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  1. City = Windermere
11900 Lake Butler Boulevard
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Details for 11900 Lake Butler Boulevard, WINDERMERE, FL 34786
Single Family
  1. Price: $18,500,000.00
  2. Price sqft: $813.97 / sqft
  3. Previous Price: $20,000,000
  4. Last Price Change: 09/13/25
  5. Days On Market: 300
  6. Bedrooms: 7
  7. Baths: 9
  8. Garage / Parking Spaces: 6
  9. Bldg sqft: 22728
  10. Acreage: 3.75 acres
  11. Pool: Yes
  12. Spa/HotTub: Yes
  13. Waterfront: Yes
  14. Wateraccess: Yes
  15. Waterfront Type: Lake Front,Lake Privileges
  16. 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
  7. High School: Olympia
  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: 235
  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
  7. High School: Olympia
  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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9621 Windy Ridge Road
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Details for 9621 Windy Ridge Road, WINDERMERE, FL 34786
Single Family
  1. Price: $13,650,000.00
  2. Price sqft: $497.59 / sqft
  3. Previous Price: $13,700,000
  4. Last Price Change: 12/10/25
  5. Days On Market: 158
  6. Bedrooms: 9
  7. Baths: 16
  8. Garage / Parking Spaces: 8
  9. Bldg sqft: 27432
  10. Acreage: 2.50 acres
  11. Pool: Yes
  12. Waterfront: No
  13. Year Built: 2025
MLS#: O6333091
  1. County: ORANGE
  2. City: WINDERMERE
  3. Zipcode: 34786
  4. Subdivision: Windsor Hill
  5. Provided by: CITARELLI REALTY GROUP LLC
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Under Construction. Experience unmatched privacy, prestige, and personalization with this brand new mansion on 2.5 pristine acres in the heart of Windermere. Tucked against protected government land t
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4226 Downeast Lane
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Details for 4226 Downeast Lane, WINDERMERE, FL 34786
Land
  1. Price: $11,800,000.00
  2. Days On Market: 24
  3. Acreage: 9.03 acres
  4. Pool: No
  5. Waterfront: Yes
  6. Wateraccess: Yes
  7. Waterfront Type: Lake Privileges
  8. Year Built: Not Available
MLS#: O6367852
  1. County: ORANGE
  2. City: WINDERMERE
  3. Zipcode: 34786
  4. Elementary School: Windermere Elem
  5. Middle School: Chain of Lakes
  6. High School: Olympia
  7. Provided by: COLDWELL BANKER RESIDENTIAL RE
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Exceptional development opportunity, currently r ce zoning should allow for 3 lakefront luxury home sites discover over 5+acres of waterfront land with 300 feet of pristine shoreline on lake down, par
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4226 Downeast Lane
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Details for 4226 Downeast Lane, WINDERMERE, FL 34786
Single Family
  1. Price: $11,800,000.00
  2. Price sqft: $1,385.63 / sqft
  3. Previous Price: $14,800,000
  4. Last Price Change: 12/17/25
  5. Days On Market: 77
  6. Bedrooms: 5
  7. Baths: 3
  8. Garage / Parking Spaces: 4
  9. Bldg sqft: 8516
  10. Acreage: 9.03 acres
  11. Pool: Yes
  12. Waterfront: Yes
  13. Wateraccess: Yes
  14. Waterfront Type: Lake Front
  15. Year Built: 1980
MLS#: O6355233
  1. County: ORANGE
  2. City: WINDERMERE
  3. Zipcode: 34786
  4. Elementary School: Windermere Elem
  5. Middle School: Chain of Lakes
  6. High School: Olympia
  7. Provided by: COLDWELL BANKER RESIDENTIAL RE
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Exceptional DEVELOPMENT OPPORTUNITY, currently R CE zoning should allow for 3 Lakefront Luxury Home Sites Discover over 5+acres of waterfront land with 300 feet of pristine shoreline on LAKE DOWN, pa
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6149 Grosvenor Shore Dr
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Details for 6149 Grosvenor Shore Dr, WINDERMERE, FL 34786
Single Family
  1. Price: $9,999,000.00
  2. Price sqft: $1,096.14 / sqft
  3. Days On Market: 60
  4. Bedrooms: 6
  5. Baths: 8
  6. Garage / Parking Spaces: 7
  7. Bldg sqft: 9122
  8. Acreage: 2.65 acres
  9. Pool: Yes
  10. Spa/HotTub: Yes
  11. Waterfront: Yes
  12. Wateraccess: Yes
  13. Waterfront Type: Lake Privileges
  14. Year Built: 2013
MLS#: O6356355
  1. County: ORANGE
  2. City: WINDERMERE
  3. Zipcode: 34786
  4. Subdivision: Keenes Pointe
  5. Elementary School: Windermere Elem
  6. Middle School: Bridgewater
  7. High School: Windermere
  8. Provided by: SOUTHERN REALTY GROUP LLC
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Keene's Pointe Stunning lakefront home on Lake Tibet of the famed Butler Chain of Lakes. No detail was spared in this completely renovated home boasting formal living and dining rooms, family and me
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6137 Grosvenor Shore Drive
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Details for 6137 Grosvenor Shore Drive, WINDERMERE, FL 34786
Single Family
  1. Price: $8,995,000.00
  2. Price sqft: $602.32 / sqft
  3. Previous Price: $9,500,000
  4. Last Price Change: 11/15/25
  5. Days On Market: 281
  6. Bedrooms: 6
  7. Baths: 9
  8. Garage / Parking Spaces: 5
  9. Bldg sqft: 14934
  10. Acreage: 2.20 acres
  11. Pool: Yes
  12. Spa/HotTub: Yes
  13. Waterfront: Yes
  14. Wateraccess: Yes
  15. Waterfront Type: Lake Privileges,Riparian Rights
  16. Year Built: 2010
MLS#: O6294487
  1. County: ORANGE
  2. City: WINDERMERE
  3. Zipcode: 34786
  4. Subdivision: Keenes Pointe
  5. Elementary School: Windermere Elem
  6. Middle School: Bridgewater
  7. High School: Windermere
  8. Provided by: PREMIER SOTHEBY'S INTL. REALTY
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Experience luxury lakefront living on a grand scale in this custom built Modern Mediterranean estate on Lake Tibet, part of the pristine Butler Chain of Lakes. The three story residence spans 9,571 sq
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6507 Rosella Court
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Details for 6507 Rosella Court, WINDERMERE, FL 34786
Single Family
  1. Price: $7,750,000.00
  2. Price sqft: $532.28 / sqft
  3. Days On Market: 66
  4. Bedrooms: 7
  5. Baths: 8
  6. Garage / Parking Spaces: 4
  7. Bldg sqft: 14560
  8. Acreage: 2.19 acres
  9. Pool: Yes
  10. Spa/HotTub: Yes
  11. Waterfront: Yes
  12. Wateraccess: Yes
  13. Waterfront Type: Lake Privileges
  14. Year Built: 2007
MLS#: O6353035
  1. County: ORANGE
  2. City: WINDERMERE
  3. Zipcode: 34786
  4. Subdivision: Keenes Pointe 46104
  5. Provided by: DEANNA MARIE SECHREST
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Luxury Living at its finest in one of Windermere's most unique Waterfront properties, with 2+ acres in the exclusive Keene's Pointe community. Soak up the Florida sunshine in the very private garden o
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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: 7
  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
  7. High School: Olympia
  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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9259 Tibet Pointe Cir
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Details for 9259 Tibet Pointe Cir, WINDERMERE, FL 34786
Single Family
  1. Price: $6,800,000.00
  2. Price sqft: $826.75 / sqft
  3. Days On Market: 227
  4. Bedrooms: 5
  5. Baths: 6
  6. Garage / Parking Spaces: 4
  7. Bldg sqft: 8225
  8. Acreage: 2.21 acres
  9. Pool: Yes
  10. Waterfront: Yes
  11. Wateraccess: Yes
  12. Waterfront Type: Lake Privileges
  13. Year Built: 2007
MLS#: O6312645
  1. County: ORANGE
  2. City: WINDERMERE
  3. Zipcode: 34786
  4. Subdivision: Keenes Pointe
  5. Elementary School: Windermere Elem
  6. Middle School: Bridgewater
  7. High School: Windermere
  8. Provided by: SOUTHERN REALTY GROUP LLC
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Welcome to 9259 Tibet Pointe Circle, an extraordinary lakefront residence nestled within the highly sought after guard gated community of Keenes Pointe. Completely renovated in 2025, this exquisite ho
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Listings provided courtesy of The Hernando County Association of Realtors MLS.
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Datafeed Last updated on January 9, 2026 @ 12:00 am
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