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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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  • 220 W READING WAY, WINTER PARK, FL 32789

    $1,195,00024 Days on yellowkey   MLS ID: O6405775

    2 Days Off yellowkey (back on 5/14/2026)

    For Sale O6405775 - 220 W READING WAY, WINTER PARK, FL 32789 8 photos

    Bed: 4   Bath: 3.0
    Liv Area Sq Ft: 2723
       Built: 1947   Tax: $14,025 (2025)
    Community: Forest Hills
    Spa: No

    Single Family


    Estimated Monthly Payment: $7,716 (change assumption)
    Mortgage ($6,548) + Taxes in 2025 ($1,169)


    Taxes:$14,025

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 1354 TIERRA CIR, WINTER PARK, FL 32792

    $425,000504 Days on yellowkey   MLS ID: O6271121

    For Sale O6271121 - 1354 TIERRA CIR, WINTER PARK, FL 32792 31 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1827
       Built: 1969
    Monthly Fee: $2
       Tax: $3,812 (2023)
    Community: Casa Aloma
    Single Family


    Estimated Monthly Payment: $2,648 (change assumption)
    Mortgage ($2,329) + Fees ($2) + Taxes in 2023 ($318)


    Taxes:$3,812

    Elementary School: English Estates Elementary

    High School: Lake Howell High

    Tax Year: 2023

    Middle School: Tuskawilla Middle


  • 7517 LAUREL SPRINGS DR, WINTER PARK, FL 32792

    $399,9904 Days on yellowkey   MLS ID: O6411247

    For Sale O6411247 - 7517 LAUREL SPRINGS DR, WINTER PARK, FL 32792 53 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1678
       Built: 1972   Tax: $6,116 (2025)
    Community: Laurel Springs
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $2,701 (change assumption)
    Mortgage ($2,192) + Taxes in 2025 ($510)


    Taxes:$6,116

    Elementary School: Aloma Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 2299 VIA TUSCANY, WINTER PARK, FL 32789

    $2,150,000209 Days on yellowkey   MLS ID: O6355858

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

    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


  • 2503 TAHOE CIR #2503, WINTER PARK, FL 32792

    $250,00060 Days on yellowkey   MLS ID: O6395130

    For Sale O6395130 - 2503 TAHOE CIR #2503, WINTER PARK, FL 32792 20 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1173
       Built: 1981   Tax: $506 (2025)
    Community: Cedarwood Village 1
    Condo


    Estimated Monthly Payment: $1,412 (change assumption)
    Mortgage ($1,370) + Taxes in 2025 ($42)


    Taxes:$506

    Elementary School: English Estates Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


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

    $236,80095 Days on yellowkey   MLS ID: O6385942

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

    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


  • 2215 WOODCREST DR, WINTER PARK, FL 32792

    $719,00018 Days on yellowkey   MLS ID: O6407540

    For Sale O6407540 - 2215 WOODCREST DR, WINTER PARK, FL 32792 39 photos

    Bed: 4   Bath: 2.0
    Liv Area Sq Ft: 1688
       Built: 1960   Tax: $4,090 (2025)
    Community: Kenilworth Estates 1St Add
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,280 (change assumption)
    Mortgage ($3,940) + Taxes in 2025 ($341)


    Taxes:$4,090

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 700 MELROSE AVE #H4, WINTER PARK, FL 32789

    $290,00010 Days on yellowkey   MLS ID: O6409318

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

    For Sale O6409318 - 700 MELROSE AVE #H4, WINTER PARK, FL 32789 43 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1074
       Built: 1964
    Monthly Fee: $699
       Tax: $851 (2025)
    Community: Winter Park Gardens Condo
    Condo


    Estimated Monthly Payment: $2,359 (change assumption)
    Mortgage ($1,589) + Fees ($699) + Taxes in 2025 ($71)


    Taxes:$851

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1885 TEMPLE DR, WINTER PARK, FL 32789

    $2,225,000201 Days on yellowkey   MLS ID: O6359471

    For Sale O6359471 - 1885 TEMPLE DR, WINTER PARK, FL 32789 53 photos

    Bed: 5   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3691
       Built: 1963   Tax: $6,073 (2025)
    Community: Lugano Terrace
    Spa: No

    Single Family


    Estimated Monthly Payment: $12,698 (change assumption)
    Mortgage ($12,191) + Taxes in 2025 ($506)


    Taxes:$6,073

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 2052 LEANNE CT, WINTER PARK, FL 32792

    $445,000118 Days on yellowkey   MLS ID: O6379323

    REDUCED by $5,000 (1.1%) on 05/28/2026

    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: $2,570 (change assumption)
    Mortgage ($2,438) + Taxes in 2024 ($132)


    Taxes:$1,581

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 3207 LOWNDES DR, WINTER PARK, FL 32792

    $485,000122 Days on yellowkey   MLS ID: O6362285

    0 Days Off yellowkey (back on 5/31/2026)

    REDUCED by $10,000 (2.0%) on 04/23/2026

    For Sale O6362285 - 3207 LOWNDES DR, WINTER PARK, FL 32792 31 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 2028
       Built: 1967   Tax: $4,172 (2024)
    Community: Georgetown Estates
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,005 (change assumption)
    Mortgage ($2,657) + Taxes in 2024 ($348)


    Taxes:$4,172

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Maitland Middle


  • 2383 SUN VALLEY CIR #2383, WINTER PARK, FL 32792

    $259,00042 Days on yellowkey   MLS ID: O6400674

    REDUCED by $10,000 (3.7%) on 05/24/2026

    For Sale O6400674 - 2383 SUN VALLEY CIR #2383, WINTER PARK, FL 32792 32 photos

    Bed: 2   Bath: 2.5
    Liv Area Sq Ft: 1295
       Built: 1985
    Monthly Fee: $499
       Tax: $2,560 (2024)
    Community: Cedarwood Village 1
    Condo


    Estimated Monthly Payment: $2,131 (change assumption)
    Mortgage ($1,419) + Fees ($499) + Taxes in 2024 ($213)


    Taxes:$2,560

    Elementary School: English Estates Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 1420 MAGNOLIA AVE, WINTER PARK, FL 32789

    $1,750,00026 Days on yellowkey   MLS ID: O6404564

    For Sale O6404564 - 1420 MAGNOLIA AVE, WINTER PARK, FL 32789 67 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3174
       Built: 2015   Tax: $21,173 (2025)
    Community: Lake Knowles Terrace Add 02
    Spa: No

    Single Family


    Estimated Monthly Payment: $11,353 (change assumption)
    Mortgage ($9,589) + Taxes in 2025 ($1,764)


    Taxes:$21,173

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 1741 MIZELL AVE, WINTER PARK, FL 32789

    $1,095,00010 Days on yellowkey   MLS ID: O6410059

    For Sale O6410059 - 1741 MIZELL AVE, WINTER PARK, FL 32789 41 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2015
       Built: 1982   Tax: $11,682 (2025)
    Community: Lake Monte Sub
    Single Family


    Estimated Monthly Payment: $6,973 (change assumption)
    Mortgage ($6,000) + Taxes in 2025 ($974)


    Taxes:$11,682

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 616 BRECHIN DR, WINTER PARK, FL 32792

    $1,045,00010 Days on yellowkey   MLS ID: O6409911

    For Sale O6409911 - 616 BRECHIN DR, WINTER PARK, FL 32792 43 photos

    Bed: 4   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 2638
       Built: 1961   Tax: $4,251 (2025)
    Community: Kenilworth Shores Sec 04
    Single Family


    Estimated Monthly Payment: $6,080 (change assumption)
    Mortgage ($5,726) + Taxes in 2025 ($354)


    Taxes:$4,251

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 2361 MULBRY DR, WINTER PARK, FL 32789

    $2,289,00046 Days on yellowkey   MLS ID: O6396840

    REDUCED by $36,000 (1.5%) on 05/28/2026

    For Sale O6396840 - 2361 MULBRY DR, WINTER PARK, FL 32789 80 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 3111
       Built: 2026   Tax: $6,436 (2025)
    Community: Lake Forest Park
    Single Family


    Estimated Monthly Payment: $13,079 (change assumption)
    Mortgage ($12,542) + Taxes in 2025 ($536)


    Taxes:$6,436

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 1565 FOREST AVE, WINTER PARK, FL 32789

    $1,650,00048 Days on yellowkey   MLS ID: O6398694

    REDUCED by $100,000 (5.7%) on 05/11/2026

    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: $9,274 (change assumption)
    Mortgage ($9,041) + 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


  • 1130 PARK NORTH PLACE, WINTER PARK, FL 32789

    $2,495,00067 Days on yellowkey   MLS ID: O6392394

    REDUCED by $155,000 (5.8%) on 04/22/2026

    For Sale O6392394 - 1130 PARK NORTH PLACE, WINTER PARK, FL 32789 41 photos

    Bed: 5   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 4011
       Built: 1968   Tax: $9,744 (2025)
    Community: Park North
    Single Family


    Estimated Monthly Payment: $14,483 (change assumption)
    Mortgage ($13,671) + Taxes in 2025 ($812)


    Taxes:$9,744

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 2823 WRIGHT AVE, WINTER PARK, FL 32789

    $899,90080 Days on yellowkey   MLS ID: O6390670

    REDUCED by $30,000 (3.2%) on 05/07/2026

    For Sale O6390670 - 2823 WRIGHT AVE, WINTER PARK, FL 32789 19 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1536
       Built: 1958   Tax: $9,119 (2025)
    Community: Lake Forest Park
    Single Family


    Estimated Monthly Payment: $5,691 (change assumption)
    Mortgage ($4,931) + Taxes in 2025 ($760)


    Taxes:$9,119

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 948 POINCIANA LN, WINTER PARK, FL 32789

    $3,174,000140 Days on yellowkey   MLS ID: O6372165

    REDUCED by $25,000 (0.8%) on 04/25/2026

    For Sale O6372165 - 948 POINCIANA LN, WINTER PARK, FL 32789 57 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3676
       Built: 2001   Tax: $19,753 (2025)
    Community: Maitland Shores First Add
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $19,037 (change assumption)
    Mortgage ($17,391) + Taxes in 2025 ($1,646)


    Taxes:$19,753

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland 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.