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  1. School = Olympia High
Details for 11900 Lake Butler Boulevard, WINDERMERE, FL 34786
Single Family
  1. Price: $18,500,000.00
  2. Price sqft: $813.97 / sqft
  3. Previous Price: $20,000,000
  4. Last Price Change: 12/29/25
  5. Days On Market: 313
  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 Middle
  7. High School: Olympia High
  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
Details for 5525 Isleworth Country Club Dr, WINDERMERE, FL 34786
Single Family
  1. Price: $14,250,000.00
  2. Price sqft: $1,156.75 / sqft
  3. Days On Market: 248
  4. Bedrooms: 5
  5. Baths: 6
  6. Garage / Parking Spaces: 6
  7. Bldg sqft: 12319
  8. Acreage: 1.02 acres
  9. Pool: Yes
  10. Spa/HotTub: Yes
  11. Waterfront: No
  12. Year Built: 1999
MLS#: O6304800
  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: ISLEWORTH REALTY LLC
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One or more photo(s) has been virtually staged. Exceptional in both style and scale, this extraordinary Isleworth estate represents the pinnacle of luxury living in one of the finest golf club communi
Details for 9639 Westover Roberts Road, WINDERMERE, FL 34786
Single Family
  1. Price: $6,395,000.00
  2. Price sqft: $324.52 / sqft
  3. Days On Market: 136
  4. Bedrooms: 5
  5. Baths: 9
  6. Garage / Parking Spaces: 7
  7. Bldg sqft: 19706
  8. Acreage: 4.43 acres
  9. Pool: Yes
  10. Spa/HotTub: Yes
  11. Waterfront: Yes
  12. Wateraccess: Yes
  13. Waterfront Type: Lake Front
  14. 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 Middle
  7. High School: Olympia High
  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
Details for 5243 Isleworth Country Club Drive, WINDERMERE, FL 34786
Single Family
  1. Price: $5,325,000.00
  2. Price sqft: $734.89 / sqft
  3. Days On Market: 105
  4. Bedrooms: 4
  5. Baths: 6
  6. Garage / Parking Spaces: 3
  7. Bldg sqft: 7246
  8. Acreage: 0.51 acres
  9. Pool: Yes
  10. Waterfront: No
  11. 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 Middle
  7. High School: Olympia High
  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
Details for 1003 Down Reserve Court, WINDERMERE, FL 34786
Single Family
  1. Price: $4,999,999.00
  2. Price sqft: $472.90 / sqft
  3. Previous Price: $5,499,999
  4. Last Price Change: 12/29/25
  5. Days On Market: 94
  6. Bedrooms: 6
  7. Baths: 8
  8. Garage / Parking Spaces: 6
  9. Bldg sqft: 10573
  10. Acreage: 0.69 acres
  11. Pool: Yes
  12. Spa/HotTub: Yes
  13. Waterfront: No
  14. Year Built: 2025
MLS#: O6353952
  1. County: ORANGE
  2. City: WINDERMERE
  3. Zipcode: 34786
  4. Subdivision: Lake Down Reserve
  5. Elementary School: Wyndham Lakes Elementary
  6. Middle School: Chain of Lakes Middle
  7. High School: Olympia High
  8. Provided by: PREMIER SOTHEBYS INT'L REALTY
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Welcome to a rare modern estate in an intimate gated enclave. Imagine 6,816 square feet of fully furnished luxury with six bedrooms, six full baths and two half baths. Every detail of this custom buil
Details for 9575 Westover Roberts Road, WINDERMERE, FL 34786
Single Family
  1. Price: $4,925,000.00
  2. Price sqft: $352.37 / sqft
  3. Days On Market: 72
  4. Bedrooms: 7
  5. Baths: 8
  6. Garage / Parking Spaces: 6
  7. Bldg sqft: 13977
  8. Acreage: 5.44 acres
  9. Pool: Yes
  10. Spa/HotTub: Yes
  11. Waterfront: Yes
  12. Wateraccess: Yes
  13. Waterfront Type: Lake Front
  14. Year Built: 2008
MLS#: O6357873
  1. County: ORANGE
  2. City: WINDERMERE
  3. Zipcode: 34786
  4. Subdivision: Gotha Town
  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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Discover Bella Olivia: a grand mediterranean estate perched high above Lake Olivia showcasing sweeping lake views, private gates, and an expansive luxury residence spanning over 8,900 square feet of l
Details for 5036 Latrobe Drive, WINDERMERE, FL 34786
Single Family
  1. Price: $4,900,000.00
  2. Price sqft: $163.03 / sqft
  3. Days On Market: 111
  4. Bedrooms: 5
  5. Baths: 5
  6. Garage / Parking Spaces: 3
  7. Bldg sqft: 30056
  8. Acreage: 0.69 acres
  9. Pool: Yes
  10. Waterfront: Yes
  11. Wateraccess: Yes
  12. Waterfront Type: Lake Front
  13. Year Built: 1990
MLS#: O6346003
  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: ISLEWORTH REALTY LLC
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Within the gates of the renowned Isleworth Golf & Country Club, this beautiful lakefront estate captures the essence of timeless luxury and gracious living. Poised on the shores of Lake Bessie, the 5,
Details for 11002 Lake Butler Boulevard, WINDERMERE, FL 34786
Single Family
  1. Price: $4,200,000.00
  2. Price sqft: $460.17 / sqft
  3. Days On Market: 291
  4. Bedrooms: 5
  5. Baths: 8
  6. Garage / Parking Spaces: 10
  7. Bldg sqft: 9127
  8. Acreage: 1.15 acres
  9. Pool: Yes
  10. Waterfront: Yes
  11. Wateraccess: Yes
  12. Waterfront Type: Lake Privileges
  13. Year Built: 1954
MLS#: O6284922
  1. County: ORANGE
  2. City: WINDERMERE
  3. Zipcode: 34786
  4. Subdivision: Metcalf Park Rep
  5. Elementary School: Windermere Elem
  6. Middle School: Gotha Middle
  7. High School: Olympia High
  8. Provided by: SERENDIPITY REALTY LLC
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Back on the Market! Lakefront Living in the Heart of Windermere A Rare Opportunity for Multigenerational Luxury Situated along the tranquil, open waters of Wauseon Baypart of the world renown
Details for 1206 Sutter Avenue, GOTHA, FL 34734
Single Family
  1. Price: $3,995,000.00
  2. Price sqft: $441.14 / sqft
  3. Days On Market: 16
  4. Bedrooms: 5
  5. Baths: 6
  6. Garage / Parking Spaces: 4
  7. Bldg sqft: 9056
  8. Acreage: 0.78 acres
  9. Pool: Yes
  10. Waterfront: No
  11. Year Built: 2024
MLS#: O6371168
  1. County: ORANGE
  2. City: GOTHA
  3. Zipcode: 34734
  4. Subdivision: Gotha Town
  5. Elementary School: Thornebrooke Elem
  6. Middle School: Gotha Middle
  7. High School: Olympia High
  8. Provided by: DOUGLAS ELLIMAN
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One or more photo(s) has been virtually staged. Welcome to 1206 Sutter Avenue, a truly exceptional estate and the crown jewel of Gotha, Floridawhere refined luxury meets modern innovation. This 2025 b
Details for 5050 Isleworth Country Club Drive, WINDERMERE, FL 34786
Single Family
  1. Price: $3,975,000.00
  2. Price sqft: $820.77 / sqft
  3. Days On Market: 13
  4. Bedrooms: 4
  5. Baths: 5
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 4843
  8. Acreage: 0.52 acres
  9. Pool: Yes
  10. Spa/HotTub: Yes
  11. Waterfront: No
  12. Year Built: 1987
MLS#: O6372348
  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: COMPASS FLORIDA LLC
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Situated on the 6th fairway along the course of Isleworth Golf & Country Club, this updated golf front sparkles with new porcelain tile throughout and modern chandeliers. This single story residence w