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 - 447 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:
  • 5275 PINE LILY CIR, WINTER PARK, FL 32792

    $665,000123 Days on yellowkey   MLS ID: O6377988

    0 Days Off yellowkey (back on 4/27/2026)

    For Sale O6377988 - 5275 PINE LILY CIR, WINTER PARK, FL 32792 34 photos

    Bed: 5   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 3152
       Built: 2014
    Monthly Fee: $182
       Tax: $7,425 (2024)
    Community: Sanctuary At Aloma
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $4,444 (change assumption)
    Mortgage ($3,644) + Fees ($182) + Taxes in 2024 ($619)


    Taxes:$7,425

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 2503 VERSAILLES AVE, WINTER PARK, FL 32789

    $2,184,000174 Days on yellowkey   MLS ID: O6365961

    0 Days Off yellowkey (back on 4/27/2026)

    REDUCED by $166,000 (7.1%) on 04/04/2026

    For Sale O6365961 - 2503 VERSAILLES AVE, WINTER PARK, FL 32789 53 photos

    Bed: 5   Bath: 4.0   Gar: 3
    Liv Area Sq Ft: 4026
       Built: 2015   Tax: $15,760 (2024)
    Community: Fontainebleau
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $13,280 (change assumption)
    Mortgage ($11,967) + Taxes in 2024 ($1,313)


    Taxes:$15,760

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Maitland Middle


  • 1540 MILLER AVE, WINTER PARK, FL 32789

    $1,399,90050 Days on yellowkey   MLS ID: O6398421

    For Sale O6398421 - 1540 MILLER AVE, WINTER PARK, FL 32789 55 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2984
       Built: 2026   Tax: $3,573 (2025)
    Community: Lawndale
    Spa: No

    Single Family


    Estimated Monthly Payment: $7,968 (change assumption)
    Mortgage ($7,670) + Taxes in 2025 ($298)


    Taxes:$3,573

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park Middle


  • 1951 CANNY CV, WINTER PARK, FL 32792

    $444,900171 Days on yellowkey   MLS ID: O6367023

    For Sale O6367023 - 1951 CANNY CV, WINTER PARK, FL 32792 64 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1782
       Built: 2023
    Monthly Fee: $375
       Tax: $6,889 (2025)
    Community: Grayson Square
    Townhouse


    Estimated Monthly Payment: $3,387 (change assumption)
    Mortgage ($2,438) + Fees ($375) + Taxes in 2025 ($574)


    Taxes:$6,889

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 1807 MAGNOLIA AVE, WINTER PARK, FL 32789

    $1,199,00047 Days on yellowkey   MLS ID: O6396616

    0 Days Off yellowkey (back on 4/25/2026)

    For Sale O6396616 - 1807 MAGNOLIA AVE, WINTER PARK, FL 32789 38 photos

    Bed: 5   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2618
       Built: 2026   Tax: $4,720 (2025)
    Community: Temple Terrace
    Spa: No

    Single Family


    Estimated Monthly Payment: $6,963 (change assumption)
    Mortgage ($6,570) + Taxes in 2025 ($393)


    Taxes:$4,720

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 259 E CANTON AVE #259, WINTER PARK, FL 32789

    $619,00084 Days on yellowkey   MLS ID: O6389246

    1 Days Off yellowkey (back on 4/25/2026)

    REDUCED by $10,000 (1.6%) on 04/19/2026

    For Sale O6389246 - 259 E CANTON AVE #259, WINTER PARK, FL 32789 36 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1040
       Built: 1971   Tax: $3,603 (2025)
    Community: Village Winterset Inc
    Condo


    Estimated Monthly Payment: $3,692 (change assumption)
    Mortgage ($3,392) + Taxes in 2025 ($300)


    Taxes:$3,603

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 291 LEWFIELD CIR #291, WINTER PARK, FL 32792

    $144,000106 Days on yellowkey   MLS ID: O6382547

    For Sale O6382547 - 291 LEWFIELD CIR #291, WINTER PARK, FL 32792 32 photos

    Bed: 1   Bath: 1.0
    Liv Area Sq Ft: 678
       Built: 1973
    Monthly Fee: $350
       Tax: $1,942 (2025)
    Community: Stratford Winter Park
    Condo


    Estimated Monthly Payment: $1,301 (change assumption)
    Mortgage ($789) + Fees ($350) + Taxes in 2025 ($162)


    Taxes:$1,942

    Elementary School: English Estates Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 2020 COCOS CT, WINTER PARK, FL 32792

    $458,99081 Days on yellowkey   MLS ID: O6389901

    1 Days Off yellowkey (back on 4/24/2026)

    REDUCED by $1,000 (0.2%) on 04/17/2026

    For Sale O6389901 - 2020 COCOS CT, WINTER PARK, FL 32792 22 photos

    Bed: 3   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1715
       Built: 1966   Tax: $1,410 (2024)
    Community: Eastbrook Sub Unit 8
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,632 (change assumption)
    Mortgage ($2,515) + Taxes in 2024 ($117)


    Taxes:$1,410

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 106 S INTERLACHEN AVE #518, WINTER PARK, FL 32789

    $1,950,00042 Days on yellowkey   MLS ID: O6400228

    For Sale O6400228 - 106 S INTERLACHEN AVE #518, WINTER PARK, FL 32789 58 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1807
       Built: 1971   Tax: $14,974 (2025)
    Community: Cloisters Condo
    Condo


    Estimated Monthly Payment: $11,933 (change assumption)
    Mortgage ($10,685) + Taxes in 2025 ($1,248)


    Taxes:$14,974

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 7429 DANIEL WEBSTER DR #14 (#C), WINTER PARK, FL 32792

    $133,00040 Days on yellowkey   MLS ID: O6400425

    For Sale O6400425 - 7429 DANIEL WEBSTER DR #14 (#C), WINTER PARK, FL 32792 17 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1036
       Built: 1974
    Monthly Fee: $640
       Tax: $1,916 (2025)
    Community: The Colonies
    Spa: No

    Condo


    Estimated Monthly Payment: $1,528 (change assumption)
    Mortgage ($729) + Fees ($640) + Taxes in 2025 ($160)


    Taxes:$1,916

    Elementary School: Cheney Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 1695 LEE RD #C202, WINTER PARK, FL 32789

    $205,000455 Days on yellowkey   MLS ID: O6285607

    REDUCED by $5,000 (2.4%) on 04/23/2026

    For Sale O6285607 - 1695 LEE RD #C202, WINTER PARK, FL 32789 1 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1149
       Built: 1966   Tax: $2,126 (2024)
    Community: Waterfall Cove At Winter Park
    Condo


    Estimated Monthly Payment: $1,300 (change assumption)
    Mortgage ($1,123) + Taxes in 2024 ($177)


    Taxes:$2,126

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 802 HAMILTON PLACE CT, WINTER PARK, FL 32789

    $1,349,00046 Days on yellowkey   MLS ID: O6398373

    For Sale O6398373 - 802 HAMILTON PLACE CT, WINTER PARK, FL 32789 37 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2843
       Built: 2018
    Monthly Fee: $142
       Tax: $9,300 (2025)
    Community: Hamilton Place
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $8,309 (change assumption)
    Mortgage ($7,392) + Fees ($142) + Taxes in 2025 ($775)


    Taxes:$9,300

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 1751 GOODRICH AVE, WINTER PARK, FL 32789

    $1,425,000124 Days on yellowkey   MLS ID: O6377936

    REDUCED by $50,000 (3.4%) on 04/23/2026

    For Sale O6377936 - 1751 GOODRICH AVE, WINTER PARK, FL 32789 50 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2170
       Built: 2016   Tax: $9,263 (2024)
    Community: Sylvan Heights
    Single Family


    Estimated Monthly Payment: $8,580 (change assumption)
    Mortgage ($7,808) + Taxes in 2024 ($772)


    Taxes:$9,263

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Glenridge Middle


  • 2305 COLDSTREAM DRIVE, WINTER PARK, FL 32792

    $1,825,00063 Days on yellowkey   MLS ID: O6393049

    1 Days Off yellowkey (back on 4/23/2026)

    For Sale O6393049 - 2305 COLDSTREAM DRIVE, WINTER PARK, FL 32792 23 photos

    Bed: 5   Bath: 5.5   Gar: 2
    Liv Area Sq Ft: 3655
       Built: 2026   Tax: $7,014 (2025)
    Community: Brookshire Heights
    Single Family


    Estimated Monthly Payment: $10,584 (change assumption)
    Mortgage ($10,000) + Taxes in 2025 ($585)


    Taxes:$7,014

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 2713 EASTERN PKWY, WINTER PARK, FL 32789

    $670,00053 Days on yellowkey   MLS ID: O6398076

    0 Days Off yellowkey (back on 4/22/2026)

    For Sale O6398076 - 2713 EASTERN PKWY, WINTER PARK, FL 32789 44 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1304
       Built: 1988   Tax: $2,713 (2025)
    Community: Parklando
    Single Family


    Estimated Monthly Payment: $3,897 (change assumption)
    Mortgage ($3,671) + Taxes in 2025 ($226)


    Taxes:$2,713

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 225 LEWFIELD CIR #225, WINTER PARK, FL 32792

    $220,000364 Days on yellowkey   MLS ID: O6314817

    For Sale O6314817 - 225 LEWFIELD CIR #225, WINTER PARK, FL 32792 33 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 953
       Built: 1973
    Monthly Fee: $465
       Tax: $1,020 (2024)
    Community: Stratford A Winter Park Condo
    Condo


    Estimated Monthly Payment: $1,755 (change assumption)
    Mortgage ($1,205) + Fees ($465) + Taxes in 2024 ($85)


    Taxes:$1,020

    Elementary School: English Estates Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 2401 SUN VALLEY CIR #2401, WINTER PARK, FL 32792

    $265,00069 Days on yellowkey   MLS ID: S5146437

    REDUCED by $20,000 (7.0%) on 04/21/2026

    For Sale S5146437 - 2401 SUN VALLEY CIR #2401, WINTER PARK, FL 32792 26 photos

    Bed: 2   Bath: 2.5
    Liv Area Sq Ft: 1495
       Built: 1984   Tax: $3,702 (2024)
    Community: Cedarwood Village 1
    Condo


    Estimated Monthly Payment: $1,761 (change assumption)
    Mortgage ($1,452) + Taxes in 2024 ($308)


    Taxes:$3,702

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 1792 CHILEAN LN, WINTER PARK, FL 32792

    $325,000131 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


  • 1849 VIBURNUM LN, WINTER PARK, FL 32792

    $425,000299 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


  • 744 CORNWALL RD, WINTER PARK, FL 32792

    $695,000305 Days on yellowkey   MLS ID: O6332168

    REDUCED by $20,000 (2.8%) on 04/15/2026

    For Sale O6332168 - 744 CORNWALL RD, WINTER PARK, FL 32792 59 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1968
       Built: 1968   Tax: $5,359 (2024)
    Community: Winter Park Pines
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,255 (change assumption)
    Mortgage ($3,808) + Taxes in 2024 ($447)


    Taxes:$5,359

    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.