REFINE SEARCH
Status
Keywords
Price
 
Bedrooms
Bathrooms
Garages
Liv Area Sq Ft
Min Year
Max Year
Property Types
No Image
Age Restricted
Foreclosure
Short Sale
Pets Allowed
Furnished
Pool
Spa
Reduced Price
Back on yellowkey
Possible Short Term Rental
Carports
Max Association Fee (monthly)
Max Monthly Payment
Search

Homes For Sale in Winter Park 32789 - 244 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

Sort:
  • 1510 MILLER AVE, WINTER PARK, FL 32789

    $1,599,900249 Days on yellowkey   MLS ID: O6350503

    REDUCED by $35,000 (2.1%) on 05/13/2026

    For Sale O6350503 - 1510 MILLER AVE, WINTER PARK, FL 32789 70 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3252
       Built: 2026   Tax: $3,573 (2025)
    Community: Lawndale
    Single Family


    Estimated Monthly Payment: $9,064 (change assumption)
    Mortgage ($8,766) + Taxes in 2025 ($298)


    Taxes:$3,573

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park Middle


  • 231 CHELTON CIR, WINTER PARK, FL 32789

    $4,950,0003 Days on yellowkey   MLS ID: O6414890

    For Sale O6414890 - 231 CHELTON CIR, WINTER PARK, FL 32789 67 photos

    Bed: 4   Bath: 6.0   Gar: 3
    Liv Area Sq Ft: 5550
       Built: 2018   Tax: $56,866 (2025)
    Community: Forest Hills
    Spa: No

    Single Family


    Estimated Monthly Payment: $31,861 (change assumption)
    Mortgage ($27,123) + Taxes in 2025 ($4,739)


    Taxes:$56,866

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 1221 RICHMOND RD, WINTER PARK, FL 32789

    $4,995,0005 Days on yellowkey   MLS ID: O6407648

    For Sale O6407648 - 1221 RICHMOND RD, WINTER PARK, FL 32789 48 photos

    Bed: 5   Bath: 5.5   Gar: 2
    Liv Area Sq Ft: 5164
       Built: 2024   Tax: $22,030 (2025)
    Community: Virginia Heights Rep
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $29,205 (change assumption)
    Mortgage ($27,369) + Taxes in 2025 ($1,836)


    Taxes:$22,030

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 641 NORTHWOOD CIRCLE, WINTER PARK, FL 32789

    $1,795,00012 Days on yellowkey   MLS ID: O6412554

    For Sale O6412554 - 641 NORTHWOOD CIRCLE, WINTER PARK, FL 32789 36 photos

    Bed: 3   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 2756
       Built: 2023   Tax: $18,393 (2025)
    Community: Winter Park Oasis
    Single Family


    Estimated Monthly Payment: $11,368 (change assumption)
    Mortgage ($9,835) + Taxes in 2025 ($1,533)


    Taxes:$18,393

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 2974 CHANTILLY AVE, WINTER PARK, FL 32789

    $550,0007 Days on yellowkey   MLS ID: O6412851

    For Sale O6412851 - 2974 CHANTILLY AVE, WINTER PARK, FL 32789 26 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1433
       Built: 1960   Tax: $1,178 (2025)
    Community: Winter Park Manor
    Single Family


    Estimated Monthly Payment: $3,112 (change assumption)
    Mortgage ($3,014) + Taxes in 2025 ($98)


    Taxes:$1,178

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 1651 WESTCHESTER AVE, WINTER PARK, FL 32789

    $1,175,00071 Days on yellowkey   MLS ID: O6384358

    0 Days Off yellowkey (back on 6/9/2026)

    REDUCED by $100,000 (7.8%) on 06/01/2026

    For Sale O6384358 - 1651 WESTCHESTER AVE, WINTER PARK, FL 32789 47 photos

    Bed: 3   Bath: 2.5   Gar: 1
    Liv Area Sq Ft: 2426
       Built: 1938   Tax: $10,973 (2025)
    Community: Orwin Manor Westminster Sec
    Single Family


    Estimated Monthly Payment: $7,353 (change assumption)
    Mortgage ($6,438) + Taxes in 2025 ($914)


    Taxes:$10,973

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park Middle


  • 2500 LEE RD #220, WINTER PARK, FL 32789

    $199,9005 Days on yellowkey   MLS ID: O6411927

    For Sale O6411927 - 2500 LEE RD #220, WINTER PARK, FL 32789 28 photos

    Bed: 2   Bath: 1.0
    Liv Area Sq Ft: 851
       Built: 1969
    Monthly Fee: $292
       Tax: $2,015 (2025)
    Community: Lakeside Manor Apts Condo
    Condo


    Estimated Monthly Payment: $1,555 (change assumption)
    Mortgage ($1,095) + Fees ($292) + Taxes in 2025 ($168)


    Taxes:$2,015

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park Middle


  • 1750 CAROLLEE LANE, WINTER PARK, FL 32789

    $1,820,00085 Days on yellowkey   MLS ID: O6391179

    REDUCED by $70,000 (3.7%) on 05/26/2026

    For Sale O6391179 - 1750 CAROLLEE LANE, WINTER PARK, FL 32789 46 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3249
       Built: 2012   Tax: $24,658 (2025)
    Community: Green Terrace V/140 Lot 3 Blk B
    Single Family


    Estimated Monthly Payment: $12,027 (change assumption)
    Mortgage ($9,972) + Taxes in 2025 ($2,055)


    Taxes:$24,658

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 1441 CARDINAL CT, WINTER PARK, FL 32789

    $4,285,00059 Days on yellowkey   MLS ID: O6399395

    For Sale O6399395 - 1441 CARDINAL CT, WINTER PARK, FL 32789 85 photos

    Bed: 4   Bath: 5.5   Gar: 2
    Liv Area Sq Ft: 4066
       Built: 2022   Tax: $47,740 (2025)
    Community: Winflor Court
    Spa: No

    Single Family


    Estimated Monthly Payment: $27,457 (change assumption)
    Mortgage ($23,479) + Taxes in 2025 ($3,978)


    Taxes:$47,740

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 700 MELROSE AVE #F 21, WINTER PARK, FL 32789

    $235,9008 Days on yellowkey   MLS ID: O6413612

    For Sale O6413612 - 700 MELROSE AVE #F 21, WINTER PARK, FL 32789 27 photos

    Bed: 1   Bath: 1.0
    Liv Area Sq Ft: 787
       Built: 1964   Tax: $1,123 (2025)
    Community: Winter Park Gdns Condo
    Condo


    Estimated Monthly Payment: $1,386 (change assumption)
    Mortgage ($1,293) + Taxes in 2025 ($94)


    Taxes:$1,123

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1611 CHESTNUT AVE, WINTER PARK, FL 32789

    $1,070,00044 Days on yellowkey   MLS ID: O6402502

    REDUCED by $30,000 (2.7%) on 06/10/2026

    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: $6,162 (change assumption)
    Mortgage ($5,863) + Taxes in 2025 ($299)


    Taxes:$3,590

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 700 MELROSE AVE #K25, WINTER PARK, FL 32789

    $245,0004 Days on yellowkey   MLS ID: O6414821

    For Sale O6414821 - 700 MELROSE AVE #K25, WINTER PARK, FL 32789 30 photos

    Bed: 1   Bath: 1.0
    Liv Area Sq Ft: 787
       Built: 1964   Tax: $3,196 (2025)
    Community: Winter Park Gardens Condo
    Condo


    Estimated Monthly Payment: $1,609 (change assumption)
    Mortgage ($1,342) + Taxes in 2025 ($266)


    Taxes:$3,196

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 685 OVERSPIN DR, WINTER PARK, FL 32789

    $629,0003 Days on yellowkey   MLS ID: O6415537

    For Sale O6415537 - 685 OVERSPIN DR, WINTER PARK, FL 32789 26 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2112
       Built: 2003   Tax: $8,533 (2025)
    Community: Dubsdread Heights
    Single Family


    Estimated Monthly Payment: $4,158 (change assumption)
    Mortgage ($3,446) + Taxes in 2025 ($711)


    Taxes:$8,533

    Elementary School: Princeton Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park Middle


  • 2500 LEE RD #104, WINTER PARK, FL 32789

    $259,9993 Days on yellowkey   MLS ID: TB8517242

    For Sale TB8517242 - 2500 LEE RD #104, WINTER PARK, FL 32789 24 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 956
       Built: 1969
    Monthly Fee: $431
       Tax: $2,327 (2025)
    Community: Lakeside Manor Apts Condo
    Spa: No

    Condo


    Estimated Monthly Payment: $2,050 (change assumption)
    Mortgage ($1,425) + Fees ($431) + Taxes in 2025 ($194)


    Taxes:$2,327

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1473 BERKSHIRE AVE, WINTER PARK, FL 32789

    $1,429,0003 Days on yellowkey   MLS ID: O6415098

    For Sale O6415098 - 1473 BERKSHIRE AVE, WINTER PARK, FL 32789 38 photos

    Bed: 5   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 2351
       Built: 2025   Tax: $5,773 (2025)
    Community: Orwin Manor Westminster Sec
    Single Family


    Estimated Monthly Payment: $8,311 (change assumption)
    Mortgage ($7,830) + Taxes in 2025 ($481)


    Taxes:$5,773

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park Middle


  • 721 PANSY AVE, WINTER PARK, FL 32789

    $1,850,000235 Days on yellowkey   MLS ID: O6352857

    REDUCED by $75,000 (3.9%) on 06/10/2026

    For Sale O6352857 - 721 PANSY AVE, WINTER PARK, FL 32789 29 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 2653
       Built: 2018   Tax: $15,480 (2025)
    Community: Villa View Park
    Single Family


    Estimated Monthly Payment: $11,427 (change assumption)
    Mortgage ($10,137) + Taxes in 2025 ($1,290)


    Taxes:$15,480

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 2889 ROUEN AVE, WINTER PARK, FL 32789

    $375,00053 Days on yellowkey   MLS ID: L4961275

    REDUCED by $24,500 (6.1%) on 06/01/2026

    For Sale L4961275 - 2889 ROUEN AVE, WINTER PARK, FL 32789 10 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1144
       Built: 1959   Tax: $5,061 (2025)
    Community: Winter Park Manor
    Single Family


    Estimated Monthly Payment: $2,477 (change assumption)
    Mortgage ($2,055) + Taxes in 2025 ($422)


    Taxes:$5,061

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 525 OLOLU DR, WINTER PARK, FL 32789

    $515,00044 Days on yellowkey   MLS ID: S5148431

    0 Days Off yellowkey (back on 6/10/2026)

    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


  • 649 N PARK AVE, WINTER PARK, FL 32789

    $3,500,00011 Days on yellowkey   MLS ID: O6411141

    For Sale O6411141 - 649 N PARK AVE, WINTER PARK, FL 32789 44 photos

    Bed: 3   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 3180
       Built: 2019
    Monthly Fee: $948
       Tax: $22,599 (2025)
    Community: Park Hill
    Townhouse


    Estimated Monthly Payment: $22,009 (change assumption)
    Mortgage ($19,178) + Fees ($948) + Taxes in 2025 ($1,883)


    Taxes:$22,599

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 2408 LAFAYETTE AVE, WINTER PARK, FL 32789

    $1,495,00064 Days on yellowkey   MLS ID: O6397694

    1 Days Off yellowkey (back on 6/10/2026)

    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




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.