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  1. School = Olympia High
11900 Lake Butler Boulevard
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Details for 11900 Lake Butler Boulevard, WINDERMERE, FL 34786
Single Family
  1. Price: $20,000,000.00
  2. Price sqft: $879.97 / sqft
  3. Days On Market: 82
  4. Bedrooms: 7
  5. Baths: 9
  6. Garage / Parking Spaces: 6
  7. Bldg sqft: 22728
  8. Acreage: 3.75 acres
  9. Pool: Yes
  10. Spa/HotTub: Yes
  11. Waterfront: Yes
  12. Wateraccess: Yes
  13. Waterfront Type: Lake Front,Lake
  14. Year Built: 2014
MLS#: O6275556
  1. County: ORANGE
  2. City: WINDERMERE
  3. Zipcode: 34786
  4. Subdivision: Metcalf Park Rep
  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 Sunset Isle: an iconic waterfront estate compound capturing timeless elegance on Windermeres largest and most prestigious Lake Butler, offering captivating unobstructed views from its 700 f
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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: 17
  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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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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4200 Down Point Lane
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Details for 4200 Down Point Lane, WINDERMERE, FL 34786
Single Family
  1. Price: $11,900,000.00
  2. Price sqft: $671.86 / sqft
  3. Previous Price: $12,900,000
  4. Last Price Change: 02/25/25
  5. Days On Market: 486
  6. Bedrooms: 6
  7. Baths: 9
  8. Garage / Parking Spaces: 4
  9. Bldg sqft: 17712
  10. Acreage: 1.60 acres
  11. Pool: Yes
  12. Spa/HotTub: Yes
  13. Waterfront: Yes
  14. Wateraccess: Yes
  15. Waterfront Type: Lake
  16. Year Built: 2001
MLS#: O6176070
  1. County: ORANGE
  2. City: WINDERMERE
  3. Zipcode: 34786
  4. Subdivision: Down Point Sub
  5. Elementary School: Windermere Elem
  6. Middle School: Chain of Lakes Middle
  7. High School: Olympia High
  8. Provided by: REVEL REALTY LLC
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Nestled along almost 1,000 of the highly sought after Butler Chain of Lakes in Windermere, this exquisite Mediterranean estate beckons with unrivaled opulence. Beyond a private gate, a 2 acre peninsul
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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: 366
  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
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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: 155
  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
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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: 470
  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
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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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5745 Emerington Crescent
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Details for 5745 Emerington Crescent, ORLANDO, FL 32819
Single Family
  1. Price: $4,940,000.00
  2. Price sqft: $429.90 / sqft
  3. Previous Price: $4,990,000
  4. Last Price Change: 02/07/25
  5. Days On Market: 441
  6. Bedrooms: 7
  7. Baths: 8
  8. Garage / Parking Spaces: 6
  9. Bldg sqft: 11491
  10. Acreage: 1.08 acres
  11. Pool: Yes
  12. Spa/HotTub: Yes
  13. Waterfront: Yes
  14. Wateraccess: Yes
  15. Waterfront Type: Lake
  16. Year Built: 2011
MLS#: O6184236
  1. County: ORANGE
  2. City: ORLANDO
  3. Zipcode: 32819
  4. Subdivision: Emerson Pointe
  5. Elementary School: Dr. Phillips Elem
  6. Middle School: Chain of Lakes Middle
  7. High School: Olympia High
  8. Provided by: EXP REALTY LLC
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Welcome to a residence where the essence of lakeside opulence meets the prestige of Bay Hill's championship golf course, creating a haven of unparalleled sophistication and relaxation. Lying within th
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225 Magnolia Street
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Details for 225 Magnolia Street, WINDERMERE, FL 34786
Single Family
  1. Price: $4,899,000.00
  2. Price sqft: $504.53 / sqft
  3. Days On Market: 73
  4. Bedrooms: 7
  5. Baths: 11
  6. Garage / Parking Spaces: 3
  7. Bldg sqft: 9710
  8. Acreage: 1.09 acres
  9. Pool: Yes
  10. Spa/HotTub: Yes
  11. Waterfront: Yes
  12. Wateraccess: Yes
  13. Waterfront Type: Beach Front,Lake
  14. Year Built: 2019
MLS#: O6292745
  1. County: ORANGE
  2. City: WINDERMERE
  3. Zipcode: 34786
  4. Subdivision: Windermere Town
  5. Elementary School: Windermere Elem
  6. Middle School: Gotha Middle
  7. High School: Olympia High
  8. Provided by: COMPASS FLORIDA LLC
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LAKEFRONT GRANDEUR IN WINDERMERE | A MASTERPIECE ON LAKE DOWN Unveiling a rare opportunity to own an architectural masterpiece on the famed Butler Chain of Lakesa residence that redefines lakefront l
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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: 16
  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
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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: 5
  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
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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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