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 - 384 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:
  • 2501 TAHOE CIR, WINTER PARK, FL 32792

    $259,90089 Days on yellowkey   MLS ID: O6378209

    2 Days Off yellowkey (back on 4/21/2026)

    REDUCED by $10,000 (3.7%) on 04/05/2026

    For Sale O6378209 - 2501 TAHOE CIR, WINTER PARK, FL 32792 36 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1495
       Built: 1981   Tax: $3,757 (2025)
    Community: Cedarwood Village 1
    Condo


    Estimated Monthly Payment: $1,737 (change assumption)
    Mortgage ($1,424) + Taxes in 2025 ($313)


    Taxes:$3,757

    Elementary School: English Estates Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 7301 CEDAR CREEK CT #66, WINTER PARK, FL 32792

    $187,50019 Days on yellowkey   MLS ID: O6397477

    For Sale O6397477 - 7301 CEDAR CREEK CT #66, WINTER PARK, FL 32792 44 photos

    Bed: 2   Bath: 2.5
    Liv Area Sq Ft: 1031
       Built: 1983
    Monthly Fee: $10
       Tax: $2,731 (2025)
    Community: Hidden Oaks Condo Ph 04
    Condo


    Estimated Monthly Payment: $1,265 (change assumption)
    Mortgage ($1,027) + Fees ($10) + Taxes in 2025 ($228)


    Taxes:$2,731

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 3028 GEORGE MASON AVE #J-7E, WINTER PARK, FL 32792

    $105,00013 Days on yellowkey   MLS ID: O6398380

    0 Days Off yellowkey (back on 4/20/2026)

    For Sale O6398380 - 3028 GEORGE MASON AVE #J-7E, WINTER PARK, FL 32792 25 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1088
       Built: 1974
    Monthly Fee: $427
       Tax: $1,989 (2025)
    Community: Colonies
    Condo


    Estimated Monthly Payment: $1,168 (change assumption)
    Mortgage ($575) + Fees ($427) + Taxes in 2025 ($166)


    Taxes:$1,989

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1792 CHILEAN LN, WINTER PARK, FL 32792

    $325,00096 Days on yellowkey   MLS ID: O6375881

    1 Days Off yellowkey (back on 4/21/2026)

    For Sale O6375881 - 1792 CHILEAN LN, WINTER PARK, FL 32792 30 photos

    Bed: 3   Bath: 1.0
    Liv Area Sq Ft: 984
       Built: 1959   Tax: $2,677 (2024)
    Community: Eastbrook Sub Unit 05
    Single Family


    Estimated Monthly Payment: $2,004 (change assumption)
    Mortgage ($1,781) + Taxes in 2024 ($223)


    Taxes:$2,677

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 1529 HOLTS GROVE CIR, WINTER PARK, FL 32789

    $2,795,00027 Days on yellowkey   MLS ID: O6395062

    REDUCED by $55,000 (1.9%) on 04/21/2026

    For Sale O6395062 - 1529 HOLTS GROVE CIR, WINTER PARK, FL 32789 84 photos

    Bed: 4   Bath: 5.0   Gar: 3
    Liv Area Sq Ft: 4356
       Built: 2005
    Monthly Fee: $262
       Tax: $21,342 (2025)
    Community: Windsong Lakeside Sec 02 43/71
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $17,355 (change assumption)
    Mortgage ($15,315) + Fees ($262) + Taxes in 2025 ($1,779)


    Taxes:$21,342

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 7506 CRANES CREEK CT #30, WINTER PARK, FL 32792

    $365,0008 Days on yellowkey   MLS ID: S5148231

    For Sale S5148231 - 7506 CRANES CREEK CT #30, WINTER PARK, FL 32792 20 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1861
       Built: 2006
    Monthly Fee: $181
       Tax: $1,974 (2025)
    Community: Cranes Creek
    Townhouse


    Estimated Monthly Payment: $2,345 (change assumption)
    Mortgage ($2,000) + Fees ($181) + Taxes in 2025 ($165)


    Taxes:$1,974

    Elementary School: Aloma Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 5330 TANGERINE AVE, WINTER PARK, FL 32792

    $354,90013 Days on yellowkey   MLS ID: O6399019

    0 Days Off yellowkey (back on 4/15/2026)

    For Sale O6399019 - 5330 TANGERINE AVE, WINTER PARK, FL 32792 32 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1642
       Built: 1976   Tax: $1,296 (2024)
    Community: Wrenwood
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,053 (change assumption)
    Mortgage ($1,945) + Taxes in 2024 ($108)


    Taxes:$1,296

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 2681 FITZHUGH RD, WINTER PARK, FL 32792

    $750,00068 Days on yellowkey   MLS ID: O6383699

    0 Days Off yellowkey (back on 4/20/2026)

    For Sale O6383699 - 2681 FITZHUGH RD, WINTER PARK, FL 32792 55 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2375
       Built: 1966   Tax: $5,903 (2024)
    Community: Winter Park Pines Merrie Oaks
    Single Family


    Estimated Monthly Payment: $4,601 (change assumption)
    Mortgage ($4,109) + Taxes in 2024 ($492)


    Taxes:$5,903

    Elementary School: Aloma Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Glenridge Middle


  • 1849 VIBURNUM LN, WINTER PARK, FL 32792

    $425,000264 Days on yellowkey   MLS ID: O6333863

    For Sale O6333863 - 1849 VIBURNUM LN, WINTER PARK, FL 32792 27 photos

    Bed: 4   Bath: 2.0
    Liv Area Sq Ft: 1627
       Built: 1961   Tax: $3,645 (2024)
    Community: Eastbrook Sub Unit 05
    Single Family


    Estimated Monthly Payment: $2,632 (change assumption)
    Mortgage ($2,329) + Taxes in 2024 ($304)


    Taxes:$3,645

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 1905 BONANZA CT, WINTER PARK, FL 32792

    $490,00012 Days on yellowkey   MLS ID: O6398772

    0 Days Off yellowkey (back on 4/20/2026)

    For Sale O6398772 - 1905 BONANZA CT, WINTER PARK, FL 32792 35 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1774
       Built: 1968   Tax: $5,015 (2024)
    Community: Eastbrook Sub Unit 13
    Single Family


    Estimated Monthly Payment: $3,103 (change assumption)
    Mortgage ($2,685) + Taxes in 2024 ($418)


    Taxes:$5,015

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 1177 KENWOOD AVE, WINTER PARK, FL 32789

    $1,870,00046 Days on yellowkey   MLS ID: O6390592

    REDUCED by $100,000 (5.1%) on 04/01/2026

    For Sale O6390592 - 1177 KENWOOD AVE, WINTER PARK, FL 32789 57 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 4363
       Built: 2007   Tax: $16,206 (2025)
    Community: Dixie Terrace
    Spa: No

    Single Family


    Estimated Monthly Payment: $11,597 (change assumption)
    Mortgage ($10,246) + Taxes in 2025 ($1,351)


    Taxes:$16,206

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2500 LEE RD #208, WINTER PARK, FL 32789

    $180,000382 Days on yellowkey   MLS ID: O6297570

    For Sale O6297570 - 2500 LEE RD #208, WINTER PARK, FL 32789 49 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 956
       Built: 1969
    Monthly Fee: $432
       Tax: $1,519 (2025)
    Community: Lakeside Manor Apts Condo
    Condo


    Estimated Monthly Payment: $1,545 (change assumption)
    Mortgage ($986) + Fees ($432) + Taxes in 2025 ($127)


    Taxes:$1,519

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park Middle


  • 1841 HARLAND PARK DR, WINTER PARK, FL 32789

    $1,895,000120 Days on yellowkey   MLS ID: O6369653

    0 Days Off yellowkey (back on 4/11/2026)

    For Sale O6369653 - 1841 HARLAND PARK DR, WINTER PARK, FL 32789 78 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3470
       Built: 2014
    Monthly Fee: $262
       Tax: $21,031 (2024)
    Community: Windsong-Knowles Place
    Single Family


    Estimated Monthly Payment: $12,398 (change assumption)
    Mortgage ($10,383) + Fees ($262) + Taxes in 2024 ($1,753)


    Taxes:$21,031

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Glenridge Middle


  • 5331 OAK CT, WINTER PARK, FL 32792

    $460,000286 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


  • 1052 MANCHESTER CIR, WINTER PARK, FL 32792

    $470,00094 Days on yellowkey   MLS ID: O6376260

    REDUCED by $5,000 (1.1%) on 04/13/2026

    For Sale O6376260 - 1052 MANCHESTER CIR, WINTER PARK, FL 32792 41 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1703
       Built: 1983   Tax: $5,216 (2025)
    Community: Howell Estates 1St Add
    Single Family


    Estimated Monthly Payment: $3,010 (change assumption)
    Mortgage ($2,575) + Taxes in 2025 ($435)


    Taxes:$5,216

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 1870 WALKER AVE, WINTER PARK, FL 32789

    $1,399,00046 Days on yellowkey   MLS ID: O6390504

    REDUCED by $26,000 (1.8%) on 04/19/2026

    For Sale O6390504 - 1870 WALKER AVE, WINTER PARK, FL 32789 21 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2046
       Built: 2026   Tax: $3,981 (2025)
    Community: Osceola Heights
    Single Family


    Estimated Monthly Payment: $7,997 (change assumption)
    Mortgage ($7,666) + Taxes in 2025 ($332)


    Taxes:$3,981

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 2020 VIA TUSCANY, WINTER PARK, FL 32789

    $4,195,00012 Days on yellowkey   MLS ID: O6400063

    0 Days Off yellowkey (back on 4/20/2026)

    For Sale O6400063 - 2020 VIA TUSCANY, WINTER PARK, FL 32789 94 photos

    Bed: 4   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 4665
       Built: 2026   Tax: $12,585 (2025)
    Community: Tuscania
    Single Family


    Estimated Monthly Payment: $24,034 (change assumption)
    Mortgage ($22,986) + Taxes in 2025 ($1,049)


    Taxes:$12,585

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 639 FRIAR RD, WINTER PARK, FL 32792

    $795,00026 Days on yellowkey   MLS ID: O6395715

    1 Days Off yellowkey (back on 4/20/2026)

    For Sale O6395715 - 639 FRIAR RD, WINTER PARK, FL 32792 50 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 1950
       Built: 1967   Tax: $3,415 (2025)
    Community: Winter Park Pines
    Single Family


    Estimated Monthly Payment: $4,641 (change assumption)
    Mortgage ($4,356) + Taxes in 2025 ($285)


    Taxes:$3,415

    Elementary School: Aloma Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 188 LEWFIELD CIR #188, WINTER PARK, FL 32792

    $129,99056 Days on yellowkey   MLS ID: O6387291

    REDUCED by $9,010 (6.5%) on 04/20/2026

    For Sale O6387291 - 188 LEWFIELD CIR #188, WINTER PARK, FL 32792 27 photos

    Bed: 1   Bath: 1.0
    Liv Area Sq Ft: 678
       Built: 1973   Tax: $424 (2024)
    Community: Stratford A Winter Park Condo
    Condo


    Estimated Monthly Payment: $748 (change assumption)
    Mortgage ($712) + Taxes in 2024 ($35)


    Taxes:$424

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 2087 LAURELWOOD WAY, WINTER PARK, FL 32792

    $659,000224 Days on yellowkey   MLS ID: O6344482

    REDUCED by $5,000 (0.8%) on 04/20/2026

    For Sale O6344482 - 2087 LAURELWOOD WAY, WINTER PARK, FL 32792 30 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1920
       Built: 2019
    Monthly Fee: $236
       Tax: $4,680 (2024)
    Community: Preserve At Hawks Crest
    Single Family


    Estimated Monthly Payment: $4,237 (change assumption)
    Mortgage ($3,611) + Fees ($236) + Taxes in 2024 ($390)


    Taxes:$4,680

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla 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.