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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: 18
  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
Exceptional in both style and scale, this extraordinary Isleworth estate represents the pinnacle of luxury living in one of the finest golf club communities in the world. Designed by architect Terry I
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9832 Laurel Valley Drive
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Details for 9832 Laurel Valley Drive, WINDERMERE, FL 34786
Single Family
  1. Price: $9,490,000.00
  2. Price sqft: $741.64 / sqft
  3. Previous Price: $9,900,000
  4. Last Price Change: 05/30/25
  5. Days On Market: 367
  6. Bedrooms: 6
  7. Baths: 10
  8. Garage / Parking Spaces: 4
  9. Bldg sqft: 12796
  10. Acreage: 0.60 acres
  11. Pool: Yes
  12. Spa/HotTub: Yes
  13. Waterfront: Yes
  14. Wateraccess: Yes
  15. Waterfront Type: Lake Privileges
  16. Year Built: 2004
MLS#: O6211352
  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. Introducing an exquisitely remodeled three level Isleworth home on Lake Butler in the renowned Butler Chain of Lakes. Boasting a spacious 11,100 square
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5271 Isleworth Country Club Drive
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Details for 5271 Isleworth Country Club Drive, WINDERMERE, FL 34786
Single Family
  1. Price: $8,775,000.00
  2. Price sqft: $529.41 / sqft
  3. Days On Market: 156
  4. Bedrooms: 7
  5. Baths: 13
  6. Garage / Parking Spaces: 6
  7. Bldg sqft: 16575
  8. Acreage: 1.17 acres
  9. Pool: Yes
  10. Spa/HotTub: Yes
  11. Waterfront: No
  12. Year Built: 2013
MLS#: O6267644
  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
Welcome to this grand residence nestled on a sprawling 1.17 acre lot originally hand selected by golf legend Arnold Palmer. Perfectly positioned to capture breathtaking views of the first and tenth ho
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5507 Worsham Court
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Details for 5507 Worsham Court, WINDERMERE, FL 34786
Single Family
  1. Price: $7,500,000.00
  2. Price sqft: $436.15 / sqft
  3. Previous Price: $7,850,000
  4. Last Price Change: 05/22/25
  5. Days On Market: 471
  6. Bedrooms: 5
  7. Baths: 11
  8. Garage / Parking Spaces: 4
  9. Bldg sqft: 17196
  10. Acreage: 0.98 acres
  11. Pool: Yes
  12. Spa/HotTub: Yes
  13. Waterfront: No
  14. Year Built: 2008
MLS#: O6180706
  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
  9. mfrmls
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Presenting one of Isleworths most iconic mansions: magnificent and grand, impressively positioned along the 14th fairway of the Isleworth golf course, behind the secured and guarded gates of one of th
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9724 Chestnut Ridge Dr
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Details for 9724 Chestnut Ridge Dr, WINDERMERE, FL 34786
Single Family
  1. Price: $4,800,000.00
  2. Price sqft: $588.09 / sqft
  3. Days On Market: 17
  4. Bedrooms: 5
  5. Baths: 6
  6. Garage / Parking Spaces: 6
  7. Bldg sqft: 8162
  8. Acreage: 0.56 acres
  9. Pool: Yes
  10. Spa/HotTub: Yes
  11. Waterfront: Yes
  12. Wateraccess: Yes
  13. Waterfront Type: Lake Front
  14. Year Built: 1990
MLS#: O6310606
  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
Experience refined lakefront living in this exceptional estate, ideally located within the renowned Isleworth Golf & Country Club. Set along the shores of Lake Bessie on a beautifully landscaped 0.56
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9724 Chestnut Ridge Dr
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Details for 9724 Chestnut Ridge Dr, Windermere, FL 34786
Single Family
  1. Price: $4,800,000.00
  2. Price sqft: $588.09 / sqft
  3. Days On Market: 17
  4. Bedrooms: 5
  5. Baths: 6
  6. Garage / Parking Spaces: 6
  7. Bldg sqft: 8162
  8. Acreage: 0.56 acres
  9. Pool: Yes
  10. Waterfront: Yes
  11. Wateraccess: Yes
  12. Waterfront Type: LakeFront,LakePrivileges
  13. Year Built: 1990
MLS#: O6310606
  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
  9. Provided through
  10. DMCA Notice
Experience refined lakefront living in this exceptional estate, ideally located within the renowned Isleworth Golf & Country Club. Set along the shores of Lake Bessie on a beautifully landscaped 0.56
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5157 Latrobe Drive
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Details for 5157 Latrobe Drive, WINDERMERE, FL 34786
Single Family
  1. Price: $4,777,000.00
  2. Price sqft: $651.71 / sqft
  3. Days On Market: 6
  4. Bedrooms: 6
  5. Baths: 9
  6. Garage / Parking Spaces: 3
  7. Bldg sqft: 7330
  8. Acreage: 0.51 acres
  9. Pool: Yes
  10. Waterfront: No
  11. Year Built: 1989
MLS#: O6312420
  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: BAY STREET GROUP FLORIDA LLC
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Newly built in 2019 a rare find in the community! Sunlit single storey layout, bright in every corner ! Panoramic views of Hole 4 from the living room! Live the legendary lifestyle in this fully reb
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5157 Latrobe Drive
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Details for 5157 Latrobe Drive, Windermere, FL 34786
Single Family
  1. Price: $4,777,000.00
  2. Price sqft: $651.71 / sqft
  3. Days On Market: 6
  4. Bedrooms: 6
  5. Baths: 9
  6. Garage / Parking Spaces: 3
  7. Bldg sqft: 7330
  8. Acreage: 0.51 acres
  9. Pool: Yes
  10. Community Pool: Yes
  11. Waterfront: No
  12. Year Built: 1989
MLS#: O6312420
  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: BAY STREET GROUP FLORIDA LLC
  9. Provided through
  10. DMCA Notice
Newly built in 2019 a rare find in the community! Sunlit single storey layout, bright in every corner ! Panoramic views of Hole 4 from the living room! Live the legendary lifestyle in this fully reb
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9844 Laurel Valley Drive
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Details for 9844 Laurel Valley Drive, WINDERMERE, FL 34786
Single Family
  1. Price: $4,700,000.00
  2. Price sqft: $646.76 / sqft
  3. Previous Price: $4,950,000
  4. Last Price Change: 03/31/25
  5. Days On Market: 492
  6. Bedrooms: 5
  7. Baths: 6
  8. Garage / Parking Spaces: 3
  9. Bldg sqft: 7267
  10. Acreage: 0.59 acres
  11. Pool: Yes
  12. Waterfront: Yes
  13. Wateraccess: Yes
  14. Waterfront Type: Lake
  15. Year Built: 1989
MLS#: O6173216
  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
This classic luxury estate is situated along the picturesque Butler Chain of lakes on Lake Butler, within the gates of the renowned Isleworth community. Spanning over 5,000 square feet, the traditiona
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5126 Fairway Oaks Dr
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Details for 5126 Fairway Oaks Dr, WINDERMERE, FL 34786
Single Family
  1. Price: $4,495,000.00
  2. Price sqft: $622.06 / sqft
  3. Previous Price: $4,790,000
  4. Last Price Change: 03/17/25
  5. Days On Market: 231
  6. Bedrooms: 5
  7. Baths: 5
  8. Garage / Parking Spaces: 2
  9. Bldg sqft: 7226
  10. Acreage: 0.50 acres
  11. Pool: Yes
  12. Spa/HotTub: Yes
  13. Waterfront: No
  14. Year Built: 1990
MLS#: S5113369
  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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Water and Golf views illuminate this unparalleled luxury home. Fully remodeled five bedroom pool home within the distinguished Isleworth Golf Community, ideally situated along the 12 hole of the cham
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Datafeed Last updated on June 7, 2025 @ 12:00 am
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