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5525 Isleworth Country Club Dr
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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: 335
  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
  7. High School: Olympia
  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
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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: 65
  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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5074 Isleworth Country Club Drive
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Details for 5074 Isleworth Country Club Drive, WINDERMERE, FL 34786
Single Family
  1. Price: $7,595,000.00
  2. Price sqft: $847.56 / sqft
  3. Days On Market: 95
  4. Bedrooms: 5
  5. Baths: 7
  6. Garage / Parking Spaces: 3
  7. Bldg sqft: 8961
  8. Acreage: 0.54 acres
  9. Pool: Yes
  10. Waterfront: No
  11. Year Built: 1988
MLS#: O6373191
  1. County: ORANGE
  2. City: WINDERMERE
  3. Zipcode: 34786
  4. Subdivision: Isleworth
  5. Provided by: MEMARPOURI REALTY LLC
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Luxury living perfectly positioned along the 6th fairway in the world renowned guard gated community of Isleworth. This exceptional estate offers over 6,900 square feet of completely remodeled space
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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: $6,150,000.00
  2. Price sqft: $514.56 / sqft
  3. Previous Price: $6,950,000
  4. Last Price Change: 04/16/26
  5. Days On Market: 107
  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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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: 192
  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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5186 Vardon Drive
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Details for 5186 Vardon Drive, WINDERMERE, FL 34786
Single Family
  1. Price: $4,960,000.00
  2. Price sqft: $629.84 / sqft
  3. Previous Price: $5,680,000
  4. Last Price Change: 02/24/26
  5. Days On Market: 64
  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. Presenting a newly remodeled luxury estate ideally positioned along Isleworths renowned championship golf course, showcasing stunning views of the signa
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5151 Latrobe Dr
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Details for 5151 Latrobe Dr, WINDERMERE, FL 34786
Single Family
  1. Price: $4,100,000.00
  2. Price sqft: $571.67 / sqft
  3. Days On Market: 30
  4. Bedrooms: 4
  5. Baths: 5
  6. Garage / Parking Spaces: 3
  7. Bldg sqft: 7172
  8. Acreage: 0.51 acres
  9. Pool: Yes
  10. Waterfront: No
  11. Year Built: 2000
MLS#: O6392380
  1. County: ORANGE
  2. City: WINDERMERE
  3. Zipcode: 34786
  4. Subdivision: Isleworth
  5. Provided by: ISLEWORTH REALTY LLC
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Positioned along the stunning 4th fairway of the renowned Isleworth Golf & Country Club, this exceptional single story estate offers four bedrooms and more than 5,300 square feet of meticulously craft
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9648 Mccormick Place
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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: 205
  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
  7. High School: Olympia
  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
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4812 Alexandra Garden Court
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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: 228
  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
  7. High School: Olympia
  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 Southpoint built residence boasts a captivating courtyard floor plan that pro
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5001 Latrobe Drive
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Details for 5001 Latrobe Drive, WINDERMERE, FL 34786
Single Family
  1. Price: $3,499,999.00
  2. Price sqft: $598.80 / sqft
  3. Days On Market: 33
  4. Bedrooms: 5
  5. Baths: 5
  6. Garage / Parking Spaces: 3
  7. Bldg sqft: 5845
  8. Acreage: 0.61 acres
  9. Pool: Yes
  10. Waterfront: No
  11. Year Built: 1990
MLS#: O6389183
  1. County: ORANGE
  2. City: WINDERMERE
  3. Zipcode: 34786
  4. Subdivision: Isleworth
  5. Provided by: Q BOUTIQUE SPECIALTY REALTY INC
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One or more photo(s) has been virtually staged. Dont miss this rare opportunity to own a stunning estate home in the prestigious Isleworth Golf & Country Club, perfectly positioned on a quiet cul de s
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