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Homes For Sale in Winter Park 32789 - 234 homes

32789 zip code is located in Orange County, Florida. Find homes for sale in Winter Park 32789 from the Multiple Listing Service (MLS). Our REALTORS® can assist you in your search for Winter Park 32789 homes for sale.

Location: Winter Park , 32789

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  • 1523 MILLER AVE, WINTER PARK, FL 32789

    $1,499,999148 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


  • 721 DUNBAR ST, WINTER PARK, FL 32789

    $399,99927 Days on yellowkey   MLS ID: O6405338

    1 Days Off yellowkey (back on 5/13/2026)

    For Sale O6405338 - 721 DUNBAR ST, WINTER PARK, FL 32789 36 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1018
       Built: 1950   Tax: $5,267 (2025)
    Community: Carver Town
    Single Family


    Estimated Monthly Payment: $2,631 (change assumption)
    Mortgage ($2,192) + Taxes in 2025 ($439)


    Taxes:$5,267

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 1500 GAY RD #5, WINTER PARK, FL 32789

    $170,000119 Days on yellowkey   MLS ID: S5143213

    0 Days Off yellowkey (back on 5/13/2026)

    REDUCED by $15,000 (8.1%) on 04/29/2026

    For Sale S5143213 - 1500 GAY RD #5, WINTER PARK, FL 32789 17 photos

    Bed: 1   Bath: 1.0
    Liv Area Sq Ft: 732
       Built: 1972   Tax: $2,098 (2024)
    Community: Chateaux Du Lac
    Condo


    Estimated Monthly Payment: $1,106 (change assumption)
    Mortgage ($931) + Taxes in 2024 ($175)


    Taxes:$2,098

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 433 CAROLINA AVE, WINTER PARK, FL 32789

    $1,395,00024 Days on yellowkey   MLS ID: O6406911

    0 Days Off yellowkey (back on 5/11/2026)

    For Sale O6406911 - 433 CAROLINA AVE, WINTER PARK, FL 32789 1 photos

    Bed: 5   Bath: 3.5
    Liv Area Sq Ft: 2771
       Built: 2018   Tax: $16,685 (2025)
    Community: Winter Park
    Single Family


    Estimated Monthly Payment: $9,034 (change assumption)
    Mortgage ($7,644) + Taxes in 2025 ($1,390)


    Taxes:$16,685

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 432 W SWOOPE AVE, WINTER PARK, FL 32789

    $695,000134 Days on yellowkey   MLS ID: O6375719

    For Sale O6375719 - 432 W SWOOPE AVE, WINTER PARK, FL 32789 20 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2317
       Built: 2014
    Monthly Fee: $463
       Tax: $9,138 (2025)
    Community: Swoope Park
    Townhouse


    Estimated Monthly Payment: $5,033 (change assumption)
    Mortgage ($3,808) + Fees ($463) + Taxes in 2025 ($761)


    Taxes:$9,138

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 40 PALMER AVE, WINTER PARK, FL 32789

    $6,950,000115 Days on yellowkey   MLS ID: O6380444

    For Sale O6380444 - 40 PALMER AVE, WINTER PARK, FL 32789 17 photos

    Bed: 5   Bath: 5.5   Gar: 4
    Liv Area Sq Ft: 5905
       Built: 2026   Tax: $12,774 (2024)
    Community: Robert Dhu Macdonald Park
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $39,146 (change assumption)
    Mortgage ($38,081) + Taxes in 2024 ($1,065)


    Taxes:$12,774

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Maitland Middle


  • 1745 INDIANA AVE #J, WINTER PARK, FL 32789

    $524,00031 Days on yellowkey   MLS ID: O6402920

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

    For Sale O6402920 - 1745 INDIANA AVE #J, WINTER PARK, FL 32789 22 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1616
       Built: 2008
    Monthly Fee: $464
       Tax: $6,444 (2025)
    Community: La Casas De Indiana
    Condo


    Estimated Monthly Payment: $3,872 (change assumption)
    Mortgage ($2,871) + Fees ($464) + Taxes in 2025 ($537)


    Taxes:$6,444

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park Middle


  • 250 CORTLAND AVE, WINTER PARK, FL 32789

    $950,00062 Days on yellowkey   MLS ID: O6395137

    For Sale O6395137 - 250 CORTLAND AVE, WINTER PARK, FL 32789 46 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2114
       Built: 1981   Tax: $4,370 (2024)
    Community: Cortland Park
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $5,569 (change assumption)
    Mortgage ($5,205) + Taxes in 2024 ($364)


    Taxes:$4,370

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Glenridge Middle


  • 2408 LAFAYETTE AVE, WINTER PARK, FL 32789

    $1,495,00055 Days on yellowkey   MLS ID: O6397694

    For Sale O6397694 - 2408 LAFAYETTE AVE, WINTER PARK, FL 32789 31 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2838
       Built: 2024   Tax: $3,770 (2024)
    Community: Winter Park Village
    Spa: No

    Single Family


    Estimated Monthly Payment: $8,506 (change assumption)
    Mortgage ($8,192) + Taxes in 2024 ($314)


    Taxes:$3,770

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Maitland Middle


  • 1836 GRINNELL TER, WINTER PARK, FL 32789

    $999,000118 Days on yellowkey   MLS ID: O6380457

    REDUCED by $51,000 (4.9%) on 05/06/2026

    For Sale O6380457 - 1836 GRINNELL TER, WINTER PARK, FL 32789 24 photos

    Bed: 3   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1907
       Built: 1995   Tax: $11,979 (2025)
    Community: Lake Virginia
    Single Family


    Estimated Monthly Payment: $6,472 (change assumption)
    Mortgage ($5,474) + Taxes in 2025 ($998)


    Taxes:$11,979

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 541 W CANTON AVE, WINTER PARK, FL 32789

    $2,800,00075 Days on yellowkey   MLS ID: O6389829

    For Sale O6389829 - 541 W CANTON AVE, WINTER PARK, FL 32789 51 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3553
       Built: 2024   Tax: $4,692 (2024)
    Community: Winter Park
    Single Family


    Estimated Monthly Payment: $15,733 (change assumption)
    Mortgage ($15,342) + Taxes in 2024 ($391)


    Taxes:$4,692

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Maitland Middle


  • 525 OLOLU DR, WINTER PARK, FL 32789

    $515,00035 Days on yellowkey   MLS ID: S5148431

    For Sale S5148431 - 525 OLOLU DR, WINTER PARK, FL 32789 42 photos

    Bed: 3   Bath: 3.0
    Liv Area Sq Ft: 1786
       Built: 1966   Tax: $2,249 (2025)
    Community: Killarney Circle
    Single Family


    Estimated Monthly Payment: $3,009 (change assumption)
    Mortgage ($2,822) + Taxes in 2025 ($187)


    Taxes:$2,249

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


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

    $4,200,00027 Days on yellowkey   MLS ID: O6406437

    For Sale O6406437 - 141 W LAKE SUE AVE, WINTER PARK, FL 32789 5 photos

    Bed: 5   Bath: 6.0   Gar: 4
    Liv Area Sq Ft: 5500
       Built: 2027   Tax: $11,049 (2025)
    Community: Virginia Heights
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $23,934 (change assumption)
    Mortgage ($23,013) + Taxes in 2025 ($921)


    Taxes:$11,049

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 408 HOLT AVE, WINTER PARK, FL 32789

    $745,00027 Days on yellowkey   MLS ID: O6405857

    For Sale O6405857 - 408 HOLT AVE, WINTER PARK, FL 32789 34 photos

    Bed: 2   Bath: 0.0
    Liv Area Sq Ft: 1440
       Built: 1942   Tax: $5,765 (2025)
    Community: Trotters Rep
    Spa: No

    Apartment


    Estimated Monthly Payment: $4,562 (change assumption)
    Mortgage ($4,082) + Taxes in 2025 ($480)


    Taxes:$5,765

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 1723 CHESTNUT AVE, WINTER PARK, FL 32789

    $1,125,00028 Days on yellowkey   MLS ID: O6402563

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

    For Sale O6402563 - 1723 CHESTNUT AVE, WINTER PARK, FL 32789 40 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2608
       Built: 1962   Tax: $4,880 (2025)
    Community: Conwill Estates
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $6,571 (change assumption)
    Mortgage ($6,164) + Taxes in 2025 ($407)


    Taxes:$4,880

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 1550 NORFOLK AVE, WINTER PARK, FL 32789

    $725,00035 Days on yellowkey   MLS ID: O6402927

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

    For Sale O6402927 - 1550 NORFOLK AVE, WINTER PARK, FL 32789 29 photos

    Bed: 3   Bath: 2.0   Gar: 3
    Liv Area Sq Ft: 1762
       Built: 1949   Tax: $3,951 (2025)
    Community: Orwin Manor Stratford Sec
    Single Family


    Estimated Monthly Payment: $4,302 (change assumption)
    Mortgage ($3,973) + Taxes in 2025 ($329)


    Taxes:$3,951

    Elementary School: Princeton Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park Middle


  • 1405 MILLER AVE, WINTER PARK, FL 32789

    $899,00094 Days on yellowkey   MLS ID: O6386405

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

    REDUCED by $51,000 (5.4%) on 04/22/2026

    For Sale O6386405 - 1405 MILLER AVE, WINTER PARK, FL 32789 46 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1884
       Built: 2023
    Monthly Fee: $200
       Tax: $8,200 (2025)
    Community: H Vanwies Sub
    Townhouse


    Estimated Monthly Payment: $5,809 (change assumption)
    Mortgage ($4,926) + Fees ($200) + Taxes in 2025 ($683)


    Taxes:$8,200

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park Middle


  • 2550 VENETIAN WAY, WINTER PARK, FL 32789

    $2,399,00090 Days on yellowkey   MLS ID: O6388219

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

    REDUCED by $51,000 (2.1%) on 04/23/2026

    For Sale O6388219 - 2550 VENETIAN WAY, WINTER PARK, FL 32789 65 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 5051
       Built: 2008   Tax: $16,724 (2024)
    Community: Maitland Shores First Add
    Single Family


    Estimated Monthly Payment: $14,539 (change assumption)
    Mortgage ($13,145) + Taxes in 2024 ($1,394)


    Taxes:$16,724

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Maitland Middle


  • 640 ARJAY WAY, WINTER PARK, FL 32789

    $1,890,000135 Days on yellowkey   MLS ID: O6372947

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

    REDUCED by $35,000 (1.8%) on 04/22/2026

    For Sale O6372947 - 640 ARJAY WAY, WINTER PARK, FL 32789 46 photos

    Bed: 5   Bath: 4.0   Gar: 3
    Liv Area Sq Ft: 3953
       Built: 1958   Tax: $11,586 (2024)
    Community: Timberlane Shores
    Single Family


    Estimated Monthly Payment: $11,321 (change assumption)
    Mortgage ($10,356) + Taxes in 2024 ($965)


    Taxes:$11,586

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Audubon Park K-8


  • 1701 GOODRICH AVE, WINTER PARK, FL 32789

    $739,00045 Days on yellowkey   MLS ID: O6400278

    For Sale O6400278 - 1701 GOODRICH AVE, WINTER PARK, FL 32789 44 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1528
       Built: 1950   Tax: $5,023 (2025)
    Community: Sylvan Hgts
    Single Family


    Estimated Monthly Payment: $4,468 (change assumption)
    Mortgage ($4,049) + Taxes in 2025 ($419)


    Taxes:$5,023

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle




Why Bother Searching Elsewhere for 32789 Homes for Sale and Other Winter Park Real Estate?

32789, Winter Park home, townhome, condo, villa, and other listing rental 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 the 32789 zip code. You can use our website to view Multiple Listing Service (MLS) data on 32789, 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 32789, 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.