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Displaying: For Sale

Location: Winter Park

Property Type(s): Single Family

Beds: 4 to 4

Winter Park - 126 properties found

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  • 1516 MILLER AVE, WINTER PARK, FL 32789

    $1,549,90024 Days on yellowkey   MLS ID: O6412745

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

    For Sale O6412745 - 1516 MILLER AVE, WINTER PARK, FL 32789 9 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3144
       Built: 2026   Tax: $4,868 (2025)
    Community: Lawndale
    Spa: No

    Single Family


    Estimated Monthly Payment: $8,898 (change assumption)
    Mortgage ($8,492) + Taxes in 2025 ($406)


    Taxes:$4,868

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 607 ELLEN DR, WINTER PARK, FL 32789

    $1,449,900247 Days on yellowkey   MLS ID: O6354269

    REDUCED by $50,000 (3.3%) on 05/23/2026

    For Sale O6354269 - 607 ELLEN DR, WINTER PARK, FL 32789 34 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 2812
       Built: 2025
    Monthly Fee: $76
       Tax: $4,224 (2024)
    Community: Lake Killarney Shores
    Spa: No

    Single Family


    Estimated Monthly Payment: $8,372 (change assumption)
    Mortgage ($7,944) + Fees ($76) + Taxes in 2024 ($352)


    Taxes:$4,224

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2024

    Middle School: College Park Middle


  • 2228 HOWARD DR, WINTER PARK, FL 32789

    $2,460,00043 Days on yellowkey   MLS ID: O6407733

    For Sale O6407733 - 2228 HOWARD DR, WINTER PARK, FL 32789 9 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3294
       Built: 2026   Tax: $3,647 (2025)
    Community: Lake Forest Park
    Single Family


    Estimated Monthly Payment: $13,783 (change assumption)
    Mortgage ($13,479) + Taxes in 2025 ($304)


    Taxes:$3,647

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 316 BECKETT CT, WINTER PARK, FL 32792

    $450,00029 Days on yellowkey   MLS ID: O6411108

    For Sale O6411108 - 316 BECKETT CT, WINTER PARK, FL 32792 33 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1651
       Built: 1966   Tax: $2,232 (2025)
    Community: Winter Park Pines Merrie Oaks
    Single Family


    Estimated Monthly Payment: $2,652 (change assumption)
    Mortgage ($2,466) + Taxes in 2025 ($186)


    Taxes:$2,232

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • WINTER PARK, FL 32792

    $430,000105 Days on yellowkey   MLS ID: S5145631

    REDUCED by $10,000 (2.3%) on 04/15/2026

    For Sale S5145631 - WINTER PARK, FL 32792 11 photos

    Bed: 4   Bath: 2.0
    Liv Area Sq Ft: 1296
       Built: 1958   Tax: $4,968 (2025)
    Community: Winter Park Estates
    Single Family


    Estimated Monthly Payment: $2,770 (change assumption)
    Mortgage ($2,356) + Taxes in 2025 ($414)


    Taxes:$4,968

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 4348 STEED TER, WINTER PARK, FL 32792

    $824,00048 Days on yellowkey   MLS ID: O6406018

    0 Days Off yellowkey (back on 5/26/2026)

    For Sale O6406018 - 4348 STEED TER, WINTER PARK, FL 32792 74 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 3040
       Built: 1989
    Monthly Fee: $29
       Tax: $3,652 (2024)
    Community: Kings Cove
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,848 (change assumption)
    Mortgage ($4,515) + Fees ($29) + Taxes in 2024 ($304)


    Taxes:$3,652

    Elementary School: Red Bug Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Tuskawilla Middle


  • 1780 BRYAN AVE, WINTER PARK, FL 32789

    $849,000197 Days on yellowkey   MLS ID: O6365369

    For Sale O6365369 - 1780 BRYAN AVE, WINTER PARK, FL 32789 8 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1617
       Built: 1952   Tax: $7,345 (2024)
    Community: Lakeview Terrace
    Single Family


    Estimated Monthly Payment: $5,264 (change assumption)
    Mortgage ($4,652) + Taxes in 2024 ($612)


    Taxes:$7,345

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 2232 BANCHORY ROAD, WINTER PARK, FL 32792

    $1,115,00052 Days on yellowkey   MLS ID: O6404702

    REDUCED by $45,000 (3.9%) on 05/21/2026

    For Sale O6404702 - 2232 BANCHORY ROAD, WINTER PARK, FL 32792 44 photos

    Bed: 4   Bath: 3.0   Gar: 1
    Liv Area Sq Ft: 2597
       Built: 1966   Tax: $11,186 (2025)
    Community: Brookshire Heights 4Th Add
    Single Family


    Estimated Monthly Payment: $7,042 (change assumption)
    Mortgage ($6,109) + Taxes in 2025 ($932)


    Taxes:$11,186

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2512 EASTBROOK BLVD, WINTER PARK, FL 32792

    $390,00035 Days on yellowkey   MLS ID: O6409544

    For Sale O6409544 - 2512 EASTBROOK BLVD, WINTER PARK, FL 32792 42 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1607
       Built: 1967   Tax: $4,171 (2025)
    Community: Eastbrook Sub Unit 8
    Single Family


    Estimated Monthly Payment: $2,485 (change assumption)
    Mortgage ($2,137) + Taxes in 2025 ($348)


    Taxes:$4,171

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1910 GLENCOE RD, WINTER PARK, FL 32789

    $3,290,00052 Days on yellowkey   MLS ID: O6403246

    2 Days Off yellowkey (back on 5/21/2026)

    For Sale O6403246 - 1910 GLENCOE RD, WINTER PARK, FL 32789 49 photos

    Bed: 4   Bath: 5.5   Gar: 2
    Liv Area Sq Ft: 3788
       Built: 2026   Tax: $8,634 (2025)
    Community: Forest Hills
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $18,746 (change assumption)
    Mortgage ($18,027) + Taxes in 2025 ($720)


    Taxes:$8,634

    Elementary School: Audubon Park K8

    High School: Winter Park High

    Tax Year: 2025

    Middle School: None


  • 1347 CHAPMAN CIR, WINTER PARK, FL 32789

    $1,395,00041 Days on yellowkey   MLS ID: O6408189

    0 Days Off yellowkey (back on 5/20/2026)

    For Sale O6408189 - 1347 CHAPMAN CIR, WINTER PARK, FL 32789 51 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2922
       Built: 2013
    Monthly Fee: $268
       Tax: $16,875 (2025)
    Community: Windsong Elizabeths Walk
    Spa: No

    Single Family


    Estimated Monthly Payment: $9,318 (change assumption)
    Mortgage ($7,644) + Fees ($268) + Taxes in 2025 ($1,406)


    Taxes:$16,875

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • 363 N PHELPS AVE, WINTER PARK, FL 32789

    $1,249,00063 Days on yellowkey   MLS ID: O6401811

    For Sale O6401811 - 363 N PHELPS AVE, WINTER PARK, FL 32789 36 photos

    Bed: 4   Bath: 3.0
    Liv Area Sq Ft: 2871
       Built: 1950   Tax: $8,856 (2025)
    Community: Sylvan Park
    Single Family


    Estimated Monthly Payment: $7,582 (change assumption)
    Mortgage ($6,844) + Taxes in 2025 ($738)


    Taxes:$8,856

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Glenridge Middle


  • WINTER PARK, FL 32789

    $1,249,90044 Days on yellowkey   MLS ID: O6406381

    For Sale O6406381 - WINTER PARK, FL 32789 25 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2936
       Built: 2026   Tax: $3,539 (2025)
    Community: Lawndale
    Single Family


    Estimated Monthly Payment: $7,144 (change assumption)
    Mortgage ($6,849) + Taxes in 2025 ($295)


    Taxes:$3,539

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1903 N PARK AVE, WINTER PARK, FL 32789

    $1,695,000155 Days on yellowkey   MLS ID: O6375766

    REDUCED by $100,000 (5.6%) on 05/14/2026

    For Sale O6375766 - 1903 N PARK AVE, WINTER PARK, FL 32789 42 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 2807
       Built: 2020   Tax: $17,232 (2025)
    Community: Twin Acres
    Single Family


    Estimated Monthly Payment: $10,723 (change assumption)
    Mortgage ($9,287) + Taxes in 2025 ($1,436)


    Taxes:$17,232

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 814 DENSMORE DR, WINTER PARK, FL 32792

    $425,00070 Days on yellowkey   MLS ID: O6399773

    2 Days Off yellowkey (back on 5/13/2026)

    For Sale O6399773 - 814 DENSMORE DR, WINTER PARK, FL 32792 24 photos

    Bed: 4   Bath: 2.0
    Liv Area Sq Ft: 1610
       Built: 1960   Tax: $5,402 (2025)
    Community: Winter Park Estates
    Single Family


    Estimated Monthly Payment: $2,779 (change assumption)
    Mortgage ($2,329) + Taxes in 2025 ($450)


    Taxes:$5,402

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Maitland Middle


  • 770 W WEBSTER AVE, WINTER PARK, FL 32789

    $725,000357 Days on yellowkey   MLS ID: O6323574

    1 Days Off yellowkey (back on 4/11/2026)

    For Sale O6323574 - 770 W WEBSTER AVE, WINTER PARK, FL 32789 34 photos

    Bed: 4   Bath: 2.0
    Liv Area Sq Ft: 1008
       Built: 1967   Tax: $4,856 (2024)
    Community: Capens Add
    Single Family


    Estimated Monthly Payment: $4,377 (change assumption)
    Mortgage ($3,973) + Taxes in 2024 ($405)


    Taxes:$4,856

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2024

    Middle School: Maitland Middle


  • Lot #21 KAROLINA AVE, WINTER PARK, FL 32789

    $944,890104 Days on yellowkey   MLS ID: O6387812

    For Sale O6387812 - Lot #21 KAROLINA AVE, WINTER PARK, FL 32789 9 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2662
       Built: 2025   Tax: $2,207 (2024)
    Community: Karolina On Killarney
    Single Family


    Estimated Monthly Payment: $5,361 (change assumption)
    Mortgage ($5,177) + Taxes in 2024 ($184)


    Taxes:$2,207

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2024

    Middle School: Maitland Middle


  • 1131 WILDMEADOW RUN, WINTER PARK, FL 32792

    $825,00093 Days on yellowkey   MLS ID: O6392218

    For Sale O6392218 - 1131 WILDMEADOW RUN, WINTER PARK, FL 32792 28 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2589
       Built: 2020
    Monthly Fee: $165
       Tax: $5,312 (2024)
    Community: Meadows At Hawks Crest
    Single Family


    Estimated Monthly Payment: $5,128 (change assumption)
    Mortgage ($4,520) + Fees ($165) + Taxes in 2024 ($443)


    Taxes:$5,312

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2024

    Middle School: Sanford Middle


  • 2627 AMBERGATE RD, WINTER PARK, FL 32792

    $510,0001199 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


  • 501 LAKEVIEW AVE, WINTER PARK, FL 32789

    $1,390,000342 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






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