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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: 160
  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#: O6411343
  1. County: ORANGE
  2. City: WINDERMERE
  3. Zipcode: 34786
  4. Elementary School: Thornebrooke Elem
  5. Middle School: Gotha Middle
  6. High School: Olympia High
  7. Provided by: STOCKWORTH REALTY GROUP
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Showcasing Central Floridas most iconic lakefront estate: an 18 acre compound with 614 feet of pristine frontage on Lake Down on The Butler Chain of Lakes. The Windy Ridge Estate is comprised of multi
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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: 181
  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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5192 Vardon Drive
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Details for 5192 Vardon Drive, WINDERMERE, FL 34786
Single Family
  1. Price: $19,500,000.00
  2. Price sqft: $952.33 / sqft
  3. Days On Market: 53
  4. Bedrooms: 6
  5. Baths: 10
  6. Garage / Parking Spaces: 5
  7. Bldg sqft: 20476
  8. Acreage: 2.27 acres
  9. Pool: Yes
  10. Spa/HotTub: Yes
  11. Waterfront: Yes
  12. Wateraccess: Yes
  13. Waterfront Type: Lake Privileges
  14. Year Built: 2006
MLS#: O6441344
  1. County: ORANGE
  2. City: WINDERMERE
  3. Zipcode: 34786
  4. Subdivision: Isleworth Amd 03
  5. Elementary School: Windermere Elem
  6. Middle School: Chain of Lakes Middle
  7. High School: Windermere High School
  8. Provided by: IRWIN REALTY GROUP LLC
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Timeless elegance and extraordinary privacy define this magnificent lakefront estate within the renowned Isleworth Golf & Country Club. Gracefully positioned on Lake Blanche along the coveted Butler
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6119 Grosvenor Shore Drive
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Details for 6119 Grosvenor Shore Drive, WINDERMERE, FL 34786
Single Family
  1. Price: $15,900,000.00
  2. Price sqft: $751.35 / sqft
  3. Days On Market: 117
  4. Bedrooms: 8
  5. Baths: 11
  6. Garage / Parking Spaces: 7
  7. Bldg sqft: 21162
  8. Acreage: 4.23 acres
  9. Pool: Yes
  10. Waterfront: Yes
  11. Wateraccess: Yes
  12. Waterfront Type: Lake Front,Lake Privileges
  13. Year Built: 2014
MLS#: O6421205
  1. County: ORANGE
  2. City: WINDERMERE
  3. Zipcode: 34786
  4. Subdivision: Keenes Point
  5. Elementary School: Windermere Elem
  6. Middle School: Bridgewater Middle
  7. High School: Windermere High School
  8. Provided by: PREMIER SOTHEBY'S INTL. REALTY
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Experience luxury lakefront living on a grand scale in this exquisite estate on Lake Tibet, part of the pristine Butler Chain of Lakes in Windermere. This custom built masterpiece by Goehring & Morgan
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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: 208
  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 Middle
  7. High School: Windermere High School
  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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3057 Porto Lago Court
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Details for 3057 Porto Lago Court, WINDERMERE, FL 34786
Single Family
  1. Price: $13,995,000.00
  2. Price sqft: $879.64 / sqft
  3. Days On Market: 148
  4. Bedrooms: 6
  5. Baths: 11
  6. Garage / Parking Spaces: 8
  7. Bldg sqft: 15910
  8. Acreage: 1.13 acres
  9. Pool: Yes
  10. Spa/HotTub: Yes
  11. Waterfront: Yes
  12. Wateraccess: Yes
  13. Waterfront Type: Lake Front,Lake Privileges
  14. Year Built: 2026
MLS#: O6411245
  1. County: ORANGE
  2. City: WINDERMERE
  3. Zipcode: 34786
  4. Subdivision: Lake Down Pointe 50 42
  5. Elementary School: Thornebrooke Elem
  6. Middle School: Gotha Middle
  7. High School: Olympia High
  8. Provided by: STOCKWORTH REALTY GROUP
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BRAND NEW ESTATE. A truly exceptional one of one on the shores of Lake Down, boasting over 12,000SF, 6BR's, 6/5BA's, and unmatched multigenerational flexibility. Designed by Mark Nasrallah and curated
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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: $11,900,000.00
  2. Price sqft: $951.24 / sqft
  3. Previous Price: $12,500,000
  4. Last Price Change: 11/01/26
  5. Days On Market: 269
  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 Middle
  7. High School: Olympia High
  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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4226 Downeast Lane
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Details for 4226 Downeast Lane, WINDERMERE, FL 34786
Single Family
  1. Price: $9,250,000.00
  2. Price sqft: $1,086.19 / sqft
  3. Previous Price: $9,750,000
  4. Last Price Change: 10/22/26
  5. Days On Market: 381
  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 Middle
  6. High School: Olympia High
  7. Provided by: COLDWELL BANKER RESIDENTIAL RE
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NEW DRAMATIC PRICE IMPROVEMENT on this exceptional 5+ acre LAKE DOWN development opportunity, offering 300 feet of pristine shoreline on the coveted BUTLER CHAIN of Lakes and positioned on the best si
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4226 Downeast Lane
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Details for 4226 Downeast Lane, WINDERMERE, FL 34786
Land
  1. Price: $9,250,000.00
  2. Previous Price: $9,750,000
  3. Last Price Change: 10/22/26
  4. Days On Market: 327
  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 Middle
  6. High School: Olympia High
  7. Provided by: COLDWELL BANKER RESIDENTIAL RE
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NEW DRAMATIC PRICE IMPROVEMENT on this exceptional 5+ acre Lake Down development opportunity, offering 300 feet of pristine shoreline on the coveted BUTLER CHAIN of Lakes and positioned on the best si
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12422 Park Avenue
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Details for 12422 Park Avenue, WINDERMERE, FL 34786
Land
  1. Price: $8,695,000.00
  2. Days On Market: 145
  3. Acreage: 2.19 acres
  4. Pool: No
  5. Waterfront: Yes
  6. Wateraccess: Yes
  7. Waterfront Type: Lake Front,Lake Privileges
  8. Year Built: Not Available
MLS#: O6416090
  1. County: ORANGE
  2. City: WINDERMERE
  3. Zipcode: 34786
  4. Subdivision: Chaine Du Lac
  5. Elementary School: Windermere Elem
  6. Middle School: Bridgewater Middle
  7. High School: Windermere High School
  8. Provided by: JULIAN PROPERTIES, INC.
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WELCOME TO PARK AVENUE. This tremendous opportunity offers 2.19 acres of sprawling possibilities over 2 parcels with Southeastern exposure and sweeping lake views. Nestled on the gorgeous shoreline of
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