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Displaying: For Sale

Location: Winter Park

Property Type(s): Single Family

Living Area Square Feet: 2500 to 2999

Winter Park - 35 properties found

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  • 616 BRECHIN DR, WINTER PARK, FL 32792

    $1,045,00033 Days on yellowkey   MLS ID: O6409911

    For Sale O6409911 - 616 BRECHIN DR, WINTER PARK, FL 32792 44 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


  • 2111 MALLARD CIR, WINTER PARK, FL 32789

    $1,245,00062 Days on yellowkey   MLS ID: O6401350

    REDUCED by $50,000 (3.9%) on 06/04/2026

    For Sale O6401350 - 2111 MALLARD CIR, WINTER PARK, FL 32789 28 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2667
       Built: 1973   Tax: $7,352 (2025)
    Community: Quail Hollow
    Spa: No

    Single Family


    Estimated Monthly Payment: $7,434 (change assumption)
    Mortgage ($6,822) + Taxes in 2025 ($613)


    Taxes:$7,352

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 240 N PHELPS AVE, WINTER PARK, FL 32789

    $2,250,00013 Days on yellowkey   MLS ID: O6415360

    For Sale O6415360 - 240 N PHELPS AVE, WINTER PARK, FL 32789 41 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 2889
       Built: 2026   Tax: $6,605 (2025)
    Community: Sylvan Heights
    Single Family


    Estimated Monthly Payment: $12,879 (change assumption)
    Mortgage ($12,328) + Taxes in 2025 ($550)


    Taxes:$6,605

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 3135 HEARTLEAF PL, WINTER PARK, FL 32792

    $649,00033 Days on yellowkey   MLS ID: O6410276

    REDUCED by $10,900 (1.7%) on 06/17/2026

    For Sale O6410276 - 3135 HEARTLEAF PL, WINTER PARK, FL 32792 36 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2749
       Built: 1994
    Monthly Fee: $20
       Tax: $2,825 (2025)
    Community: Lost Creek
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,812 (change assumption)
    Mortgage ($3,556) + Fees ($20) + Taxes in 2025 ($235)


    Taxes:$2,825

    Elementary School: Red Bug Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 2454 BROOKSHIRE AVE, WINTER PARK, FL 32792

    $1,399,000118 Days on yellowkey   MLS ID: O6384924

    2 Days Off yellowkey (back on 6/22/2026)

    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


  • 446 MELROSE AVE, WINTER PARK, FL 32789

    $1,625,00058 Days on yellowkey   MLS ID: O6402113

    REDUCED by $70,000 (4.1%) on 06/18/2026

    For Sale O6402113 - 446 MELROSE AVE, WINTER PARK, FL 32789 39 photos

    Bed: 4   Bath: 2.0
    Liv Area Sq Ft: 2640
       Built: 1987   Tax: $20,217 (2025)
    Community: Virginia Heights Rep
    Spa: No

    Single Family


    Estimated Monthly Payment: $10,589 (change assumption)
    Mortgage ($8,904) + Taxes in 2025 ($1,685)


    Taxes:$20,217

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Audubon Park K-8


  • 641 NORTHWOOD CIRCLE, WINTER PARK, FL 32789

    $1,795,00023 Days on yellowkey   MLS ID: O6412554

    For Sale O6412554 - 641 NORTHWOOD CIRCLE, WINTER PARK, FL 32789 41 photos

    Bed: 3   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 2756
       Built: 2023   Tax: $18,393 (2025)
    Community: Winter Park Oasis
    Single Family


    Estimated Monthly Payment: $11,368 (change assumption)
    Mortgage ($9,835) + Taxes in 2025 ($1,533)


    Taxes:$18,393

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 1369 BLUE STEM LN, WINTER PARK, FL 32792

    $825,00078 Days on yellowkey   MLS ID: O6396971

    For Sale O6396971 - 1369 BLUE STEM LN, WINTER PARK, FL 32792 46 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2589
       Built: 2021
    Monthly Fee: $413
       Tax: $6,074 (2024)
    Community: Landings At Hawks Crest
    Single Family


    Estimated Monthly Payment: $5,440 (change assumption)
    Mortgage ($4,520) + Fees ($413) + Taxes in 2024 ($506)


    Taxes:$6,074

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 2430 CHANTILLY AVE, WINTER PARK, FL 32789

    $1,665,00041 Days on yellowkey   MLS ID: O6401352

    For Sale O6401352 - 2430 CHANTILLY AVE, WINTER PARK, FL 32789 49 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 2916
       Built: 2026   Tax: $4,730 (2025)
    Community: Winter Park Village
    Spa: No

    Single Family


    Estimated Monthly Payment: $9,517 (change assumption)
    Mortgage ($9,123) + Taxes in 2025 ($394)


    Taxes:$4,730

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 2702 PARKLAND DR, WINTER PARK, FL 32789

    $1,139,75075 Days on yellowkey   MLS ID: O6397997

    REDUCED by $35,250 (3.0%) on 05/18/2026

    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: $6,684 (change assumption)
    Mortgage ($6,245) + 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


  • 785 N PHELPS AVE, WINTER PARK, FL 32789

    $1,900,00091 Days on yellowkey   MLS ID: O6393117

    REDUCED by $89,000 (4.5%) on 06/05/2026

    For Sale O6393117 - 785 N PHELPS AVE, WINTER PARK, FL 32789 41 photos

    Bed: 5   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2964
       Built: 2026   Tax: $9,172 (2025)
    Community: Comstock Park
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $11,175 (change assumption)
    Mortgage ($10,411) + Taxes in 2025 ($764)


    Taxes:$9,172

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 2501 LAFAYETTE AVE, WINTER PARK, FL 32789

    $1,795,0007 Days on yellowkey   MLS ID: O6416565

    For Sale O6416565 - 2501 LAFAYETTE AVE, WINTER PARK, FL 32789 22 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 2819
       Built: 2026   Tax: $4,608 (2026)
    Community: Winter Park Village
    Single Family


    Estimated Monthly Payment: $10,219 (change assumption)
    Mortgage ($9,835) + Taxes in 2026 ($384)


    Taxes:$4,608

    Elementary School: None

    High School: None

    Tax Year: 2026

    Middle School: None


  • 1220 WOODMERE DR, WINTER PARK, FL 32789

    $1,700,00012 Days on yellowkey   MLS ID: O6415611

    0 Days Off yellowkey (back on 6/17/2026)

    For Sale O6415611 - 1220 WOODMERE DR, WINTER PARK, FL 32789 44 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2815
       Built: 1996   Tax: $7,845 (2025)
    Community: Woodmere Terrace Rep
    Single Family


    Estimated Monthly Payment: $9,969 (change assumption)
    Mortgage ($9,315) + Taxes in 2025 ($654)


    Taxes:$7,845

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 1981 BLUE RIDGE RD, WINTER PARK, FL 32789

    $1,150,00054 Days on yellowkey   MLS ID: O6402961

    For Sale O6402961 - 1981 BLUE RIDGE RD, WINTER PARK, FL 32789 52 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2750
       Built: 1963   Tax: $11,270 (2025)
    Community: Timberlane Shores
    Single Family


    Estimated Monthly Payment: $7,240 (change assumption)
    Mortgage ($6,301) + Taxes in 2025 ($939)


    Taxes:$11,270

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: None


  • 721 PANSY AVE, WINTER PARK, FL 32789

    $1,850,000246 Days on yellowkey   MLS ID: O6352857

    REDUCED by $75,000 (3.9%) on 06/10/2026

    For Sale O6352857 - 721 PANSY AVE, WINTER PARK, FL 32789 29 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 2653
       Built: 2018   Tax: $15,480 (2025)
    Community: Villa View Park
    Single Family


    Estimated Monthly Payment: $11,427 (change assumption)
    Mortgage ($10,137) + Taxes in 2025 ($1,290)


    Taxes:$15,480

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 1090 WILDMEADOW RUN, WINTER PARK, FL 32792

    $835,00089 Days on yellowkey   MLS ID: O6394208

    REDUCED by $10,000 (1.2%) on 06/02/2026

    For Sale O6394208 - 1090 WILDMEADOW RUN, WINTER PARK, FL 32792 37 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2589
       Built: 2021
    Monthly Fee: $243
       Tax: $6,258 (2024)
    Community: Hawks Crest
    Single Family


    Estimated Monthly Payment: $5,340 (change assumption)
    Mortgage ($4,575) + Fees ($243) + Taxes in 2024 ($521)


    Taxes:$6,258

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 1611 CHESTNUT AVE, WINTER PARK, FL 32789

    $1,070,00055 Days on yellowkey   MLS ID: O6402502

    REDUCED by $30,000 (2.7%) on 06/10/2026

    For Sale O6402502 - 1611 CHESTNUT AVE, WINTER PARK, FL 32789 45 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 2916
       Built: 1973   Tax: $3,590 (2025)
    Community: Lake Knowles Terrace
    Single Family


    Estimated Monthly Payment: $6,162 (change assumption)
    Mortgage ($5,863) + Taxes in 2025 ($299)


    Taxes:$3,590

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 2408 LAFAYETTE AVE, WINTER PARK, FL 32789

    $1,495,00075 Days on yellowkey   MLS ID: O6397694

    1 Days Off yellowkey (back on 6/10/2026)

    For Sale O6397694 - 2408 LAFAYETTE AVE, WINTER PARK, FL 32789 31 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2838
       Built: 2024   Tax: $3,770 (2024)
    Community: Winter Park Village
    Spa: No

    Single Family


    Estimated Monthly Payment: $8,506 (change assumption)
    Mortgage ($8,192) + Taxes in 2024 ($314)


    Taxes:$3,770

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Maitland Middle


  • 2220 FAIRGLENN WAY, WINTER PARK, FL 32792

    $629,90068 Days on yellowkey   MLS ID: O6399993

    0 Days Off yellowkey (back on 6/10/2026)

    REDUCED by $20,000 (3.1%) on 06/08/2026

    For Sale O6399993 - 2220 FAIRGLENN WAY, WINTER PARK, FL 32792 53 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: $3,784 (change assumption)
    Mortgage ($3,451) + 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


  • 3312 HEARTWOOD AVE, WINTER PARK, FL 32792

    $465,000249 Days on yellowkey   MLS ID: O6352582

    2 Days Off yellowkey (back on 6/8/2026)

    REDUCED by $19,000 (3.9%) on 04/08/2026

    For Sale O6352582 - 3312 HEARTWOOD AVE, WINTER PARK, FL 32792 36 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2878
       Built: 1983   Tax: $2,183 (2025)
    Community: Bel-Aire Pines
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,730 (change assumption)
    Mortgage ($2,548) + Taxes in 2025 ($182)


    Taxes:$2,183

    Elementary School: Aloma Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


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