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Winter Park Homes For Sale & Real Estate - 444 homes

Winter Park homes for sale are located in Seminole County, Florida. Find homes in Winter Park for sale with data from the Multiple Listing Service (MLS). Our REALTORS® can assist you in your real estate search for Winter Park houses.

Location: Winter Park

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  • 3330 COLEUS CT, WINTER PARK, FL 32792

    $384,900109 Days on yellowkey   MLS ID: O6378218

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

    For Sale O6378218 - 3330 COLEUS CT, WINTER PARK, FL 32792 36 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1988
       Built: 1968   Tax: $5,410 (2024)
    Community: Eastbrook Sub Unit 14
    Single Family


    Estimated Monthly Payment: $2,560 (change assumption)
    Mortgage ($2,109) + Taxes in 2024 ($451)


    Taxes:$5,410

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 721 DUNBAR ST, WINTER PARK, FL 32789

    $399,99922 Days on yellowkey   MLS ID: O6405338

    1 Days Off yellowkey (back on 5/13/2026)

    For Sale O6405338 - 721 DUNBAR ST, WINTER PARK, FL 32789 36 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1018
       Built: 1950   Tax: $5,267 (2025)
    Community: Carver Town
    Single Family


    Estimated Monthly Payment: $2,631 (change assumption)
    Mortgage ($2,192) + Taxes in 2025 ($439)


    Taxes:$5,267

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 1500 GAY RD #5, WINTER PARK, FL 32789

    $170,000114 Days on yellowkey   MLS ID: S5143213

    0 Days Off yellowkey (back on 5/13/2026)

    REDUCED by $15,000 (8.1%) on 04/29/2026

    For Sale S5143213 - 1500 GAY RD #5, WINTER PARK, FL 32789 17 photos

    Bed: 1   Bath: 1.0
    Liv Area Sq Ft: 732
       Built: 1972   Tax: $2,098 (2024)
    Community: Chateaux Du Lac
    Condo


    Estimated Monthly Payment: $1,106 (change assumption)
    Mortgage ($931) + Taxes in 2024 ($175)


    Taxes:$2,098

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 311 SCOTTSDALE SQ #311, WINTER PARK, FL 32792

    $109,900217 Days on yellowkey   MLS ID: O6355536

    For Sale O6355536 - 311 SCOTTSDALE SQ #311, WINTER PARK, FL 32792 8 photos

    Bed: 1   Bath: 1.0
    Liv Area Sq Ft: 785
       Built: 1974
    Monthly Fee: $2,097
       Tax: $1,271 (2024)
    Community: Winter Park Woods Condo
    Condo


    Estimated Monthly Payment: $2,805 (change assumption)
    Mortgage ($602) + Fees ($2,097) + Taxes in 2024 ($106)


    Taxes:$1,271

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 1624 BARCELONA WAY, WINTER PARK, FL 32789

    $2,250,000191 Days on yellowkey   MLS ID: O6362124

    REDUCED by $25,000 (1.1%) on 04/17/2026

    For Sale O6362124 - 1624 BARCELONA WAY, WINTER PARK, FL 32789 62 photos

    Bed: 3   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 3818
       Built: 1972
    Monthly Fee: $87
       Tax: $12,501 (2024)
    Community: Sevilla
    Spa: No

    Single Family


    Estimated Monthly Payment: $13,457 (change assumption)
    Mortgage ($12,328) + Fees ($87) + Taxes in 2024 ($1,042)


    Taxes:$12,501

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Audubon Park K-8


  • 188 LEWFIELD CIR #188, WINTER PARK, FL 32792

    $129,99088 Days on yellowkey   MLS ID: O6387291

    1 Days Off yellowkey (back on 5/12/2026)

    REDUCED by $9,010 (6.5%) on 04/20/2026

    For Sale O6387291 - 188 LEWFIELD CIR #188, WINTER PARK, FL 32792 27 photos

    Bed: 1   Bath: 1.0
    Liv Area Sq Ft: 678
       Built: 1973   Tax: $424 (2024)
    Community: Stratford A Winter Park Condo
    Condo


    Estimated Monthly Payment: $748 (change assumption)
    Mortgage ($712) + Taxes in 2024 ($35)


    Taxes:$424

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 2225 WINTER WOODS BLVD, WINTER PARK, FL 32792

    $375,00047 Days on yellowkey   MLS ID: O6398734

    1 Days Off yellowkey (back on 5/12/2026)

    For Sale O6398734 - 2225 WINTER WOODS BLVD, WINTER PARK, FL 32792 37 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1473
       Built: 1968
    Monthly Fee: $2
       Tax: $3,236 (2024)
    Community: Winter Woods Unit 01
    Single Family


    Estimated Monthly Payment: $2,326 (change assumption)
    Mortgage ($2,055) + Fees ($2) + Taxes in 2024 ($270)


    Taxes:$3,236

    Elementary School: English Estates Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 433 CAROLINA AVE, WINTER PARK, FL 32789

    $1,395,00019 Days on yellowkey   MLS ID: O6406911

    0 Days Off yellowkey (back on 5/11/2026)

    For Sale O6406911 - 433 CAROLINA AVE, WINTER PARK, FL 32789 1 photos

    Bed: 5   Bath: 3.5
    Liv Area Sq Ft: 2771
       Built: 2018   Tax: $16,685 (2025)
    Community: Winter Park
    Single Family


    Estimated Monthly Payment: $9,034 (change assumption)
    Mortgage ($7,644) + Taxes in 2025 ($1,390)


    Taxes:$16,685

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 432 W SWOOPE AVE, WINTER PARK, FL 32789

    $695,000129 Days on yellowkey   MLS ID: O6375719

    For Sale O6375719 - 432 W SWOOPE AVE, WINTER PARK, FL 32789 20 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2317
       Built: 2014
    Monthly Fee: $463
       Tax: $9,138 (2025)
    Community: Swoope Park
    Townhouse


    Estimated Monthly Payment: $5,033 (change assumption)
    Mortgage ($3,808) + Fees ($463) + Taxes in 2025 ($761)


    Taxes:$9,138

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 40 PALMER AVE, WINTER PARK, FL 32789

    $6,950,000110 Days on yellowkey   MLS ID: O6380444

    For Sale O6380444 - 40 PALMER AVE, WINTER PARK, FL 32789 17 photos

    Bed: 5   Bath: 5.5   Gar: 4
    Liv Area Sq Ft: 5905
       Built: 2026   Tax: $12,774 (2024)
    Community: Robert Dhu Macdonald Park
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $39,146 (change assumption)
    Mortgage ($38,081) + Taxes in 2024 ($1,065)


    Taxes:$12,774

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Maitland Middle


  • 1745 INDIANA AVE #J, WINTER PARK, FL 32789

    $524,00026 Days on yellowkey   MLS ID: O6402920

    1 Days Off yellowkey (back on 5/8/2026)

    For Sale O6402920 - 1745 INDIANA AVE #J, WINTER PARK, FL 32789 22 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1616
       Built: 2008
    Monthly Fee: $464
       Tax: $6,444 (2025)
    Community: La Casas De Indiana
    Condo


    Estimated Monthly Payment: $3,872 (change assumption)
    Mortgage ($2,871) + Fees ($464) + Taxes in 2025 ($537)


    Taxes:$6,444

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park Middle


  • 1427 LAKE FLORENCE WAY, WINTER PARK, FL 32792

    $639,000191 Days on yellowkey   MLS ID: TB8449992

    1 Days Off yellowkey (back on 5/11/2026)

    REDUCED by $36,000 (5.3%) on 05/06/2026

    For Sale TB8449992 - 1427 LAKE FLORENCE WAY, WINTER PARK, FL 32792 32 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2193
       Built: 2019
    Monthly Fee: $186
       Tax: $5,586 (2024)
    Community: Lake Florence Preserve
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $4,153 (change assumption)
    Mortgage ($3,501) + Fees ($186) + Taxes in 2024 ($465)


    Taxes:$5,586

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 819 DENSMORE DR, WINTER PARK, FL 32792

    $375,00023 Days on yellowkey   MLS ID: O6405658

    3 Days Off yellowkey (back on 5/11/2026)

    For Sale O6405658 - 819 DENSMORE DR, WINTER PARK, FL 32792 39 photos

    Bed: 3   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1300
       Built: 1961   Tax: $5,225 (2025)
    Community: Winter Park Estates Sec 2
    Single Family


    Estimated Monthly Payment: $2,490 (change assumption)
    Mortgage ($2,055) + Taxes in 2025 ($435)


    Taxes:$5,225

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 250 CORTLAND AVE, WINTER PARK, FL 32789

    $950,00057 Days on yellowkey   MLS ID: O6395137

    For Sale O6395137 - 250 CORTLAND AVE, WINTER PARK, FL 32789 46 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2114
       Built: 1981   Tax: $4,370 (2024)
    Community: Cortland Park
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $5,569 (change assumption)
    Mortgage ($5,205) + Taxes in 2024 ($364)


    Taxes:$4,370

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Glenridge Middle


  • 2408 LAFAYETTE AVE, WINTER PARK, FL 32789

    $1,495,00050 Days on yellowkey   MLS ID: O6397694

    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


  • 1836 GRINNELL TER, WINTER PARK, FL 32789

    $999,000113 Days on yellowkey   MLS ID: O6380457

    REDUCED by $51,000 (4.9%) on 05/06/2026

    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: $6,472 (change assumption)
    Mortgage ($5,474) + Taxes in 2025 ($998)


    Taxes:$11,979

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 541 W CANTON AVE, WINTER PARK, FL 32789

    $2,800,00070 Days on yellowkey   MLS ID: O6389829

    For Sale O6389829 - 541 W CANTON AVE, WINTER PARK, FL 32789 51 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3553
       Built: 2024   Tax: $4,692 (2024)
    Community: Winter Park
    Single Family


    Estimated Monthly Payment: $15,733 (change assumption)
    Mortgage ($15,342) + Taxes in 2024 ($391)


    Taxes:$4,692

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Maitland Middle


  • 525 OLOLU DR, WINTER PARK, FL 32789

    $515,00030 Days on yellowkey   MLS ID: S5148431

    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


  • 3374 HAMLET LOOP, WINTER PARK, FL 32792

    $370,00030 Days on yellowkey   MLS ID: O6403488

    For Sale O6403488 - 3374 HAMLET LOOP, WINTER PARK, FL 32792 42 photos

    Bed: 3   Bath: 2.5   Gar: 1
    Liv Area Sq Ft: 1397
       Built: 1994
    Monthly Fee: $63
       Tax: $5,326 (2024)
    Community: Villas Of Casselberry Ph 3
    Single Family


    Estimated Monthly Payment: $2,534 (change assumption)
    Mortgage ($2,027) + Fees ($63) + Taxes in 2024 ($444)


    Taxes:$5,326

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 2482 ROXBURY RD, WINTER PARK, FL 32789

    $400,00022 Days on yellowkey   MLS ID: O6406443

    For Sale O6406443 - 2482 ROXBURY RD, WINTER PARK, FL 32789 20 photos

    Bed: 2   Bath: 1.0
    Liv Area Sq Ft: 913
       Built: 1948   Tax: $5,020 (2025)
    Community: Glencoe
    Single Family


    Estimated Monthly Payment: $2,610 (change assumption)
    Mortgage ($2,192) + Taxes in 2025 ($418)


    Taxes:$5,020

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park Middle




Why Bother Searching Elsewhere for Winter Park Homes for Sale and Other Real Estate?

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 houses for sale in Winter Park . You can use our website to view Multiple Listing Service (MLS) data on 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 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.