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  1. Subdivision Like Isleworth
  2. Listing Status = Active
5192 Vardon Drive
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Details for 5192 Vardon Drive, WINDERMERE, FL 34786
Single Family
  1. Price: $19,500,000.00
  2. Price sqft: $952.33 / sqft
  3. Days On Market: 53
  4. Bedrooms: 6
  5. Baths: 10
  6. Garage / Parking Spaces: 5
  7. Bldg sqft: 20476
  8. Acreage: 2.27 acres
  9. Pool: Yes
  10. Spa/HotTub: Yes
  11. Waterfront: Yes
  12. Wateraccess: Yes
  13. Waterfront Type: Lake Privileges
  14. Year Built: 2006
MLS#: O6441344
  1. County: ORANGE
  2. City: WINDERMERE
  3. Zipcode: 34786
  4. Subdivision: Isleworth Amd 03
  5. Elementary School: Windermere Elem
  6. Middle School: Chain of Lakes Middle
  7. High School: Windermere High School
  8. Provided by: IRWIN REALTY GROUP LLC
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Timeless elegance and extraordinary privacy define this magnificent lakefront estate within the renowned Isleworth Golf & Country Club. Gracefully positioned on Lake Blanche along the coveted Butler
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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: $11,900,000.00
  2. Price sqft: $951.24 / sqft
  3. Previous Price: $12,500,000
  4. Last Price Change: 11/01/26
  5. Days On Market: 269
  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 Middle
  7. High School: Olympia High
  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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5092 Isleworth Country Club Drive
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Details for 5092 Isleworth Country Club Drive, WINDERMERE, FL 34786
Single Family
  1. Price: $8,500,000.00
  2. Price sqft: $823.72 / sqft
  3. Days On Market: 39
  4. Bedrooms: 4
  5. Baths: 5
  6. Garage / Parking Spaces: 4
  7. Bldg sqft: 10319
  8. Acreage: 0.93 acres
  9. Pool: Yes
  10. Spa/HotTub: Yes
  11. Waterfront: No
  12. Year Built: 1995
MLS#: O6446272
  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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Set along the front nine of Isleworth championship golf course with breathtaking views of Hole 6, this grand estate occupies an oversized lot along Isleworths main drive and has been beautifully reima
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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: $7,250,000.00
  2. Price sqft: $784.97 / sqft
  3. Previous Price: $7,595,000
  4. Last Price Change: 10/07/26
  5. Days On Market: 299
  6. Bedrooms: 5
  7. Baths: 7
  8. Garage / Parking Spaces: 3
  9. Bldg sqft: 9236
  10. Acreage: 0.54 acres
  11. Pool: Yes
  12. Spa/HotTub: Yes
  13. Waterfront: No
  14. Year Built: 1988
MLS#: O6373191
  1. County: ORANGE
  2. City: WINDERMERE
  3. Zipcode: 34786
  4. Subdivision: Isleworth
  5. Provided by: MEM REALTY GROUP
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A masterfully reimagined golf front estate, this residence offers an unparalleled standard of luxury within the acclaimed guard gated community of Isleworth. Completely reimagined and expanded, the re
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5373 Isleworth Country Club Drive
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Details for 5373 Isleworth Country Club Drive, WINDERMERE, FL 34786
Single Family
  1. Price: $7,200,000.00
  2. Price sqft: $938.11 / sqft
  3. Days On Market: 62
  4. Bedrooms: 5
  5. Baths: 6
  6. Garage / Parking Spaces: 3
  7. Bldg sqft: 7675
  8. Acreage: 0.52 acres
  9. Pool: Yes
  10. Spa/HotTub: Yes
  11. Waterfront: No
  12. Year Built: 1988
MLS#: O6439156
  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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Impressively elegant NEW CONSTRUCTION Isleworth estate, prominently positioned on the 17th fairway of the championship golf course, with sweeping Lake Louise vistas beyond. This home was completely g
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6055 Louise Cove Drive
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Details for 6055 Louise Cove Drive, WINDERMERE, FL 34786
Single Family
  1. Price: $6,850,000.00
  2. Price sqft: $793.19 / sqft
  3. Previous Price: $6,900,000
  4. Last Price Change: 10/21/26
  5. Days On Market: 93
  6. Bedrooms: 5
  7. Baths: 6
  8. Garage / Parking Spaces: 3
  9. Bldg sqft: 8636
  10. Acreage: 1.03 acres
  11. Pool: Yes
  12. Spa/HotTub: Yes
  13. Waterfront: Yes
  14. Wateraccess: Yes
  15. Waterfront Type: Lake Privileges
  16. Year Built: 2001
MLS#: O6430931
  1. County: ORANGE
  2. City: WINDERMERE
  3. Zipcode: 34786
  4. Subdivision: Isleworth West
  5. Elementary School: Windermere Elem
  6. Middle School: Bridgewater Middle
  7. High School: Windermere High School
  8. Provided by: STOCKWORTH REALTY GROUP
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Stately and elegant lakefront estate showcasing the best of Isleworth West. This grand home spans more than 7,000 square feet with 5 bedrooms of which, four are on the ground floor plus office, gym,
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9921 Lake Louise Drive
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Details for 9921 Lake Louise Drive, WINDERMERE, FL 34786
Single Family
  1. Price: $6,650,000.00
  2. Price sqft: $606.48 / sqft
  3. Days On Market: 100
  4. Bedrooms: 5
  5. Baths: 7
  6. Garage / Parking Spaces: 4
  7. Bldg sqft: 10965
  8. Acreage: 1.14 acres
  9. Pool: Yes
  10. Spa/HotTub: Yes
  11. Waterfront: No
  12. Year Built: 2003
MLS#: O6429164
  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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Positioned along the back nine of Isleworths renowned championship golf course, this exceptional estate spans nearly 7,000 square feet and has been thoughtfully reimagined through an extensive three y
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6462 Deacon Cir
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Details for 6462 Deacon Cir, WINDERMERE, FL 34786
Single Family
  1. Price: $6,595,000.00
  2. Price sqft: $728.17 / sqft
  3. Previous Price: $6,499,999
  4. Last Price Change: 09/21/26
  5. Days On Market: 180
  6. Bedrooms: 5
  7. Baths: 6
  8. Garage / Parking Spaces: 3
  9. Bldg sqft: 9057
  10. Acreage: 0.64 acres
  11. Pool: Yes
  12. Spa/HotTub: Yes
  13. Waterfront: Yes
  14. Wateraccess: Yes
  15. Waterfront Type: Lake Privileges
  16. Year Built: 1990
MLS#: O6407107
  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 Isleworth Golf & Country Club, along the shores of Lake Chase, this exceptional lakefront offers a refined and contemporary waterfront lifestyle. Ideally positioned near the drivin
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9316 Gladys Garden Ct
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Details for 9316 Gladys Garden Ct, WINDERMERE, FL 34786
Single Family
  1. Price: $6,500,000.00
  2. Price sqft: $633.47 / sqft
  3. Days On Market: 133
  4. Bedrooms: 5
  5. Baths: 7
  6. Garage / Parking Spaces: 3
  7. Bldg sqft: 10261
  8. Acreage: 0.26 acres
  9. Pool: Yes
  10. Waterfront: No
  11. Year Built: 2026
MLS#: O6420326
  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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Virtually Staged. An exceptional new construction offering within The Gardens of Isleworth, this newly completed residence by premier custom homebuilder Goehring & Morgan presents a rare opportunity t
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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: $5,975,000.00
  2. Price sqft: $499.92 / sqft
  3. Previous Price: $6,000,000
  4. Last Price Change: 09/22/26
  5. Days On Market: 311
  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 Middle
  7. High School: Olympia High
  8. Provided by: DOUGLAS ELLIMAN
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Virtually Staged. Newly renovated, this private Isleworth residence offers a rare balance of architectural authority, thoughtful design, and quiet indulgence. Spanning approximately 8,000 square feet
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