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Homes For Sale in Winter Park 32789 - 215 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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  • 1830 EDWIN BLVD, WINTER PARK, FL 32789

    $679,80018 Days on yellowkey   MLS ID: O6400055

    For Sale O6400055 - 1830 EDWIN BLVD, WINTER PARK, FL 32789 52 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1287
       Built: 1957   Tax: $3,955 (2025)
    Community: Campo Bello
    Single Family


    Estimated Monthly Payment: $4,054 (change assumption)
    Mortgage ($3,725) + Taxes in 2025 ($330)


    Taxes:$3,955

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 2500 LEE RD #122, WINTER PARK, FL 32789

    $179,00062 Days on yellowkey   MLS ID: O6384082

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

    For Sale O6384082 - 2500 LEE RD #122, WINTER PARK, FL 32789 25 photos

    Bed: 1   Bath: 1.0
    Liv Area Sq Ft: 645
       Built: 1969   Tax: $428 (2024)
    Community: Lakeside Manor Apts Condo
    Condo


    Estimated Monthly Payment: $1,016 (change assumption)
    Mortgage ($981) + Taxes in 2024 ($36)


    Taxes:$428

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2024

    Middle School: College Park Middle


  • 1821 PINETREE RD, WINTER PARK, FL 32789

    $6,997,0003 Days on yellowkey   MLS ID: O6395725

    For Sale O6395725 - 1821 PINETREE RD, WINTER PARK, FL 32789 63 photos

    Bed: 5   Bath: 6.5   Gar: 2
    Liv Area Sq Ft: 5006
       Built: 2018   Tax: $71,518 (2025)
    Community: Sicilian Shores
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $44,299 (change assumption)
    Mortgage ($38,339) + Taxes in 2025 ($5,960)


    Taxes:$71,518

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 1611 CHESTNUT AVE, WINTER PARK, FL 32789

    $1,100,0004 Days on yellowkey   MLS ID: O6402502

    For Sale O6402502 - 1611 CHESTNUT AVE, WINTER PARK, FL 32789 45 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 2916
       Built: 1973   Tax: $3,590 (2025)
    Community: Lake Knowles Terrace
    Single Family


    Estimated Monthly Payment: $6,326 (change assumption)
    Mortgage ($6,027) + Taxes in 2025 ($299)


    Taxes:$3,590

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 1660 WALNUT AVE, WINTER PARK, FL 32789

    $1,650,0007 Days on yellowkey   MLS ID: O6395277

    For Sale O6395277 - 1660 WALNUT AVE, WINTER PARK, FL 32789 43 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2249
       Built: 2026   Tax: $6,297 (2025)
    Community: Lake Knowles Terrace
    Spa: No

    Single Family


    Estimated Monthly Payment: $9,566 (change assumption)
    Mortgage ($9,041) + Taxes in 2025 ($525)


    Taxes:$6,297

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 363 N PHELPS AVE, WINTER PARK, FL 32789

    $1,249,00011 Days on yellowkey   MLS ID: O6401811

    For Sale O6401811 - 363 N PHELPS AVE, WINTER PARK, FL 32789 38 photos

    Bed: 4   Bath: 3.0
    Liv Area Sq Ft: 2871
       Built: 1950   Tax: $8,856 (2025)
    Community: Sylvan Park
    Single Family


    Estimated Monthly Payment: $7,582 (change assumption)
    Mortgage ($6,844) + Taxes in 2025 ($738)


    Taxes:$8,856

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 785 N PHELPS AVE, WINTER PARK, FL 32789

    $1,989,00040 Days on yellowkey   MLS ID: O6393117

    REDUCED by $60,000 (2.9%) on 04/23/2026

    For Sale O6393117 - 785 N PHELPS AVE, WINTER PARK, FL 32789 41 photos

    Bed: 5   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2964
       Built: 2026   Tax: $9,172 (2025)
    Community: Comstock Park
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $11,663 (change assumption)
    Mortgage ($10,898) + Taxes in 2025 ($764)


    Taxes:$9,172

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 640 ARJAY WAY, WINTER PARK, FL 32789

    $1,890,000104 Days on yellowkey   MLS ID: O6372947

    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


  • 1751 GLENCOE RD, WINTER PARK, FL 32789

    $3,490,000181 Days on yellowkey   MLS ID: O6339739

    REDUCED by $100,000 (2.8%) on 04/23/2026

    For Sale O6339739 - 1751 GLENCOE RD, WINTER PARK, FL 32789 45 photos

    Bed: 5   Bath: 6.0   Gar: 2
    Liv Area Sq Ft: 4520
       Built: 2025   Tax: $12,895 (2024)
    Community: Forest Hills
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $20,197 (change assumption)
    Mortgage ($19,123) + Taxes in 2024 ($1,075)


    Taxes:$12,895

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Audubon Park K-8


  • 1473 BERKSHIRE AVE, WINTER PARK, FL 32789

    $1,499,000316 Days on yellowkey   MLS ID: O6320741

    For Sale O6320741 - 1473 BERKSHIRE AVE, WINTER PARK, FL 32789 53 photos

    Bed: 5   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 2895
       Built: 2025   Tax: $5,730 (2024)
    Community: Orwin Manor Westminster Sec
    Single Family


    Estimated Monthly Payment: $8,691 (change assumption)
    Mortgage ($8,213) + Taxes in 2024 ($478)


    Taxes:$5,730

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2024

    Middle School: College Park Middle


  • 1981 BLUE RIDGE RD, WINTER PARK, FL 32789

    $1,150,0003 Days on yellowkey   MLS ID: O6402961

    For Sale O6402961 - 1981 BLUE RIDGE RD, WINTER PARK, FL 32789 52 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2750
       Built: 1963   Tax: $11,270 (2025)
    Community: Timberlane Shores
    Single Family


    Estimated Monthly Payment: $7,240 (change assumption)
    Mortgage ($6,301) + Taxes in 2025 ($939)


    Taxes:$11,270

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: None


  • 147 S INTERLACHEN AVE #202, WINTER PARK, FL 32789

    $2,272,00093 Days on yellowkey   MLS ID: L4959060

    REDUCED by $178,000 (7.3%) on 05/02/2026

    For Sale L4959060 - 147 S INTERLACHEN AVE #202, WINTER PARK, FL 32789 31 photos

    Bed: 3   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3272
       Built: 1990   Tax: $18,439 (2024)
    Community: 147 Interlachen Place
    Condo


    Estimated Monthly Payment: $13,986 (change assumption)
    Mortgage ($12,449) + Taxes in 2024 ($1,537)


    Taxes:$18,439

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 1807 HAMMERLIN AVE #G, WINTER PARK, FL 32789

    $550,00048 Days on yellowkey   MLS ID: O6391277

    REDUCED by $30,000 (5.2%) on 04/28/2026

    For Sale O6391277 - 1807 HAMMERLIN AVE #G, WINTER PARK, FL 32789 25 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1818
       Built: 2006   Tax: $6,197 (2025)
    Community: Terrazo Del Sol
    Condo


    Estimated Monthly Payment: $3,530 (change assumption)
    Mortgage ($3,014) + Taxes in 2025 ($516)


    Taxes:$6,197

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 1351 MAGNOLIA AVE, WINTER PARK, FL 32789

    $3,100,0003 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


  • 1695 LEE RD #B210, WINTER PARK, FL 32789

    $109,000102 Days on yellowkey   MLS ID: O6375872

    For Sale O6375872 - 1695 LEE RD #B210, WINTER PARK, FL 32789 27 photos

    Bed: 1   Bath: 1.0
    Liv Area Sq Ft: 638
       Built: 1966   Tax: $1,493 (2024)
    Community: Waterfall Cove
    Spa: No

    Condo


    Estimated Monthly Payment: $722 (change assumption)
    Mortgage ($597) + Taxes in 2024 ($124)


    Taxes:$1,493

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 101 S NEW YORK AVE #302, WINTER PARK, FL 32789

    $1,450,00040 Days on yellowkey   MLS ID: O6390752

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

    REDUCED by $130,000 (8.2%) on 04/24/2026

    For Sale O6390752 - 101 S NEW YORK AVE #302, WINTER PARK, FL 32789 40 photos

    Bed: 3   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3174
       Built: 2009
    Monthly Fee: $1,263
       Tax: $19,802 (2025)
    Community: Winter Park Residential
    Condo


    Estimated Monthly Payment: $10,858 (change assumption)
    Mortgage ($7,945) + Fees ($1,263) + Taxes in 2025 ($1,650)


    Taxes:$19,802

    Elementary School: None

    High School: Winter Park High

    Tax Year: 2025

    Middle School: None


  • 1836 GRINNELL TER, WINTER PARK, FL 32789

    $1,050,00087 Days on yellowkey   MLS ID: O6380457

    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: $6,752 (change assumption)
    Mortgage ($5,753) + Taxes in 2025 ($998)


    Taxes:$11,979

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 150 DANA WAY, WINTER PARK, FL 32789

    $3,799,00038 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


  • 2299 VIA TUSCANY, WINTER PARK, FL 32789

    $2,200,000181 Days on yellowkey   MLS ID: O6355858

    For Sale O6355858 - 2299 VIA TUSCANY, WINTER PARK, FL 32789 60 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3986
       Built: 1953   Tax: $13,185 (2025)
    Community: Maitland Shores
    Single Family


    Estimated Monthly Payment: $13,153 (change assumption)
    Mortgage ($12,054) + Taxes in 2025 ($1,099)


    Taxes:$13,185

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 1781 INDIANA AVE #A, WINTER PARK, FL 32789

    $545,00082 Days on yellowkey   MLS ID: O6381195

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

    REDUCED by $20,000 (3.5%) on 04/14/2026

    For Sale O6381195 - 1781 INDIANA AVE #A, WINTER PARK, FL 32789 47 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1616
       Built: 2008
    Monthly Fee: $464
       Tax: $6,026 (2024)
    Community: Las Casas De Indiana
    Townhouse


    Estimated Monthly Payment: $3,952 (change assumption)
    Mortgage ($2,986) + Fees ($464) + Taxes in 2024 ($502)


    Taxes:$6,026

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2024

    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.