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  1. School = Olympia High
Details for 11900 Lake Butler Boulevard, WINDERMERE, FL 34786
Single Family
  1. Price: $20,000,000.00
  2. Price sqft: $879.97 / sqft
  3. Days On Market: 179
  4. Bedrooms: 7
  5. Baths: 9
  6. Garage / Parking Spaces: 6
  7. Bldg sqft: 22728
  8. Acreage: 3.75 acres
  9. Pool: Yes
  10. Spa/HotTub: Yes
  11. Waterfront: Yes
  12. Wateraccess: Yes
  13. Waterfront Type: Lake Front,Lake Privileges
  14. 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: 114
  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 4200 Down Point Lane, WINDERMERE, FL 34786
Single Family
  1. Price: $11,900,000.00
  2. Price sqft: $671.86 / sqft
  3. Previous Price: $12,900,000
  4. Last Price Change: 09/03/25
  5. Days On Market: 583
  6. Bedrooms: 6
  7. Baths: 9
  8. Garage / Parking Spaces: 4
  9. Bldg sqft: 17712
  10. Acreage: 1.60 acres
  11. Pool: Yes
  12. Spa/HotTub: Yes
  13. Waterfront: Yes
  14. Wateraccess: Yes
  15. Waterfront Type: Lake Privileges
  16. Year Built: 2001
MLS#: O6176070
  1. County: ORANGE
  2. City: WINDERMERE
  3. Zipcode: 34786
  4. Subdivision: Down Point Sub
  5. Elementary School: Windermere Elem
  6. Middle School: Chain of Lakes Middle
  7. High School: Olympia High
  8. Provided by: REVEL REALTY LLC
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Nestled along almost 1,000 of the highly sought after Butler Chain of Lakes in Windermere, this exquisite Mediterranean estate beckons with unrivaled opulence. Beyond a private gate, a 2 acre peninsul
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: 2
  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 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: 2
  4. Bedrooms: 5
  5. Baths: 9
  6. Garage / Parking Spaces: 7
  7. Bldg sqft: 19706
  8. Acreage: 4.43 acres
  9. Pool: Yes
  10. Waterfront: Yes
  11. Wateraccess: Yes
  12. Waterfront Type: LakeFront,LakePrivileges
  13. 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 5199 Latrobe Drive, WINDERMERE, FL 34786
Single Family
  1. Price: $5,494,000.00
  2. Price sqft: $829.66 / sqft
  3. Days On Market: 97
  4. Bedrooms: 5
  5. Baths: 7
  6. Garage / Parking Spaces: 4
  7. Bldg sqft: 6622
  8. Acreage: 0.52 acres
  9. Pool: Yes
  10. Spa/HotTub: Yes
  11. Waterfront: No
  12. Year Built: 1993
MLS#: O6315618
  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: COLDWELL BANKER RESIDENTIAL RE
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Nestled in the exclusive and coveted gated community of Isleworth, this fully remodeled, turn key golf estate is positioned along Isleworths famed championship golf course. This remarkable golf front
Details for 5745 Emerington Crescent, ORLANDO, FL 32819
Single Family
  1. Price: $4,940,000.00
  2. Price sqft: $429.90 / sqft
  3. Previous Price: $4,990,000
  4. Last Price Change: 06/30/25
  5. Days On Market: 538
  6. Bedrooms: 7
  7. Baths: 8
  8. Garage / Parking Spaces: 6
  9. Bldg sqft: 11491
  10. Acreage: 1.08 acres
  11. Pool: Yes
  12. Spa/HotTub: Yes
  13. Waterfront: Yes
  14. Wateraccess: Yes
  15. Waterfront Type: Lake Privileges
  16. Year Built: 2011
MLS#: O6184236
  1. County: ORANGE
  2. City: ORLANDO
  3. Zipcode: 32819
  4. Subdivision: Emerson Pointe
  5. Elementary School: Dr. Phillips Elem
  6. Middle School: Chain of Lakes Middle
  7. High School: Olympia High
  8. Provided by: EXP REALTY LLC
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Welcome to a residence where the essence of lakeside opulence meets the prestige of Bay Hill's championship golf course, creating a haven of unparalleled sophistication and relaxation. Lying within th
Details for 225 Magnolia Street, WINDERMERE, FL 34786
Single Family
  1. Price: $4,899,000.00
  2. Price sqft: $504.53 / sqft
  3. Days On Market: 170
  4. Bedrooms: 7
  5. Baths: 11
  6. Garage / Parking Spaces: 3
  7. Bldg sqft: 9710
  8. Acreage: 1.09 acres
  9. Pool: Yes
  10. Spa/HotTub: Yes
  11. Waterfront: Yes
  12. Wateraccess: Yes
  13. Waterfront Type: Beach Front,Lake Privileges
  14. Year Built: 2019
MLS#: O6292745
  1. County: ORANGE
  2. City: WINDERMERE
  3. Zipcode: 34786
  4. Subdivision: Windermere Town
  5. Elementary School: Windermere Elem
  6. Middle School: Gotha Middle
  7. High School: Olympia High
  8. Provided by: COMPASS FLORIDA LLC
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LAKEFRONT GRANDEUR IN WINDERMERE | A MASTERPIECE ON LAKE DOWN Unveiling a rare opportunity to own an architectural masterpiece on the famed Butler Chain of Lakesa residence that redefines lakefront l
Details for 10545 Down Lakeview Circle, WINDERMERE, FL 34786
Single Family
  1. Price: $3,795,000.00
  2. Price sqft: $379.92 / sqft
  3. Days On Market: 61
  4. Bedrooms: 5
  5. Baths: 7
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 9989
  8. Acreage: 2.78 acres
  9. Pool: Yes
  10. Spa/HotTub: Yes
  11. Waterfront: Yes
  12. Wateraccess: Yes
  13. Waterfront Type: Lake Privileges
  14. Year Built: 1987
MLS#: O6324706
  1. County: ORANGE
  2. City: WINDERMERE
  3. Zipcode: 34786
  4. Subdivision: Lakes
  5. Elementary School: Thornebrooke Elem
  6. Middle School: Gotha Middle
  7. High School: Olympia High
  8. Provided by: COLONIALTOWN REALTY
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Enjoy stunning sunsets from your private estate with expansive views, located on Lake Down, the prestigious Butler Chain of Lakes in Windermere. This well appointed property features 2.78 acres with f
Details for 4812 Alexandra Garden Court, WINDERMERE, FL 34786
Single Family
  1. Price: $3,699,000.00
  2. Price sqft: $495.38 / sqft
  3. Days On Market: 7
  4. Bedrooms: 3
  5. Baths: 5
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 7467
  8. Acreage: 0.26 acres
  9. Pool: Yes
  10. Spa/HotTub: Yes
  11. Waterfront: No
  12. Year Built: 2007
MLS#: O6339134
  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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Luxury villa living within the exclusive Gardens of Isleworth, part of the Isleworth Golf & Country Club. This exceptional residence boasts a captivating courtyard floor plan that provides breathtakin