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4226 Downeast Lane
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Details for 4226 Downeast Lane, WINDERMERE, FL 34786
Single Family
  1. Price: $14,800,000.00
  2. Price sqft: $1,737.91 / sqft
  3. Days On Market: 12
  4. Bedrooms: 5
  5. Baths: 3
  6. Garage / Parking Spaces: 4
  7. Bldg sqft: 8516
  8. Acreage: 9.03 acres
  9. Pool: Yes
  10. Waterfront: Yes
  11. Wateraccess: Yes
  12. Waterfront Type: Lake Front
  13. 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 Middle
  6. High School: Olympia High
  7. Provided by: COLDWELL BANKER RESIDENTIAL RE
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Exceptional DEVELOPMENT OPPORTUNITY,R CE zoning may allow for 3 Lakefront Luxury Home Sites + Additional Lots on these two parcels. Discover over 9 acres of waterfront land with 300 feet of pristine
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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: 170
  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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9935 Lake Louise Drive
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Details for 9935 Lake Louise Drive, WINDERMERE, FL 34786
Single Family
  1. Price: $12,995,000.00
  2. Price sqft: $520.84 / sqft
  3. Days On Market: 55
  4. Bedrooms: 7
  5. Baths: 10
  6. Garage / Parking Spaces: 6
  7. Bldg sqft: 24950
  8. Acreage: 2.14 acres
  9. Pool: Yes
  10. Spa/HotTub: Yes
  11. Waterfront: Yes
  12. Wateraccess: Yes
  13. Waterfront Type: Lake Front,Lake Privileges
  14. Year Built: 2012
MLS#: O6340680
  1. County: ORANGE
  2. City: WINDERMERE
  3. Zipcode: 34786
  4. Subdivision: Isleworth 01 Amd
  5. Elementary School: Windermere Elem
  6. Middle School: Chain of Lakes Middle
  7. High School: Olympia High
  8. Provided by: IRWIN REALTY GROUP LLC
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Experience the pinnacle of luxury living in this extraordinary lakefront estate located in the world renowned Isleworth Golf & Country Club. Positioned on 2.14 private acres along Lake Louise, part of
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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: $10,900,000.00
  2. Price sqft: $615.40 / sqft
  3. Previous Price: $11,900,000
  4. Last Price Change: 09/29/25
  5. Days On Market: 639
  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 Privileges
  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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9639 Westover Roberts Road
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Details for 9639 Westover Roberts Road, WINDERMERE, FL 34786
Single Family
  1. Price: $6,395,000.00
  2. Price sqft: $324.52 / sqft
  3. Days On Market: 58
  4. Bedrooms: 5
  5. Baths: 9
  6. Garage / Parking Spaces: 7
  7. Bldg sqft: 19706
  8. Acreage: 4.43 acres
  9. Pool: Yes
  10. Spa/HotTub: Yes
  11. Waterfront: Yes
  12. Wateraccess: Yes
  13. Waterfront Type: Lake Front
  14. Year Built: 2017
MLS#: O6341883
  1. County: ORANGE
  2. City: WINDERMERE
  3. Zipcode: 34786
  4. Subdivision: Gotha Town
  5. Elementary School: Thornebrooke Elem
  6. Middle School: Gotha Middle
  7. High School: Olympia High
  8. Provided by: STOCKWORTH REALTY GROUP
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Welcome to a residence that transcends even the highest expectations of luxury living! This is a once in a lifetime estate where architecture, scale, and location combine to create an experience that
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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: 48
  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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1003 Down Reserve Court
New Construction
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Details for 1003 Down Reserve Court, WINDERMERE, FL 34786
Single Family
  1. Price: $5,499,999.00
  2. Price sqft: $520.19 / sqft
  3. Days On Market: 16
  4. Bedrooms: 6
  5. Baths: 8
  6. Garage / Parking Spaces: 6
  7. Bldg sqft: 10573
  8. Acreage: 0.69 acres
  9. Pool: Yes
  10. Spa/HotTub: Yes
  11. Waterfront: No
  12. Year Built: 2025
MLS#: O6353952
  1. County: ORANGE
  2. City: WINDERMERE
  3. Zipcode: 34786
  4. Subdivision: Lake Down Reserve
  5. Elementary School: Wyndham Lakes Elementary
  6. Middle School: Chain of Lakes Middle
  7. High School: Olympia High
  8. Provided by: PREMIER SOTHEBYS INT'L REALTY
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Welcome to a rare modern estate inside an intimate gated enclave, offering 6,816 square feet of fully furnished luxury with six bedrooms, six full baths and two half baths. Every detail of this custom
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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: 153
  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: 27
  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: 33
  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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