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9508 Windy Ridge Road
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Details for 9508 Windy Ridge Road, WINDERMERE, FL 34786
Single Family
  1. Price: $30,000,000.00
  2. Price sqft: $639.85 / sqft
  3. Days On Market: 160
  4. Bedrooms: 7
  5. Baths: 14
  6. Garage / Parking Spaces: 12
  7. Bldg sqft: 46886
  8. Acreage: 18.16 acres
  9. Pool: Yes
  10. Spa/HotTub: Yes
  11. Waterfront: Yes
  12. Wateraccess: Yes
  13. Waterfront Type: Lake Front,Lake Privileges
  14. Year Built: 2011
MLS#: O6411343
  1. County: ORANGE
  2. City: WINDERMERE
  3. Zipcode: 34786
  4. Elementary School: Thornebrooke Elem
  5. Middle School: Gotha Middle
  6. High School: Olympia High
  7. Provided by: STOCKWORTH REALTY GROUP
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Showcasing Central Floridas most iconic lakefront estate: an 18 acre compound with 614 feet of pristine frontage on Lake Down on The Butler Chain of Lakes. The Windy Ridge Estate is comprised of multi
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3057 Porto Lago Court
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Details for 3057 Porto Lago Court, WINDERMERE, FL 34786
Single Family
  1. Price: $13,995,000.00
  2. Price sqft: $879.64 / sqft
  3. Days On Market: 148
  4. Bedrooms: 6
  5. Baths: 11
  6. Garage / Parking Spaces: 8
  7. Bldg sqft: 15910
  8. Acreage: 1.13 acres
  9. Pool: Yes
  10. Spa/HotTub: Yes
  11. Waterfront: Yes
  12. Wateraccess: Yes
  13. Waterfront Type: Lake Front,Lake Privileges
  14. Year Built: 2026
MLS#: O6411245
  1. County: ORANGE
  2. City: WINDERMERE
  3. Zipcode: 34786
  4. Subdivision: Lake Down Pointe 50 42
  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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BRAND NEW ESTATE. A truly exceptional one of one on the shores of Lake Down, boasting over 12,000SF, 6BR's, 6/5BA's, and unmatched multigenerational flexibility. Designed by Mark Nasrallah and curated
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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: $11,900,000.00
  2. Price sqft: $951.24 / sqft
  3. Previous Price: $12,500,000
  4. Last Price Change: 11/01/26
  5. Days On Market: 269
  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
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4226 Downeast Lane
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Details for 4226 Downeast Lane, WINDERMERE, FL 34786
Land
  1. Price: $9,250,000.00
  2. Previous Price: $9,750,000
  3. Last Price Change: 10/22/26
  4. Days On Market: 327
  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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NEW DRAMATIC PRICE IMPROVEMENT on this exceptional 5+ acre Lake Down development opportunity, offering 300 feet of pristine shoreline on the coveted BUTLER CHAIN of Lakes and positioned on the best si
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4226 Downeast Lane
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Details for 4226 Downeast Lane, WINDERMERE, FL 34786
Single Family
  1. Price: $9,250,000.00
  2. Price sqft: $1,086.19 / sqft
  3. Previous Price: $9,750,000
  4. Last Price Change: 10/22/26
  5. Days On Market: 381
  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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NEW DRAMATIC PRICE IMPROVEMENT on this exceptional 5+ acre LAKE DOWN development opportunity, offering 300 feet of pristine shoreline on the coveted BUTLER CHAIN of Lakes and positioned on the best si
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5092 Isleworth Country Club Drive
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Details for 5092 Isleworth Country Club Drive, WINDERMERE, FL 34786
Single Family
  1. Price: $8,500,000.00
  2. Price sqft: $823.72 / sqft
  3. Days On Market: 39
  4. Bedrooms: 4
  5. Baths: 5
  6. Garage / Parking Spaces: 4
  7. Bldg sqft: 10319
  8. Acreage: 0.93 acres
  9. Pool: Yes
  10. Spa/HotTub: Yes
  11. Waterfront: No
  12. Year Built: 1995
MLS#: O6446272
  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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Set along the front nine of Isleworth championship golf course with breathtaking views of Hole 6, this grand estate occupies an oversized lot along Isleworths main drive and has been beautifully reima
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724 W 2nd Avenue
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Details for 724 W 2nd Avenue, WINDERMERE, FL 34786
Single Family
  1. Price: $7,500,000.00
  2. Price sqft: $722.13 / sqft
  3. Days On Market: 111
  4. Bedrooms: 6
  5. Baths: 8
  6. Garage / Parking Spaces: 4
  7. Bldg sqft: 10386
  8. Acreage: 1.10 acres
  9. Pool: Yes
  10. Spa/HotTub: Yes
  11. Waterfront: Yes
  12. Wateraccess: Yes
  13. Waterfront Type: Lake Front,Lake Privileges
  14. Year Built: 2024
MLS#: O6426995
  1. County: ORANGE
  2. City: WINDERMERE
  3. Zipcode: 34786
  4. Subdivision: Windermere
  5. Elementary School: Windermere Elem
  6. Middle School: Gotha Middle
  7. High School: Olympia High
  8. Provided by: THE SIMON SIMAAN GROUP
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Under contract accepting backup offers. Welcome to an extraordinary lakefront estate on the prestigious shores of Lake Butler with 182 feet of water frontage, where timeless architecture, exceptional
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5373 Isleworth Country Club Drive
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Details for 5373 Isleworth Country Club Drive, WINDERMERE, FL 34786
Single Family
  1. Price: $7,200,000.00
  2. Price sqft: $938.11 / sqft
  3. Days On Market: 62
  4. Bedrooms: 5
  5. Baths: 6
  6. Garage / Parking Spaces: 3
  7. Bldg sqft: 7675
  8. Acreage: 0.52 acres
  9. Pool: Yes
  10. Spa/HotTub: Yes
  11. Waterfront: No
  12. Year Built: 1988
MLS#: O6439156
  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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Impressively elegant NEW CONSTRUCTION Isleworth estate, prominently positioned on the 17th fairway of the championship golf course, with sweeping Lake Louise vistas beyond. This home was completely g
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9117 Bay Point Drive
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Details for 9117 Bay Point Drive, ORLANDO, FL 32819
Single Family
  1. Price: $6,995,000.00
  2. Price sqft: $869.70 / sqft
  3. Days On Market: 159
  4. Bedrooms: 5
  5. Baths: 8
  6. Garage / Parking Spaces: 3
  7. Bldg sqft: 8043
  8. Acreage: 0.33 acres
  9. Pool: Yes
  10. Waterfront: Yes
  11. Wateraccess: Yes
  12. Waterfront Type: Lake Privileges
  13. Year Built: 2026
MLS#: S5150268
  1. County: ORANGE
  2. City: ORLANDO
  3. Zipcode: 32819
  4. Subdivision: Bay Point
  5. Elementary School: Dr. Phillips Elem
  6. Middle School: Southwest Middle
  7. High School: Olympia High
  8. Provided by: SERHANT
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An exceptional opportunity to own a NEWLY CONSTRUCTED luxury waterfront estate within the exclusive gated enclave of Bay Point at Bay Hill. This remarkable residence offers over 6,400 square feet of t
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9061 Ron Den Lane
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Details for 9061 Ron Den Lane, WINDERMERE, FL 34786
Single Family
  1. Price: $6,800,000.00
  2. Price sqft: $868.23 / sqft
  3. Previous Price: $6,900,000
  4. Last Price Change: 09/16/26
  5. Days On Market: 145
  6. Bedrooms: 5
  7. Baths: 7
  8. Garage / Parking Spaces: 4
  9. Bldg sqft: 7832
  10. Acreage: 0.47 acres
  11. Pool: Yes
  12. Waterfront: Yes
  13. Wateraccess: Yes
  14. Waterfront Type: Lake Privileges
  15. Year Built: 2024
MLS#: O6417446
  1. County: ORANGE
  2. City: WINDERMERE
  3. Zipcode: 34786
  4. Subdivision: Down Acres Estates
  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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A rare architectural statement on Lake Down, this extraordinary contemporary waterfront estate redefines luxury living in the heart of Windermere. Positioned on the prestigious Butler Chain of Lakes,
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