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Winter Park Homes For Sale & Real Estate - 416 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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  • 3463 ARNEL DR, WINTER PARK, FL 32792

    $404,900135 Days on yellowkey   MLS ID: O6390301

    0 Days Off yellowkey (back on 7/28/2026)

    REDUCED by $5,000 (1.2%) on 07/24/2026

    For Sale O6390301 - 3463 ARNEL DR, WINTER PARK, FL 32792 35 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: $2,606 (change assumption)
    Mortgage ($2,219) + Taxes in 2024 ($387)


    Taxes:$4,648

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 256 LEWFIELD CIR #256, WINTER PARK, FL 32792

    $184,900200 Days on yellowkey   MLS ID: O6367842

    1 Days Off yellowkey (back on 6/19/2026)

    For Sale O6367842 - 256 LEWFIELD CIR #256, WINTER PARK, FL 32792 55 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 927
       Built: 1973
    Monthly Fee: $465
       Tax: $1,916 (2025)
    Community: Stratford A Winter Park Condo
    Condo


    Estimated Monthly Payment: $1,638 (change assumption)
    Mortgage ($1,013) + Fees ($465) + Taxes in 2025 ($160)


    Taxes:$1,916

    Elementary School: English Estates Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 7327 FOREST HILL CT #223, WINTER PARK, FL 32792

    $175,00087 Days on yellowkey   MLS ID: O6403841

    REDUCED by $5,000 (2.8%) on 07/28/2026

    For Sale O6403841 - 7327 FOREST HILL CT #223, WINTER PARK, FL 32792 24 photos

    Bed: 2   Bath: 2.5
    Liv Area Sq Ft: 1031
       Built: 1984
    Monthly Fee: $450
       Tax: $2,597 (2025)
    Community: Hidden Oaks Condo Ph 12
    Condo


    Estimated Monthly Payment: $1,625 (change assumption)
    Mortgage ($959) + Fees ($450) + Taxes in 2025 ($216)


    Taxes:$2,597

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1840 ASTER DR, WINTER PARK, FL 32792

    $414,90059 Days on yellowkey   MLS ID: O6412364

    REDUCED by $5,000 (1.2%) on 07/28/2026

    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: $2,345 (change assumption)
    Mortgage ($2,273) + Taxes in 2025 ($72)


    Taxes:$864

    Elementary School: Red Bug Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 1404 BORDER DR, WINTER PARK, FL 32789

    $1,150,00062 Days on yellowkey   MLS ID: O6412140

    REDUCED by $25,000 (2.1%) on 07/01/2026

    For Sale O6412140 - 1404 BORDER DR, WINTER PARK, FL 32789 38 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 2469
       Built: 2023   Tax: $16,220 (2025)
    Community: Winter Park Village
    Single Family


    Estimated Monthly Payment: $7,653 (change assumption)
    Mortgage ($6,301) + Taxes in 2025 ($1,352)


    Taxes:$16,220

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 102 BELL PL, WINTER PARK, FL 32792

    $1,399,000107 Days on yellowkey   MLS ID: O6398118

    For Sale O6398118 - 102 BELL PL, WINTER PARK, FL 32792 46 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2459
       Built: 2025   Tax: $4,224 (2025)
    Community: Eastgate Sub
    Spa: No

    Single Family


    Estimated Monthly Payment: $8,018 (change assumption)
    Mortgage ($7,666) + Taxes in 2025 ($352)


    Taxes:$4,224

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 723 SYMONDS AVE, WINTER PARK, FL 32789

    $1,800,00063 Days on yellowkey   MLS ID: O6406823

    For Sale O6406823 - 723 SYMONDS AVE, WINTER PARK, FL 32789 50 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 3065
       Built: 2023   Tax: $15,884 (2025)
    Community: Horton Aaron
    Single Family


    Estimated Monthly Payment: $11,186 (change assumption)
    Mortgage ($9,863) + Taxes in 2025 ($1,324)


    Taxes:$15,884

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 433 GILBERT RD, WINTER PARK, FL 32792

    $675,0003 Days on yellowkey   MLS ID: O6428430

    For Sale O6428430 - 433 GILBERT RD, WINTER PARK, FL 32792 36 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1770
       Built: 1965   Tax: $4,032 (2025)
    Community: Winter Park Pines
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,035 (change assumption)
    Mortgage ($3,699) + Taxes in 2025 ($336)


    Taxes:$4,032

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 338 BLUE HERON DR, WINTER PARK, FL 32789

    $840,00061 Days on yellowkey   MLS ID: O6410174

    REDUCED by $25,000 (2.9%) on 07/28/2026

    For Sale O6410174 - 338 BLUE HERON DR, WINTER PARK, FL 32789 44 photos

    Bed: 3   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2017
       Built: 1960   Tax: $6,647 (2025)
    Community: Flamingo Shores
    Single Family


    Estimated Monthly Payment: $5,157 (change assumption)
    Mortgage ($4,603) + Taxes in 2025 ($554)


    Taxes:$6,647

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park Middle


  • 1398 GROVE TER, WINTER PARK, FL 32789

    $1,995,000105 Days on yellowkey   MLS ID: O6399698

    REDUCED by $100,000 (4.8%) on 07/28/2026

    For Sale O6399698 - 1398 GROVE TER, WINTER PARK, FL 32789 58 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3450
       Built: 2004   Tax: $24,548 (2025)
    Community: Sylvan Lake Shores
    Spa: No

    Single Family


    Estimated Monthly Payment: $12,977 (change assumption)
    Mortgage ($10,931) + Taxes in 2025 ($2,046)


    Taxes:$24,548

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 651 DARCEY DR, WINTER PARK, FL 32792

    $500,0003 Days on yellowkey   MLS ID: O6428379

    0 Days Off yellowkey (back on 7/27/2026)

    For Sale O6428379 - 651 DARCEY DR, WINTER PARK, FL 32792 1 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1866
       Built: 1967   Tax: $7,847 (2025)
    Community: Brookshire Heights
    Single Family


    Estimated Monthly Payment: $3,394 (change assumption)
    Mortgage ($2,740) + Taxes in 2025 ($654)


    Taxes:$7,847

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 2702 PARKLAND DR, WINTER PARK, FL 32789

    $1,049,000111 Days on yellowkey   MLS ID: O6397997

    REDUCED by $50,000 (4.5%) on 07/21/2026

    For Sale O6397997 - 2702 PARKLAND DR, WINTER PARK, FL 32789 48 photos

    Bed: 5   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2656
       Built: 1949   Tax: $5,269 (2025)
    Community: Parklando
    Single Family


    Estimated Monthly Payment: $6,187 (change assumption)
    Mortgage ($5,748) + Taxes in 2025 ($439)


    Taxes:$5,269

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 341 E READING WAY, WINTER PARK, FL 32789

    $1,625,00030 Days on yellowkey   MLS ID: O6420387

    REDUCED by $70,000 (4.1%) on 07/28/2026

    For Sale O6420387 - 341 E READING WAY, WINTER PARK, FL 32789 57 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 3723
       Built: 2007   Tax: $20,249 (2026)
    Community: Charmont
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $10,591 (change assumption)
    Mortgage ($8,904) + Taxes in 2026 ($1,687)


    Taxes:$20,249

    Elementary School: None

    High School: Winter Park High

    Tax Year: 2026

    Middle School: Audubon Park K-8


  • 1320 GLADIOLAS DR, WINTER PARK, FL 32792

    $474,00062 Days on yellowkey   MLS ID: O6412139

    REDUCED by $1,000 (0.2%) on 07/28/2026

    For Sale O6412139 - 1320 GLADIOLAS DR, WINTER PARK, FL 32792 43 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1624
       Built: 1983   Tax: $1,380 (2025)
    Community: Garden Lake Estates Unit 3
    Single Family


    Estimated Monthly Payment: $2,712 (change assumption)
    Mortgage ($2,597) + Taxes in 2025 ($115)


    Taxes:$1,380

    Elementary School: Red Bug Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 145 SCOTTSDALE SQ, WINTER PARK, FL 32792

    $99,90015 Days on yellowkey   MLS ID: O6424788

    0 Days Off yellowkey (back on 7/28/2026)

    For Sale O6424788 - 145 SCOTTSDALE SQ, WINTER PARK, FL 32792 33 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1020
       Built: 1974
    Monthly Fee: $880
       Tax: $1,552 (2025)
    Community: Winter Park Woods Condo
    Condo


    Estimated Monthly Payment: $1,557 (change assumption)
    Mortgage ($547) + Fees ($880) + Taxes in 2025 ($129)


    Taxes:$1,552

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 240 KILLARNEY DR, WINTER PARK, FL 32789

    $1,275,00013 Days on yellowkey   MLS ID: O6415977

    For Sale O6415977 - 240 KILLARNEY DR, WINTER PARK, FL 32789 13 photos

    Bed: 3   Bath: 2.5
    Liv Area Sq Ft: 1329
       Built: 1947   Tax: $6,161 (2025)
    Community: Killarney Estates
    Single Family


    Estimated Monthly Payment: $7,500 (change assumption)
    Mortgage ($6,986) + Taxes in 2025 ($513)


    Taxes:$6,161

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park Middle


  • 230 KILLARNEY DR, WINTER PARK, FL 32789

    $1,250,00013 Days on yellowkey   MLS ID: O6415950

    For Sale O6415950 - 230 KILLARNEY DR, WINTER PARK, FL 32789 13 photos

    Bed: 4   Bath: 1.0
    Liv Area Sq Ft: 1260
       Built: 1925   Tax: $5,754 (2025)
    Community: Killarney Estates
    Single Family


    Estimated Monthly Payment: $7,329 (change assumption)
    Mortgage ($6,849) + Taxes in 2025 ($480)


    Taxes:$5,754

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2025

    Middle School: College Park Middle


  • 1529 HOLTS GROVE CIR, WINTER PARK, FL 32789

    $2,699,000120 Days on yellowkey   MLS ID: O6395062

    0 Days Off yellowkey (back on 6/15/2026)

    REDUCED by $96,000 (3.4%) on 05/20/2026

    For Sale O6395062 - 1529 HOLTS GROVE CIR, WINTER PARK, FL 32789 77 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
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $16,829 (change assumption)
    Mortgage ($14,789) + 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


  • 1695 LEE RD #A116, WINTER PARK, FL 32789

    $135,00029 Days on yellowkey   MLS ID: O6420863

    For Sale O6420863 - 1695 LEE RD #A116, WINTER PARK, FL 32789 18 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1149
       Built: 1966   Tax: $2,263 (2025)
    Community: Waterfall Cove
    Condo


    Estimated Monthly Payment: $928 (change assumption)
    Mortgage ($740) + Taxes in 2025 ($189)


    Taxes:$2,263

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1438 TIERRA CIR, WINTER PARK, FL 32792

    $514,90089 Days on yellowkey   MLS ID: O6403855

    REDUCED by $5,000 (1.0%) on 06/24/2026

    For Sale O6403855 - 1438 TIERRA CIR, WINTER PARK, FL 32792 36 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1627
       Built: 1968   Tax: $1,630 (2024)
    Community: Casa Aloma
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,957 (change assumption)
    Mortgage ($2,821) + Taxes in 2024 ($136)


    Taxes:$1,630

    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.