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  1. Subdivision Like Isleworth
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: 214
  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
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9826 Laurel Valley Drive
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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: 91
  4. Bedrooms: 5
  5. Baths: 6
  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: EXP REALTY 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
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5199 Latrobe Drive
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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: 196
  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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One or more photo(s) has been virtually staged. Nestled in the exclusive and coveted gated community of Isleworth, this fully remodeled, turn key golf estate is positioned along Isleworths famed champ
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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: 70
  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: 77
  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: 84
  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: 106
  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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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: 124
  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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4711 Joanna Garden Ct
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Details for 4711 Joanna Garden Ct, WINDERMERE, FL 34786
Single Family
  1. Price: $3,250,000.00
  2. Price sqft: $512.46 / sqft
  3. Days On Market: 36
  4. Bedrooms: 3
  5. Baths: 4
  6. Garage / Parking Spaces: 3
  7. Bldg sqft: 6342
  8. Acreage: 0.26 acres
  9. Pool: Yes
  10. Spa/HotTub: Yes
  11. Waterfront: No
  12. Year Built: 2007
MLS#: O6359789
  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 exclusive Gardens of Isleworth enclave within Isleworth Golf & Country Club, this exquisite residence exemplifies refined Florida living. Crafted by Pellegrini Homes with profession
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6120 Payne Stewart Dr
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Details for 6120 Payne Stewart Dr, WINDERMERE, FL 34786
Single Family
  1. Price: $2,700,000.00
  2. Price sqft: $609.07 / sqft
  3. Previous Price: $2,799,000
  4. Last Price Change: 12/10/25
  5. Days On Market: 284
  6. Bedrooms: 4
  7. Baths: 5
  8. Garage / Parking Spaces: 3
  9. Bldg sqft: 4433
  10. Acreage: 0.34 acres
  11. Pool: No
  12. Waterfront: No
  13. Year Built: 1987
MLS#: O6288273
  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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Isleworth nestled in Windermere, this 600 acre community, is a prestigious residential enclave nestled along the Butler Chain of Lakes. This charming villa is in walking distance to Isleworth Golf &
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Tropic Shores Realty - Crystal River
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Listings provided courtesy of The Hernando County Association of Realtors MLS.
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Datafeed Last updated on December 19, 2025 @ 12:00 am
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