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- School = Windermere Elem
Single Family
- Price: $20,000,000.00
- Price sqft: $879.97 / sqft
- Days On Market: 160
- 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
- Year Built: 2014
MLS#: O6275556
- County: ORANGE
- City: WINDERMERE
- Zipcode: 34786
- Subdivision: Metcalf Park Rep
- Elementary School: Windermere Elem
- Middle School: Chain of Lakes
- High School: Olympia
- Provided by: STOCKWORTH REALTY GROUP
- 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
Single Family
- Price: $14,250,000.00
- Price sqft: $1,156.75 / sqft
- Days On Market: 95
- Bedrooms: 5
- Baths: 6
- Garage / Parking Spaces: 6
- Bldg sqft: 12319
- Acreage: 1.02 acres
- Pool: Yes
- Spa/HotTub: Yes
- Waterfront: No
- Year Built: 1999
MLS#: O6304800
- County: ORANGE
- City: WINDERMERE
- Zipcode: 34786
- Subdivision: Isleworth
- Elementary School: Windermere Elem
- Middle School: Chain of Lakes
- High School: Olympia
- Provided by: ISLEWORTH REALTY LLC
- 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
Single Family
- Price: $11,900,000.00
- Price sqft: $671.86 / sqft
- Days On Market: 564
- Bedrooms: 6
- Baths: 9
- Garage / Parking Spaces: 4
- Bldg sqft: 17712
- Acreage: 1.60 acres
- Pool: Yes
- Spa/HotTub: Yes
- Waterfront: Yes
- Wateraccess: Yes
- Waterfront Type: Lake
- Year Built: 2001
MLS#: O6176070
- County: ORANGE
- City: WINDERMERE
- Zipcode: 34786
- Subdivision: Down Point Sub
- Elementary School: Windermere Elem
- Middle School: Chain of Lakes
- High School: Olympia
- Provided by: REVEL REALTY LLC
- DMCA Notice
Nestled along almost 1,000 of the highly sought after Butler Chain of Lakes in Windermere, this exquisite Mediterranean estate beckons with unrivaled opulence. Beyond a private gate, a 2 acre peninsul
Single Family
- Price: $9,500,000.00
- Price sqft: $636.13 / sqft
- Days On Market: 141
- Bedrooms: 6
- Baths: 9
- Garage / Parking Spaces: 5
- Bldg sqft: 14934
- Acreage: 2.20 acres
- Pool: Yes
- Spa/HotTub: Yes
- Waterfront: Yes
- Wateraccess: Yes
- Waterfront Type: Lake Privileges,Riparian Rights
- Year Built: 2010
MLS#: O6294487
- County: ORANGE
- City: WINDERMERE
- Zipcode: 34786
- Subdivision: Keenes Pointe
- Elementary School: Windermere Elem
- Middle School: Bridgewater
- High School: Windermere
- Provided by: PREMIER SOTHEBY'S INTL. REALTY
- 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
Single Family
- Price: $8,499,000.00
- Price sqft: $664.19 / sqft
- Previous Price: $9,490,000
- Last Price Change: 07/08/25
- Days On Market: 444
- Bedrooms: 6
- Baths: 10
- Garage / Parking Spaces: 4
- Bldg sqft: 12796
- Acreage: 0.60 acres
- Pool: Yes
- Spa/HotTub: Yes
- Waterfront: Yes
- Wateraccess: Yes
- Waterfront Type: Lake Privileges
- Year Built: 2004
MLS#: O6211352
- County: ORANGE
- City: WINDERMERE
- Zipcode: 34786
- Subdivision: Isleworth
- Elementary School: Windermere Elem
- Middle School: Chain of Lakes
- High School: Olympia
- Provided by: ISLEWORTH REALTY LLC
- DMCA Notice
One or more photo(s) has been virtually staged. Introducing an exquisitely remodeled three level Isleworth home on Lake Butler in the renowned Butler Chain of Lakes. Boasting a spacious 11,100 square
Land
- Price: $8,250,000.00
- Days On Market: 52
- Acreage: 2.19 acres
- Pool: No
- Waterfront: Yes
- Wateraccess: Yes
- Waterfront Type: Lake Front,Lake Privileges
- Year Built: Not Available
MLS#: O6322995
- County: ORANGE
- City: WINDERMERE
- Zipcode: 34786
- Subdivision: Chaine Du Lac
- Elementary School: Windermere Elem
- Middle School: Bridgewater
- High School: Windermere
- Provided by: JULIAN PROPERTIES, INC.
- DMCA Notice
WELCOME TO PARK AVENUE. This tremendous opportunity offers 2.19 acres of sprawling possibilities with Southeastern exposure and sweeping lake views. Nestled on the gorgeous shoreline of Lake Butler am
Single Family
- Price: $7,500,000.00
- Price sqft: $627.72 / sqft
- Days On Market: 79
- Bedrooms: 5
- Baths: 8
- Garage / Parking Spaces: 4
- Bldg sqft: 11948
- Acreage: 1.74 acres
- Pool: Yes
- Waterfront: Yes
- Wateraccess: Yes
- Waterfront Type: Lake
- Year Built: 2006
MLS#: O6315165
- County: ORANGE
- City: Windermere
- Zipcode: 34786
- Subdivision: Reserve At Lake Butler Sound 4
- Elementary School: Windermere Elem
- Middle School: Bridgewater
- High School: Windermere
- Provided by: THE SIMON SIMAAN GROUP
- Provided through
- DMCA Notice
Step into timeless elegance, luxury, and sophisticated living. Located in the exclusive man gated community of Lake Butler Soundone of Central Floridas most prestigious communities. From the moment yo
Single Family
- Price: $7,500,000.00
- Price sqft: $627.72 / sqft
- Days On Market: 79
- Bedrooms: 5
- Baths: 8
- Garage / Parking Spaces: 4
- Bldg sqft: 11948
- Acreage: 1.74 acres
- Pool: Yes
- Spa/HotTub: Yes
- Waterfront: Yes
- Wateraccess: Yes
- Waterfront Type: Lake Privileges
- Year Built: 2006
MLS#: O6315165
- County: ORANGE
- City: WINDERMERE
- Zipcode: 34786
- Subdivision: Reserve At Lake Butler Sound 4
- Elementary School: Windermere Elem
- Middle School: Bridgewater Middle
- High School: Windermere High School
- Provided by: THE SIMON SIMAAN GROUP
- DMCA Notice
Step into timeless elegance, luxury, and sophisticated living. Located in the exclusive man gated community of Lake Butler Soundone of Central Floridas most prestigious communities. From the moment yo
Single Family
- Price: $5,494,000.00
- Price sqft: $829.66 / sqft
- Days On Market: 78
- Bedrooms: 5
- Baths: 7
- Garage / Parking Spaces: 4
- Bldg sqft: 6622
- Acreage: 0.52 acres
- Pool: Yes
- Spa/HotTub: Yes
- Waterfront: No
- Year Built: 1993
MLS#: O6315618
- County: ORANGE
- City: WINDERMERE
- Zipcode: 34786
- Subdivision: Isleworth
- Elementary School: Windermere Elem
- Middle School: Chain of Lakes
- High School: Olympia
- Provided by: COLDWELL BANKER RESIDENTIAL RE
- DMCA Notice
Nestled in the exclusive and coveted gated community of Isleworth, this fully remodeled, turn key golf estate is positioned along Isleworths famed championship golf course. This remarkable golf front
Single Family
- Price: $5,489,000.00
- Price sqft: $437.13 / sqft
- Days On Market: 4
- Bedrooms: 6
- Baths: 9
- Garage / Parking Spaces: 4
- Bldg sqft: 12557
- Acreage: 0.51 acres
- Pool: Yes
- Spa/HotTub: Yes
- Waterfront: Yes
- Wateraccess: Yes
- Waterfront Type: Pond
- Year Built: 2011
MLS#: O6336879
- County: ORANGE
- City: WINDERMERE
- Zipcode: 34786
- Subdivision: Keenes Pointe
- Elementary School: Windermere Elem
- Middle School: Bridgewater
- High School: Windermere
- Provided by: SOUTHERN REALTY GROUP LLC
- DMCA Notice
Welcome to a stunning, fully furnished, professionally designed home nestled within the guard gates of Keenes Pointe in Windermere. This exceptional residence boasts 8,305 sq ft of luxurious living sp

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Listings provided courtesy of The Hernando County Association of Realtors MLS.
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