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Winter Park Homes For Sale & Real Estate - 446 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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  • 2922 REEF KNOT PL, WINTER PARK, FL 32792

    $1,149,000360 Days on yellowkey   MLS ID: O6316445

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

    For Sale O6316445 - 2922 REEF KNOT PL, WINTER PARK, FL 32792 49 photos

    Bed: 4   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 3153
       Built: 2019
    Monthly Fee: $186
       Tax: $10,521 (2024)
    Community: Lake Florence Preserve
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $7,358 (change assumption)
    Mortgage ($6,296) + Fees ($186) + Taxes in 2024 ($877)


    Taxes:$10,521

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 2627 AMBERGATE RD, WINTER PARK, FL 32792

    $510,0001177 Days on yellowkey   MLS ID: O6093816

    For Sale O6093816 - 2627 AMBERGATE RD, WINTER PARK, FL 32792 19 photos

    Bed: 4   Bath: 3.0   Gar: 1
    Liv Area Sq Ft: 1805
       Built: 1959   Tax: $4,750 (2022)
    Community: Winter Park Estates
    Single Family


    Estimated Monthly Payment: $3,190 (change assumption)
    Mortgage ($2,794) + Taxes in 2022 ($396)


    Taxes:$4,750

    Elementary School: None

    High School: None

    Tax Year: 2022

    Middle School: None


  • 1351 MAGNOLIA AVE, WINTER PARK, FL 32789

    $3,100,00033 Days on yellowkey   MLS ID: O6404105

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

    For Sale O6404105 - 1351 MAGNOLIA AVE, WINTER PARK, FL 32789 1 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3460
       Built: 2026   Tax: $9,720 (2025)
    Community: Lake Knowles Terrace Add 02
    Single Family


    Estimated Monthly Payment: $17,796 (change assumption)
    Mortgage ($16,986) + Taxes in 2025 ($810)


    Taxes:$9,720

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2237 WOODCREST DR, WINTER PARK, FL 32792

    $490,00033 Days on yellowkey   MLS ID: O6404115

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

    For Sale O6404115 - 2237 WOODCREST DR, WINTER PARK, FL 32792 1 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1492
       Built: 1959   Tax: $1,919 (2025)
    Community: Kenilworth Estates 1St Add
    Single Family


    Estimated Monthly Payment: $2,845 (change assumption)
    Mortgage ($2,685) + Taxes in 2025 ($160)


    Taxes:$1,919

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 200 SAINT ANDREWS BLVD #315, WINTER PARK, FL 32792

    $169,000110 Days on yellowkey   MLS ID: V4947283

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

    For Sale V4947283 - 200 SAINT ANDREWS BLVD #315, WINTER PARK, FL 32792 43 photos

    Bed: 1   Bath: 1.0
    Liv Area Sq Ft: 793
       Built: 1970
    Monthly Fee: $451
       Tax: $873 (2024)
    Community: Four Seasons Condo
    Condo


    Estimated Monthly Payment: $1,450 (change assumption)
    Mortgage ($926) + Fees ($451) + Taxes in 2024 ($73)


    Taxes:$873

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Glenridge Middle


  • 150 DANA WAY, WINTER PARK, FL 32789

    $3,799,00068 Days on yellowkey   MLS ID: O6394012

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

    For Sale O6394012 - 150 DANA WAY, WINTER PARK, FL 32789 81 photos

    Bed: 5   Bath: 5.0   Gar: 2
    Liv Area Sq Ft: 4451
       Built: 2026   Tax: $14,010 (2025)
    Community: Charmont
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $21,983 (change assumption)
    Mortgage ($20,816) + Taxes in 2025 ($1,168)


    Taxes:$14,010

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 1781 INDIANA AVE #A, WINTER PARK, FL 32789

    $545,000112 Days on yellowkey   MLS ID: O6381195

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

    REDUCED by $20,000 (3.5%) on 04/14/2026

    For Sale O6381195 - 1781 INDIANA AVE #A, WINTER PARK, FL 32789 47 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1616
       Built: 2008
    Monthly Fee: $464
       Tax: $6,026 (2024)
    Community: Las Casas De Indiana
    Townhouse


    Estimated Monthly Payment: $3,952 (change assumption)
    Mortgage ($2,986) + Fees ($464) + Taxes in 2024 ($502)


    Taxes:$6,026

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2024

    Middle School: College Park Middle


  • 1354 INDIANA AVE, WINTER PARK, FL 32789

    $589,90090 Days on yellowkey   MLS ID: O6387500

    For Sale O6387500 - 1354 INDIANA AVE, WINTER PARK, FL 32789 39 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1269
       Built: 1947   Tax: $5,352 (2024)
    Community: Metzingers Add
    Single Family


    Estimated Monthly Payment: $3,678 (change assumption)
    Mortgage ($3,232) + Taxes in 2024 ($446)


    Taxes:$5,352

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 2220 FAIRGLENN WAY, WINTER PARK, FL 32792

    $649,90047 Days on yellowkey   MLS ID: O6399993

    REDUCED by $25,000 (3.7%) on 04/30/2026

    For Sale O6399993 - 2220 FAIRGLENN WAY, WINTER PARK, FL 32792 54 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2636
       Built: 1986
    Monthly Fee: $53
       Tax: $3,357 (2025)
    Community: Quail Run
    Single Family


    Estimated Monthly Payment: $3,894 (change assumption)
    Mortgage ($3,561) + Fees ($53) + Taxes in 2025 ($280)


    Taxes:$3,357

    Elementary School: Red Bug Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 100 S INTERLACHEN AVE #101, WINTER PARK, FL 32789

    $1,299,000104 Days on yellowkey   MLS ID: O6382597

    For Sale O6382597 - 100 S INTERLACHEN AVE #101, WINTER PARK, FL 32789 53 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1734
       Built: 1971   Tax: $9,362 (2025)
    Community: Cloisters Condo
    Condo


    Estimated Monthly Payment: $7,898 (change assumption)
    Mortgage ($7,118) + Taxes in 2025 ($780)


    Taxes:$9,362

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 726/720 N PENNSYLVANIA AVE, WINTER PARK, FL 32789

    $1,185,99935 Days on yellowkey   MLS ID: O6402984

    For Sale O6402984 - 726/720 N PENNSYLVANIA AVE, WINTER PARK, FL 32789 37 photos

    Bed: 6   Bath: 0.0
    Liv Area Sq Ft: 2282
       Built: 2015   Tax: $5,170 (2025)
    Community: Morseland Sub
    Apartment


    Estimated Monthly Payment: $6,929 (change assumption)
    Mortgage ($6,498) + Taxes in 2025 ($431)


    Taxes:$5,170

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 420 OHIO ST, WINTER PARK, FL 32789

    $1,360,00036 Days on yellowkey   MLS ID: O6399541

    For Sale O6399541 - 420 OHIO ST, WINTER PARK, FL 32789 8 photos

    Bed: 5   Bath: 5.5   Gar: 2
    Liv Area Sq Ft: 3735
       Built: 2026   Tax: $1,281 (2025)
    Community: Karolina On Killarney
    Single Family


    Estimated Monthly Payment: $7,559 (change assumption)
    Mortgage ($7,452) + Taxes in 2025 ($107)


    Taxes:$1,281

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 501 LAKEVIEW AVE, WINTER PARK, FL 32789

    $1,390,000320 Days on yellowkey   MLS ID: O6325192

    For Sale O6325192 - 501 LAKEVIEW AVE, WINTER PARK, FL 32789 59 photos

    Bed: 4   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3253
       Built: 2026   Tax: $2,820 (2024)
    Community: Killarney Estates
    Single Family


    Estimated Monthly Payment: $7,851 (change assumption)
    Mortgage ($7,616) + Taxes in 2024 ($235)


    Taxes:$2,820

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2024

    Middle School: College Park Middle


  • 7484 CANFORD CT #8, WINTER PARK, FL 32792

    $250,00037 Days on yellowkey   MLS ID: O6402492

    For Sale O6402492 - 7484 CANFORD CT #8, WINTER PARK, FL 32792 25 photos

    Bed: 3   Bath: 2.5
    Liv Area Sq Ft: 1578
       Built: 1974   Tax: $2,121 (2025)
    Community: Whisperwood Condo
    Condo


    Estimated Monthly Payment: $1,547 (change assumption)
    Mortgage ($1,370) + Taxes in 2025 ($177)


    Taxes:$2,121

    Elementary School: Cheney Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 3245 COLEUS CT, WINTER PARK, FL 32792

    $379,90066 Days on yellowkey   MLS ID: O6390829

    REDUCED by $10,000 (2.6%) on 04/28/2026

    For Sale O6390829 - 3245 COLEUS CT, WINTER PARK, FL 32792 18 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1529
       Built: 1968   Tax: $986 (2024)
    Community: Eastbrook Sub Unit 14
    Single Family


    Estimated Monthly Payment: $2,164 (change assumption)
    Mortgage ($2,082) + Taxes in 2024 ($82)


    Taxes:$986

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 2384 SUN VALLEY CIR, WINTER PARK, FL 32792

    $269,90093 Days on yellowkey   MLS ID: O6386755

    REDUCED by $5,000 (1.8%) on 04/28/2026

    For Sale O6386755 - 2384 SUN VALLEY CIR, WINTER PARK, FL 32792 36 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1311
       Built: 1983   Tax: $688 (2024)
    Community: Cedarwood Village 1
    Condo


    Estimated Monthly Payment: $1,536 (change assumption)
    Mortgage ($1,479) + Taxes in 2024 ($57)


    Taxes:$688

    Elementary School: English Estates Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 2454 BROOKSHIRE AVE, WINTER PARK, FL 32792

    $1,399,00097 Days on yellowkey   MLS ID: O6384924

    1 Days Off yellowkey (back on 4/28/2026)

    For Sale O6384924 - 2454 BROOKSHIRE AVE, WINTER PARK, FL 32792 34 photos

    Bed: 4   Bath: 3.5   Gar: 1
    Liv Area Sq Ft: 2509
       Built: 2023   Tax: $11,586 (2024)
    Community: Brookshire Heights 1St Add
    Single Family


    Estimated Monthly Payment: $8,631 (change assumption)
    Mortgage ($7,666) + Taxes in 2024 ($966)


    Taxes:$11,586

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Glenridge Middle


  • 632 COUNTRY CLUB DR, WINTER PARK, FL 32789

    $1,050,000585 Days on yellowkey   MLS ID: O6250417

    0 Days Off yellowkey (back on 9/29/2025)

    For Sale O6250417 - 632 COUNTRY CLUB DR, WINTER PARK, FL 32789 36 photos

    Bed: 3   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 2342
       Built: 1952   Tax: $4,638 (2023)
    Community: Lords Sub
    Spa: No

    Single Family


    Estimated Monthly Payment: $6,140 (change assumption)
    Mortgage ($5,753) + Taxes in 2023 ($387)


    Taxes:$4,638

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2023

    Middle School: College Park Middle


  • 1521 HERON WOOD PL, WINTER PARK, FL 32792

    $925,000117 Days on yellowkey   MLS ID: O6379884

    For Sale O6379884 - 1521 HERON WOOD PL, WINTER PARK, FL 32792 74 photos

    Bed: 4   Bath: 2.0
    Liv Area Sq Ft: 3950
       Built: 1983   Tax: $6,494 (2024)
    Community: None
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $5,610 (change assumption)
    Mortgage ($5,068) + Taxes in 2024 ($541)


    Taxes:$6,494

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 121 STEFANIK RD, WINTER PARK, FL 32792

    $317,500224 Days on yellowkey   MLS ID: A4669103

    For Sale A4669103 - 121 STEFANIK RD, WINTER PARK, FL 32792 11 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1392
       Built: 1949   Tax: $3,581 (2024)
    Community: Slovak Village
    Single Family


    Estimated Monthly Payment: $2,038 (change assumption)
    Mortgage ($1,740) + Taxes in 2024 ($298)


    Taxes:$3,581

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None




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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.