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Homes For Sale in Winter Park 32789 - 219 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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  • 1347 CHAPMAN CIR, WINTER PARK, FL 32789

    $1,395,00075 Days on yellowkey   MLS ID: O6408189

    0 Days Off yellowkey (back on 5/20/2026)

    For Sale O6408189 - 1347 CHAPMAN CIR, WINTER PARK, FL 32789 51 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2922
       Built: 2013
    Monthly Fee: $268
       Tax: $16,875 (2025)
    Community: Windsong Elizabeths Walk
    Spa: No

    Single Family


    Estimated Monthly Payment: $9,318 (change assumption)
    Mortgage ($7,644) + Fees ($268) + Taxes in 2025 ($1,406)


    Taxes:$16,875

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 266 W LYMAN AVE, WINTER PARK, FL 32789

    $1,375,00081 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


  • 1903 N PARK AVE, WINTER PARK, FL 32789

    $1,695,000189 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


  • 432 W SWOOPE AVE, WINTER PARK, FL 32789

    $695,000189 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


  • 408 HOLT AVE, WINTER PARK, FL 32789

    $745,00082 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


  • 2500 LEE RD #202, WINTER PARK, FL 32789

    $224,999538 Days on yellowkey   MLS ID: O6277579

    REDUCED by $10,000 (4.3%) on 04/28/2026

    For Sale O6277579 - 2500 LEE RD #202, WINTER PARK, FL 32789 52 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 956
       Built: 1969
    Monthly Fee: $432
       Tax: $2,327 (2025)
    Community: Lakeside Manor Condominium Association, Inc.
    Condo


    Estimated Monthly Payment: $1,859 (change assumption)
    Mortgage ($1,233) + Fees ($432) + Taxes in 2025 ($194)


    Taxes:$2,327

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park Middle


  • 150 DANA WAY, WINTER PARK, FL 32789

    $3,799,000124 Days on yellowkey   MLS ID: O6394012

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

    For Sale O6394012 - 150 DANA WAY, WINTER PARK, FL 32789 81 photos

    Bed: 5   Bath: 5.0   Gar: 2
    Liv Area Sq Ft: 4451
       Built: 2026   Tax: $14,010 (2025)
    Community: Charmont
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $21,983 (change assumption)
    Mortgage ($20,816) + Taxes in 2025 ($1,168)


    Taxes:$14,010

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 726/720 N PENNSYLVANIA AVE, WINTER PARK, FL 32789

    $1,185,99991 Days on yellowkey   MLS ID: O6402984

    For Sale O6402984 - 726/720 N PENNSYLVANIA AVE, WINTER PARK, FL 32789 37 photos

    Bed: 6   Bath: 0.0
    Liv Area Sq Ft: 2282
       Built: 2015   Tax: $5,170 (2025)
    Community: Morseland Sub
    Apartment


    Estimated Monthly Payment: $6,929 (change assumption)
    Mortgage ($6,498) + Taxes in 2025 ($431)


    Taxes:$5,170

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 632 COUNTRY CLUB DR, WINTER PARK, FL 32789

    $1,050,000641 Days on yellowkey   MLS ID: O6250417

    0 Days Off yellowkey (back on 9/29/2025)

    For Sale O6250417 - 632 COUNTRY CLUB DR, WINTER PARK, FL 32789 36 photos

    Bed: 3   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 2342
       Built: 1952   Tax: $4,638 (2023)
    Community: Lords Sub
    Spa: No

    Single Family


    Estimated Monthly Payment: $6,140 (change assumption)
    Mortgage ($5,753) + Taxes in 2023 ($387)


    Taxes:$4,638

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2023

    Middle School: College Park Middle


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

    $205,000512 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


  • 811 OVERSPIN DR, WINTER PARK, FL 32789

    $349,000104 Days on yellowkey   MLS ID: O6400009

    For Sale O6400009 - 811 OVERSPIN DR, WINTER PARK, FL 32789 9 photos

    Bed: 2   Bath: 1.0   Gar: 1
    Liv Area Sq Ft: 749
       Built: 1950   Tax: $3,998 (2025)
    Community: Dubsdread Heights
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,245 (change assumption)
    Mortgage ($1,912) + Taxes in 2025 ($333)


    Taxes:$3,998

    Elementary School: Princeton Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park Middle


  • 2612 ROXBURY RD, WINTER PARK, FL 32789

    $630,000230 Days on yellowkey   MLS ID: S5139410

    For Sale S5139410 - 2612 ROXBURY RD, WINTER PARK, FL 32789 37 photos

    Bed: 5   Bath: 0.0
    Liv Area Sq Ft: 2472
       Built: 1957   Tax: $6,425 (2024)
    Community: Glencoe Sub
    Single Family


    Estimated Monthly Payment: $3,987 (change assumption)
    Mortgage ($3,452) + Taxes in 2024 ($535)


    Taxes:$6,425

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2024

    Middle School: College Park Middle


  • 2612 ROXBURY RD, WINTER PARK, FL 32789

    $630,000268 Days on yellowkey   MLS ID: S5137596

    For Sale S5137596 - 2612 ROXBURY RD, WINTER PARK, FL 32789 30 photos

    Bed: 5   Bath: 3.0
    Liv Area Sq Ft: 2472
       Built: 1957   Tax: $6,425 (2024)
    Community: Glencoe Sub
    Single Family


    Estimated Monthly Payment: $3,987 (change assumption)
    Mortgage ($3,452) + Taxes in 2024 ($535)


    Taxes:$6,425

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2024

    Middle School: College Park Middle


  • 1870 STAUNTON AVE, WINTER PARK, FL 32789

    $1,250,000117 Days on yellowkey   MLS ID: O6391469

    For Sale O6391469 - 1870 STAUNTON AVE, WINTER PARK, FL 32789 10 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2525
       Built: 1935   Tax: $1,302 (2025)
    Community: Karolina On Killarney
    Single Family


    Estimated Monthly Payment: $6,958 (change assumption)
    Mortgage ($6,849) + Taxes in 2025 ($109)


    Taxes:$1,302

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park Middle


  • 1630 ELM AVE, WINTER PARK, FL 32789

    $2,385,000135 Days on yellowkey   MLS ID: O6388606

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

    For Sale O6388606 - 1630 ELM AVE, WINTER PARK, FL 32789 15 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3408
       Built: 2026   Tax: $1,673 (2024)
    Community: Temple Estates
    Single Family


    Estimated Monthly Payment: $13,208 (change assumption)
    Mortgage ($13,068) + Taxes in 2024 ($139)


    Taxes:$1,673

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Maitland Middle


  • 1996 INDIANA AVE, WINTER PARK, FL 32789

    $249,900202 Days on yellowkey   MLS ID: O6372229

    0 Days Off yellowkey (back on 3/27/2026)

    For Sale O6372229 - 1996 INDIANA AVE, WINTER PARK, FL 32789 18 photos

    Bed: 2   Bath: 1.0
    Liv Area Sq Ft: 818
       Built: 1938   Tax: $1,401 (2024)
    Community: Lawndale
    Single Family


    Estimated Monthly Payment: $1,486 (change assumption)
    Mortgage ($1,369) + Taxes in 2024 ($117)


    Taxes:$1,401

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 1120 PRESERVE POINT DR, WINTER PARK, FL 32789

    $8,950,000296 Days on yellowkey   MLS ID: O6350054

    For Sale O6350054 - 1120 PRESERVE POINT DR, WINTER PARK, FL 32789 89 photos

    Bed: 7   Bath: 10.0
    Liv Area Sq Ft: 11255
       Built: 2009
    Community: Windsong-Preserve Point
    Single Family


    Estimated Monthly Payment: $49,040 (change assumption)
    Mortgage ($49,040)


    Taxes:

    Elementary School: None

    High School: None

    Tax Year:

    Middle School: None


  • 1137 OAKS BLVD, WINTER PARK, FL 32789

    $634,900174 Days on yellowkey   MLS ID: O6379388

    0 Days Off yellowkey (back on 3/21/2026)

    For Sale O6379388 - 1137 OAKS BLVD, WINTER PARK, FL 32789 29 photos

    Bed: 2   Bath: 1.5
    Liv Area Sq Ft: 1149
       Built: 1958
    Community: Dixie Terrace
    Single Family


    Estimated Monthly Payment: $3,479 (change assumption)
    Mortgage ($3,479)


    Taxes:

    Elementary School: None

    High School: None

    Tax Year:

    Middle School: None


  • 1289 HARMON AVE, WINTER PARK, FL 32789

    $500,000   MLS ID: O6346480

    For Sale O6346480 - 1289 HARMON AVE, WINTER PARK, FL 32789 30 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1683
       Built: 1990
    Community: Henkel Add
    Townhouse


    Estimated Monthly Payment: $2,740 (change assumption)
    Mortgage ($2,740)


    Taxes:

    Elementary School: None

    High School: None

    Tax Year:

    Middle School: None




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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.