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Winter Park Condos For Sale - 100 condos

Winter Park Condos for sale are located in Orange County, Florida. Find condos in Winter Park for sale with data from the Multiple Listing Service (MLS). Our REALTORS® can assist you in your search for Winter Park condominiums.

Location: Winter Park

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

    $245,000120 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


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

    $224,999478 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


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

    $240,00037 Days on yellowkey   MLS ID: O6401802

    2 Days Off yellowkey (back on 5/6/2026)

    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


  • 1809 HAMMERLIN AVE, WINTER PARK, FL 32789

    $549,000136 Days on yellowkey   MLS ID: O6373616

    REDUCED by $36,000 (6.2%) on 05/06/2026

    For Sale O6373616 - 1809 HAMMERLIN AVE, WINTER PARK, FL 32789 44 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1818
       Built: 2006   Tax: $5,826 (2024)
    Community: Terazzo Del Sol Condo Assn Inc
    Condo


    Estimated Monthly Payment: $3,494 (change assumption)
    Mortgage ($3,008) + Taxes in 2024 ($486)


    Taxes:$5,826

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Audubon Park K-8


  • 1000 S SEMORAN BLVD #805, WINTER PARK, FL 32792

    $174,70070 Days on yellowkey   MLS ID: O6392099

    0 Days Off yellowkey (back on 5/6/2026)

    REDUCED by $5,000 (2.8%) on 04/13/2026

    For Sale O6392099 - 1000 S SEMORAN BLVD #805, WINTER PARK, FL 32792 19 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1003
       Built: 1969
    Monthly Fee: $355
       Tax: $1,111 (2025)
    Community: Golfside Villas Condo
    Condo


    Estimated Monthly Payment: $1,405 (change assumption)
    Mortgage ($957) + Fees ($355) + Taxes in 2025 ($93)


    Taxes:$1,111

    Elementary School: None

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 150 KILLARNEY BAY CT #5, WINTER PARK, FL 32789

    $325,000316 Days on yellowkey   MLS ID: O6328063

    For Sale O6328063 - 150 KILLARNEY BAY CT #5, WINTER PARK, FL 32789 26 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1140
       Built: 1986
    Monthly Fee: $460
       Tax: $2,100 (2024)
    Community: Killarney Bay Condo
    Condo


    Estimated Monthly Payment: $2,416 (change assumption)
    Mortgage ($1,781) + Fees ($460) + Taxes in 2024 ($175)


    Taxes:$2,100

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2024

    Middle School: College Park Middle


  • 1695 LEE RD #E116, WINTER PARK, FL 32789

    $125,00026 Days on yellowkey   MLS ID: O6399346

    For Sale O6399346 - 1695 LEE RD #E116, WINTER PARK, FL 32789 29 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1149
       Built: 1966
    Monthly Fee: $624
       Tax: $2,263 (2025)
    Community: Waterfall Cove/Winter Park
    Condo


    Estimated Monthly Payment: $1,497 (change assumption)
    Mortgage ($685) + Fees ($624) + Taxes in 2025 ($189)


    Taxes:$2,263

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


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

    $179,00073 Days on yellowkey   MLS ID: O6391256

    3 Days Off yellowkey (back on 5/4/2026)

    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


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

    $179,00088 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


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

    $99,000101 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


  • 200 SAINT ANDREWS BLVD #315, WINTER PARK, FL 32792

    $169,000106 Days on yellowkey   MLS ID: V4947283

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

    For Sale V4947283 - 200 SAINT ANDREWS BLVD #315, WINTER PARK, FL 32792 43 photos

    Bed: 1   Bath: 1.0
    Liv Area Sq Ft: 793
       Built: 1970
    Monthly Fee: $451
       Tax: $873 (2024)
    Community: Four Seasons Condo
    Condo


    Estimated Monthly Payment: $1,450 (change assumption)
    Mortgage ($926) + Fees ($451) + Taxes in 2024 ($73)


    Taxes:$873

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Glenridge Middle


  • 100 S INTERLACHEN AVE #101, WINTER PARK, FL 32789

    $1,299,000100 Days on yellowkey   MLS ID: O6382597

    For Sale O6382597 - 100 S INTERLACHEN AVE #101, WINTER PARK, FL 32789 53 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1734
       Built: 1971   Tax: $9,362 (2025)
    Community: Cloisters Condo
    Condo


    Estimated Monthly Payment: $7,898 (change assumption)
    Mortgage ($7,118) + Taxes in 2025 ($780)


    Taxes:$9,362

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 7484 CANFORD CT #8, WINTER PARK, FL 32792

    $250,00033 Days on yellowkey   MLS ID: O6402492

    For Sale O6402492 - 7484 CANFORD CT #8, WINTER PARK, FL 32792 25 photos

    Bed: 3   Bath: 2.5
    Liv Area Sq Ft: 1578
       Built: 1974   Tax: $2,121 (2025)
    Community: Whisperwood Condo
    Condo


    Estimated Monthly Payment: $1,547 (change assumption)
    Mortgage ($1,370) + Taxes in 2025 ($177)


    Taxes:$2,121

    Elementary School: Cheney Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 2384 SUN VALLEY CIR, WINTER PARK, FL 32792

    $269,90089 Days on yellowkey   MLS ID: O6386755

    REDUCED by $5,000 (1.8%) on 04/28/2026

    For Sale O6386755 - 2384 SUN VALLEY CIR, WINTER PARK, FL 32792 36 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1311
       Built: 1983   Tax: $688 (2024)
    Community: Cedarwood Village 1
    Condo


    Estimated Monthly Payment: $1,536 (change assumption)
    Mortgage ($1,479) + Taxes in 2024 ($57)


    Taxes:$688

    Elementary School: English Estates Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


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

    $619,00081 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


  • 291 LEWFIELD CIR #291, WINTER PARK, FL 32792

    $144,000103 Days on yellowkey   MLS ID: O6382547

    For Sale O6382547 - 291 LEWFIELD CIR #291, WINTER PARK, FL 32792 32 photos

    Bed: 1   Bath: 1.0
    Liv Area Sq Ft: 678
       Built: 1973
    Monthly Fee: $350
       Tax: $1,942 (2025)
    Community: Stratford Winter Park
    Condo


    Estimated Monthly Payment: $1,301 (change assumption)
    Mortgage ($789) + Fees ($350) + Taxes in 2025 ($162)


    Taxes:$1,942

    Elementary School: English Estates Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 106 S INTERLACHEN AVE #518, WINTER PARK, FL 32789

    $1,950,00039 Days on yellowkey   MLS ID: O6400228

    For Sale O6400228 - 106 S INTERLACHEN AVE #518, WINTER PARK, FL 32789 58 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1807
       Built: 1971   Tax: $14,974 (2025)
    Community: Cloisters Condo
    Condo


    Estimated Monthly Payment: $11,933 (change assumption)
    Mortgage ($10,685) + Taxes in 2025 ($1,248)


    Taxes:$14,974

    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

    $133,00037 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


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

    $205,000452 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


  • 7117 SWALLOW RUN #G1, WINTER PARK, FL 32792

    $236,80093 Days on yellowkey   MLS ID: O6385942

    REDUCED by $13,000 (5.2%) on 04/23/2026

    For Sale O6385942 - 7117 SWALLOW RUN #G1, WINTER PARK, FL 32792 22 photos

    Bed: 3   Bath: 2.5   Gar: 1
    Liv Area Sq Ft: 1565
       Built: 2011
    Monthly Fee: $385
       Tax: $3,776 (2024)
    Community: Village/Whisperwood
    Condo


    Estimated Monthly Payment: $1,997 (change assumption)
    Mortgage ($1,298) + Fees ($385) + Taxes in 2024 ($315)


    Taxes:$3,776

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None




Why Bother Searching Elsewhere for Winter Park Condos for Sale and Other Condominiums?

Winter Park home, townhome, condo, villa, and other listing sales 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 condos for sale in Winter Park . You can use our website to view Multiple Listing Service (MLS) data on Winter Park condos. 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 Winter Park condo 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.