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Displaying: For Sale

Location: Windermere

Property Type(s): Single Family

Price: $1,000,000+

Windermere - 178 properties found

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  • 9713 ENDICOTT CT, WINDERMERE, FL 34786

    $5,250,00053 Days on yellowkey   MLS ID: O6393891

    1 Days Off yellowkey (back on 4/21/2026)

    For Sale O6393891 - 9713 ENDICOTT CT, WINDERMERE, FL 34786 100 photos

    Bed: 6   Bath: 7.0   Gar: 6
    Liv Area Sq Ft: 7818
       Built: 2007
    Monthly Fee: $313
       Tax: $66,793 (2025)
    Community: Keenes Pointe
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $34,646 (change assumption)
    Mortgage ($28,766) + Fees ($313) + Taxes in 2025 ($5,566)


    Taxes:$66,793

    Elementary School: Windermere Elem

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 5926 BLAKEFORD DR, WINDERMERE, FL 34786

    $2,149,00094 Days on yellowkey   MLS ID: O6388716

    1 Days Off yellowkey (back on 4/17/2026)

    For Sale O6388716 - 5926 BLAKEFORD DR, WINDERMERE, FL 34786 67 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 3906
       Built: 1999
    Monthly Fee: $298
       Tax: $12,674 (2025)
    Community: Keenes Pointe
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $13,129 (change assumption)
    Mortgage ($11,775) + Fees ($298) + Taxes in 2025 ($1,056)


    Taxes:$12,674

    Elementary School: Windermere Elem

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 4812 ALEXANDRA GARDEN CT, WINDERMERE, FL 34786

    $3,699,000279 Days on yellowkey   MLS ID: O6339134

    For Sale O6339134 - 4812 ALEXANDRA GARDEN CT, WINDERMERE, FL 34786 66 photos

    Bed: 3   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 4262
       Built: 2007
    Monthly Fee: $1,146
       Tax: $45,888 (2024)
    Community: Isleworth
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $25,238 (change assumption)
    Mortgage ($20,268) + Fees ($1,146) + Taxes in 2024 ($3,824)


    Taxes:$45,888

    Elementary School: Windermere Elem

    High School: Olympia High

    Tax Year: 2024

    Middle School: Chain of Lakes Middle


  • 12488 PARK AVE, WINDERMERE, FL 34786

    $15,500,00055 Days on yellowkey   MLS ID: O6395291

    For Sale O6395291 - 12488 PARK AVE, WINDERMERE, FL 34786 68 photos

    Bed: 10   Bath: 14.5   Gar: 9
    Liv Area Sq Ft: 13425
       Built: 1996
    Monthly Fee: $633
       Tax: $56,672 (2025)
    Community: Chaine Du Lac
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $90,285 (change assumption)
    Mortgage ($84,929) + Fees ($633) + Taxes in 2025 ($4,723)


    Taxes:$56,672

    Elementary School: Windermere Elem

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 11226 MACAW CT, WINDERMERE, FL 34786

    $1,825,00057 Days on yellowkey   MLS ID: O6393210

    For Sale O6393210 - 11226 MACAW CT, WINDERMERE, FL 34786 77 photos

    Bed: 4   Bath: 4.5   Gar: 3
    Liv Area Sq Ft: 4549
       Built: 2004
    Monthly Fee: $283
       Tax: $19,332 (2025)
    Community: Keenes Pointe
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $11,894 (change assumption)
    Mortgage ($10,000) + Fees ($283) + Taxes in 2025 ($1,611)


    Taxes:$19,332

    Elementary School: Windermere Elem

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 1703 ROBERTS LANDING RD, WINDERMERE, FL 34786

    $1,520,000262 Days on yellowkey   MLS ID: O6346120

    For Sale O6346120 - 1703 ROBERTS LANDING RD, WINDERMERE, FL 34786 63 photos

    Bed: 4   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3288
       Built: 1996   Tax: $17,269 (2024)
    Community: Roberts Landing
    Single Family


    Estimated Monthly Payment: $9,768 (change assumption)
    Mortgage ($8,329) + Taxes in 2024 ($1,439)


    Taxes:$17,269

    Elementary School: Thornebrooke Elem

    High School: Olympia High

    Tax Year: 2024

    Middle School: Gotha Middle


  • 6152 GOLDEN DEWDROP TRL, WINDERMERE, FL 34786

    $1,130,00062 Days on yellowkey   MLS ID: O6396835

    For Sale O6396835 - 6152 GOLDEN DEWDROP TRL, WINDERMERE, FL 34786 3 photos

    Bed: 8   Bath: 5.0   Gar: 2
    Liv Area Sq Ft: 4830
       Built: 2012
    Monthly Fee: $133
       Tax: $14,684 (2025)
    Community: Windermere Lndgs Fd-1
    Single Family


    Estimated Monthly Payment: $7,548 (change assumption)
    Mortgage ($6,192) + Fees ($133) + Taxes in 2025 ($1,224)


    Taxes:$14,684

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 4819 ALEXANDRA GARDEN CT, WINDERMERE, FL 34786

    $3,200,000320 Days on yellowkey   MLS ID: O6330108

    For Sale O6330108 - 4819 ALEXANDRA GARDEN CT, WINDERMERE, FL 34786 44 photos

    Bed: 4   Bath: 4.5   Gar: 3
    Liv Area Sq Ft: 3745
       Built: 2006
    Monthly Fee: $1,146
       Tax: $33,607 (2024)
    Community: Isleworth
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $21,480 (change assumption)
    Mortgage ($17,534) + Fees ($1,146) + Taxes in 2024 ($2,801)


    Taxes:$33,607

    Elementary School: Windermere Elem

    High School: Olympia High

    Tax Year: 2024

    Middle School: Chain of Lakes Middle


  • 9731 CHESTNUT RIDGE DR, WINDERMERE, FL 34786

    $3,400,000297 Days on yellowkey   MLS ID: O6336655

    For Sale O6336655 - 9731 CHESTNUT RIDGE DR, WINDERMERE, FL 34786 57 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 4877
       Built: 1986
    Monthly Fee: $1,224
       Tax: $19,867 (2024)
    Community: Isleworth
    Single Family


    Estimated Monthly Payment: $21,509 (change assumption)
    Mortgage ($18,630) + Fees ($1,224) + Taxes in 2024 ($1,656)


    Taxes:$19,867

    Elementary School: Windermere Elem

    High School: Olympia High

    Tax Year: 2024

    Middle School: Chain of Lakes Middle


  • 58 MAIN ST, WINDERMERE, FL 34786

    $3,725,000124 Days on yellowkey   MLS ID: O6370886

    For Sale O6370886 - 58 MAIN ST, WINDERMERE, FL 34786 52 photos

    Bed: 5   Bath: 4.0   Gar: 3
    Liv Area Sq Ft: 4875
       Built: 1953   Tax: $21,723 (2024)
    Community: Lake Butler Park Pt Rep
    Single Family


    Estimated Monthly Payment: $22,221 (change assumption)
    Mortgage ($20,410) + Taxes in 2024 ($1,810)


    Taxes:$21,723

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 6142 GROSVENOR SHORE DR, WINDERMERE, FL 34786

    $5,150,00092 Days on yellowkey   MLS ID: O6388222

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

    For Sale O6388222 - 6142 GROSVENOR SHORE DR, WINDERMERE, FL 34786 72 photos

    Bed: 4   Bath: 5.5   Gar: 4
    Liv Area Sq Ft: 6950
       Built: 2009
    Monthly Fee: $298
       Tax: $69,198 (2026)
    Community: Keenes Pointe
    Spa: No

    Single Family


    Estimated Monthly Payment: $34,283 (change assumption)
    Mortgage ($28,218) + Fees ($298) + Taxes in 2026 ($5,767)


    Taxes:$69,198

    Elementary School: Windermere Elem

    High School: Windermere High School

    Tax Year: 2026

    Middle School: Bridgewater Middle


  • 11537 CLAYMONT CIR, WINDERMERE, FL 34786

    $1,400,00069 Days on yellowkey   MLS ID: O6395210

    For Sale O6395210 - 11537 CLAYMONT CIR, WINDERMERE, FL 34786 43 photos

    Bed: 5   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 3164
       Built: 2002
    Monthly Fee: $283
       Tax: $16,031 (2024)
    Community: Keenes Pointe Ut 04 Sec 31 48 82
    Single Family


    Estimated Monthly Payment: $9,290 (change assumption)
    Mortgage ($7,671) + Fees ($283) + Taxes in 2024 ($1,336)


    Taxes:$16,031

    Elementary School: Windermere Elem

    High School: Windermere High School

    Tax Year: 2024

    Middle School: Bridgewater Middle


  • 6109 ORTA CT, WINDERMERE, FL 34786

    $4,495,000145 Days on yellowkey   MLS ID: O6374125

    1 Days Off yellowkey (back on 3/27/2026)

    For Sale O6374125 - 6109 ORTA CT, WINDERMERE, FL 34786 64 photos

    Bed: 5   Bath: 6.0
    Liv Area Sq Ft: 5895
       Built: 2016
    Monthly Fee: $442
       Tax: $65,510 (2025)
    Community: Waterstone
    Single Family


    Estimated Monthly Payment: $30,531 (change assumption)
    Mortgage ($24,630) + Fees ($442) + Taxes in 2025 ($5,459)


    Taxes:$65,510

    Elementary School: Windermere Elem

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 12235 MONTALCINO CIRCLE, WINDERMERE, FL 34786

    $1,899,924185 Days on yellowkey   MLS ID: O6365656

    2 Days Off yellowkey (back on 3/25/2026)

    For Sale O6365656 - 12235 MONTALCINO CIRCLE, WINDERMERE, FL 34786 68 photos

    Bed: 4   Bath: 4.5
    Liv Area Sq Ft: 4550
       Built: 2018
    Community: Casa Del Lago Rep
    Single Family


    Estimated Monthly Payment: $10,410 (change assumption)
    Mortgage ($10,410)


    Taxes:

    Elementary School: None

    High School: None

    Tax Year:

    Middle School: None


  • 11339 CAMDEN PARK DR, WINDERMERE, FL 34786

    $1,490,00095 Days on yellowkey   MLS ID: O6388110

    For Sale O6388110 - 11339 CAMDEN PARK DR, WINDERMERE, FL 34786 100 photos

    Bed: 5   Bath: 4.0
    Liv Area Sq Ft: 3492
       Built: 2004
    Community: Keenes Pointe
    Single Family


    Estimated Monthly Payment: $8,164 (change assumption)
    Mortgage ($8,164)


    Taxes:

    Elementary School: None

    High School: None

    Tax Year:

    Middle School: None


  • 11002 LAKE BUTLER BLVD, WINDERMERE, FL 34786

    $3,999,999429 Days on yellowkey   MLS ID: O6284922

    For Sale O6284922 - 11002 LAKE BUTLER BLVD, WINDERMERE, FL 34786 71 photos

    Bed: 5   Bath: 7.0
    Liv Area Sq Ft: 6248
       Built: 1954
    Community: Metcalf Park Rep
    Single Family


    Estimated Monthly Payment: $21,917 (change assumption)
    Mortgage ($21,917)


    Taxes:

    Elementary School: None

    High School: None

    Tax Year:

    Middle School: None


  • 5837 CAYMUS LOOP, WINDERMERE, FL 34786

    $1,349,000122 Days on yellowkey   MLS ID: O6380732

    3 Days Off yellowkey (back on 3/20/2026)

    For Sale O6380732 - 5837 CAYMUS LOOP, WINDERMERE, FL 34786 36 photos

    Bed: 4   Bath: 3.0
    Liv Area Sq Ft: 2937
       Built: 2004
    Community: Keenes Pointe
    Single Family


    Estimated Monthly Payment: $7,392 (change assumption)
    Mortgage ($7,392)


    Taxes:

    Elementary School: None

    High School: None

    Tax Year:

    Middle School: None


  • 5243 ISLEWORTH COUNTRY CLUB DR, WINDERMERE, FL 34786

    $5,100,000   MLS ID: O6348067

    For Sale O6348067 - 5243 ISLEWORTH COUNTRY CLUB DR, WINDERMERE, FL 34786 65 photos

    Bed: 4   Bath: 5.5
    Liv Area Sq Ft: 6424
       Built: 1992
    Community: Isleworth
    Single Family


    Estimated Monthly Payment: $27,945 (change assumption)
    Mortgage ($27,945)


    Taxes:

    Elementary School: None

    High School: None

    Tax Year:

    Middle School: None






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