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  1. Subdivision Like Isleworth
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: 140
  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 9935 Lake Louise Drive, WINDERMERE, FL 34786
Single Family
  1. Price: $12,995,000.00
  2. Price sqft: $520.84 / sqft
  3. Days On Market: 24
  4. Bedrooms: 7
  5. Baths: 10
  6. Garage / Parking Spaces: 6
  7. Bldg sqft: 24950
  8. Acreage: 2.14 acres
  9. Pool: Yes
  10. Spa/HotTub: Yes
  11. Waterfront: Yes
  12. Wateraccess: Yes
  13. Waterfront Type: Lake Front,Lake Privileges
  14. Year Built: 2012
MLS#: O6340680
  1. County: ORANGE
  2. City: WINDERMERE
  3. Zipcode: 34786
  4. Subdivision: Isleworth 01 Amd
  5. Elementary School: Windermere Elem
  6. Middle School: Chain of Lakes Middle
  7. High School: Olympia High
  8. Provided by: IRWIN REALTY GROUP LLC
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Experience the pinnacle of luxury living in this extraordinary lakefront estate located in the world renowned Isleworth Golf & Country Club. Positioned on 2.14 private acres along Lake Louise, part of
Details for 5074 Isleworth Country Club Drive, WINDERMERE, FL 34786
Single Family
  1. Price: $7,995,000.00
  2. Price sqft: $892.20 / sqft
  3. Previous Price: $8,325,000
  4. Last Price Change: 10/01/25
  5. Days On Market: 110
  6. Bedrooms: 5
  7. Baths: 7
  8. Garage / Parking Spaces: 3
  9. Bldg sqft: 8961
  10. Acreage: 0.54 acres
  11. Pool: Yes
  12. Spa/HotTub: Yes
  13. Waterfront: No
  14. Year Built: 1988
MLS#: O6317868
  1. County: ORANGE
  2. City: WINDERMERE
  3. Zipcode: 34786
  4. Subdivision: Isleworth
  5. Provided by: MEMARPOURI REALTY LLC
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Experience luxury living at its finest in the high end gated community of Isleworth. Nestled on the 6th fairway of Isleworths world renowned golf course, this beautifully redesigned estate offers over
Details for 9826 Laurel Valley Drive, WINDERMERE, FL 34786
Single Family
  1. Price: $5,900,000.00
  2. Price sqft: $484.76 / sqft
  3. Days On Market: 17
  4. Bedrooms: 4
  5. Baths: 5
  6. Garage / Parking Spaces: 3
  7. Bldg sqft: 12171
  8. Acreage: 0.66 acres
  9. Pool: Yes
  10. Spa/HotTub: Yes
  11. Waterfront: Yes
  12. Wateraccess: Yes
  13. Waterfront Type: Lake Privileges
  14. Year Built: 1987
MLS#: O6345711
  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: SOUTHERN REALTY GROUP LLC
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Tucked within the gates of Isleworth Golf Community and Country Club lies a residence that feels more like a private lakeside retreat than a home. Here, more than 7,000 square feet of elegance unfolds
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: 123
  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 5036 Latrobe Drive, WINDERMERE, FL 34786
Single Family
  1. Price: $4,900,000.00
  2. Price sqft: $163.03 / sqft
  3. Days On Market: 3
  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 5036 Latrobe Drive, Windermere, FL 34786
Single Family
  1. Price: $4,900,000.00
  2. Price sqft: $163.03 / sqft
  3. Days On Market: 3
  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: LakeFront,LakePrivileges
  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
  9. Provided through
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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 9648 Mccormick Place, WINDERMERE, FL 34786
Single Family
  1. Price: $3,800,000.00
  2. Price sqft: $529.99 / sqft
  3. Days On Market: 10
  4. Bedrooms: 3
  5. Baths: 4
  6. Garage / Parking Spaces: 3
  7. Bldg sqft: 7170
  8. Acreage: 0.54 acres
  9. Pool: Yes
  10. Spa/HotTub: Yes
  11. Waterfront: No
  12. Year Built: 1988
MLS#: O6346918
  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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Stunning golf and lake views and beautifully updated grounds are hallmarks of this elegant Isleworth estate. Nestled along the front nine overlooking Isleworths 2nd fairway and beautiful Lake Chase, t
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: 32
  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
Details for 9731 Chestnut Ridge Drive, WINDERMERE, FL 34786
Single Family
  1. Price: $3,400,000.00
  2. Price sqft: $552.76 / sqft
  3. Days On Market: 50
  4. Bedrooms: 4
  5. Baths: 4
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 6151
  8. Acreage: 0.54 acres
  9. Pool: Yes
  10. Waterfront: No
  11. Year Built: 1986
MLS#: O6336655
  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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Nestled within the gates of the renowned Isleworth Golf & Country Club, this beautiful four bedroom estate offers nearly 5,000 square feet and showcases an elegant transitional style. The main level