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Winter Park Homes For Sale & Real Estate - 439 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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  • 426 WORTHINGTON DR, WINTER PARK, FL 32789

    $2,499,000Listed 06/24/2026 8:44AM   MLS ID: O6418049

    For Sale O6418049 - 426 WORTHINGTON DR, WINTER PARK, FL 32789 46 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3520
       Built: 2026   Tax: $9,459 (2025)
    Community: Kenilworth Shores Sec 01
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $14,481 (change assumption)
    Mortgage ($13,693) + Taxes in 2025 ($788)


    Taxes:$9,459

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 2889 ROUEN AVE, WINTER PARK, FL 32789

    $365,00064 Days on yellowkey   MLS ID: L4961275

    REDUCED by $10,000 (2.7%) on 06/23/2026

    For Sale L4961275 - 2889 ROUEN AVE, WINTER PARK, FL 32789 10 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1144
       Built: 1959   Tax: $5,061 (2025)
    Community: Winter Park Manor
    Single Family


    Estimated Monthly Payment: $2,422 (change assumption)
    Mortgage ($2,000) + Taxes in 2025 ($422)


    Taxes:$5,061

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2231 NAIRN DR, WINTER PARK, FL 32792

    $499,000168 Days on yellowkey   MLS ID: O6369016

    For Sale O6369016 - 2231 NAIRN DR, WINTER PARK, FL 32792 19 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1088
       Built: 1956   Tax: $3,793 (2025)
    Community: Aloma
    Single Family


    Estimated Monthly Payment: $3,050 (change assumption)
    Mortgage ($2,734) + Taxes in 2025 ($316)


    Taxes:$3,793

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 230 STRATHY LN, WINTER PARK, FL 32792

    $499,000168 Days on yellowkey   MLS ID: O6371054

    For Sale O6371054 - 230 STRATHY LN, WINTER PARK, FL 32792 12 photos

    Bed: 2   Bath: 1.0
    Liv Area Sq Ft: 920
       Built: 1957   Tax: $4,071 (2024)
    Community: Aloma
    Single Family


    Estimated Monthly Payment: $3,073 (change assumption)
    Mortgage ($2,734) + Taxes in 2024 ($339)


    Taxes:$4,071

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Glenridge Middle


  • 1649 HARMON AVE, WINTER PARK, FL 32789

    $1,299,90096 Days on yellowkey   MLS ID: O6392216

    REDUCED by $50,000 (3.7%) on 06/12/2026

    For Sale O6392216 - 1649 HARMON AVE, WINTER PARK, FL 32789 57 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3223
       Built: 2018   Tax: $11,908 (2025)
    Community: Lawndale
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $8,115 (change assumption)
    Mortgage ($7,123) + Taxes in 2025 ($992)


    Taxes:$11,908

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park Middle


  • 1662 TREMONT LN, WINTER PARK, FL 32792

    $384,90019 Days on yellowkey   MLS ID: O6414180

    1 Days Off yellowkey (back on 6/24/2026)

    REDUCED by $5,000 (1.3%) on 06/19/2026

    For Sale O6414180 - 1662 TREMONT LN, WINTER PARK, FL 32792 56 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1534
       Built: 1986
    Monthly Fee: $49
       Tax: $4,339 (2025)
    Community: Country Lane
    Single Family


    Estimated Monthly Payment: $2,520 (change assumption)
    Mortgage ($2,109) + Fees ($49) + Taxes in 2025 ($362)


    Taxes:$4,339

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1826 BANCHORY RD, WINTER PARK, FL 32789

    $779,0001 Day on yellowkey   MLS ID: O6419474

    0 Days Off yellowkey (back on 6/23/2026)

    For Sale O6419474 - 1826 BANCHORY RD, WINTER PARK, FL 32789 1 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2391
       Built: 1962   Tax: $7,662 (2025)
    Community: Kenilworth Shores Sec 06
    Single Family


    Estimated Monthly Payment: $4,907 (change assumption)
    Mortgage ($4,268) + Taxes in 2025 ($639)


    Taxes:$7,662

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 7488 WHISPERWOOD DR #28, WINTER PARK, FL 32792

    $230,0001 Day on yellowkey   MLS ID: O6419151

    For Sale O6419151 - 7488 WHISPERWOOD DR #28, WINTER PARK, FL 32792 63 photos

    Bed: 2   Bath: 2.5
    Liv Area Sq Ft: 1578
       Built: 1974
    Monthly Fee: $575
       Tax: $3,078 (2025)
    Community: Whisperwood Condo
    Condo


    Estimated Monthly Payment: $2,092 (change assumption)
    Mortgage ($1,260) + Fees ($575) + Taxes in 2025 ($257)


    Taxes:$3,078

    Elementary School: Cheney Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 1564 LAWNDALE CIR, WINTER PARK, FL 32792

    $450,0001 Day on yellowkey   MLS ID: O6418817

    For Sale O6418817 - 1564 LAWNDALE CIR, WINTER PARK, FL 32792 45 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1980
       Built: 1985
    Monthly Fee: $46
       Tax: $3,124 (2025)
    Community: Country Lane
    Single Family


    Estimated Monthly Payment: $2,772 (change assumption)
    Mortgage ($2,466) + Fees ($46) + Taxes in 2025 ($260)


    Taxes:$3,124

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 1600 LEGION DR, WINTER PARK, FL 32789

    $3,995,00011 Days on yellowkey   MLS ID: O6415591

    For Sale O6415591 - 1600 LEGION DR, WINTER PARK, FL 32789 70 photos

    Bed: 5   Bath: 5.5   Gar: 3
    Liv Area Sq Ft: 4483
       Built: 2008   Tax: $20,740 (2025)
    Community: Green Oaks Rep
    Spa: No

    Single Family


    Estimated Monthly Payment: $23,618 (change assumption)
    Mortgage ($21,890) + Taxes in 2025 ($1,728)


    Taxes:$20,740

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 1630 LASBURY AVE, WINTER PARK, FL 32789

    $2,750,00053 Days on yellowkey   MLS ID: O6404300

    4 Days Off yellowkey (back on 6/24/2026)

    For Sale O6404300 - 1630 LASBURY AVE, WINTER PARK, FL 32789 37 photos

    Bed: 5   Bath: 4.0   Gar: 3
    Liv Area Sq Ft: 4917
       Built: 2003   Tax: $14,204 (2025)
    Community: Comstock Park
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $16,252 (change assumption)
    Mortgage ($15,068) + Taxes in 2025 ($1,184)


    Taxes:$14,204

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 751 WARRENTON RD, WINTER PARK, FL 32792

    $319,9001 Day on yellowkey   MLS ID: TB8522073

    For Sale TB8522073 - 751 WARRENTON RD, WINTER PARK, FL 32792 16 photos

    Bed: 3   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1196
       Built: 1989
    Monthly Fee: $86
       Tax: $2,795 (2025)
    Community: Winter Park Pines Patio Homes
    Spa: No

    Half Duplex


    Estimated Monthly Payment: $2,072 (change assumption)
    Mortgage ($1,753) + Fees ($86) + Taxes in 2025 ($233)


    Taxes:$2,795

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1565 FOREST AVE, WINTER PARK, FL 32789

    $1,495,00071 Days on yellowkey   MLS ID: O6398694

    REDUCED by $155,000 (9.4%) on 06/15/2026

    For Sale O6398694 - 1565 FOREST AVE, WINTER PARK, FL 32789 37 photos

    Bed: 4   Bath: 2.0
    Liv Area Sq Ft: 2163
       Built: 1925   Tax: $2,803 (2025)
    Community: Ellno Willo
    Single Family


    Estimated Monthly Payment: $8,425 (change assumption)
    Mortgage ($8,192) + Taxes in 2025 ($234)


    Taxes:$2,803

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 240 ORANGE TERRACE DR, WINTER PARK, FL 32789

    $470,000321 Days on yellowkey   MLS ID: O6330690

    REDUCED by $9,900 (2.1%) on 06/23/2026

    For Sale O6330690 - 240 ORANGE TERRACE DR, WINTER PARK, FL 32789 32 photos

    Bed: 4   Bath: 2.0
    Liv Area Sq Ft: 1718
       Built: 1955   Tax: $6,210 (2024)
    Community: Orange Terrace
    Single Family


    Estimated Monthly Payment: $3,093 (change assumption)
    Mortgage ($2,575) + Taxes in 2024 ($518)


    Taxes:$6,210

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2024

    Middle School: Robinswood Middle


  • 2052 LEANNE CT, WINTER PARK, FL 32792

    $440,000141 Days on yellowkey   MLS ID: O6379323

    REDUCED by $5,000 (1.1%) on 06/17/2026

    For Sale O6379323 - 2052 LEANNE CT, WINTER PARK, FL 32792 30 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2264
       Built: 1969   Tax: $1,581 (2024)
    Community: Eastbrook Sub Unit 15
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,543 (change assumption)
    Mortgage ($2,411) + Taxes in 2024 ($132)


    Taxes:$1,581

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 1813 HARLAND PARK DR, WINTER PARK, FL 32789

    $1,875,00054 Days on yellowkey   MLS ID: O6403483

    REDUCED by $120,000 (6.0%) on 05/28/2026

    For Sale O6403483 - 1813 HARLAND PARK DR, WINTER PARK, FL 32789 59 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3551
       Built: 2013
    Monthly Fee: $268
       Tax: $23,539 (2025)
    Community: Windsong - Knowles Place
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $12,503 (change assumption)
    Mortgage ($10,274) + Fees ($268) + Taxes in 2025 ($1,962)


    Taxes:$23,539

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 413 W MORSE BLVD, WINTER PARK, FL 32789

    $2,695,00018 Days on yellowkey   MLS ID: O6412134

    For Sale O6412134 - 413 W MORSE BLVD, WINTER PARK, FL 32789 29 photos

    Bed: 3   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3048
       Built: 2018
    Monthly Fee: $386
       Tax: $19,919 (2026)
    Community: Town Of Winter Park
    Townhouse


    Estimated Monthly Payment: $16,813 (change assumption)
    Mortgage ($14,767) + Fees ($386) + Taxes in 2026 ($1,660)


    Taxes:$19,919

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2026

    Middle School: Maitland Middle


  • 926 ENCLAVE PL, WINTER PARK, FL 32792

    $2,235,00035 Days on yellowkey   MLS ID: O6408030

    For Sale O6408030 - 926 ENCLAVE PL, WINTER PARK, FL 32792 5 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 4150
       Built: 2026
    Monthly Fee: $124
       Tax: $9,900 (2026)
    Community: The Enclave Winter Park
    Single Family


    Estimated Monthly Payment: $13,195 (change assumption)
    Mortgage ($12,246) + 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


  • 1840 ASTER DR, WINTER PARK, FL 32792

    $439,90023 Days on yellowkey   MLS ID: O6412364

    REDUCED by $10,000 (2.2%) on 06/21/2026

    For Sale O6412364 - 1840 ASTER DR, WINTER PARK, FL 32792 20 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1667
       Built: 1978   Tax: $864 (2025)
    Community: Garden Lake Estates Unit 1
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,482 (change assumption)
    Mortgage ($2,410) + Taxes in 2025 ($72)


    Taxes:$864

    Elementary School: Red Bug Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 2500 LEE RD #208, WINTER PARK, FL 32789

    $175,000439 Days on yellowkey   MLS ID: O6297570

    REDUCED by $5,000 (2.8%) on 05/14/2026

    For Sale O6297570 - 2500 LEE RD #208, WINTER PARK, FL 32789 49 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 956
       Built: 1969
    Monthly Fee: $432
       Tax: $1,519 (2025)
    Community: Lakeside Manor Apts Condo
    Condo


    Estimated Monthly Payment: $1,517 (change assumption)
    Mortgage ($959) + Fees ($432) + Taxes in 2025 ($127)


    Taxes:$1,519

    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.