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Winter Park Homes For Sale & Real Estate - 302 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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  • 352 CAMBRIDGE BLVD, WINTER PARK, FL 32789

    $650,00074 Days on yellowkey   MLS ID: O6375545

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

    For Sale O6375545 - 352 CAMBRIDGE BLVD, WINTER PARK, FL 32789 37 photos

    Bed: 5   Bath: 3.0
    Liv Area Sq Ft: 1917
       Built: 1920   Tax: $9,806 (2024)
    Community: Glencoe Sub
    Single Family


    Estimated Monthly Payment: $4,379 (change assumption)
    Mortgage ($3,562) + Taxes in 2024 ($817)


    Taxes:$9,806

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 352 CAMBRIDGE BLVD, WINTER PARK, FL 32789

    $650,00069 Days on yellowkey   MLS ID: O6377540

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

    For Sale O6377540 - 352 CAMBRIDGE BLVD, WINTER PARK, FL 32789 37 photos

    Bed: 5   Bath: 0.0
    Liv Area Sq Ft: 1917
       Built: 1920   Tax: $9,806 (2024)
    Community: Glencoe Sub
    Apartment


    Estimated Monthly Payment: $4,379 (change assumption)
    Mortgage ($3,562) + Taxes in 2024 ($817)


    Taxes:$9,806

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 2500 LEE RD #229, WINTER PARK, FL 32789

    $245,00066 Days on yellowkey   MLS ID: O6377616

    For Sale O6377616 - 2500 LEE RD #229, WINTER PARK, FL 32789 41 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 956
       Built: 1969   Tax: $2,613 (2024)
    Community: Lakeside Manor Apts Condo
    Condo


    Estimated Monthly Payment: $1,560 (change assumption)
    Mortgage ($1,342) + Taxes in 2024 ($218)


    Taxes:$2,613

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 2519 WINDWARD WAY, WINTER PARK, FL 32792

    $279,50014 Days on yellowkey   MLS ID: O6392291

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

    For Sale O6392291 - 2519 WINDWARD WAY, WINTER PARK, FL 32792 28 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1105
       Built: 1976
    Monthly Fee: $99
       Tax: $3,155 (2024)
    Community: Windward Square Sec 1
    Townhouse


    Estimated Monthly Payment: $1,893 (change assumption)
    Mortgage ($1,531) + Fees ($99) + Taxes in 2024 ($263)


    Taxes:$3,155

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 2052 LEANNE CT, WINTER PARK, FL 32792

    $456,00062 Days on yellowkey   MLS ID: O6379323

    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
    Single Family


    Estimated Monthly Payment: $2,630 (change assumption)
    Mortgage ($2,499) + Taxes in 2024 ($132)


    Taxes:$1,581

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 2501 TAHOE CIR, WINTER PARK, FL 32792

    $259,90067 Days on yellowkey   MLS ID: O6378209

    REDUCED by $10,000 (3.7%) on 04/05/2026

    For Sale O6378209 - 2501 TAHOE CIR, WINTER PARK, FL 32792 36 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1495
       Built: 1981   Tax: $3,757 (2025)
    Community: Cedarwood Village 1
    Condo


    Estimated Monthly Payment: $1,737 (change assumption)
    Mortgage ($1,424) + Taxes in 2025 ($313)


    Taxes:$3,757

    Elementary School: English Estates Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 720 W WEBSTER AVE, WINTER PARK, FL 32789

    $550,00032 Days on yellowkey   MLS ID: G5108643

    For Sale G5108643 - 720 W WEBSTER AVE, WINTER PARK, FL 32789 43 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1356
       Built: 1950   Tax: $5,128 (2024)
    Community: Carver Town
    Single Family


    Estimated Monthly Payment: $3,441 (change assumption)
    Mortgage ($3,014) + Taxes in 2024 ($427)


    Taxes:$5,128

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Maitland Middle


  • 2412 CHANTILLY AVE, WINTER PARK, FL 32789

    $2,395,00054 Days on yellowkey   MLS ID: O6381552

    For Sale O6381552 - 2412 CHANTILLY AVE, WINTER PARK, FL 32789 61 photos

    Bed: 5   Bath: 6.5   Gar: 3
    Liv Area Sq Ft: 4506
       Built: 2026   Tax: $4,779 (2025)
    Community: Winter Park Village
    Single Family


    Estimated Monthly Payment: $13,521 (change assumption)
    Mortgage ($13,123) + Taxes in 2025 ($398)


    Taxes:$4,779

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 250 CORTLAND AVE, WINTER PARK, FL 32789

    $950,0003 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
    Single Family


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


    Taxes:$4,370

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 150 DANA WAY, WINTER PARK, FL 32789

    $3,799,00010 Days on yellowkey   MLS ID: O6394012

    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
    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


  • 2401 ANTILLES DR, WINTER PARK, FL 32792

    $320,000152 Days on yellowkey   MLS ID: O6357934

    For Sale O6357934 - 2401 ANTILLES DR, WINTER PARK, FL 32792 33 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1719
       Built: 1977
    Monthly Fee: $95

    Community: Windward Square Sec 1
    Townhouse


    Estimated Monthly Payment: $1,848 (change assumption)
    Mortgage ($1,753) + Fees ($95) + Taxes in 2024 ($0)


    Taxes:$0

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 3463 ARNEL DR, WINTER PARK, FL 32792

    $479,90020 Days on yellowkey   MLS ID: O6390301

    For Sale O6390301 - 3463 ARNEL DR, WINTER PARK, FL 32792 58 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1770
       Built: 1967   Tax: $4,648 (2024)
    Community: Eastbrook Sub Unit 11
    Single Family


    Estimated Monthly Payment: $3,017 (change assumption)
    Mortgage ($2,630) + Taxes in 2024 ($387)


    Taxes:$4,648

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 1742 TEMPLE DR, WINTER PARK, FL 32789

    $3,449,99963 Days on yellowkey   MLS ID: O6378905

    REDUCED by $99,991 (2.8%) on 04/05/2026

    For Sale O6378905 - 1742 TEMPLE DR, WINTER PARK, FL 32789 73 photos

    Bed: 4   Bath: 5.0   Gar: 2
    Liv Area Sq Ft: 3658
       Built: 2003   Tax: $22,077 (2024)
    Community: Lake Knowles Terrace Add 02
    Single Family


    Estimated Monthly Payment: $20,743 (change assumption)
    Mortgage ($18,904) + Taxes in 2024 ($1,840)


    Taxes:$22,077

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 4872 ORANGE AVE, WINTER PARK, FL 32792

    $375,00060 Days on yellowkey   MLS ID: O6380333

    1 Days Off yellowkey (back on 4/5/2026)

    For Sale O6380333 - 4872 ORANGE AVE, WINTER PARK, FL 32792 18 photos

    Bed: 3   Bath: 2.5
    Liv Area Sq Ft: 1881
       Built: 1960   Tax: $4,494 (2024)
    Community: Suburban Homes First Add
    Single Family


    Estimated Monthly Payment: $2,429 (change assumption)
    Mortgage ($2,055) + Taxes in 2024 ($374)


    Taxes:$4,494

    Elementary School: Lakemont Elem

    High School: None

    Tax Year: 2024

    Middle School: Maitland Middle


  • 781 NORTHWOOD CIR, WINTER PARK, FL 32789

    $775,0005 Days on yellowkey   MLS ID: O6394119

    0 Days Off yellowkey (back on 4/5/2026)

    For Sale O6394119 - 781 NORTHWOOD CIR, WINTER PARK, FL 32789 33 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1566
       Built: 1971   Tax: $6,931 (2025)
    Community: Winter Park Oasis
    Single Family


    Estimated Monthly Payment: $4,824 (change assumption)
    Mortgage ($4,246) + Taxes in 2025 ($578)


    Taxes:$6,931

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 141 GLENRIDGE WAY, WINTER PARK, FL 32789

    $3,250,00010 Days on yellowkey   MLS ID: O6393616

    For Sale O6393616 - 141 GLENRIDGE WAY, WINTER PARK, FL 32789 66 photos

    Bed: 5   Bath: 4.5   Gar: 3
    Liv Area Sq Ft: 5243
       Built: 2008   Tax: $40,155 (2025)
    Community: Charmont
    Single Family


    Estimated Monthly Payment: $21,154 (change assumption)
    Mortgage ($17,808) + Taxes in 2025 ($3,346)


    Taxes:$40,155

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 2175 MARSH SEDGE LN, WINTER PARK, FL 32792

    $845,00012 Days on yellowkey   MLS ID: O6393503

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

    For Sale O6393503 - 2175 MARSH SEDGE LN, WINTER PARK, FL 32792 44 photos

    Bed: 5   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3188
       Built: 2019
    Monthly Fee: $236
       Tax: $9,100 (2025)
    Community: Hawks Crest
    Single Family


    Estimated Monthly Payment: $5,624 (change assumption)
    Mortgage ($4,630) + Fees ($236) + Taxes in 2025 ($758)


    Taxes:$9,100

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 7445 BETTY ST, WINTER PARK, FL 32792

    $435,0005 Days on yellowkey   MLS ID: OM721366

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

    For Sale OM721366 - 7445 BETTY ST, WINTER PARK, FL 32792 76 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1576
       Built: 1983   Tax: $3,769 (2025)
    Community: Wrenwood Unit 3 4Th Add
    Single Family


    Estimated Monthly Payment: $2,698 (change assumption)
    Mortgage ($2,384) + Taxes in 2025 ($314)


    Taxes:$3,769

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 1529 HOLTS GROVE CIR, WINTER PARK, FL 32789

    $2,850,0005 Days on yellowkey   MLS ID: O6395062

    For Sale O6395062 - 1529 HOLTS GROVE CIR, WINTER PARK, FL 32789 84 photos

    Bed: 4   Bath: 5.0   Gar: 3
    Liv Area Sq Ft: 4356
       Built: 2005
    Monthly Fee: $262
       Tax: $21,342 (2025)
    Community: Windsong Lakeside Sec 02 43/71
    Single Family


    Estimated Monthly Payment: $17,657 (change assumption)
    Mortgage ($15,616) + Fees ($262) + Taxes in 2025 ($1,779)


    Taxes:$21,342

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 1183 WILDMEADOW RUN, WINTER PARK, FL 32792

    $830,00045 Days on yellowkey   MLS ID: O6379772

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

    For Sale O6379772 - 1183 WILDMEADOW RUN, WINTER PARK, FL 32792 44 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3020
       Built: 2020
    Monthly Fee: $150
       Tax: $5,682 (2024)
    Community: Meadows At Hawks Crest
    Single Family


    Estimated Monthly Payment: $5,171 (change assumption)
    Mortgage ($4,548) + Fees ($150) + Taxes in 2024 ($474)


    Taxes:$5,682

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None




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.