkey   MLS ID: O6406803

    For Sale O6406803 - 910 ENCLAVE PL, WINTER PARK, FL 32792 4 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3620
       Built: 2027
    Monthly Fee: $124
       Tax: $9,900 (2026)
    Community: The Enclave Winter Park
    Single Family


    Estimated Monthly Payment: $11,354 (change assumption)
    Mortgage ($10,405) + 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


  • 926 ENCLAVE PL, WINTER PARK, FL 32792

    $2,235,00040 Days on yellowkey   MLS ID: O6408030

    For Sale O6408030 - 926 ENCLAVE PL, WINTER PARK, FL 32792 6 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 4150
       Built: 2026
    Monthly Fee: $124
       Tax: $9,900 (2026)
    Community: The Enclave Winter Park
    Single Family


    Estimated Monthly Payment: $13,195 (change assumption)
    Mortgage ($12,246) + 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


  • 1000 S SEMORAN BLVD BLVD #603, WINTER PARK, FL 32792

    $99,9004 Days on yellowkey   MLS ID: O6420027

    For Sale O6420027 - 1000 S SEMORAN BLVD BLVD #603, WINTER PARK, FL 32792 17 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1003
       Built: 1969   Tax: $1,878 (2025)
    Community: Golfside Villas Condo
    Condo


    Estimated Monthly Payment: $704 (change assumption)
    Mortgage ($547) + Taxes in 2025 ($157)


    Taxes:$1,878

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 3037 ANTIQUE OAKS CIR #156, WINTER PARK, FL 32792

    $154,9004 Days on yellowkey   MLS ID: O6420008

    For Sale O6420008 - 3037 ANTIQUE OAKS CIR #156, WINTER PARK, FL 32792 21 photos

    Bed: 1   Bath: 1.0
    Liv Area Sq Ft: 749
       Built: 1984   Tax: $2,058 (2025)
    Community: Parkview Village
    Condo


    Estimated Monthly Payment: $1,020 (change assumption)
    Mortgage ($849) + Taxes in 2025 ($172)


    Taxes:$2,058

    Elementary School: Aloma Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 2774 BANCHORY RD, WINTER PARK, FL 32792

    $645,0004 Days on yellowkey   MLS ID: O6418821

    For Sale O6418821 - 2774 BANCHORY RD, WINTER PARK, FL 32792 34 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1560
       Built: 1965   Tax: $7,220 (2025)
    Community: Winter Park Pines
    Single Family


    Estimated Monthly Payment: $4,136 (change assumption)
    Mortgage ($3,534) + Taxes in 2025 ($602)


    Taxes:$7,220

    Elementary School: Aloma Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 2803 BANCHORY RD, WINTER PARK, FL 32792

    $474,00031 Days on yellowkey   MLS ID: O6404011

    REDUCED by $21,000 (4.2%) on 06/26/2026

    For Sale O6404011 - 2803 BANCHORY RD, WINTER PARK, FL 32792 31 photos

    Bed: 4   Bath: 2.0
    Liv Area Sq Ft: 1596
       Built: 1965
    Monthly Fee: $5
       Tax: $2,458 (2025)
    Community: Winter Park Pines
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,807 (change assumption)
    Mortgage ($2,597) + Fees ($5) + Taxes in 2025 ($205)


    Taxes:$2,458

    Elementary School: Aloma Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 2052 LEANNE CT, WINTER PARK, FL 32792

    $440,000146 Days on yellowkey   MLS ID: O6379323

    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


  • 147 S INTERLACHEN AVE #202, WINTER PARK, FL 32789

    $2,095,000149 Days on yellowkey   MLS ID: L4959060

    REDUCED by $75,000 (3.5%) on 06/04/2026

    For Sale L4959060 - 147 S INTERLACHEN AVE #202, WINTER PARK, FL 32789 31 photos

    Bed: 3   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3272
       Built: 1990   Tax: $18,439 (2024)
    Community: 147 Interlachen Place
    Condo


    Estimated Monthly Payment: $13,016 (change assumption)
    Mortgage ($11,479) + Taxes in 2024 ($1,537)


    Taxes:$18,439

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 2500 LEE RD #222, WINTER PARK, FL 32789

    $184,9005 Days on yellowkey   MLS ID: O6419663

    For Sale O6419663 - 2500 LEE RD #222, WINTER PARK, FL 32789 22 photos

    Bed: 1   Bath: 1.0
    Liv Area Sq Ft: 645
       Built: 1969
    Monthly Fee: $292
       Tax: $926 (2024)
    Community: Lakeside Manor
    Condo


    Estimated Monthly Payment: $1,382 (change assumption)
    Mortgage ($1,013) + Fees ($292) + Taxes in 2024 ($77)


    Taxes:$926

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 7577 DOCKSIDE ST, WINTER PARK, FL 32792

    $360,00027 Days on yellowkey   MLS ID: O6412514

    REDUCED by $10,000 (2.7%) on 06/25/2026

    For Sale O6412514 - 7577 DOCKSIDE ST, WINTER PARK, FL 32792 30 photos

    Bed: 3   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1245
       Built: 1977   Tax: $3,722 (2025)
    Community: Woodcrest Unit 6
    Single Family


    Estimated Monthly Payment: $2,283 (change assumption)
    Mortgage ($1,973) + Taxes in 2025 ($310)


    Taxes:$3,722

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 946 ENCLAVE PL, WINTER PARK, FL 32792

    $2,175,00032 Days on yellowkey   MLS ID: O6411633

    For Sale O6411633 - 946 ENCLAVE PL, WINTER PARK, FL 32792 3 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3989
       Built: 2026
    Monthly Fee: $375
       Tax: $9,900 (2026)
    Community: The Enclave Winter Park
    Single Family


    Estimated Monthly Payment: $13,118 (change assumption)
    Mortgage ($11,918) + Fees ($375) + Taxes in 2026 ($825)


    Taxes:$9,900

    Elementary School: None

    High School: None

    Tax Year: 2026

    Middle School: None




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.