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  1. Subdivision Like Isleworth
  2. Listing Status = Active
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: 263
  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
  9. mfrmls
  10. DMCA Notice
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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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: 23
  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: $6,950,000.00
  2. Price sqft: $581.49 / sqft
  3. Days On Market: 35
  4. Bedrooms: 7
  5. Baths: 7
  6. Garage / Parking Spaces: 3
  7. Bldg sqft: 11952
  8. Acreage: 0.56 acres
  9. Pool: Yes
  10. Spa/HotTub: Yes
  11. Waterfront: Yes
  12. Wateraccess: Yes
  13. Waterfront Type: Pond
  14. 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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Private showings are easily accommodated, including same day requests. Newly renovated and fully turnkey, this private Isleworth residence offers a rare balance of architectural authority, thoughtfu
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6117 Louise Cove Drive
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Details for 6117 Louise Cove Drive, WINDERMERE, FL 34786
Single Family
  1. Price: $5,400,000.00
  2. Price sqft: $694.80 / sqft
  3. Days On Market: 27
  4. Bedrooms: 4
  5. Baths: 5
  6. Garage / Parking Spaces: 3
  7. Bldg sqft: 7772
  8. Acreage: 0.79 acres
  9. Pool: Yes
  10. Waterfront: Yes
  11. Wateraccess: Yes
  12. Waterfront Type: Lake Privileges
  13. Year Built: 2002
MLS#: O6372197
  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: ISLEWORTH REALTY LLC
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Nestled along the shores of Lake Louise within Isleworth West, this exceptional two story estate represents the finest in lakefront living. Offering four bedrooms, four and a half baths, and more than
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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: $5,325,000.00
  2. Price sqft: $734.89 / sqft
  3. Days On Market: 119
  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
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5036 Latrobe Drive
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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: 126
  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,
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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: 133
  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
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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: 155
  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
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5050 Isleworth Country Club Drive
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Details for 5050 Isleworth Country Club Drive, WINDERMERE, FL 34786
Single Family
  1. Price: $3,690,000.00
  2. Price sqft: $761.92 / sqft
  3. Previous Price: $3,975,000
  4. Last Price Change: 01/24/26
  5. Days On Market: 27
  6. Bedrooms: 4
  7. Baths: 5
  8. Garage / Parking Spaces: 2
  9. Bldg sqft: 4843
  10. Acreage: 0.52 acres
  11. Pool: Yes
  12. Spa/HotTub: Yes
  13. Waterfront: No
  14. 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
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9731 Chestnut Ridge Drive
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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: 173
  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
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Tropic Shores Realty - Crystal River
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Datafeed Last updated on February 6, 2026 @ 12:00 am
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