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 = Chain Of Lakes Middle
  2. Listing Status = Active
11900 Lake Butler Boulevard
Virtual Tour
Reduced
More Like This
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
  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.
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: $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: 67
  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
  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: $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
  8. mfrmls
  9. DMCA Notice
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
Listing Details and 27 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: $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: 179
  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
  8. mfrmls
  9. DMCA Notice
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
Listing Details and 28 Additional Pictures
Request more information about this listing.
5186 Vardon Drive
Virtual Tour
More Like This
Active
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: 66
  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
  9. mfrmls
  10. DMCA Notice
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,
Listing Details and 60 Additional Pictures
Request more information about this listing.
9725 Chestnut Ridge Drive
Virtual Tour
Reduced
More Like This
Active
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
  9. mfrmls
  10. DMCA Notice
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
Listing Details and 56 Additional Pictures
Request more information about this listing.
1330 Lake Olivia
Virtual Tour
New Construction
More Like This
Active
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
  9. mfrmls
  10. DMCA Notice
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
Listing Details and 12 Additional Pictures
Request more information about this listing.
5243 Isleworth Country Club Drive
Virtual Tour
More Like This
Active
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
  9. mfrmls
  10. DMCA Notice
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
Listing Details and 64 Additional Pictures
Request more information about this listing.
5070 Down Point Lane
Virtual Tour
More Like This
Active
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: 54
  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
  8. mfrmls
  9. DMCA Notice
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
Listing Details and 56 Additional Pictures
Request more information about this listing.
5745 Emerington Crescent
Virtual Tour
More Like This
Active
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
  9. mfrmls
  10. DMCA Notice
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
Listing Details and 99 Additional Pictures
Request more information about this listing.
Liked Listings