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Winter Park Homes For Sale & Real Estate - 444 homes

Winter Park homes for sale are located in Orange 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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  • 930 ENCLAVE PL, WINTER PARK, FL 32792

    $2,050,00016 Days on yellowkey   MLS ID: O6403032

    For Sale O6403032 - 930 ENCLAVE PL, WINTER PARK, FL 32792 4 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3813
       Built: 2026
    Monthly Fee: $124
       Tax: $9,900 (2026)
    Community: The Enclave Winter Park
    Single Family


    Estimated Monthly Payment: $12,182 (change assumption)
    Mortgage ($11,233) + Fees ($124) + Taxes in 2026 ($825)


    Taxes:$9,900

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2026

    Middle School: Maitland Middle


  • 2500 LEE RD #237, WINTER PARK, FL 32789

    $169,000144 Days on yellowkey   MLS ID: V4946519

    For Sale V4946519 - 2500 LEE RD #237, WINTER PARK, FL 32789 23 photos

    Bed: 1   Bath: 1.0
    Liv Area Sq Ft: 645
       Built: 1969   Tax: $2,227 (2024)
    Community: Lakeside Manor Apts Condo
    Condo


    Estimated Monthly Payment: $1,112 (change assumption)
    Mortgage ($926) + Taxes in 2024 ($186)


    Taxes:$2,227

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2024

    Middle School: College Park Middle


  • 2217 SUSSEX RD, WINTER PARK, FL 32792

    $519,999190 Days on yellowkey   MLS ID: O6362648

    For Sale O6362648 - 2217 SUSSEX RD, WINTER PARK, FL 32792 34 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2092
       Built: 1968   Tax: $4,939 (2024)
    Community: Winter Woods Unit 01
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,261 (change assumption)
    Mortgage ($2,849) + Taxes in 2024 ($412)


    Taxes:$4,939

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 1707 HARMON AVE, WINTER PARK, FL 32789

    $695,00011 Days on yellowkey   MLS ID: O6409180

    For Sale O6409180 - 1707 HARMON AVE, WINTER PARK, FL 32789 37 photos

    Bed: 3   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1669
       Built: 1927   Tax: $4,658 (2025)
    Community: Lawndale
    Single Family


    Estimated Monthly Payment: $4,196 (change assumption)
    Mortgage ($3,808) + Taxes in 2025 ($388)


    Taxes:$4,658

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park Middle


  • 2299 VIA TUSCANY, WINTER PARK, FL 32789

    $2,150,000207 Days on yellowkey   MLS ID: O6355858

    REDUCED by $50,000 (2.3%) on 05/27/2026

    For Sale O6355858 - 2299 VIA TUSCANY, WINTER PARK, FL 32789 60 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3986
       Built: 1953   Tax: $13,185 (2025)
    Community: Maitland Shores
    Single Family


    Estimated Monthly Payment: $12,879 (change assumption)
    Mortgage ($11,781) + Taxes in 2025 ($1,099)


    Taxes:$13,185

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 1307 FORMOSA AVE, WINTER PARK, FL 32789

    $373,80039 Days on yellowkey   MLS ID: O6400711

    1 Days Off yellowkey (back on 5/27/2026)

    REDUCED by $100 (0.0%) on 05/26/2026

    For Sale O6400711 - 1307 FORMOSA AVE, WINTER PARK, FL 32789 33 photos

    Bed: 2   Bath: 1.0   Gar: 1
    Liv Area Sq Ft: 1150
       Built: 1946   Tax: $6,007 (2025)
    Community: Golfview
    Single Family


    Estimated Monthly Payment: $2,549 (change assumption)
    Mortgage ($2,048) + Taxes in 2025 ($501)


    Taxes:$6,007

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 340 KILLARNEY BAY CT #4-4, WINTER PARK, FL 32789

    $395,00015 Days on yellowkey   MLS ID: O6407259

    REDUCED by $15,000 (3.7%) on 05/25/2026

    For Sale O6407259 - 340 KILLARNEY BAY CT #4-4, WINTER PARK, FL 32789 37 photos

    Bed: 2   Bath: 2.5
    Liv Area Sq Ft: 1428
       Built: 1986   Tax: $1,080 (2025)
    Community: Killarney Bay Condo
    Condo


    Estimated Monthly Payment: $2,254 (change assumption)
    Mortgage ($2,164) + Taxes in 2025 ($90)


    Taxes:$1,080

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park Middle


  • 731 BONGART ROAD, WINTER PARK, FL 32792

    $499,00023 Days on yellowkey   MLS ID: O6406004

    For Sale O6406004 - 731 BONGART ROAD, WINTER PARK, FL 32792 44 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 1526
       Built: 1961   Tax: $5,910 (2025)
    Community: Winter Park Estates
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,227 (change assumption)
    Mortgage ($2,734) + Taxes in 2025 ($493)


    Taxes:$5,910

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 1695 LEE RD #E204, WINTER PARK, FL 32789

    $115,000171 Days on yellowkey   MLS ID: O6366205

    REDUCED by $9,900 (7.9%) on 04/03/2026

    For Sale O6366205 - 1695 LEE RD #E204, WINTER PARK, FL 32789 27 photos

    Bed: 2   Bath: 1.0
    Liv Area Sq Ft: 881
       Built: 1966
    Monthly Fee: $482
       Tax: $1,917 (2024)
    Community: Waterfall Cove
    Condo


    Estimated Monthly Payment: $1,272 (change assumption)
    Mortgage ($630) + Fees ($482) + Taxes in 2024 ($160)


    Taxes:$1,917

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 269 E CANTON AVE #269, WINTER PARK, FL 32789

    $989,5009 Days on yellowkey   MLS ID: O6404706

    For Sale O6404706 - 269 E CANTON AVE #269, WINTER PARK, FL 32789 44 photos

    Bed: 1   Bath: 1.5
    Liv Area Sq Ft: 1109
       Built: 1971
    Monthly Fee: $1,039
       Tax: $3,470 (2025)
    Community: Village Winterset Inc
    Condo


    Estimated Monthly Payment: $6,750 (change assumption)
    Mortgage ($5,422) + Fees ($1,039) + Taxes in 2025 ($289)


    Taxes:$3,470

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 607 ELLEN DR, WINTER PARK, FL 32789

    $1,449,900221 Days on yellowkey   MLS ID: O6354269

    REDUCED by $50,000 (3.3%) on 05/23/2026

    For Sale O6354269 - 607 ELLEN DR, WINTER PARK, FL 32789 34 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 2812
       Built: 2025
    Monthly Fee: $76
       Tax: $4,224 (2024)
    Community: Lake Killarney Shores
    Spa: No

    Single Family


    Estimated Monthly Payment: $8,372 (change assumption)
    Mortgage ($7,944) + Fees ($76) + Taxes in 2024 ($352)


    Taxes:$4,224

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2024

    Middle School: College Park Middle


  • WINTER PARK, FL 32792

    $430,00079 Days on yellowkey   MLS ID: S5145631

    REDUCED by $10,000 (2.3%) on 04/15/2026

    For Sale S5145631 - WINTER PARK, FL 32792 11 photos

    Bed: 4   Bath: 2.0
    Liv Area Sq Ft: 1296
       Built: 1958   Tax: $4,968 (2025)
    Community: Winter Park Estates
    Single Family


    Estimated Monthly Payment: $2,770 (change assumption)
    Mortgage ($2,356) + Taxes in 2025 ($414)


    Taxes:$4,968

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1120 WISCONSIN AVE, WINTER PARK, FL 32789

    $1,095,0004 Days on yellowkey   MLS ID: O6406800

    For Sale O6406800 - 1120 WISCONSIN AVE, WINTER PARK, FL 32789 37 photos

    Bed: 3   Bath: 3.5   Gar: 1
    Liv Area Sq Ft: 2213
       Built: 2021   Tax: $10,451 (2025)
    Community: Henkel Add
    Single Family


    Estimated Monthly Payment: $6,871 (change assumption)
    Mortgage ($6,000) + Taxes in 2025 ($871)


    Taxes:$10,451

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park Middle


  • 193 LEWFIELD CIR, WINTER PARK, FL 32792

    $248,9004 Days on yellowkey   MLS ID: O6409075

    For Sale O6409075 - 193 LEWFIELD CIR, WINTER PARK, FL 32792 33 photos

    Bed: 2   Bath: 2.5
    Liv Area Sq Ft: 1300
       Built: 1973
    Monthly Fee: $533
       Tax: $2,286 (2025)
    Community: Stratford A Winter Park Condo
    Condo


    Estimated Monthly Payment: $2,087 (change assumption)
    Mortgage ($1,364) + Fees ($533) + Taxes in 2025 ($191)


    Taxes:$2,286

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 676 DUNBLANE DR, WINTER PARK, FL 32792

    $699,000176 Days on yellowkey   MLS ID: O6365557

    0 Days Off yellowkey (back on 5/26/2026)

    REDUCED by $51,000 (6.8%) on 05/12/2026

    For Sale O6365557 - 676 DUNBLANE DR, WINTER PARK, FL 32792 35 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1827
       Built: 1962   Tax: $5,584 (2024)
    Community: Kenilworth Shores Sec 04
    Single Family


    Estimated Monthly Payment: $4,295 (change assumption)
    Mortgage ($3,830) + Taxes in 2024 ($465)


    Taxes:$5,584

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Glenridge Middle


  • 4772 TANGERINE AVE #4772, WINTER PARK, FL 32792

    $199,00022 Days on yellowkey   MLS ID: O6405042

    For Sale O6405042 - 4772 TANGERINE AVE #4772, WINTER PARK, FL 32792 25 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1058
       Built: 1973   Tax: $2,825 (2025)
    Community: Wrenwood Condo
    Condo


    Estimated Monthly Payment: $1,326 (change assumption)
    Mortgage ($1,090) + Taxes in 2025 ($235)


    Taxes:$2,825

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 1812 KILLARNEY DR, WINTER PARK, FL 32789

    $400,0006 Days on yellowkey   MLS ID: G5112648

    0 Days Off yellowkey (back on 5/26/2026)

    For Sale G5112648 - 1812 KILLARNEY DR, WINTER PARK, FL 32789 10 photos

    Bed: 4   Bath: 2.0
    Liv Area Sq Ft: 1048
       Built: 1950   Tax: $4,779 (2025)
    Community: Karolina On Killarney
    Single Family


    Estimated Monthly Payment: $2,590 (change assumption)
    Mortgage ($2,192) + Taxes in 2025 ($398)


    Taxes:$4,779

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1261 INDIANA AVE, WINTER PARK, FL 32789

    $539,00040 Days on yellowkey   MLS ID: O6400698

    For Sale O6400698 - 1261 INDIANA AVE, WINTER PARK, FL 32789 29 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1660
       Built: 2005
    Monthly Fee: $360
       Tax: $2,892 (2025)
    Community: Townhomes/Harper Place
    Townhouse


    Estimated Monthly Payment: $3,554 (change assumption)
    Mortgage ($2,953) + Fees ($360) + Taxes in 2025 ($241)


    Taxes:$2,892

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park Middle


  • 240 N PHELPS AVE, WINTER PARK, FL 32789

    $2,279,00082 Days on yellowkey   MLS ID: O6389035

    For Sale O6389035 - 240 N PHELPS AVE, WINTER PARK, FL 32789 68 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 2889
       Built: 2026   Tax: $6,605 (2025)
    Community: Sylvan Heights
    Spa: No

    Single Family


    Estimated Monthly Payment: $13,038 (change assumption)
    Mortgage ($12,487) + Taxes in 2025 ($550)


    Taxes:$6,605

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 1473 BERKSHIRE AVE, WINTER PARK, FL 32789

    $1,479,000342 Days on yellowkey   MLS ID: O6320741

    REDUCED by $20,000 (1.3%) on 05/10/2026

    For Sale O6320741 - 1473 BERKSHIRE AVE, WINTER PARK, FL 32789 53 photos

    Bed: 5   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 2895
       Built: 2025   Tax: $5,730 (2024)
    Community: Orwin Manor Westminster Sec
    Single Family


    Estimated Monthly Payment: $8,581 (change assumption)
    Mortgage ($8,104) + Taxes in 2024 ($478)


    Taxes:$5,730

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2024

    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.