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Winter Park Condos For Sale - 101 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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  • 1000 S SEMORAN BLVD #306, WINTER PARK, FL 32792

    $138,00017 Days on yellowkey   MLS ID: R4911525

    REDUCED by $10,000 (6.8%) on 07/13/2026

    For Sale R4911525 - 1000 S SEMORAN BLVD #306, WINTER PARK, FL 32792 13 photos

    Bed: 1   Bath: 1.0
    Liv Area Sq Ft: 796
       Built: 1969   Tax: $1,987 (2025)
    Community: Golfside Villas Condo
    Condo


    Estimated Monthly Payment: $922 (change assumption)
    Mortgage ($756) + Taxes in 2025 ($166)


    Taxes:$1,987

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1695 LEE RD #B108, WINTER PARK, FL 32789

    $89,9999 Days on yellowkey   MLS ID: O6422568

    For Sale O6422568 - 1695 LEE RD #B108, WINTER PARK, FL 32789 15 photos

    Bed: 1   Bath: 1.0
    Liv Area Sq Ft: 638
       Built: 1966
    Monthly Fee: $347
       Tax: $1,781 (2025)
    Community: Waterfall Cove Of Winter Park
    Condo


    Estimated Monthly Payment: $989 (change assumption)
    Mortgage ($493) + Fees ($347) + Taxes in 2025 ($148)


    Taxes:$1,781

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1695 LEE RD #D211, WINTER PARK, FL 32789

    $109,00099 Days on yellowkey   MLS ID: O6396190

    REDUCED by $5,000 (4.4%) on 07/06/2026

    For Sale O6396190 - 1695 LEE RD #D211, WINTER PARK, FL 32789 28 photos

    Bed: 2   Bath: 1.0
    Liv Area Sq Ft: 881
       Built: 1966   Tax: $2,051 (2025)
    Community: Waterfall Cove/Winter Park
    Condo


    Estimated Monthly Payment: $768 (change assumption)
    Mortgage ($597) + Taxes in 2025 ($171)


    Taxes:$2,051

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 205 LEWFIELD CIR #205, WINTER PARK, FL 32792

    $182,900185 Days on yellowkey   MLS ID: S5141588

    REDUCED by $37,100 (16.9%) on 06/20/2026

    For Sale S5141588 - 205 LEWFIELD CIR #205, WINTER PARK, FL 32792 24 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 927
       Built: 1973   Tax: $796 (2024)
    Community: Stratford A Winter Park Condo
    Condo


    Estimated Monthly Payment: $1,069 (change assumption)
    Mortgage ($1,002) + Taxes in 2024 ($66)


    Taxes:$796

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 101 S NEW YORK AVE #311, WINTER PARK, FL 32789

    $1,849,90029 Days on yellowkey   MLS ID: O6416927

    For Sale O6416927 - 101 S NEW YORK AVE #311, WINTER PARK, FL 32789 39 photos

    Bed: 3   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3112
       Built: 2008
    Monthly Fee: $1,303
       Tax: $20,039 (2025)
    Community: Winter Park Residential
    Condo


    Estimated Monthly Payment: $13,109 (change assumption)
    Mortgage ($10,136) + Fees ($1,303) + Taxes in 2025 ($1,670)


    Taxes:$20,039

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 1500 GAY RD #17D, WINTER PARK, FL 32789

    $249,90059 Days on yellowkey   MLS ID: O6408516

    REDUCED by $10,000 (3.8%) on 07/08/2026

    For Sale O6408516 - 1500 GAY RD #17D, WINTER PARK, FL 32789 38 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1026
       Built: 1972   Tax: $3,244 (2025)
    Community: Chateaux Du Lac
    Spa: No

    Condo


    Estimated Monthly Payment: $1,640 (change assumption)
    Mortgage ($1,369) + Taxes in 2025 ($270)


    Taxes:$3,244

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


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

    $290,000226 Days on yellowkey   MLS ID: O6362403

    REDUCED by $8,000 (2.7%) on 06/28/2026

    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: $1,836 (change assumption)
    Mortgage ($1,589) + Taxes in 2025 ($247)


    Taxes:$2,965

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park Middle


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

    $515,000121 Days on yellowkey   MLS ID: O6391277

    REDUCED by $10,000 (1.9%) on 06/15/2026

    For Sale O6391277 - 1807 HAMMERLIN AVE #G, WINTER PARK, FL 32789 29 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: $3,338 (change assumption)
    Mortgage ($2,822) + 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


  • 283 LEWFIELD CIR #283, WINTER PARK, FL 32792

    $142,50014 Days on yellowkey   MLS ID: O6420915

    1 Days Off yellowkey (back on 7/12/2026)

    For Sale O6420915 - 283 LEWFIELD CIR #283, WINTER PARK, FL 32792 23 photos

    Bed: 1   Bath: 1.0
    Liv Area Sq Ft: 678
       Built: 1973   Tax: $1,729 (2025)
    Community: Stratford A Winter Park Condo
    Condo


    Estimated Monthly Payment: $925 (change assumption)
    Mortgage ($781) + Taxes in 2025 ($144)


    Taxes:$1,729

    Elementary School: English Estates Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 303 SCOTTSDALE SQ #303, WINTER PARK, FL 32792

    $80,0006 Days on yellowkey   MLS ID: O6424296

    For Sale O6424296 - 303 SCOTTSDALE SQ #303, WINTER PARK, FL 32792 3 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1020
       Built: 1974   Tax: $1,392 (2025)
    Community: Winter Park Woods Condo
    Condo


    Estimated Monthly Payment: $554 (change assumption)
    Mortgage ($438) + Taxes in 2025 ($116)


    Taxes:$1,392

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 2450 GRAND TETON CIR #2450, WINTER PARK, FL 32792

    $255,0006 Days on yellowkey   MLS ID: O6418973

    For Sale O6418973 - 2450 GRAND TETON CIR #2450, WINTER PARK, FL 32792 37 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1311
       Built: 1981   Tax: $889 (2025)
    Community: Cedarwood Village 1
    Spa: No

    Condo


    Estimated Monthly Payment: $1,471 (change assumption)
    Mortgage ($1,397) + Taxes in 2025 ($74)


    Taxes:$889

    Elementary School: English Estates Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 106 S INTERLACHEN AVE #118, WINTER PARK, FL 32789

    $1,295,000160 Days on yellowkey   MLS ID: O6380506

    3 Days Off yellowkey (back on 7/10/2026)

    REDUCED by $65,000 (4.8%) on 06/08/2026

    For Sale O6380506 - 106 S INTERLACHEN AVE #118, WINTER PARK, FL 32789 55 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1834
       Built: 1971   Tax: $9,767 (2025)
    Community: Cloisters Condo
    Condo


    Estimated Monthly Payment: $7,910 (change assumption)
    Mortgage ($7,096) + Taxes in 2025 ($814)


    Taxes:$9,767

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 3381 CEDAR SPRINGS PL #151, WINTER PARK, FL 32792

    $179,90021 Days on yellowkey   MLS ID: O6419959

    For Sale O6419959 - 3381 CEDAR SPRINGS PL #151, WINTER PARK, FL 32792 32 photos

    Bed: 2   Bath: 2.5
    Liv Area Sq Ft: 1031
       Built: 1984   Tax: $197 (2025)
    Community: Hidden. Oaks
    Spa: No

    Condo


    Estimated Monthly Payment: $1,002 (change assumption)
    Mortgage ($986) + Taxes in 2025 ($16)


    Taxes:$197

    Elementary School: Aloma Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 7471 CANFORD CT #19, WINTER PARK, FL 32792

    $199,000280 Days on yellowkey   MLS ID: G5103114

    For Sale G5103114 - 7471 CANFORD CT #19, WINTER PARK, FL 32792 15 photos

    Bed: 2   Bath: 1.5
    Liv Area Sq Ft: 1393
       Built: 1974   Tax: $2,750 (2024)
    Community: Whisperwood Condo
    Condo


    Estimated Monthly Payment: $1,320 (change assumption)
    Mortgage ($1,090) + Taxes in 2024 ($229)


    Taxes:$2,750

    Elementary School: Cheney Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Glenridge Middle


  • 311 E MORSE BLVD #7-19, WINTER PARK, FL 32789

    $284,900199 Days on yellowkey   MLS ID: O6368912

    REDUCED by $5,000 (1.7%) on 05/21/2026

    For Sale O6368912 - 311 E MORSE BLVD #7-19, WINTER PARK, FL 32789 27 photos

    Bed: 1   Bath: 1.0
    Liv Area Sq Ft: 482
       Built: 1960
    Monthly Fee: $870
       Tax: $3,161 (2024)
    Community: Whispering Waters
    Condo


    Estimated Monthly Payment: $2,694 (change assumption)
    Mortgage ($1,561) + Fees ($870) + Taxes in 2024 ($263)


    Taxes:$3,161

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Audubon Park K-8


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

    $144,000150 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


  • 184 SANDLEWOOD TRL ##2, WINTER PARK, FL 32789

    $299,000159 Days on yellowkey   MLS ID: O6380753

    1 Days Off yellowkey (back on 6/29/2026)

    REDUCED by $13,000 (4.2%) on 06/18/2026

    For Sale O6380753 - 184 SANDLEWOOD TRL ##2, WINTER PARK, FL 32789 29 photos

    Bed: 2   Bath: 2.5
    Liv Area Sq Ft: 1133
       Built: 1985
    Monthly Fee: $310
       Tax: $2,915 (2025)
    Community: Sandlewood Creek Condo Ph 10
    Condo


    Estimated Monthly Payment: $2,191 (change assumption)
    Mortgage ($1,638) + Fees ($310) + Taxes in 2025 ($243)


    Taxes:$2,915

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 3371 RIVER VIEW WAY #46, WINTER PARK, FL 32792

    $205,00076 Days on yellowkey   MLS ID: O6403947

    29 Days Off yellowkey (back on 7/8/2026)

    For Sale O6403947 - 3371 RIVER VIEW WAY #46, WINTER PARK, FL 32792 45 photos

    Bed: 3   Bath: 2.5
    Liv Area Sq Ft: 1151
       Built: 1983
    Monthly Fee: $450
       Tax: $2,986 (2025)
    Community: Hidden Oaks Condo Ph 03
    Condo


    Estimated Monthly Payment: $1,822 (change assumption)
    Mortgage ($1,123) + Fees ($450) + Taxes in 2025 ($249)


    Taxes:$2,986

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


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

    $2,070,000166 Days on yellowkey   MLS ID: L4959060

    REDUCED by $25,000 (1.2%) on 07/08/2026

    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: $12,879 (change assumption)
    Mortgage ($11,342) + Taxes in 2024 ($1,537)


    Taxes:$18,439

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 1809 HAMMERLIN AVE, WINTER PARK, FL 32789

    $549,000183 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




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.