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  1. City = Windermere
  2. Listing Status = Active
Details for 5074 Isleworth Country Club Drive, WINDERMERE, FL 34786
Single Family
  1. Price: $7,595,000.00
  2. Price sqft: $847.56 / sqft
  3. Days On Market: 104
  4. Bedrooms: 5
  5. Baths: 7
  6. Garage / Parking Spaces: 3
  7. Bldg sqft: 8961
  8. Acreage: 0.54 acres
  9. Pool: Yes
  10. Waterfront: No
  11. Year Built: 1988
MLS#: O6373191
  1. County: ORANGE
  2. City: WINDERMERE
  3. Zipcode: 34786
  4. Subdivision: Isleworth
  5. Provided by: MEMARPOURI REALTY LLC
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  7. DMCA Notice
Luxury living perfectly positioned along the 6th fairway in the world renowned guard gated community of Isleworth. This exceptional estate offers over 6,900 square feet of completely remodeled space
Details for 5186 Vardon Drive, WINDERMERE, FL 34786
Single Family
  1. Price: $6,980,000.00
  2. Price sqft: $886.35 / sqft
  3. Previous Price: $4,960,000
  4. Last Price Change: 04/18/26
  5. Days On Market: 73
  6. Bedrooms: 4
  7. Baths: 5
  8. Garage / Parking Spaces: 3
  9. Bldg sqft: 7875
  10. Acreage: 1.01 acres
  11. Pool: Yes
  12. Waterfront: No
  13. Year Built: 1990
MLS#: O6382040
  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: FLORIDA REALTY INVESTMENTS
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One or more photo(s) has been virtually staged. Fully reimagined golf front estate in the prestigious Isleworth community with sweeping views of the iconic 3rd hole. Situated on approximately 1 acre,
Details for 9259 Tibet Pointe Cir, WINDERMERE, FL 34786
Single Family
  1. Price: $6,499,000.00
  2. Price sqft: $790.15 / sqft
  3. Previous Price: $6,699,000
  4. Last Price Change: 04/08/26
  5. Days On Market: 336
  6. Bedrooms: 5
  7. Baths: 6
  8. Garage / Parking Spaces: 4
  9. Bldg sqft: 8225
  10. Acreage: 2.21 acres
  11. Pool: Yes
  12. Waterfront: Yes
  13. Wateraccess: Yes
  14. Waterfront Type: Lake Privileges
  15. 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
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: 232
  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
  7. High School: Olympia
  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
Details for 9725 Chestnut Ridge Drive, WINDERMERE, FL 34786
Single Family
  1. Price: $6,150,000.00
  2. Price sqft: $514.56 / sqft
  3. Previous Price: $6,950,000
  4. Last Price Change: 04/16/26
  5. Days On Market: 116
  6. Bedrooms: 7
  7. Baths: 7
  8. Garage / Parking Spaces: 3
  9. Bldg sqft: 11952
  10. Acreage: 0.56 acres
  11. Pool: Yes
  12. Spa/HotTub: Yes
  13. Waterfront: Yes
  14. Wateraccess: Yes
  15. Waterfront Type: Pond
  16. 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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Newly renovated, this private Isleworth residence offers a rare balance of architectural authority, thoughtful design, and quiet indulgence. Spanning approximately 8,000 square feet, the home unfolds
Details for 5138 Fairway Oaks Dr, WINDERMERE, FL 34786
Single Family
  1. Price: $5,500,000.00
  2. Price sqft: $930.47 / sqft
  3. Days On Market: 3
  4. Bedrooms: 4
  5. Baths: 5
  6. Garage / Parking Spaces: 3
  7. Bldg sqft: 5911
  8. Acreage: 0.50 acres
  9. Pool: Yes
  10. Spa/HotTub: Yes
  11. Waterfront: No
  12. Year Built: 1994
MLS#: O6401757
  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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Set along Isleworths signature 12th fairway, this fully reimagined estate captures the essence of refined golf course living within the renowned Isleworth Golf & Country Clubrecognized among the fines
Details for 1330 Lake Olivia, WINDERMERE, FL 34786
Single Family
  1. Price: $5,500,000.00
  2. Price sqft: $598.09 / sqft
  3. Days On Market: 33
  4. Bedrooms: 6
  5. Baths: 8
  6. Garage / Parking Spaces: 4
  7. Bldg sqft: 9196
  8. Acreage: 1.62 acres
  9. Pool: Yes
  10. Spa/HotTub: Yes
  11. Waterfront: No
  12. 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
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: 201
  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
Details for 9721 Carillon Park Drive, WINDERMERE, FL 34786
Single Family
  1. Price: $5,000,000.00
  2. Price sqft: $398.18 / sqft
  3. Previous Price: $5,489,000
  4. Last Price Change: 03/30/26
  5. Days On Market: 253
  6. Bedrooms: 6
  7. Baths: 9
  8. Garage / Parking Spaces: 4
  9. Bldg sqft: 12557
  10. Acreage: 0.51 acres
  11. Pool: Yes
  12. Spa/HotTub: Yes
  13. Waterfront: Yes
  14. Wateraccess: Yes
  15. Waterfront Type: Pond
  16. Year Built: 2011
MLS#: O6336879
  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: DOUGLAS ELLIMAN
  9. mfrmls
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Welcome to 9721 carillon park dr, windermere, fl 34786, a stunning estate inside the guard gated community of keenes pointe. This extraordinary residence offers 8,305 square feet of luxury living spa
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: 61
  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
  8. mfrmls
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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