Windermere, FL Real Estate

311 Properties Found.
Sorted By:
9508 WINDY RIDGE ROAD WINDERMERE FL 34786
Photo of 9508 WINDY RIDGE ROAD, WINDERMERE, FL 34786
$30,000,000  7 Beds | 13 Baths
9508 WINDY RIDGE ROAD  WINDERMERE, FL 34786
11900 LAKE BUTLER BOULEVARD WINDERMERE FL 34786
Photo of 11900 LAKE BUTLER BOULEVARD, WINDERMERE, FL 34786
$18,500,000  7 Beds | 8.5 Baths
11900 LAKE BUTLER BOULEVARD  WINDERMERE, FL 34786
5525 ISLEWORTH COUNTRY CLUB DR WINDERMERE FL 34786
Photo of 5525 ISLEWORTH COUNTRY CLUB DR, WINDERMERE, FL 34786
$14,250,000  5 Beds | 5.5 Baths
5525 ISLEWORTH COUNTRY CLUB DR  WINDERMERE, FL 34786
9323 GLADYS GARDEN COURT WINDERMERE FL 34786
Photo of 9323 GLADYS GARDEN COURT, WINDERMERE, FL 34786
$12,500,000  6 Beds | 8 Baths
9323 GLADYS GARDEN COURT  WINDERMERE, FL 34786
4226 DOWNEAST LANE WINDERMERE FL 34786
Photo of 4226 DOWNEAST LANE, WINDERMERE, FL 34786
$10,500,000  0 Baths
4226 DOWNEAST LANE  WINDERMERE, FL 34786
4226 DOWNEAST LANE WINDERMERE FL 34786
Photo of 4226 DOWNEAST LANE, WINDERMERE, FL 34786
$10,500,000  5 Beds | 3 Baths
4226 DOWNEAST LANE  WINDERMERE, FL 34786
6149 GROSVENOR SHORE DR WINDERMERE FL 34786
Photo of 6149 GROSVENOR SHORE DR, WINDERMERE, FL 34786
$9,999,000  6 Beds | 7 Baths
6149 GROSVENOR SHORE DR  WINDERMERE, FL 34786
6137 GROSVENOR SHORE DRIVE WINDERMERE FL 34786
Photo of 6137 GROSVENOR SHORE DRIVE, WINDERMERE, FL 34786
$8,995,000  6 Beds | 7.5 Baths
6137 GROSVENOR SHORE DRIVE  WINDERMERE, FL 34786
9343 TIBET POINTE CIRCLE WINDERMERE FL 34786
Photo of 9343 TIBET POINTE CIRCLE, WINDERMERE, FL 34786
$7,950,000  7 Beds | 9 Baths
9343 TIBET POINTE CIRCLE  WINDERMERE, FL 34786
5074 ISLEWORTH COUNTRY CLUB DRIVE WINDERMERE FL 34786
Photo of 5074 ISLEWORTH COUNTRY CLUB DRIVE, WINDERMERE, FL 34786
$7,595,000  5 Beds | 6.5 Baths
5074 ISLEWORTH COUNTRY CLUB DRIVE  WINDERMERE, FL 34786
9725 CHESTNUT RIDGE DRIVE WINDERMERE FL 34786
Photo of 9725 CHESTNUT RIDGE DRIVE, WINDERMERE, FL 34786
$6,950,000  7 Beds | 6 Baths
9725 CHESTNUT RIDGE DRIVE  WINDERMERE, FL 34786
11 MAIN STREET WINDERMERE FL 34786
Photo of 11 MAIN STREET, WINDERMERE, FL 34786
$6,700,000  5 Beds | 5 Baths
11 MAIN STREET  WINDERMERE, FL 34786
Listings Courtesy of Mid-Florida Regional MLS as distributed by MLSGrid. Based on information submitted to the MLS GRID as of 4/10/2026 8:07 PM. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information..
Brokers make an effort to deliver accurate information, but buyers should independently verify any information on which they will rely in a transaction. All properties are subject to prior sale, change or withdrawal. Neither nor any listing broker shall be responsible for any typographical errors, misinformation, or misprints, and they shall be held totally harmless from any damages arising from reliance upon this data. This data is provided exclusively for consumer -- personal, non-commercial use and may not be used for any purpose other than to identify prospective properties they may be interested in purchasing. © 2026 Mid-Florida Regional MLS.