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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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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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800 W 2nd Avenue
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Details for 800 W 2nd Avenue, WINDERMERE, FL 34786
Single Family
  1. Price: $5,600,000.00
  2. Price sqft: $686.53 / sqft
  3. Previous Price: $5,999,000
  4. Last Price Change: 11/07/26
  5. Days On Market: 109
  6. Bedrooms: 5
  7. Baths: 5
  8. Garage / Parking Spaces: 3
  9. Bldg sqft: 8157
  10. Acreage: 0.45 acres
  11. Pool: Yes
  12. Spa/HotTub: Yes
  13. Waterfront: Yes
  14. Wateraccess: Yes
  15. Waterfront Type: Lake Privileges
  16. Year Built: 1993
MLS#: O6422976
  1. County: ORANGE
  2. City: WINDERMERE
  3. Zipcode: 34786
  4. Subdivision: Aladar On Lake Butler
  5. Elementary School: Windermere Elem
  6. Middle School: Gotha Middle
  7. High School: Olympia High
  8. Provided by: ONE LUXURY INTERNATIONAL LLC
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Set beneath a canopy of majestic live oaks along the shores of the Butler Chain of Lakes, this timeless estate has been comprehensively reimagined to blend enduring architecture with modern luxury. Re
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9615 Windy Ridge Road
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Details for 9615 Windy Ridge Road, WINDERMERE, FL 34786
Single Family
  1. Price: $5,300,000.00
  2. Price sqft: $388.05 / sqft
  3. Days On Market: 25
  4. Bedrooms: 6
  5. Baths: 8
  6. Garage / Parking Spaces: 4
  7. Bldg sqft: 13658
  8. Acreage: 2.49 acres
  9. Pool: Yes
  10. Waterfront: No
  11. Year Built: 2007
MLS#: O6449197
  1. County: ORANGE
  2. City: WINDERMERE
  3. Zipcode: 34786
  4. Subdivision: Windsor Hill
  5. Elementary School: Thornebrooke Elem
  6. Middle School: Gotha Middle
  7. High School: Olympia High
  8. Provided by: KELLER WILLIAMS CLASSIC
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Under contract accepting backup offers. A palm framed pool and spa, a balcony connected game room and a dedicated theater give this Mediterranean inspired estate a distinctive rhythm of outdoor relaxa
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Windy Ridge Road
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Details for Windy Ridge Road, WINDERMERE, FL 34786
Land
  1. Price: $5,250,000.00
  2. Previous Price: $4,500,000
  3. Last Price Change: 09/11/26
  4. Days On Market: 65
  5. Acreage: 2.90 acres
  6. Pool: No
  7. Waterfront: Yes
  8. Wateraccess: Yes
  9. Waterfront Type: Lake Front,Lake Privileges
  10. Year Built: Not Available
MLS#: O6439497
  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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Exceptional lakefront opportunity to build on one of the most coveted sites along The Butler Chain of Lakes. This prime and elevated lot is 215 feet wide and one of three being carved out of a larger
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Windy Ridge Road
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Details for Windy Ridge Road, WINDERMERE, FL 34786
Land
  1. Price: $4,750,000.00
  2. Previous Price: $4,250,000
  3. Last Price Change: 09/11/26
  4. Days On Market: 65
  5. Acreage: 2.10 acres
  6. Pool: No
  7. Waterfront: Yes
  8. Wateraccess: Yes
  9. Waterfront Type: Lake Front,Lake Privileges
  10. Year Built: Not Available
MLS#: O6439342
  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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Exceptional lakefront opportunity to build on one of the most coveted sites along The Butler Chain of Lakes. This prime and elevated lot is 175 feet wide and one of three being carved out of a larger
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9575 Westover Roberts Road
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Details for 9575 Westover Roberts Road, WINDERMERE, FL 34786
Single Family
  1. Price: $4,750,000.00
  2. Price sqft: $339.84 / sqft
  3. Previous Price: $4,850,000
  4. Last Price Change: 09/18/26
  5. Days On Market: 363
  6. Bedrooms: 7
  7. Baths: 8
  8. Garage / Parking Spaces: 6
  9. Bldg sqft: 13977
  10. Acreage: 5.44 acres
  11. Pool: Yes
  12. Spa/HotTub: Yes
  13. Waterfront: Yes
  14. Wateraccess: Yes
  15. Waterfront Type: Lake Front
  16. Year Built: 2008
MLS#: O6357873
  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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Discover Bella Olivia: a grand mediterranean estate perched high above Lake Olivia showcasing sweeping lake views, private gates, and an expansive luxury residence spanning over 8,900 square feet of l
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9602 Maywood Drive
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Details for 9602 Maywood Drive, WINDERMERE, FL 34786
Single Family
  1. Price: $4,350,000.00
  2. Price sqft: $565.23 / sqft
  3. Days On Market: 34
  4. Bedrooms: 5
  5. Baths: 5
  6. Garage / Parking Spaces: 5
  7. Bldg sqft: 7696
  8. Acreage: 1.33 acres
  9. Pool: Yes
  10. Spa/HotTub: Yes
  11. Waterfront: Yes
  12. Wateraccess: Yes
  13. Waterfront Type: Lake Front,Lake Privileges
  14. Year Built: 2005
MLS#: O6446848
  1. County: ORANGE
  2. City: WINDERMERE
  3. Zipcode: 34786
  4. Subdivision: Lake Down Shores
  5. Elementary School: Thornebrooke Elem
  6. Middle School: Gotha Middle
  7. High School: Olympia High
  8. Provided by: DIAMOND REAL ESTATE GROUP
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Welcome to 9602 Maywood Drive, a privately gated lakefront estate on Windermere's prestigious Butler Chain of Lakes. The home was reimagined through a renovation of more than $1 million by the award w
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Windy Ridge Road
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Details for Windy Ridge Road, WINDERMERE, FL 34786
Land
  1. Price: $4,250,000.00
  2. Previous Price: $4,500,000
  3. Last Price Change: 09/11/26
  4. Days On Market: 65
  5. Acreage: 1.10 acres
  6. Pool: No
  7. Waterfront: Yes
  8. Wateraccess: Yes
  9. Waterfront Type: Lake Front,Lake Privileges
  10. Year Built: Not Available
MLS#: O6439500
  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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Exceptional lakefront opportunity to build on one of the most coveted sites along The Butler Chain of Lakes. This prime and elevated lot is 158 feet wide and one of four being carved out of a larger c
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