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  1. School = Olympia High
9508 Windy Ridge Road
9508 Windy Ridge Road
Single Family
  1. Price: $28,500,000.00
  2. Price sqft: $558.82 / sqft
  3. Days On Market: 220
  4. Bedrooms: 7
  5. Baths: 14
  6. Garage / Parking Spaces: 10
  7. Bldg sqft: 51000
  8. Acreage: 10.00 acres
  9. Pool: Yes
  10. Waterfront: Yes
  11. Wateraccess: Yes
  12. Year Built: 2011
MLS#: O5746245
  1. County: ORANGE
  2. City: WINDERMERE
  3. Zipcode: 34786
  4. Subdivision: Acreage & Unrec
  5. Elementary School: Thornebrooke Elem
  6. High School: Olympia High
  7. Provided by: STOCKWORTH REALTY GROUP
Private Windermere lakefront compound with 18 acres on The Butler Chain of Lakes offering an unparalleled presence and prestige in Central Florida's most desirable location. This walled and gated esta [Read More]
9912 Lake Louise Drive
9912 Lake Louise Drive
Single Family
  1. Price: $23,000,000.00
  2. Price sqft: $903.17 / sqft
  3. Days On Market: 348
  4. Bedrooms: 11
  5. Baths: 14
  6. Garage / Parking Spaces: 40
  7. Bldg sqft: 25466
  8. Acreage: 0.00 acres
  9. Pool: Yes
  10. Spa/HotTub: Yes
  11. Waterfront: Yes
  12. Wateraccess: Yes
  13. Year Built: 1999
MLS#: O5714911
  1. County: ORANGE
  2. City: WINDERMERE
  3. Zipcode: 34786
  4. Subdivision: Isleworth 02 Amd
  5. Elementary School: Windermere Elem
  6. High School: Olympia High
  7. Provided by: EXP REALTY LLC
An exquisite waterfront estate within one of Orlando's most sought after golf community of Isleworth Country Club. This impressive mansion offers car enthusiasts a dream showcase garage that can accom [Read More]
5372 Isleworth Country Club Drive
5372 Isleworth Country Club Drive
Single Family
  1. Price: $7,790,000.00
  2. Price sqft: $588.81 / sqft
  3. Days On Market: 420
  4. Bedrooms: 8
  5. Baths: 9
  6. Garage / Parking Spaces: 3
  7. Bldg sqft: 13230
  8. Acreage: 0.00 acres
  9. Pool: Yes
  10. Waterfront: No
  11. Year Built: 2004
MLS#: O5700351
  1. County: ORANGE
  2. City: WINDERMERE
  3. Zipcode: 34786
  4. Subdivision: Isleworth 01 Amd
  5. Elementary School: Windermere Elem
  6. High School: Olympia High
  7. Provided by: REGAL R.E. PROFESSIONALS LLC
This exquisite one of a kind Isleworth masterpiece features unparalleled details and craftsmanship throughout. From the hand carved millwork to the imported marble fireplaces and over 115 Italian marb [Read More]
5318 Isleworth Country Club Drive
5318 Isleworth Country Club Drive
Single Family
  1. Price: $6,750,000.00
  2. Price sqft: $548.87 / sqft
  3. Days On Market: 378
  4. Bedrooms: 6
  5. Baths: 10
  6. Garage / Parking Spaces: 4
  7. Bldg sqft: 12298
  8. Acreage: 0.00 acres
  9. Pool: Yes
  10. Spa/HotTub: Yes
  11. Waterfront: No
  12. Year Built: 2006
MLS#: O5713515
  1. County: ORANGE
  2. City: WINDERMERE
  3. Zipcode: 34786
  4. Subdivision: Isleworth
  5. Elementary School: Windermere Elem
  6. High School: Olympia High
  7. Provided by: ISLEWORTH REALTY LLC
Characterized by a lovely English garden designed to maximize its prime golf front location, this estate is unparalleled in Isleworth. Beyond the circular driveway with fountain and porte cochere entr [Read More]
5139 Fairway Oaks Drive
5139 Fairway Oaks Drive
Single Family
  1. Price: $5,685,000.00
  2. Price sqft: $509.27 / sqft
  3. Days On Market: 69
  4. Bedrooms: 6
  5. Baths: 9
  6. Garage / Parking Spaces: 4
  7. Bldg sqft: 11163
  8. Acreage: 1.00 acres
  9. Pool: Yes
  10. Waterfront: Yes
  11. Wateraccess: Yes
  12. Year Built: 2009
MLS#: O5775789
  1. County: ORANGE
  2. City: WINDERMERE
  3. Zipcode: 34786
  4. Subdivision: Isleworth
  5. Elementary School: Windermere Elem
  6. High School: Olympia High
  7. Provided by: ISLEWORTH REALTY LLC
Seller Requirement: Buyer must produce proof of funds at full listing price. Nestled on a picturesque home site along the shores of Lake Bessie, this commanding waterfront residence blends a Spanish M [Read More]
5020 Down Point Lane
5020 Down Point Lane
Single Family
  1. Price: $4,949,000.00
  2. Price sqft: $514.40 / sqft
  3. Days On Market: 433
  4. Bedrooms: 5
  5. Baths: 8
  6. Garage / Parking Spaces: 6
  7. Bldg sqft: 9621
  8. Acreage: 0.00 acres
  9. Pool: No
  10. Waterfront: Yes
  11. Wateraccess: Yes
  12. Year Built: 2005
MLS#: O5701437
  1. County: ORANGE
  2. City: WINDERMERE
  3. Zipcode: 34786
  4. Subdivision: Sunset Bay Rep
  5. Elementary School: Windermere Elem
  6. High School: Olympia High
  7. Provided by: REGAL R.E. PROFESSIONALS LLC
Villa Constantia is the epitome of luxury Windermere lake front living. Designed by legendary architect John Henry this exquisite lake front mansion is perfectly positioned on Lake Down, part of the r [Read More]
6342 Deacon Circle
6342 Deacon Circle
Single Family
  1. Price: $4,900,000.00
  2. Price sqft: $699.20 / sqft
  3. Days On Market: 276
  4. Bedrooms: 5
  5. Baths: 6
  6. Garage / Parking Spaces: 3
  7. Bldg sqft: 7008
  8. Acreage: 1.00 acres
  9. Pool: Yes
  10. Waterfront: Yes
  11. Wateraccess: Yes
  12. Year Built: 1991
MLS#: O5735188
  1. County: ORANGE
  2. City: WINDERMERE
  3. Zipcode: 34786
  4. Subdivision: Isleworth
  5. Elementary School: Windermere Elem
  6. High School: Olympia High
  7. Provided by: ISLEWORTH REALTY LLC
Nestled along the lake in the heart of Isleworth, this fully updated residence offers a prime location overlooking Lake Isleworth with direct access to the renowned Butler Chain of Lakes. The five bed [Read More]
9520 Windy Ridge Road
9520 Windy Ridge Road
Land
  1. Price: $4,900,000.00
  2. Days On Market: 186
  3. Acreage: 5.00 acres
  4. Pool: No
  5. Waterfront: Yes
  6. Wateraccess: Yes
  7. Year Built: Not Available
MLS#: O5752665
  1. County: ORANGE
  2. City: WINDERMERE
  3. Zipcode: 34786
  4. Subdivision: Acreage & Unrec
  5. Elementary School: Thornebrooke Elem
  6. High School: Olympia High
  7. Provided by: STOCKWORTH REALTY GROUP
Exceptional lakefront opportunity. May be developed into a cluster of multiple luxury homes or build your dream mansion behind the secured walls of Windermeres largest estate. Perched above Lake Down [Read More]
5501 Isleworth Country Club Drive
5501 Isleworth Country Club Drive
Single Family
  1. Price: $4,800,000.00
  2. Price sqft: $690.05 / sqft
  3. Days On Market: 252
  4. Bedrooms: 6
  5. Baths: 8
  6. Garage / Parking Spaces: 4
  7. Bldg sqft: 6956
  8. Acreage: 1.00 acres
  9. Pool: Yes
  10. Spa/HotTub: Yes
  11. Waterfront: No
  12. Wateraccess: Yes
  13. Year Built: 2007
MLS#: O5740376
  1. County: ORANGE
  2. City: WINDERMERE
  3. Zipcode: 34786
  4. Subdivision: Isleworth
  5. Elementary School: Windermere Elem
  6. High School: Olympia High
  7. Provided by: IRWIN REALTY GROUP LLC
Located on the 14th hole of the World Famous Isleworth Golf Course this magnificent property is truly one of the most spectacular estates in the area. Breathtaking views from every room in the house.C [Read More]
9711 Deacon Court
9711 Deacon Court
Single Family
  1. Price: $4,395,000.00
  2. Price sqft: $523.21 / sqft
  3. Days On Market: 55
  4. Bedrooms: 5
  5. Baths: 5
  6. Garage / Parking Spaces: 4
  7. Bldg sqft: 8400
  8. Acreage: 0.00 acres
  9. Pool: Yes
  10. Waterfront: Yes
  11. Wateraccess: Yes
  12. Year Built: 1990
MLS#: O5777309
  1. County: ORANGE
  2. City: WINDERMERE
  3. Zipcode: 34786
  4. Subdivision: Isleworth
  5. Elementary School: Windermere Elem
  6. High School: Olympia High
  7. Provided by: REGAL R.E. PROFESSIONALS LLC
Stunning Butler Chain lake front estate nestled along the shores of Lake Isleworth. Located in renowned Isleworth Golf and Country Club this sprawling estate offers one of a kind panoramic sunset view [Read More]