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  1. Zipcode = 34786
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9508 Windy Ridge Road
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Details for 9508 Windy Ridge Road, WINDERMERE, FL 34786
Single Family
  1. Price: $30,000,000.00
  2. Price sqft: $639.85 / sqft
  3. Days On Market: 55
  4. Bedrooms: 7
  5. Baths: 14
  6. Garage / Parking Spaces: 12
  7. Bldg sqft: 46886
  8. Acreage: 18.16 acres
  9. Pool: Yes
  10. Spa/HotTub: Yes
  11. Waterfront: Yes
  12. Wateraccess: Yes
  13. Waterfront Type: Lake Front,Lake Privileges
  14. Year Built: 2011
MLS#: O6388674
  1. County: ORANGE
  2. City: WINDERMERE
  3. Zipcode: 34786
  4. Elementary School: Thornebrooke Elem
  5. Middle School: Gotha
  6. High School: Olympia
  7. Provided by: DOUGLAS ELLIMAN
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Presenting Windy Ridge Estate on 18 gated acres with 614 feet of pristine frontage on Lake Down, Butler Chain of Lakes. Manicured grounds, panoramic water views, and over 50,000 SF across multiple str
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5603 Marleon Drive
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Details for 5603 Marleon Drive, Windermere, FL 34786
Single Family
  1. Price: $27,000,000.00
  2. Price sqft: $786.71 / sqft
  3. Days On Market: 0
  4. Bedrooms: 7
  5. Baths: 10
  6. Garage / Parking Spaces: 10
  7. Bldg sqft: 34320
  8. Acreage: 11.58 acres
  9. Pool: Yes
  10. Waterfront: Yes
  11. Wateraccess: Yes
  12. Waterfront Type: LakeFront,LakePrivileges
  13. Year Built: 2008
MLS#: O6404938
  1. County: ORANGE
  2. City: Windermere
  3. Zipcode: 34786
  4. Subdivision: Na
  5. Provided by: PREMIER SOTHEBYS INT'L REALTY
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A rare legacy estate of extraordinary scale and architectural significance, this magnificent lakefront compound spans over 22,000 square feet across more than 11 private acres with over 440 feet of pr
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5603 Marleon Drive
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Details for 5603 Marleon Drive, WINDERMERE, FL 34786
Single Family
  1. Price: $27,000,000.00
  2. Price sqft: $786.71 / sqft
  3. Days On Market: 0
  4. Bedrooms: 7
  5. Baths: 10
  6. Garage / Parking Spaces: 10
  7. Bldg sqft: 34320
  8. Acreage: 11.58 acres
  9. Pool: Yes
  10. Spa/HotTub: Yes
  11. Waterfront: Yes
  12. Wateraccess: Yes
  13. Waterfront Type: Lake Front
  14. Year Built: 2008
MLS#: O6404938
  1. County: ORANGE
  2. City: WINDERMERE
  3. Zipcode: 34786
  4. Provided by: PREMIER SOTHEBYS INT'L REALTY
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A rare legacy estate of extraordinary scale and architectural significance, this magnificent lakefront compound spans over 22,000 square feet across more than 11 private acres with over 440 feet of pr
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11900 Lake Butler Boulevard
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Details for 11900 Lake Butler Boulevard, WINDERMERE, FL 34786
Single Family
  1. Price: $17,250,000.00
  2. Price sqft: $758.98 / sqft
  3. Previous Price: $18,500,000
  4. Last Price Change: 04/16/26
  5. Days On Market: 422
  6. Bedrooms: 7
  7. Baths: 9
  8. Garage / Parking Spaces: 6
  9. Bldg sqft: 22728
  10. Acreage: 3.75 acres
  11. Pool: Yes
  12. Spa/HotTub: Yes
  13. Waterfront: Yes
  14. Wateraccess: Yes
  15. Waterfront Type: Lake Front,Lake Privileges
  16. Year Built: 2014
MLS#: O6275556
  1. County: ORANGE
  2. City: WINDERMERE
  3. Zipcode: 34786
  4. Subdivision: Metcalf Park Rep
  5. Elementary School: Windermere Elem
  6. Middle School: Chain of Lakes
  7. High School: Olympia
  8. Provided by: STOCKWORTH REALTY GROUP
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Presenting Sunset Isle: an iconic waterfront estate compound capturing timeless elegance on Windermeres largest and most prestigious Lake Butler, offering captivating unobstructed views from its 700 f
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12488 Park Avenue
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Details for 12488 Park Avenue, WINDERMERE, FL 34786
Single Family
  1. Price: $15,500,000.00
  2. Price sqft: $878.09 / sqft
  3. Days On Market: 26
  4. Bedrooms: 10
  5. Baths: 17
  6. Garage / Parking Spaces: 9
  7. Bldg sqft: 17652
  8. Acreage: 2.75 acres
  9. Pool: Yes
  10. Spa/HotTub: Yes
  11. Waterfront: Yes
  12. Wateraccess: Yes
  13. Waterfront Type: Lake Privileges
  14. Year Built: 1996
MLS#: O6395291
  1. County: ORANGE
  2. City: WINDERMERE
  3. Zipcode: 34786
  4. Subdivision: Chaine Du Lac
  5. Elementary School: Windermere Elem
  6. Middle School: Bridgewater
  7. High School: Windermere
  8. Provided by: ONE LUXURY INTERNATIONAL LLC
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Commanding a rare 2.75 acre lakefront setting on the coveted Butler Chain of Lakes, this extraordinary Windermere estate is a true work of art. Recently completed after a meticulous, ground up transfo
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9621 Windy Ridge Road
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Details for 9621 Windy Ridge Road, WINDERMERE, FL 34786
Single Family
  1. Price: $13,540,000.00
  2. Price sqft: $493.58 / sqft
  3. Previous Price: $13,550,000
  4. Last Price Change: 05/01/26
  5. Days On Market: 21
  6. Bedrooms: 9
  7. Baths: 16
  8. Garage / Parking Spaces: 8
  9. Bldg sqft: 27432
  10. Acreage: 2.50 acres
  11. Pool: Yes
  12. Waterfront: No
  13. Year Built: 2025
MLS#: O6400740
  1. County: ORANGE
  2. City: WINDERMERE
  3. Zipcode: 34786
  4. Subdivision: Windsor Hill
  5. Provided by: CITARELLI REALTY GROUP LLC
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Under Construction. Under Construction. Experience unmatched privacy, prestige, and personalization with this brand new mansion on 2.5 pristine acres in the heart of Windermere. Tucked against protect
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9323 Gladys Garden Court
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Details for 9323 Gladys Garden Court, WINDERMERE, FL 34786
Single Family
  1. Price: $12,500,000.00
  2. Price sqft: $999.20 / sqft
  3. Previous Price: $13,995,000
  4. Last Price Change: 04/04/26
  5. Days On Market: 87
  6. Bedrooms: 6
  7. Baths: 10
  8. Garage / Parking Spaces: 4
  9. Bldg sqft: 12510
  10. Acreage: 0.26 acres
  11. Pool: Yes
  12. Waterfront: No
  13. Year Built: 2026
MLS#: O6381880
  1. County: ORANGE
  2. City: WINDERMERE
  3. Zipcode: 34786
  4. Subdivision: Isleworth
  5. Elementary School: Windermere Elem
  6. Middle School: Chain of Lakes
  7. High School: Olympia
  8. Provided by: CORCORAN PREMIER REALTY
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Brand new construction and fully furnished! Architecturally refined and intentionally designed by Ashley Martin Home, this custom estate is a masterclass in proportion, craftsmanship, and quiet luxury
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6149 Grosvenor Shore Dr
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Details for 6149 Grosvenor Shore Dr, WINDERMERE, FL 34786
Single Family
  1. Price: $10,900,000.00
  2. Price sqft: $1,194.91 / sqft
  3. Previous Price: $9,999,000
  4. Last Price Change: 04/25/26
  5. Days On Market: 182
  6. Bedrooms: 6
  7. Baths: 8
  8. Garage / Parking Spaces: 7
  9. Bldg sqft: 9122
  10. Acreage: 2.65 acres
  11. Pool: Yes
  12. Spa/HotTub: Yes
  13. Waterfront: Yes
  14. Wateraccess: Yes
  15. Waterfront Type: Lake Privileges
  16. Year Built: 2013
MLS#: O6356355
  1. County: ORANGE
  2. City: WINDERMERE
  3. Zipcode: 34786
  4. Subdivision: Keenes Pointe
  5. Elementary School: Windermere Elem
  6. Middle School: Bridgewater
  7. High School: Windermere
  8. Provided by: SOUTHERN REALTY GROUP LLC
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Keene's Pointe Stunning lakefront home on Lake Tibet of the famed Butler Chain of Lakes. No detail was spared in this completely renovated home boasting formal living and dining rooms, family and me
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4226 Downeast Lane
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Details for 4226 Downeast Lane, WINDERMERE, FL 34786
Single Family
  1. Price: $10,500,000.00
  2. Price sqft: $1,232.97 / sqft
  3. Previous Price: $11,800,000
  4. Last Price Change: 04/09/26
  5. Days On Market: 199
  6. Bedrooms: 5
  7. Baths: 3
  8. Garage / Parking Spaces: 4
  9. Bldg sqft: 8516
  10. Acreage: 9.03 acres
  11. Pool: Yes
  12. Waterfront: Yes
  13. Wateraccess: Yes
  14. Waterfront Type: Lake Front
  15. Year Built: 1980
MLS#: O6355233
  1. County: ORANGE
  2. City: WINDERMERE
  3. Zipcode: 34786
  4. Elementary School: Windermere Elem
  5. Middle School: Chain of Lakes
  6. High School: Olympia
  7. Provided by: COLDWELL BANKER RESIDENTIAL RE
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Dramatic price improvement. Exceptional development opportunity, currently r ce zoning should allow for 3 luxury home sites discover over 5+acres of waterfront land with 300 feet of pristine shorelin
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4226 Downeast Lane
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Details for 4226 Downeast Lane, WINDERMERE, FL 34786
Land
  1. Price: $10,500,000.00
  2. Previous Price: $11,800,000
  3. Last Price Change: 04/09/26
  4. Days On Market: 146
  5. Acreage: 9.03 acres
  6. Pool: No
  7. Waterfront: Yes
  8. Wateraccess: Yes
  9. Waterfront Type: Lake Privileges
  10. Year Built: Not Available
MLS#: O6367852
  1. County: ORANGE
  2. City: WINDERMERE
  3. Zipcode: 34786
  4. Elementary School: Windermere Elem
  5. Middle School: Chain of Lakes
  6. High School: Olympia
  7. Provided by: COLDWELL BANKER RESIDENTIAL RE
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Dramatic price improvement. Exceptional development opportunity, currently r ce zoning should allow for 3 luxury home sites discover over 5+acres of waterfront land with 300 feet of pristine shoreline
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