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 - 449 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:
  • 1813 HARLAND PARK DR, WINTER PARK, FL 32789

    $1,875,00034 Days on yellowkey   MLS ID: O6403483

    REDUCED by $120,000 (6.0%) on 05/28/2026

    For Sale O6403483 - 1813 HARLAND PARK DR, WINTER PARK, FL 32789 59 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3551
       Built: 2013
    Monthly Fee: $268
       Tax: $23,539 (2025)
    Community: Windsong - Knowles Place
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $12,503 (change assumption)
    Mortgage ($10,274) + Fees ($268) + Taxes in 2025 ($1,962)


    Taxes:$23,539

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 5275 PINE LILY CIR, WINTER PARK, FL 32792

    $665,000125 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


  • 2823 WRIGHT AVE, WINTER PARK, FL 32789

    $899,90083 Days on yellowkey   MLS ID: O6390670

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

    REDUCED by $30,000 (3.2%) on 05/07/2026

    For Sale O6390670 - 2823 WRIGHT AVE, WINTER PARK, FL 32789 19 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1536
       Built: 1958   Tax: $9,119 (2025)
    Community: Lake Forest Park
    Single Family


    Estimated Monthly Payment: $5,691 (change assumption)
    Mortgage ($4,931) + Taxes in 2025 ($760)


    Taxes:$9,119

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 5503 ALBERT DR, WINTER PARK, FL 32792

    $405,0001 Day on yellowkey   MLS ID: S5151098

    For Sale S5151098 - 5503 ALBERT DR, WINTER PARK, FL 32792 57 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1366
       Built: 1978   Tax: $4,123 (2025)
    Community: Howell Branch Woods
    Single Family


    Estimated Monthly Payment: $2,563 (change assumption)
    Mortgage ($2,219) + Taxes in 2025 ($344)


    Taxes:$4,123

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1510 MILLER AVE, WINTER PARK, FL 32789

    $1,599,900240 Days on yellowkey   MLS ID: O6350503

    REDUCED by $35,000 (2.1%) on 05/13/2026

    For Sale O6350503 - 1510 MILLER AVE, WINTER PARK, FL 32789 70 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3252
       Built: 2026   Tax: $3,573 (2025)
    Community: Lawndale
    Single Family


    Estimated Monthly Payment: $9,064 (change assumption)
    Mortgage ($8,766) + Taxes in 2025 ($298)


    Taxes:$3,573

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park Middle


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

    $114,000176 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


  • 1695 LEE RD #D211, WINTER PARK, FL 32789

    $114,00057 Days on yellowkey   MLS ID: O6396190

    For Sale O6396190 - 1695 LEE RD #D211, WINTER PARK, FL 32789 28 photos

    Bed: 2   Bath: 1.0
    Liv Area Sq Ft: 881
       Built: 1966   Tax: $2,051 (2025)
    Community: Waterfall Cove/Winter Park
    Condo


    Estimated Monthly Payment: $796 (change assumption)
    Mortgage ($625) + Taxes in 2025 ($171)


    Taxes:$2,051

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1250 FORMOSA AVE, WINTER PARK, FL 32789

    $560,0001 Day on yellowkey   MLS ID: O6412954

    For Sale O6412954 - 1250 FORMOSA AVE, WINTER PARK, FL 32789 37 photos

    Bed: 3   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 1937
       Built: 2022
    Monthly Fee: $252
       Tax: $8,328 (2025)
    Community: Urban Green 12
    Townhouse


    Estimated Monthly Payment: $4,014 (change assumption)
    Mortgage ($3,068) + Fees ($252) + Taxes in 2025 ($694)


    Taxes:$8,328

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1920 HEATHWOOD DR, WINTER PARK, FL 32792

    $370,00071 Days on yellowkey   MLS ID: O6393303

    For Sale O6393303 - 1920 HEATHWOOD DR, WINTER PARK, FL 32792 37 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1978
       Built: 1980   Tax: $4,895 (2025)
    Community: Cedar Ridge Unit 1
    Single Family


    Estimated Monthly Payment: $2,435 (change assumption)
    Mortgage ($2,027) + Taxes in 2025 ($408)


    Taxes:$4,895

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


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

    $1,899,90044 Days on yellowkey   MLS ID: O6400228

    REDUCED by $50,100 (2.6%) on 06/03/2026

    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: $11,658 (change assumption)
    Mortgage ($10,410) + 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


  • 2648 GALLIANO CIR, WINTER PARK, FL 32792

    $355,000100 Days on yellowkey   MLS ID: S5144547

    For Sale S5144547 - 2648 GALLIANO CIR, WINTER PARK, FL 32792 39 photos

    Bed: 2   Bath: 2.5   Gar: 1
    Liv Area Sq Ft: 1550
       Built: 2004
    Monthly Fee: $175
       Tax: $4,736 (2024)
    Community: Vistas At Lake Howell
    Single Family


    Estimated Monthly Payment: $2,515 (change assumption)
    Mortgage ($1,945) + Fees ($175) + Taxes in 2024 ($395)


    Taxes:$4,736

    Elementary School: Sterling Park Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 1351 MAGNOLIA AVE, WINTER PARK, FL 32789

    $3,100,00034 Days on yellowkey   MLS ID: O6404105

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

    For Sale O6404105 - 1351 MAGNOLIA AVE, WINTER PARK, FL 32789 1 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3460
       Built: 2026   Tax: $9,720 (2025)
    Community: Lake Knowles Terrace Add 02
    Single Family


    Estimated Monthly Payment: $17,796 (change assumption)
    Mortgage ($16,986) + Taxes in 2025 ($810)


    Taxes:$9,720

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 240 ORANGE TERRACE DR, WINTER PARK, FL 32789

    $479,900301 Days on yellowkey   MLS ID: O6330690

    REDUCED by $100 (0.0%) on 06/03/2026

    For Sale O6330690 - 240 ORANGE TERRACE DR, WINTER PARK, FL 32789 32 photos

    Bed: 4   Bath: 2.0
    Liv Area Sq Ft: 1718
       Built: 1955   Tax: $6,210 (2024)
    Community: Orange Terrace
    Single Family


    Estimated Monthly Payment: $3,147 (change assumption)
    Mortgage ($2,630) + Taxes in 2024 ($518)


    Taxes:$6,210

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2024

    Middle School: Robinswood Middle


  • 1618 INDIANA AVE, WINTER PARK, FL 32789

    $675,00052 Days on yellowkey   MLS ID: O6398673

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

    REDUCED by $10,000 (1.5%) on 05/08/2026

    For Sale O6398673 - 1618 INDIANA AVE, WINTER PARK, FL 32789 31 photos

    Bed: 4   Bath: 0.0
    Liv Area Sq Ft: 1604
       Built: 1963   Tax: $5,477 (2025)
    Community: Lawndale
    Apartment


    Estimated Monthly Payment: $4,155 (change assumption)
    Mortgage ($3,699) + Taxes in 2025 ($456)


    Taxes:$5,477

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1437 MILLER AVE, WINTER PARK, FL 32789

    $750,00035 Days on yellowkey   MLS ID: O6403858

    1 Days Off yellowkey (back on 5/3/2026)

    For Sale O6403858 - 1437 MILLER AVE, WINTER PARK, FL 32789 1 photos

    Bed: 5   Bath: 4.0
    Liv Area Sq Ft: 2150
       Built: 1932   Tax: $6,987 (2025)
    Community: Lawndale
    Single Family


    Estimated Monthly Payment: $4,692 (change assumption)
    Mortgage ($4,109) + Taxes in 2025 ($582)


    Taxes:$6,987

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1082 WILDMEADOW RUN, WINTER PARK, FL 32792

    $650,00014 Days on yellowkey   MLS ID: O6408825

    For Sale O6408825 - 1082 WILDMEADOW RUN, WINTER PARK, FL 32792 40 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1770
       Built: 2021
    Monthly Fee: $170
       Tax: $5,154 (2025)
    Community: Meadows At Hawks Crest
    Single Family


    Estimated Monthly Payment: $4,161 (change assumption)
    Mortgage ($3,562) + Fees ($170) + Taxes in 2025 ($430)


    Taxes:$5,154

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 1651 WESTCHESTER AVE, WINTER PARK, FL 32789

    $1,175,00062 Days on yellowkey   MLS ID: O6384358

    REDUCED by $100,000 (7.8%) on 06/01/2026

    For Sale O6384358 - 1651 WESTCHESTER AVE, WINTER PARK, FL 32789 48 photos

    Bed: 3   Bath: 2.5   Gar: 1
    Liv Area Sq Ft: 2426
       Built: 1938   Tax: $10,973 (2025)
    Community: Orwin Manor Westminster Sec
    Single Family


    Estimated Monthly Payment: $7,353 (change assumption)
    Mortgage ($6,438) + Taxes in 2025 ($914)


    Taxes:$10,973

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park Middle


  • 1260 ALABAMA DR, WINTER PARK, FL 32789

    $6,900,00093 Days on yellowkey   MLS ID: O6387200

    For Sale O6387200 - 1260 ALABAMA DR, WINTER PARK, FL 32789 58 photos

    Bed: 6   Bath: 6.0   Gar: 3
    Liv Area Sq Ft: 6396
       Built: 1991   Tax: $59,749 (2025)
    Community: J Kronenberger Sub
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $42,786 (change assumption)
    Mortgage ($37,807) + Taxes in 2025 ($4,979)


    Taxes:$59,749

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 7577 DOCKSIDE ST, WINTER PARK, FL 32792

    $370,0001 Day on yellowkey   MLS ID: O6412514

    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: $2,338 (change assumption)
    Mortgage ($2,027) + Taxes in 2025 ($310)


    Taxes:$3,722

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 2054 EASTBROOK BLVD, WINTER PARK, FL 32792

    $500,0002 Days on yellowkey   MLS ID: V4949389

    For Sale V4949389 - 2054 EASTBROOK BLVD, WINTER PARK, FL 32792 2 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2031
       Built: 1966   Tax: $5,054 (2025)
    Community: Eastbrook Sub Unit 8
    Single Family


    Estimated Monthly Payment: $3,161 (change assumption)
    Mortgage ($2,740) + Taxes in 2025 ($421)


    Taxes:$5,054

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2025

    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.