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  1. School = Chain Of Lakes
  2. Listing Status = Active
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: 378
  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: 313
  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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9323 Gladys Garden Court
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Details for 9323 Gladys Garden Court, WINDERMERE, FL 34786
Single Family
  1. Price: $13,995,000.00
  2. Price sqft: $1,118.71 / sqft
  3. Days On Market: 43
  4. Bedrooms: 6
  5. Baths: 10
  6. Garage / Parking Spaces: 4
  7. Bldg sqft: 12510
  8. Acreage: 0.26 acres
  9. Pool: Yes
  10. Waterfront: No
  11. Year Built: 2026
MLS#: O6381880
  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: CORCORAN PREMIER REALTY
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Brand new construction and fully furnished! Architecturally refined and intentionally designed by Ashley Martin Home, this custom estate is a masterclass in proportion, craftsmanship, and quiet luxury
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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: 102
  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: 155
  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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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: 86
  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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1002 Down Reserve Court
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Details for 1002 Down Reserve Court, WINDERMERE, FL 34786
Single Family
  1. Price: $6,530,000.00
  2. Price sqft: $811.08 / sqft
  3. Previous Price: $6,590,000
  4. Last Price Change: 03/21/26
  5. Days On Market: 35
  6. Bedrooms: 6
  7. Baths: 6
  8. Garage / Parking Spaces: 3
  9. Bldg sqft: 8051
  10. Acreage: 1.09 acres
  11. Pool: Yes
  12. Spa/HotTub: Yes
  13. Waterfront: Yes
  14. Wateraccess: Yes
  15. Waterfront Type: Lake Front
  16. Year Built: 2021
MLS#: O6383597
  1. County: ORANGE
  2. City: WINDERMERE
  3. Zipcode: 34786
  4. Subdivision: Rosser Reserve Rep
  5. Elementary School: Windermere Elem
  6. Middle School: Chain of Lakes
  7. High School: Olympia
  8. Provided by: WRA BUSINESS & REAL ESTATE
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Luxury, architectural elegance, and an unparalleled lakefront lifestyle on the Butler Chain of Lakes in Windermere. Set on a sprawling lot of over one acre, this extraordinary waterfront estate off
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1330 Lake Olivia
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Details for 1330 Lake Olivia, WINDERMERE, FL 34786
Single Family
  1. Price: $5,500,000.00
  2. Price sqft: $866.82 / sqft
  3. Days On Market: 2
  4. Bedrooms: 6
  5. Baths: 8
  6. Garage / Parking Spaces: 4
  7. Bldg sqft: 6345
  8. Acreage: 1.62 acres
  9. Pool: Yes
  10. Waterfront: No
  11. Year Built: 2026
MLS#: S5144942
  1. County: ORANGE
  2. City: WINDERMERE
  3. Zipcode: 34786
  4. Subdivision: Lake Olivia Reserve
  5. Elementary School: Windermere Elem
  6. Middle School: Chain of Lakes
  7. High School: Windermere
  8. Provided by: EMPIRE NETWORK REALTY
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One or more photo(s) has been virtually staged. Pre Construction. To be built. This is a lakefront estate currently under construction in Windermere, set on the shores of Lake Olivia with wide, unobst
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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: $5,100,000.00
  2. Price sqft: $703.84 / sqft
  3. Previous Price: $5,325,000
  4. Last Price Change: 03/12/26
  5. Days On Market: 170
  6. Bedrooms: 4
  7. Baths: 6
  8. Garage / Parking Spaces: 3
  9. Bldg sqft: 7246
  10. Acreage: 0.51 acres
  11. Pool: Yes
  12. Waterfront: No
  13. 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
  7. High School: Olympia
  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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5070 Down Point Lane
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Details for 5070 Down Point Lane, WINDERMERE, FL 34786
Single Family
  1. Price: $4,995,000.00
  2. Price sqft: $462.54 / sqft
  3. Days On Market: 30
  4. Bedrooms: 6
  5. Baths: 7
  6. Garage / Parking Spaces: 4
  7. Bldg sqft: 10799
  8. Acreage: 2.64 acres
  9. Pool: Yes
  10. Spa/HotTub: Yes
  11. Waterfront: Yes
  12. Wateraccess: Yes
  13. Waterfront Type: Lake Privileges
  14. Year Built: 1998
MLS#: O6385276
  1. County: ORANGE
  2. City: WINDERMERE
  3. Zipcode: 34786
  4. Subdivision: Sunset Bay
  5. Elementary School: Windermere Elem
  6. Middle School: Chain of Lakes
  7. Provided by: EXP REALTY LLC
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Nestled behind the gates in the heart of Windermere, this exceptional lakefront estate commands sweeping views across the renowned Butler Chain of Lakes. Designed for refined living and effortless ent
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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 March 29, 2026 @ 12:00 am
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