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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

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  • 1600 ALABAMA DR #402, WINTER PARK, FL 32789

    $1,250,00014 Days on yellowkey   MLS ID: O6413153

    For Sale O6413153 - 1600 ALABAMA DR #402, WINTER PARK, FL 32789 38 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1574
       Built: 1981   Tax: $4,206 (2025)
    Community: Alabama Condo
    Condo


    Estimated Monthly Payment: $7,200 (change assumption)
    Mortgage ($6,849) + Taxes in 2025 ($351)


    Taxes:$4,206

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 4772 TANGERINE AVE #4772, WINTER PARK, FL 32792

    $199,00040 Days on yellowkey   MLS ID: O6405042

    0 Days Off yellowkey (back on 6/8/2026)

    For Sale O6405042 - 4772 TANGERINE AVE #4772, WINTER PARK, FL 32792 25 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1058
       Built: 1973   Tax: $2,825 (2025)
    Community: Wrenwood Condo
    Condo


    Estimated Monthly Payment: $1,326 (change assumption)
    Mortgage ($1,090) + Taxes in 2025 ($235)


    Taxes:$2,825

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 1398 GROVE TER, WINTER PARK, FL 32789

    $2,195,00062 Days on yellowkey   MLS ID: O6399698

    For Sale O6399698 - 1398 GROVE TER, WINTER PARK, FL 32789 58 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3450
       Built: 2004   Tax: $24,548 (2025)
    Community: Sylvan Lake Shores
    Spa: No

    Single Family


    Estimated Monthly Payment: $14,073 (change assumption)
    Mortgage ($12,027) + Taxes in 2025 ($2,046)


    Taxes:$24,548

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


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

    $1,100,00020 Days on yellowkey   MLS ID: O6411621

    REDUCED by $100,000 (8.3%) on 06/08/2026

    For Sale O6411621 - 241 W LAKE SUE AVE, WINTER PARK, FL 32789 60 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2304
       Built: 1950   Tax: $14,823 (2025)
    Community: Virginia Heights
    Single Family


    Estimated Monthly Payment: $7,262 (change assumption)
    Mortgage ($6,027) + Taxes in 2025 ($1,235)


    Taxes:$14,823

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 800 JUANITA RAEL, WINTER PARK, FL 32789

    $2,300,00070 Days on yellowkey   MLS ID: O6396611

    5 Days Off yellowkey (back on 6/8/2026)

    For Sale O6396611 - 800 JUANITA RAEL, WINTER PARK, FL 32789 37 photos

    Bed: 5   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 4021
       Built: 1961   Tax: $9,773 (2025)
    Community: Green Oaks Rep 02
    Spa: No

    Single Family


    Estimated Monthly Payment: $13,417 (change assumption)
    Mortgage ($12,602) + Taxes in 2025 ($814)


    Taxes:$9,773

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 1624 BARCELONA WAY, WINTER PARK, FL 32789

    $2,235,000209 Days on yellowkey   MLS ID: O6362124

    REDUCED by $15,000 (0.7%) on 05/30/2026

    For Sale O6362124 - 1624 BARCELONA WAY, WINTER PARK, FL 32789 62 photos

    Bed: 3   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 3818
       Built: 1972
    Monthly Fee: $87
       Tax: $12,501 (2024)
    Community: Sevilla
    Spa: No

    Single Family


    Estimated Monthly Payment: $13,375 (change assumption)
    Mortgage ($12,246) + Fees ($87) + Taxes in 2024 ($1,042)


    Taxes:$12,501

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Audubon Park K-8


  • 311 E MORSE BLVD #7-19, WINTER PARK, FL 32789

    $284,900170 Days on yellowkey   MLS ID: O6368912

    REDUCED by $5,000 (1.7%) on 05/21/2026

    For Sale O6368912 - 311 E MORSE BLVD #7-19, WINTER PARK, FL 32789 34 photos

    Bed: 1   Bath: 1.0
    Liv Area Sq Ft: 482
       Built: 1960
    Monthly Fee: $870
       Tax: $3,161 (2024)
    Community: Whispering Waters
    Condo


    Estimated Monthly Payment: $2,694 (change assumption)
    Mortgage ($1,561) + Fees ($870) + Taxes in 2024 ($263)


    Taxes:$3,161

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Audubon Park K-8


  • 3312 HEARTWOOD AVE, WINTER PARK, FL 32792

    $465,000242 Days on yellowkey   MLS ID: O6352582

    2 Days Off yellowkey (back on 6/8/2026)

    REDUCED by $19,000 (3.9%) on 04/08/2026

    For Sale O6352582 - 3312 HEARTWOOD AVE, WINTER PARK, FL 32792 36 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2878
       Built: 1983   Tax: $2,183 (2025)
    Community: Bel-Aire Pines
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,730 (change assumption)
    Mortgage ($2,548) + Taxes in 2025 ($182)


    Taxes:$2,183

    Elementary School: Aloma Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 1523 MILLER AVE, WINTER PARK, FL 32789

    $1,499,999161 Days on yellowkey   MLS ID: O6371649

    REDUCED by $50,001 (3.2%) on 05/14/2026

    For Sale O6371649 - 1523 MILLER AVE, WINTER PARK, FL 32789 65 photos

    Bed: 5   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 3164
       Built: 2026   Tax: $3,620 (2025)
    Community: Lawndale
    Single Family


    Estimated Monthly Payment: $8,521 (change assumption)
    Mortgage ($8,219) + Taxes in 2025 ($302)


    Taxes:$3,620

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park Middle


  • 1319 BESSMOR RD, WINTER PARK, FL 32789

    $589,00057 Days on yellowkey   MLS ID: O6400395

    REDUCED by $6,000 (1.0%) on 06/08/2026

    For Sale O6400395 - 1319 BESSMOR RD, WINTER PARK, FL 32789 13 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1126
       Built: 1956   Tax: $5,626 (2025)
    Community: Winter Park Village
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,696 (change assumption)
    Mortgage ($3,227) + Taxes in 2025 ($469)


    Taxes:$5,626

    Elementary School: Dream Lake Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 1052 MANCHESTER CIR, WINTER PARK, FL 32792

    $460,000144 Days on yellowkey   MLS ID: O6376260

    REDUCED by $10,000 (2.1%) on 05/28/2026

    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: $2,955 (change assumption)
    Mortgage ($2,520) + Taxes in 2025 ($435)


    Taxes:$5,216

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 4768 TANGERINE AVE #4768, WINTER PARK, FL 32792

    $179,000113 Days on yellowkey   MLS ID: S5144503

    REDUCED by $6,000 (3.2%) on 05/20/2026

    For Sale S5144503 - 4768 TANGERINE AVE #4768, WINTER PARK, FL 32792 17 photos

    Bed: 1   Bath: 1.0
    Liv Area Sq Ft: 753
       Built: 1973
    Monthly Fee: $280
       Tax: $1,479 (2024)
    Community: Wrenwood Condo
    Condo


    Estimated Monthly Payment: $1,384 (change assumption)
    Mortgage ($981) + Fees ($280) + Taxes in 2024 ($123)


    Taxes:$1,479

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 723 SYMONDS AVE, WINTER PARK, FL 32789

    $2,000,00020 Days on yellowkey   MLS ID: O6406823

    For Sale O6406823 - 723 SYMONDS AVE, WINTER PARK, FL 32789 50 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 3065
       Built: 2023   Tax: $15,884 (2025)
    Community: Horton Aaron
    Single Family


    Estimated Monthly Payment: $12,282 (change assumption)
    Mortgage ($10,959) + Taxes in 2025 ($1,324)


    Taxes:$15,884

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 622 PENN PL, WINTER PARK, FL 32789

    $1,895,00027 Days on yellowkey   MLS ID: TB8511228

    For Sale TB8511228 - 622 PENN PL, WINTER PARK, FL 32789 26 photos

    Bed: 3   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2767
       Built: 2001
    Monthly Fee: $222
       Tax: $12,624 (2025)
    Community: Pennsylvania Place Rep
    Single Family


    Estimated Monthly Payment: $11,657 (change assumption)
    Mortgage ($10,383) + Fees ($222) + Taxes in 2025 ($1,052)


    Taxes:$12,624

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 950 HANOVER AVE, WINTER PARK, FL 32789

    $460,00067 Days on yellowkey   MLS ID: O6398273

    REDUCED by $10,000 (2.1%) on 06/01/2026

    For Sale O6398273 - 950 HANOVER AVE, WINTER PARK, FL 32789 28 photos

    Bed: 3   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1606
       Built: 1956   Tax: $3,525 (2025)
    Community: Albert Lee Ridge 1St Add
    Single Family


    Estimated Monthly Payment: $2,814 (change assumption)
    Mortgage ($2,520) + Taxes in 2025 ($294)


    Taxes:$3,525

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1077 MINNESOTA AVE, WINTER PARK, FL 32789

    $1,395,00020 Days on yellowkey   MLS ID: O6411722

    For Sale O6411722 - 1077 MINNESOTA AVE, WINTER PARK, FL 32789 49 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 3046
       Built: 2025   Tax: $1,383 (2025)
    Community: Na
    Single Family


    Estimated Monthly Payment: $7,759 (change assumption)
    Mortgage ($7,644) + Taxes in 2025 ($115)


    Taxes:$1,383

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 193 LEWFIELD CIR, WINTER PARK, FL 32792

    $248,90022 Days on yellowkey   MLS ID: O6409075

    For Sale O6409075 - 193 LEWFIELD CIR, WINTER PARK, FL 32792 33 photos

    Bed: 2   Bath: 2.5
    Liv Area Sq Ft: 1300
       Built: 1973
    Monthly Fee: $533
       Tax: $2,286 (2025)
    Community: Stratford A Winter Park Condo
    Condo


    Estimated Monthly Payment: $2,087 (change assumption)
    Mortgage ($1,364) + Fees ($533) + Taxes in 2025 ($191)


    Taxes:$2,286

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 413 W MORSE BLVD, WINTER PARK, FL 32789

    $2,695,00011 Days on yellowkey   MLS ID: O6412134

    For Sale O6412134 - 413 W MORSE BLVD, WINTER PARK, FL 32789 28 photos

    Bed: 3   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3048
       Built: 2018
    Monthly Fee: $386
       Tax: $19,919 (2026)
    Community: Town Of Winter Park
    Townhouse


    Estimated Monthly Payment: $16,813 (change assumption)
    Mortgage ($14,767) + Fees ($386) + Taxes in 2026 ($1,660)


    Taxes:$19,919

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2026

    Middle School: Maitland Middle


  • 2648 GALLIANO CIR, WINTER PARK, FL 32792

    $355,000113 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


  • 121 STEFANIK RD, WINTER PARK, FL 32792

    $317,500238 Days on yellowkey   MLS ID: A4669103

    0 Days Off yellowkey (back on 6/7/2026)

    For Sale A4669103 - 121 STEFANIK RD, WINTER PARK, FL 32792 11 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1392
       Built: 1949   Tax: $3,581 (2024)
    Community: Slovak Village
    Single Family


    Estimated Monthly Payment: $2,038 (change assumption)
    Mortgage ($1,740) + Taxes in 2024 ($298)


    Taxes:$3,581

    Elementary School: None

    High School: None

    Tax Year: 2024

    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.