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  1. School = Olympia
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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: 56
  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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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: 423
  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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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: 88
  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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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: 147
  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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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: 200
  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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5186 Vardon Drive
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Details for 5186 Vardon Drive, WINDERMERE, FL 34786
Single Family
  1. Price: $6,980,000.00
  2. Price sqft: $886.35 / sqft
  3. Previous Price: $4,960,000
  4. Last Price Change: 04/18/26
  5. Days On Market: 88
  6. Bedrooms: 4
  7. Baths: 5
  8. Garage / Parking Spaces: 3
  9. Bldg sqft: 7875
  10. Acreage: 1.01 acres
  11. Pool: Yes
  12. Waterfront: No
  13. Year Built: 1990
MLS#: O6382040
  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: FLORIDA REALTY INVESTMENTS
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One or more photo(s) has been virtually staged. Fully reimagined golf front estate in the prestigious Isleworth community with sweeping views of the iconic 3rd hole. Situated on approximately 1 acre,
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9725 Chestnut Ridge Drive
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Details for 9725 Chestnut Ridge Drive, WINDERMERE, FL 34786
Single Family
  1. Price: $6,000,000.00
  2. Price sqft: $502.01 / sqft
  3. Previous Price: $6,150,000
  4. Last Price Change: 05/02/26
  5. Days On Market: 131
  6. Bedrooms: 7
  7. Baths: 7
  8. Garage / Parking Spaces: 3
  9. Bldg sqft: 11952
  10. Acreage: 0.56 acres
  11. Pool: Yes
  12. Spa/HotTub: Yes
  13. Waterfront: Yes
  14. Wateraccess: Yes
  15. Waterfront Type: Pond
  16. Year Built: 1999
MLS#: O6370294
  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: DOUGLAS ELLIMAN
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Newly renovated, this private Isleworth residence offers a rare balance of architectural authority, thoughtful design, and quiet indulgence. Spanning approximately 8,000 square feet, the home unfolds
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9639 Westover Roberts Road
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Details for 9639 Westover Roberts Road, WINDERMERE, FL 34786
Single Family
  1. Price: $5,900,000.00
  2. Price sqft: $299.40 / sqft
  3. Previous Price: $6,395,000
  4. Last Price Change: 04/30/26
  5. Days On Market: 246
  6. Bedrooms: 5
  7. Baths: 9
  8. Garage / Parking Spaces: 7
  9. Bldg sqft: 19706
  10. Acreage: 4.43 acres
  11. Pool: Yes
  12. Spa/HotTub: Yes
  13. Waterfront: Yes
  14. Wateraccess: Yes
  15. Waterfront Type: Lake Front
  16. Year Built: 2017
MLS#: O6341883
  1. County: ORANGE
  2. City: WINDERMERE
  3. Zipcode: 34786
  4. Subdivision: Gotha Town
  5. Elementary School: Thornebrooke Elem
  6. Middle School: Gotha
  7. High School: Olympia
  8. Provided by: STOCKWORTH REALTY GROUP
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Welcome to a residence that transcends even the highest expectations of luxury living! This is a once in a lifetime estate where architecture, scale, and location combine to create an experience that
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5138 Fairway Oaks Dr
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Details for 5138 Fairway Oaks Dr, WINDERMERE, FL 34786
Single Family
  1. Price: $5,500,000.00
  2. Price sqft: $930.47 / sqft
  3. Days On Market: 18
  4. Bedrooms: 4
  5. Baths: 5
  6. Garage / Parking Spaces: 3
  7. Bldg sqft: 5911
  8. Acreage: 0.50 acres
  9. Pool: Yes
  10. Spa/HotTub: Yes
  11. Waterfront: No
  12. Year Built: 1994
MLS#: O6401757
  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: ISLEWORTH REALTY LLC
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Set along Isleworths signature 12th fairway, this fully reimagined estate captures the essence of refined golf course living within the renowned Isleworth Golf & Country Clubrecognized among the fines
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5243 Isleworth Country Club Drive
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Details for 5243 Isleworth Country Club Drive, WINDERMERE, FL 34786
Single Family
  1. Price: $5,100,000.00
  2. Price sqft: $703.84 / sqft
  3. Previous Price: $5,325,000
  4. Last Price Change: 03/12/26
  5. Days On Market: 215
  6. Bedrooms: 4
  7. Baths: 6
  8. Garage / Parking Spaces: 3
  9. Bldg sqft: 7246
  10. Acreage: 0.51 acres
  11. Pool: Yes
  12. Waterfront: No
  13. Year Built: 1992
MLS#: O6348067
  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: STOCKWORTH REALTY GROUP
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Presenting a magnificent Isleworth golf front estate with sweeping lake views, perched above holes #2 and #9 and Lake Chase, combining a completely reimagined interior with designer elegance and moder
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Tropic Shores Realty - Crystal River
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