Skip to Main Content
Headshot for Associate Michelle Hill
  1. Michelle Hill, ABR,AHWD,PA,PSA,REALTOR ®,SFR
  2. Tropic Shores Realty
  3. Mobile: 352.247.2177
  4. 229.834.4988
Skip to Main Content
Refine Search
  1. Home
  2. Search Listings
  3. Search Results
Searching on:
  1. School = Windermere Elem
  2. Listing Status = Active
11900 Lake Butler Boulevard
Virtual Tour
More Like This
Active
Details for 11900 Lake Butler Boulevard, WINDERMERE, FL 34786
Single Family
  1. Price: $18,500,000.00
  2. Price sqft: $813.97 / sqft
  3. Previous Price: $20,000,000
  4. Last Price Change: 09/13/25
  5. Days On Market: 363
  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
  7. High School: Olympia
  8. Provided by: STOCKWORTH REALTY GROUP
  9. mfrmls
  10. DMCA Notice
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
Listing Details and 90 Additional Pictures
Request more information about this listing.
5525 Isleworth Country Club Dr
Virtual Tour
More Like This
Active
Details for 5525 Isleworth Country Club Dr, WINDERMERE, FL 34786
Single Family
  1. Price: $14,250,000.00
  2. Price sqft: $1,156.75 / sqft
  3. Days On Market: 299
  4. Bedrooms: 5
  5. Baths: 6
  6. Garage / Parking Spaces: 6
  7. Bldg sqft: 12319
  8. Acreage: 1.02 acres
  9. Pool: Yes
  10. Spa/HotTub: Yes
  11. Waterfront: No
  12. Year Built: 1999
MLS#: O6304800
  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
  9. mfrmls
  10. DMCA Notice
One or more photo(s) has been virtually staged. Exceptional in both style and scale, this extraordinary Isleworth estate represents the pinnacle of luxury living in one of the finest golf club communi
Listing Details and 99 Additional Pictures
Request more information about this listing.
9323 Gladys Garden Court
Virtual Tour
New Construction
More Like This
Active
Details for 9323 Gladys Garden Court, WINDERMERE, FL 34786
Single Family
  1. Price: $13,995,000.00
  2. Price sqft: $1,118.71 / sqft
  3. Days On Market: 29
  4. Bedrooms: 6
  5. Baths: 10
  6. Garage / Parking Spaces: 4
  7. Bldg sqft: 12510
  8. Acreage: 0.26 acres
  9. Pool: Yes
  10. Waterfront: No
  11. 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
  7. High School: Olympia
  8. Provided by: CORCORAN PREMIER REALTY
  9. mfrmls
  10. DMCA Notice
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
Listing Details and 83 Additional Pictures
Request more information about this listing.
4226 Downeast Lane
Virtual Tour
More Like This
Active
Details for 4226 Downeast Lane, WINDERMERE, FL 34786
Land
  1. Price: $11,800,000.00
  2. Days On Market: 87
  3. Acreage: 9.03 acres
  4. Pool: No
  5. Waterfront: Yes
  6. Wateraccess: Yes
  7. Waterfront Type: Lake Privileges
  8. 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
  6. High School: Olympia
  7. Provided by: COLDWELL BANKER RESIDENTIAL RE
  8. mfrmls
  9. DMCA Notice
Exceptional development opportunity, currently r ce zoning should allow for 3 lakefront luxury home sites discover over 5+acres of waterfront land with 300 feet of pristine shoreline on lake down, par
Listing Details and 16 Additional Pictures
Request more information about this listing.
4226 Downeast Lane
Virtual Tour
More Like This
Active
Details for 4226 Downeast Lane, WINDERMERE, FL 34786
Single Family
  1. Price: $11,800,000.00
  2. Price sqft: $1,385.63 / sqft
  3. Previous Price: $14,800,000
  4. Last Price Change: 12/17/25
  5. Days On Market: 141
  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
  6. High School: Olympia
  7. Provided by: COLDWELL BANKER RESIDENTIAL RE
  8. mfrmls
  9. DMCA Notice
Exceptional DEVELOPMENT OPPORTUNITY, currently R CE zoning should allow for 3 Lakefront Luxury Home Sites Discover over 5+acres of waterfront land with 300 feet of pristine shoreline on LAKE DOWN, pa
Listing Details and 17 Additional Pictures
Request more information about this listing.
6149 Grosvenor Shore Dr
Virtual Tour
More Like This
Active
Details for 6149 Grosvenor Shore Dr, WINDERMERE, FL 34786
Single Family
  1. Price: $9,999,000.00
  2. Price sqft: $1,096.14 / sqft
  3. Days On Market: 123
  4. Bedrooms: 6
  5. Baths: 8
  6. Garage / Parking Spaces: 7
  7. Bldg sqft: 9122
  8. Acreage: 2.65 acres
  9. Pool: Yes
  10. Spa/HotTub: Yes
  11. Waterfront: Yes
  12. Wateraccess: Yes
  13. Waterfront Type: Lake Privileges
  14. Year Built: 2013
MLS#: O6356355
  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
  9. mfrmls
  10. DMCA Notice
Keene's Pointe Stunning lakefront home on Lake Tibet of the famed Butler Chain of Lakes. No detail was spared in this completely renovated home boasting formal living and dining rooms, family and me
Listing Details and 74 Additional Pictures
Request more information about this listing.
6137 Grosvenor Shore Drive
Virtual Tour
More Like This
Active
Details for 6137 Grosvenor Shore Drive, WINDERMERE, FL 34786
Single Family
  1. Price: $8,995,000.00
  2. Price sqft: $602.32 / sqft
  3. Previous Price: $9,500,000
  4. Last Price Change: 11/15/25
  5. Days On Market: 344
  6. Bedrooms: 6
  7. Baths: 9
  8. Garage / Parking Spaces: 5
  9. Bldg sqft: 14934
  10. Acreage: 2.20 acres
  11. Pool: Yes
  12. Spa/HotTub: Yes
  13. Waterfront: Yes
  14. Wateraccess: Yes
  15. Waterfront Type: Lake Privileges,Riparian Rights
  16. Year Built: 2010
MLS#: O6294487
  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: PREMIER SOTHEBY'S INTL. REALTY
  9. mfrmls
  10. DMCA Notice
Experience luxury lakefront living on a grand scale in this custom built Modern Mediterranean estate on Lake Tibet, part of the pristine Butler Chain of Lakes. The three story residence spans 9,571 sq
Listing Details and 61 Additional Pictures
Request more information about this listing.
9725 Chestnut Ridge Drive
Virtual Tour
More Like This
Active
Details for 9725 Chestnut Ridge Drive, WINDERMERE, FL 34786
Single Family
  1. Price: $6,950,000.00
  2. Price sqft: $581.49 / sqft
  3. Days On Market: 71
  4. Bedrooms: 7
  5. Baths: 7
  6. Garage / Parking Spaces: 3
  7. Bldg sqft: 11952
  8. Acreage: 0.56 acres
  9. Pool: Yes
  10. Spa/HotTub: Yes
  11. Waterfront: Yes
  12. Wateraccess: Yes
  13. Waterfront Type: Pond
  14. 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
  9. mfrmls
  10. DMCA Notice
Private showings are easily accommodated, including same day requests. Newly renovated and fully turnkey, this private Isleworth residence offers a rare balance of architectural authority, thoughtfu
Listing Details and 56 Additional Pictures
Request more information about this listing.
11 Main Street
New Construction
More Like This
Active
Details for 11 Main Street, WINDERMERE, FL 34786
Single Family
  1. Price: $6,700,000.00
  2. Price sqft: $1,095.85 / sqft
  3. Days On Market: 10
  4. Bedrooms: 5
  5. Baths: 5
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 6114
  8. Acreage: 0.41 acres
  9. Pool: No
  10. Waterfront: Yes
  11. Wateraccess: Yes
  12. Waterfront Type: Canal - Freshwater
  13. Year Built: 2026
MLS#: O6387596
  1. County: ORANGE
  2. City: WINDERMERE
  3. Zipcode: 34786
  4. Subdivision: Davis Shores
  5. Elementary School: Windermere Elem
  6. Middle School: Gotha
  7. High School: Olympia
  8. Provided by: GOLDEN GROUP REALTY LLC
  9. mfrmls
  10. DMCA Notice
Under Construction. Brand New Construction in the Heart of Downtown Windermere Currently Under Construction! Walking distance to downtown events, the farmers market, food trucks, and the local bre
Listing Details and 3 Additional Pictures
Request more information about this listing.
9259 Tibet Pointe Cir
Virtual Tour
More Like This
Active
Details for 9259 Tibet Pointe Cir, WINDERMERE, FL 34786
Single Family
  1. Price: $6,699,000.00
  2. Price sqft: $814.47 / sqft
  3. Previous Price: $6,800,000
  4. Last Price Change: 02/03/26
  5. Days On Market: 291
  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
  9. mfrmls
  10. DMCA Notice
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
Listing Details and 69 Additional Pictures
Request more information about this listing.
Liked Listings