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


Displaying: For Sale

Location: Winter Park

Property Type(s): Condos

Beds: 2 to 2

Winter Park - 55 properties found

Sort:
  • 151 N ORLANDO AVE ##115, WINTER PARK, FL 32789

    $298,000153 Days on yellowkey   MLS ID: O6362403

    For Sale O6362403 - 151 N ORLANDO AVE ##115, WINTER PARK, FL 32789 22 photos

    Bed: 2   Bath: 1.0
    Liv Area Sq Ft: 710
       Built: 1960   Tax: $2,965 (2025)
    Community: Lake Killarney Condo
    Spa: No

    Condo


    Estimated Monthly Payment: $1,880 (change assumption)
    Mortgage ($1,633) + Taxes in 2025 ($247)


    Taxes:$2,965

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park Middle


  • 278 SCOTTSDALE SQ #278, WINTER PARK, FL 32792

    $99,00075 Days on yellowkey   MLS ID: O6383638

    For Sale O6383638 - 278 SCOTTSDALE SQ #278, WINTER PARK, FL 32792 27 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1020
       Built: 1974
    Monthly Fee: $880
       Tax: $1,552 (2025)
    Community: Winter Park Woods Condo
    Condo


    Estimated Monthly Payment: $1,552 (change assumption)
    Mortgage ($542) + Fees ($880) + Taxes in 2025 ($129)


    Taxes:$1,552

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 630 KILLARNEY BAY CT #3, WINTER PARK, FL 32789

    $495,00095 Days on yellowkey   MLS ID: O6375307

    For Sale O6375307 - 630 KILLARNEY BAY CT #3, WINTER PARK, FL 32789 55 photos

    Bed: 2   Bath: 2.5
    Liv Area Sq Ft: 1428
       Built: 1986   Tax: $6,595 (2025)
    Community: Killarney Bay Condo
    Condo


    Estimated Monthly Payment: $3,262 (change assumption)
    Mortgage ($2,712) + Taxes in 2025 ($550)


    Taxes:$6,595

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park Middle


  • 2317 SUN VALLEY CIR #2317, WINTER PARK, FL 32792

    $269,00017 Days on yellowkey   MLS ID: O6398500

    REDUCED by $10,000 (3.6%) on 05/01/2026

    For Sale O6398500 - 2317 SUN VALLEY CIR #2317, WINTER PARK, FL 32792 17 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1295
       Built: 1987   Tax: $1,107 (2025)
    Community: Cedarwood Village 1
    Condo


    Estimated Monthly Payment: $1,566 (change assumption)
    Mortgage ($1,474) + Taxes in 2025 ($92)


    Taxes:$1,107

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 3282 OAK LAKE PL #3282, WINTER PARK, FL 32792

    $169,5004 Days on yellowkey   MLS ID: O6403912

    For Sale O6403912 - 3282 OAK LAKE PL #3282, WINTER PARK, FL 32792 27 photos

    Bed: 2   Bath: 1.5
    Liv Area Sq Ft: 990
       Built: 1984   Tax: $2,899 (2025)
    Community: Hidden Oaks Condominium Association, Inc
    Condo


    Estimated Monthly Payment: $1,170 (change assumption)
    Mortgage ($929) + Taxes in 2025 ($242)


    Taxes:$2,899

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 100 S INTERLACHEN AVE #503, WINTER PARK, FL 32789

    $879,000236 Days on yellowkey   MLS ID: O6343006

    For Sale O6343006 - 100 S INTERLACHEN AVE #503, WINTER PARK, FL 32789 41 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1143
       Built: 1971   Tax: $7,844 (2024)
    Community: Cloisters Condo
    Condo


    Estimated Monthly Payment: $5,470 (change assumption)
    Mortgage ($4,816) + Taxes in 2024 ($654)


    Taxes:$7,844

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Audubon Park K-8


  • 639 SAINT JOHNS CT #639, WINTER PARK, FL 32792

    $199,9008 Days on yellowkey   MLS ID: O6402025

    For Sale O6402025 - 639 SAINT JOHNS CT #639, WINTER PARK, FL 32792 42 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1120
       Built: 1981   Tax: $3,077 (2025)
    Community: Winter Park Villas
    Condo


    Estimated Monthly Payment: $1,352 (change assumption)
    Mortgage ($1,095) + Taxes in 2025 ($256)


    Taxes:$3,077

    Elementary School: Aloma Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


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

    $224,999452 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 50 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


  • 3057 AARON BURR AVE #1, WINTER PARK, FL 32792

    $116,000152 Days on yellowkey   MLS ID: O6364189

    1 Days Off yellowkey (back on 4/28/2026)

    For Sale O6364189 - 3057 AARON BURR AVE #1, WINTER PARK, FL 32792 11 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1066
       Built: 1974
    Monthly Fee: $409
       Tax: $1,911 (2024)
    Community: Colonies
    Condo


    Estimated Monthly Payment: $1,204 (change assumption)
    Mortgage ($636) + Fees ($409) + Taxes in 2024 ($159)


    Taxes:$1,911

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 4790 TANGERINE AVE #4790, WINTER PARK, FL 32792

    $194,99577 Days on yellowkey   MLS ID: O6380539

    0 Days Off yellowkey (back on 4/28/2026)

    REDUCED by $20,000 (9.3%) on 04/07/2026

    For Sale O6380539 - 4790 TANGERINE AVE #4790, WINTER PARK, FL 32792 31 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1058
       Built: 1973   Tax: $2,253 (2024)
    Community: Wrenwood Condo
    Condo


    Estimated Monthly Payment: $1,256 (change assumption)
    Mortgage ($1,068) + Taxes in 2024 ($188)


    Taxes:$2,253

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Maitland Middle


  • 200 SAINT ANDREWS BLVD #2901, WINTER PARK, FL 32792

    $225,00032 Days on yellowkey   MLS ID: O6395720

    1 Days Off yellowkey (back on 4/27/2026)

    For Sale O6395720 - 200 SAINT ANDREWS BLVD #2901, WINTER PARK, FL 32792 29 photos

    Bed: 2   Bath: 1.5
    Liv Area Sq Ft: 1266
       Built: 1970
    Monthly Fee: $451
       Tax: $2,131 (2025)
    Community: Four Seasons Condo
    Condo


    Estimated Monthly Payment: $1,861 (change assumption)
    Mortgage ($1,233) + Fees ($451) + Taxes in 2025 ($178)


    Taxes:$2,131

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


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

    $261,500216 Days on yellowkey   MLS ID: O6348568

    REDUCED by $2,500 (0.9%) on 04/13/2026

    For Sale O6348568 - 1500 GAY RD #24B, WINTER PARK, FL 32789 21 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: $1,539 (change assumption)
    Mortgage ($1,433) + Taxes in 2024 ($106)


    Taxes:$1,271

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 259 E CANTON AVE #259, WINTER PARK, FL 32789

    $619,00055 Days on yellowkey   MLS ID: O6389246

    1 Days Off yellowkey (back on 4/25/2026)

    REDUCED by $10,000 (1.6%) on 04/19/2026

    For Sale O6389246 - 259 E CANTON AVE #259, WINTER PARK, FL 32789 36 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1040
       Built: 1971   Tax: $3,603 (2025)
    Community: Village Winterset Inc
    Condo


    Estimated Monthly Payment: $3,692 (change assumption)
    Mortgage ($3,392) + Taxes in 2025 ($300)


    Taxes:$3,603

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 851 MILES AVE #13, WINTER PARK, FL 32789

    $209,999137 Days on yellowkey   MLS ID: O6368234

    2 Days Off yellowkey (back on 4/24/2026)

    For Sale O6368234 - 851 MILES AVE #13, WINTER PARK, FL 32789 24 photos

    Bed: 2   Bath: 1.0
    Liv Area Sq Ft: 808
       Built: 1984   Tax: $2,694 (2025)
    Community: Aragon Condo
    Condo


    Estimated Monthly Payment: $1,375 (change assumption)
    Mortgage ($1,151) + Taxes in 2025 ($224)


    Taxes:$2,694

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 3651 N GOLDENROD RD #D101, WINTER PARK, FL 32792

    $179,00047 Days on yellowkey   MLS ID: O6391256

    REDUCED by $6,000 (3.2%) on 04/24/2026

    For Sale O6391256 - 3651 N GOLDENROD RD #D101, WINTER PARK, FL 32792 39 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 840
       Built: 1990
    Monthly Fee: $370
       Tax: $2,000 (2025)
    Community: Lancelot/Winter Park
    Condo


    Estimated Monthly Payment: $1,517 (change assumption)
    Mortgage ($981) + Fees ($370) + Taxes in 2025 ($167)


    Taxes:$2,000

    Elementary School: Aloma Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 7794 COUNTRY PL #2, WINTER PARK, FL 32792

    $241,90017 Days on yellowkey   MLS ID: O6397587

    For Sale O6397587 - 7794 COUNTRY PL #2, WINTER PARK, FL 32792 17 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1068
       Built: 1988
    Monthly Fee: $296
       Tax: $2,620 (2024)
    Community: Goldenrod Villas Condo
    Spa: No

    Condo


    Estimated Monthly Payment: $1,840 (change assumption)
    Mortgage ($1,325) + Fees ($296) + Taxes in 2024 ($218)


    Taxes:$2,620

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 1250 S DENNING DR #117, WINTER PARK, FL 32789

    $240,00011 Days on yellowkey   MLS ID: O6401802

    For Sale O6401802 - 1250 S DENNING DR #117, WINTER PARK, FL 32789 28 photos

    Bed: 2   Bath: 1.5
    Liv Area Sq Ft: 908
       Built: 1967   Tax: $2,763 (2025)
    Community: Mead Garden
    Condo


    Estimated Monthly Payment: $1,545 (change assumption)
    Mortgage ($1,315) + Taxes in 2025 ($230)


    Taxes:$2,763

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 7429 DANIEL WEBSTER DR #14 (#C), WINTER PARK, FL 32792

    $133,00011 Days on yellowkey   MLS ID: O6400425

    For Sale O6400425 - 7429 DANIEL WEBSTER DR #14 (#C), WINTER PARK, FL 32792 17 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1036
       Built: 1974
    Monthly Fee: $640
       Tax: $1,916 (2025)
    Community: The Colonies
    Spa: No

    Condo


    Estimated Monthly Payment: $1,528 (change assumption)
    Mortgage ($729) + Fees ($640) + Taxes in 2025 ($160)


    Taxes:$1,916

    Elementary School: Cheney Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 2500 LEE RD #229, WINTER PARK, FL 32789

    $245,00094 Days on yellowkey   MLS ID: O6377616

    1 Days Off yellowkey (back on 4/22/2026)

    For Sale O6377616 - 2500 LEE RD #229, WINTER PARK, FL 32789 41 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 956
       Built: 1969   Tax: $2,613 (2024)
    Community: Lakeside Manor Apts Condo
    Spa: No

    Condo


    Estimated Monthly Payment: $1,560 (change assumption)
    Mortgage ($1,342) + Taxes in 2024 ($218)


    Taxes:$2,613

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 3651 N GOLDENROD RD #D102, WINTER PARK, FL 32792

    $159,00013 Days on yellowkey   MLS ID: O6401114

    For Sale O6401114 - 3651 N GOLDENROD RD #D102, WINTER PARK, FL 32792 14 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 840
       Built: 1990
    Monthly Fee: $370
       Tax: $2,461 (2025)
    Community: Lancelot/Winter Park
    Condo


    Estimated Monthly Payment: $1,446 (change assumption)
    Mortgage ($871) + Fees ($370) + Taxes in 2025 ($205)


    Taxes:$2,461

    Elementary School: Aloma Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


123




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.