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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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  • 1500 GAY RD #24B, WINTER PARK, FL 32789

    $259,500245 Days on yellowkey   MLS ID: O6348568

    REDUCED by $2,000 (0.8%) on 05/15/2026

    For Sale O6348568 - 1500 GAY RD #24B, WINTER PARK, FL 32789 23 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1026
       Built: 1972   Tax: $1,271 (2024)
    Community: Chateaux Du Lac
    Spa: No

    Condo


    Estimated Monthly Payment: $1,528 (change assumption)
    Mortgage ($1,422) + Taxes in 2024 ($106)


    Taxes:$1,271

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 1260 ALABAMA DR, WINTER PARK, FL 32789

    $6,900,00091 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


  • 106 S INTERLACHEN AVE #118, WINTER PARK, FL 32789

    $1,360,000116 Days on yellowkey   MLS ID: O6380506

    REDUCED by $35,000 (2.5%) on 05/14/2026

    For Sale O6380506 - 106 S INTERLACHEN AVE #118, WINTER PARK, FL 32789 55 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1834
       Built: 1971   Tax: $9,767 (2025)
    Community: Cloisters Condo
    Condo


    Estimated Monthly Payment: $8,266 (change assumption)
    Mortgage ($7,452) + Taxes in 2025 ($814)


    Taxes:$9,767

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 1761 LEGION DR, WINTER PARK, FL 32789

    $3,270,000355 Days on yellowkey   MLS ID: O6302616

    REDUCED by $25,000 (0.8%) on 04/15/2026

    For Sale O6302616 - 1761 LEGION DR, WINTER PARK, FL 32789 54 photos

    Bed: 5   Bath: 5.5   Gar: 3
    Liv Area Sq Ft: 4955
       Built: 2017   Tax: $22,139 (2024)
    Community: Green Oaks Rep 02
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $19,762 (change assumption)
    Mortgage ($17,917) + Taxes in 2024 ($1,845)


    Taxes:$22,139

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Maitland Middle


  • 141 GLENRIDGE WAY, WINTER PARK, FL 32789

    $3,250,00067 Days on yellowkey   MLS ID: O6393616

    1 Days Off yellowkey (back on 5/16/2026)

    For Sale O6393616 - 141 GLENRIDGE WAY, WINTER PARK, FL 32789 66 photos

    Bed: 5   Bath: 4.5   Gar: 3
    Liv Area Sq Ft: 5243
       Built: 2008   Tax: $40,155 (2025)
    Community: Charmont
    Single Family


    Estimated Monthly Payment: $21,154 (change assumption)
    Mortgage ($17,808) + Taxes in 2025 ($3,346)


    Taxes:$40,155

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 266 W LYMAN AVE, WINTER PARK, FL 32789

    $1,375,00024 Days on yellowkey   MLS ID: O6406526

    2 Days Off yellowkey (back on 5/15/2026)

    For Sale O6406526 - 266 W LYMAN AVE, WINTER PARK, FL 32789 37 photos

    Bed: 3   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2000
       Built: 2014
    Monthly Fee: $568
       Tax: $11,410 (2024)
    Community: Lyman Ave Villas 1
    Spa: No

    Townhouse


    Estimated Monthly Payment: $9,053 (change assumption)
    Mortgage ($7,534) + Fees ($568) + Taxes in 2024 ($951)


    Taxes:$11,410

    Elementary School: None

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Audubon Park K-8


  • 2500 LEE RD #232, WINTER PARK, FL 32789

    $164,90027 Days on yellowkey   MLS ID: O6404916

    For Sale O6404916 - 2500 LEE RD #232, WINTER PARK, FL 32789 26 photos

    Bed: 1   Bath: 1.0
    Liv Area Sq Ft: 645
       Built: 1969
    Monthly Fee: $292
       Tax: $2,216 (2025)
    Community: Lakeside Manor Apts Condo
    Condo


    Estimated Monthly Payment: $1,380 (change assumption)
    Mortgage ($904) + Fees ($292) + Taxes in 2025 ($185)


    Taxes:$2,216

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1900 WINTER PARK RD, WINTER PARK, FL 32789

    $849,90036 Days on yellowkey   MLS ID: O6402566

    REDUCED by $91,100 (9.7%) on 05/15/2026

    For Sale O6402566 - 1900 WINTER PARK RD, WINTER PARK, FL 32789 22 photos

    Bed: 4   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1511
       Built: 1947   Tax: $2,803 (2025)
    Community: Charmont
    Single Family


    Estimated Monthly Payment: $4,890 (change assumption)
    Mortgage ($4,657) + Taxes in 2025 ($234)


    Taxes:$2,803

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 423 OLOLU DR, WINTER PARK, FL 32789

    $549,000145 Days on yellowkey   MLS ID: O6369976

    REDUCED by $40,000 (6.8%) on 05/14/2026

    For Sale O6369976 - 423 OLOLU DR, WINTER PARK, FL 32789 51 photos

    Bed: 3   Bath: 3.0
    Liv Area Sq Ft: 1920
       Built: 1981   Tax: $4,030 (2024)
    Community: Killarney Circle
    Single Family


    Estimated Monthly Payment: $3,344 (change assumption)
    Mortgage ($3,008) + Taxes in 2024 ($336)


    Taxes:$4,030

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2024

    Middle School: College Park Middle


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

    $175,000417 Days on yellowkey   MLS ID: O6297570

    REDUCED by $5,000 (2.8%) on 05/14/2026

    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: $1,517 (change assumption)
    Mortgage ($959) + 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


  • WINTER PARK, FL 32789

    $1,249,90021 Days on yellowkey   MLS ID: O6406381

    For Sale O6406381 - WINTER PARK, FL 32789 25 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2936
       Built: 2026   Tax: $3,539 (2025)
    Community: Lawndale
    Single Family


    Estimated Monthly Payment: $7,144 (change assumption)
    Mortgage ($6,849) + Taxes in 2025 ($295)


    Taxes:$3,539

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2600 EUSTON RD, WINTER PARK, FL 32789

    $630,00053 Days on yellowkey   MLS ID: O6397890

    For Sale O6397890 - 2600 EUSTON RD, WINTER PARK, FL 32789 36 photos

    Bed: 6   Bath: 3.0
    Liv Area Sq Ft: 3145
       Built: 1951   Tax: $7,446 (2024)
    Community: Glencoe Sub
    Single Family


    Estimated Monthly Payment: $4,072 (change assumption)
    Mortgage ($3,452) + Taxes in 2024 ($620)


    Taxes:$7,446

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 1903 N PARK AVE, WINTER PARK, FL 32789

    $1,695,000132 Days on yellowkey   MLS ID: O6375766

    REDUCED by $100,000 (5.6%) on 05/14/2026

    For Sale O6375766 - 1903 N PARK AVE, WINTER PARK, FL 32789 42 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 2807
       Built: 2020   Tax: $17,232 (2025)
    Community: Twin Acres
    Single Family


    Estimated Monthly Payment: $10,723 (change assumption)
    Mortgage ($9,287) + Taxes in 2025 ($1,436)


    Taxes:$17,232

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 1523 MILLER AVE, WINTER PARK, FL 32789

    $1,499,999146 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

    $399,99925 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

    $170,000117 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

    $1,395,00022 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

    $695,000132 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

    $6,950,000113 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

    $524,00029 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




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.