Searching on:
  1. School = Chain Of Lakes Middle
  2. Listing Status = Active
Details for 11900 Lake Butler Boulevard, WINDERMERE, FL 34786
Single Family
  1. Price: $17,250,000.00
  2. Price sqft: $758.98 / sqft
  3. Previous Price: $18,500,000
  4. Last Price Change: 04/15/26
  5. Days On Market: 401
  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 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
Details for 9323 Gladys Garden Court, WINDERMERE, FL 34786
Single Family
  1. Price: $12,500,000.00
  2. Price sqft: $999.20 / sqft
  3. Previous Price: $13,995,000
  4. Last Price Change: 04/03/26
  5. Days On Market: 66
  6. Bedrooms: 6
  7. Baths: 10
  8. Garage / Parking Spaces: 4
  9. Bldg sqft: 12510
  10. Acreage: 0.26 acres
  11. Pool: Yes
  12. Waterfront: No
  13. 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 Middle
  7. High School: Olympia High
  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
Details for 4226 Downeast Lane, WINDERMERE, FL 34786
Land
  1. Price: $10,500,000.00
  2. Previous Price: $11,800,000
  3. Last Price Change: 04/09/26
  4. Days On Market: 125
  5. Acreage: 9.03 acres
  6. Pool: No
  7. Waterfront: Yes
  8. Wateraccess: Yes
  9. Waterfront Type: Lake Privileges
  10. 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 Middle
  6. High School: Olympia High
  7. Provided by: COLDWELL BANKER RESIDENTIAL RE
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Dramatic price improvement. Exceptional development opportunity, currently r ce zoning should allow for 3 luxury home sites discover over 5+acres of waterfront land with 300 feet of pristine shoreline
Details for 4226 Downeast Lane, WINDERMERE, FL 34786
Single Family
  1. Price: $10,500,000.00
  2. Price sqft: $1,232.97 / sqft
  3. Previous Price: $11,800,000
  4. Last Price Change: 04/09/26
  5. Days On Market: 178
  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 Middle
  6. High School: Olympia High
  7. Provided by: COLDWELL BANKER RESIDENTIAL RE
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Dramatic price improvement. Exceptional development opportunity, currently r ce zoning should allow for 3 luxury home sites discover over 5+acres of waterfront land with 300 feet of pristine shorelin
Details for 5186 Vardon Drive, WINDERMERE, FL 34786
Single Family
  1. Price: $6,980,000.00
  2. Price sqft: $886.35 / sqft
  3. Days On Market: 65
  4. Bedrooms: 4
  5. Baths: 5
  6. Garage / Parking Spaces: 3
  7. Bldg sqft: 7875
  8. Acreage: 1.01 acres
  9. Pool: Yes
  10. Waterfront: No
  11. 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 Middle
  7. High School: Olympia High
  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 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: 04/15/26
  5. Days On Market: 109
  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 Middle
  7. High School: Olympia High
  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 1330 Lake Olivia, WINDERMERE, FL 34786
Single Family
  1. Price: $5,500,000.00
  2. Price sqft: $598.09 / sqft
  3. Days On Market: 25
  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 Middle
  7. High School: Windermere High School
  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: 03/11/26
  5. Days On Market: 193
  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 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
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: 53
  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 Middle
  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
Details for 5745 Emerington Crescent, ORLANDO, FL 32819
Single Family
  1. Price: $4,590,000.00
  2. Price sqft: $399.44 / sqft
  3. Days On Market: 63
  4. Bedrooms: 7
  5. Baths: 8
  6. Garage / Parking Spaces: 6
  7. Bldg sqft: 11491
  8. Acreage: 1.08 acres
  9. Pool: Yes
  10. Spa/HotTub: Yes
  11. Waterfront: Yes
  12. Wateraccess: Yes
  13. Waterfront Type: Lake Privileges
  14. Year Built: 2011
MLS#: O6382015
  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