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- School = Chain Of Lakes Middle
- Listing Status = Active
Single Family
- Price: $17,250,000.00
- Price sqft: $758.98 / sqft
- Previous Price: $18,500,000
- Last Price Change: 04/15/26
- Days On Market: 409
- Bedrooms: 7
- Baths: 9
- Garage / Parking Spaces: 6
- Bldg sqft: 22728
- Acreage: 3.75 acres
- Pool: Yes
- Spa/HotTub: Yes
- Waterfront: Yes
- Wateraccess: Yes
- Waterfront Type: Lake Front,Lake Privileges
- Year Built: 2014
MLS#: O6275556
- County: ORANGE
- City: WINDERMERE
- Zipcode: 34786
- Subdivision: Metcalf Park Rep
- Elementary School: Windermere Elem
- Middle School: Chain of Lakes Middle
- High School: Olympia High
- Provided by: STOCKWORTH REALTY GROUP
- DMCA Notice
Description
- 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
Single Family
- Price: $12,500,000.00
- Price sqft: $999.20 / sqft
- Previous Price: $13,995,000
- Last Price Change: 04/03/26
- Days On Market: 74
- Bedrooms: 6
- Baths: 10
- Garage / Parking Spaces: 4
- Bldg sqft: 12510
- Acreage: 0.26 acres
- Pool: Yes
- Waterfront: No
- Year Built: 2026
MLS#: O6381880
- County: ORANGE
- City: WINDERMERE
- Zipcode: 34786
- Subdivision: Isleworth
- Elementary School: Windermere Elem
- Middle School: Chain of Lakes Middle
- High School: Olympia High
- Provided by: CORCORAN PREMIER REALTY
- DMCA Notice
Description
- 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
Single Family
- Price: $10,500,000.00
- Price sqft: $1,232.97 / sqft
- Previous Price: $11,800,000
- Last Price Change: 04/27/26
- Days On Market: 186
- Bedrooms: 5
- Baths: 3
- Garage / Parking Spaces: 4
- Bldg sqft: 8516
- Acreage: 9.03 acres
- Pool: Yes
- Waterfront: Yes
- Wateraccess: Yes
- Waterfront Type: Lake Front
- Year Built: 1980
MLS#: O6355233
- County: ORANGE
- City: WINDERMERE
- Zipcode: 34786
- Elementary School: Windermere Elem
- Middle School: Chain of Lakes Middle
- High School: Olympia High
- Provided by: COLDWELL BANKER RESIDENTIAL RE
- DMCA Notice
Description
- 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
Land
- Price: $10,500,000.00
- Previous Price: $11,800,000
- Last Price Change: 04/09/26
- Days On Market: 133
- Acreage: 9.03 acres
- Pool: No
- Waterfront: Yes
- Wateraccess: Yes
- Waterfront Type: Lake Privileges
- Year Built: Not Available
MLS#: O6367852
- County: ORANGE
- City: WINDERMERE
- Zipcode: 34786
- Elementary School: Windermere Elem
- Middle School: Chain of Lakes Middle
- High School: Olympia High
- Provided by: COLDWELL BANKER RESIDENTIAL RE
- DMCA Notice
Description
- 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
Single Family
- Price: $6,980,000.00
- Price sqft: $886.35 / sqft
- Previous Price: $698,000
- Last Price Change: 04/20/26
- Days On Market: 73
- Bedrooms: 4
- Baths: 5
- Garage / Parking Spaces: 3
- Bldg sqft: 7875
- Acreage: 1.01 acres
- Pool: Yes
- Waterfront: No
- Year Built: 1990
MLS#: O6382040
- County: ORANGE
- City: WINDERMERE
- Zipcode: 34786
- Subdivision: Isleworth
- Elementary School: Windermere Elem
- Middle School: Chain of Lakes Middle
- High School: Olympia High
- Provided by: FLORIDA REALTY INVESTMENTS
- DMCA Notice
Description
- 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,
Single Family
- Price: $6,150,000.00
- Price sqft: $514.56 / sqft
- Previous Price: $6,950,000
- Last Price Change: 04/15/26
- Days On Market: 116
- Bedrooms: 7
- Baths: 7
- Garage / Parking Spaces: 3
- Bldg sqft: 11952
- Acreage: 0.56 acres
- Pool: Yes
- Spa/HotTub: Yes
- Waterfront: Yes
- Wateraccess: Yes
- Waterfront Type: Pond
- Year Built: 1999
MLS#: O6370294
- County: ORANGE
- City: WINDERMERE
- Zipcode: 34786
- Subdivision: Isleworth
- Elementary School: Windermere Elem
- Middle School: Chain of Lakes Middle
- High School: Olympia High
- Provided by: DOUGLAS ELLIMAN
- DMCA Notice
Description
- 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
Single Family
- Price: $5,500,000.00
- Price sqft: $930.47 / sqft
- Days On Market: 3
- Bedrooms: 4
- Baths: 5
- Garage / Parking Spaces: 3
- Bldg sqft: 5911
- Acreage: 0.50 acres
- Pool: Yes
- Spa/HotTub: Yes
- Waterfront: No
- Year Built: 1994
MLS#: O6401757
- County: ORANGE
- City: WINDERMERE
- Zipcode: 34786
- Subdivision: Isleworth
- Elementary School: Windermere Elem
- Middle School: Chain of Lakes Middle
- High School: Olympia High
- Provided by: ISLEWORTH REALTY LLC
- DMCA Notice
Description
- Set along Isleworths signature 12th fairway, this fully reimagined estate captures the essence of refined golf course living within the renowned Isleworth Golf & Country Clubrecognized among the fines
Single Family
- Price: $5,500,000.00
- Price sqft: $598.09 / sqft
- Days On Market: 33
- Bedrooms: 6
- Baths: 8
- Garage / Parking Spaces: 4
- Bldg sqft: 9196
- Acreage: 1.62 acres
- Pool: Yes
- Spa/HotTub: Yes
- Waterfront: No
- Year Built: 2026
MLS#: S5144942
- County: ORANGE
- City: WINDERMERE
- Zipcode: 34786
- Subdivision: Lake Olivia Reserve
- Elementary School: Windermere Elem
- Middle School: Chain of Lakes Middle
- High School: Windermere High School
- Provided by: EMPIRE NETWORK REALTY
- DMCA Notice
Description
- 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
Single Family
- Price: $5,100,000.00
- Price sqft: $703.84 / sqft
- Previous Price: $5,325,000
- Last Price Change: 03/11/26
- Days On Market: 201
- Bedrooms: 4
- Baths: 6
- Garage / Parking Spaces: 3
- Bldg sqft: 7246
- Acreage: 0.51 acres
- Pool: Yes
- Waterfront: No
- Year Built: 1992
MLS#: O6348067
- County: ORANGE
- City: WINDERMERE
- Zipcode: 34786
- Subdivision: Isleworth
- Elementary School: Windermere Elem
- Middle School: Chain of Lakes Middle
- High School: Olympia High
- Provided by: STOCKWORTH REALTY GROUP
- DMCA Notice
Description
- 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
Single Family
- Price: $4,995,000.00
- Price sqft: $462.54 / sqft
- Days On Market: 61
- Bedrooms: 6
- Baths: 7
- Garage / Parking Spaces: 4
- Bldg sqft: 10799
- Acreage: 2.64 acres
- Pool: Yes
- Spa/HotTub: Yes
- Waterfront: Yes
- Wateraccess: Yes
- Waterfront Type: Lake Privileges
- Year Built: 1998
MLS#: O6385276
- County: ORANGE
- City: WINDERMERE
- Zipcode: 34786
- Subdivision: Sunset Bay
- Elementary School: Windermere Elem
- Middle School: Chain of Lakes Middle
- Provided by: EXP REALTY LLC
- DMCA Notice
Description
- 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









