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  1. School = Windermere Elem
Details for 4047 Isabella Circle, WINDERMERE, FL 34786
Single Family
  1. Price: $2,850,000.00
  2. Price sqft: $270.35 / sqft
  3. Previous Price: $2,995,000
  4. Last Price Change: 10/01/25
  5. Days On Market: 181
  6. Bedrooms: 6
  7. Baths: 8
  8. Garage / Parking Spaces: 3
  9. Bldg sqft: 10542
  10. Acreage: 0.53 acres
  11. Pool: No
  12. Waterfront: No
  13. Year Built: 2019
MLS#: O6305503
  1. County: ORANGE
  2. City: WINDERMERE
  3. Zipcode: 34786
  4. Subdivision: Casabella Ph 2
  5. Elementary School: Windermere Elem
  6. Middle School: Bridgewater
  7. High School: Windermere
  8. Provided by: REAL BROKER, LLC
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$75,000 credit towards pool with acceptable offer! This exceptional 2019 built home has been transformed with nearly a full interior remodel, making it one of the most distinctive properties in the so
Details for 6120 Payne Stewart Dr, WINDERMERE, FL 34786
Single Family
  1. Price: $2,799,000.00
  2. Price sqft: $631.40 / sqft
  3. Days On Market: 238
  4. Bedrooms: 4
  5. Baths: 5
  6. Garage / Parking Spaces: 3
  7. Bldg sqft: 4433
  8. Acreage: 0.34 acres
  9. Pool: No
  10. Waterfront: No
  11. Year Built: 1987
MLS#: O6288273
  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: SOUTHERN REALTY GROUP LLC
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Isleworth nestled in Windermere, this 600 acre community, is a prestigious residential enclave nestled along the Butler Chain of Lakes. This charming villa is in walking distance to Isleworth Golf &
Details for 6102 Hampshire Court, WINDERMERE, FL 34786
Single Family
  1. Price: $2,650,000.00
  2. Price sqft: $411.81 / sqft
  3. Days On Market: 45
  4. Bedrooms: 4
  5. Baths: 6
  6. Garage / Parking Spaces: 3
  7. Bldg sqft: 6435
  8. Acreage: 0.44 acres
  9. Pool: Yes
  10. Spa/HotTub: Yes
  11. Waterfront: No
  12. Year Built: 2002
MLS#: O6344907
  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: CHARLES RUTENBERG REALTY ORLANDO
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This elegant single story Rick Watson home, located at 6102 S Hampshire Court, Windermere, FL 34786, sits on a private Jack Nicklausdesigned golf course lot in the exclusive, 24 hour manned and gated
Details for 9905 Lanai View Court, WINDERMERE, FL 34786
Single Family
  1. Price: $2,650,000.00
  2. Price sqft: $260.85 / sqft
  3. Previous Price: $2,750,000
  4. Last Price Change: 08/21/25
  5. Days On Market: 137
  6. Bedrooms: 5
  7. Baths: 8
  8. Garage / Parking Spaces: 4
  9. Bldg sqft: 10159
  10. Acreage: 0.67 acres
  11. Pool: Yes
  12. Waterfront: No
  13. Year Built: 2011
MLS#: S5129274
  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: MAXIM REALTY ORLANDO
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BACK ON THE MARKET BUYERS' FINANCE FELL THROUGH. Welcome to a home that isnt just designedits curated. Tucked behind the gates of one of Central Floridas most exclusive golf communities, 9905
Details for 9204 Tibet Pointe Circle, WINDERMERE, FL 34786
Single Family
  1. Price: $2,500,000.00
  2. Price sqft: $364.01 / sqft
  3. Days On Market: 38
  4. Bedrooms: 5
  5. Baths: 6
  6. Garage / Parking Spaces: 3
  7. Bldg sqft: 6868
  8. Acreage: 0.47 acres
  9. Pool: Yes
  10. Spa/HotTub: Yes
  11. Waterfront: No
  12. Year Built: 2007
MLS#: O6347671
  1. County: ORANGE
  2. City: WINDERMERE
  3. Zipcode: 34786
  4. Subdivision: Keenes Pointe 46104
  5. Elementary School: Windermere Elem
  6. Middle School: Bridgewater
  7. High School: Windermere
  8. Provided by: THE SIMON SIMAAN GROUP
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Your stunning Keenes Pointe custom home by Stonebridge was built for luxurious everyday living and effortless entertaining. The grand first floor features travertine and hardwood floors throughout, a
Details for 11019 Ullswater Lane, WINDERMERE, FL 34786
Single Family
  1. Price: $2,495,000.00
  2. Price sqft: $313.29 / sqft
  3. Days On Market: 25
  4. Bedrooms: 5
  5. Baths: 5
  6. Garage / Parking Spaces: 3
  7. Bldg sqft: 7964
  8. Acreage: 0.51 acres
  9. Pool: Yes
  10. Spa/HotTub: Yes
  11. Waterfront: No
  12. Year Built: 2006
MLS#: O6350027
  1. County: ORANGE
  2. City: WINDERMERE
  3. Zipcode: 34786
  4. Subdivision: Reserve At Lake Butler Sound
  5. Elementary School: Windermere Elem
  6. Middle School: Bridgewater
  7. High School: Windermere
  8. Provided by: REAL BROKER, LLC
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Welcome to 11019 Ullswater Drive, a timeless Italian inspired residence built by Brierhill Custom Homes. Set on over half an acre within the 24 hour manned gates of The Reserve at Lake Butler Sound, t
Details for 11106 Coniston Way, WINDERMERE, FL 34786
Single Family
  1. Price: $2,450,000.00
  2. Price sqft: $325.50 / sqft
  3. Days On Market: 146
  4. Bedrooms: 5
  5. Baths: 7
  6. Garage / Parking Spaces: 3
  7. Bldg sqft: 7527
  8. Acreage: 0.61 acres
  9. Pool: Yes
  10. Spa/HotTub: Yes
  11. Waterfront: No
  12. Year Built: 2008
MLS#: O6316553
  1. County: ORANGE
  2. City: WINDERMERE
  3. Zipcode: 34786
  4. Subdivision: Reserve At Lake Butler
  5. Elementary School: Windermere Elem
  6. Middle School: Bridgewater
  7. High School: Windermere
  8. Provided by: COMPASS FLORIDA LLC
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A one of a kind French Provincial estate, "The Monet," was crafted by Master Custom Builder Castleworks in 2008 and has been updated a smart home for todays buyers. This luxurious residence is situate
Details for 409 2nd Avenue, WINDERMERE, FL 34786
Single Family
  1. Price: $2,399,000.00
  2. Price sqft: $383.72 / sqft
  3. Previous Price: $2,425,000
  4. Last Price Change: 10/17/25
  5. Days On Market: 231
  6. Bedrooms: 5
  7. Baths: 5
  8. Garage / Parking Spaces: 3
  9. Bldg sqft: 6252
  10. Acreage: 0.51 acres
  11. Pool: Yes
  12. Spa/HotTub: Yes
  13. Waterfront: No
  14. Year Built: 1995
MLS#: O6290296
  1. County: ORANGE
  2. City: WINDERMERE
  3. Zipcode: 34786
  4. Subdivision: Windermere Town
  5. Elementary School: Windermere Elem
  6. Middle School: Gotha
  7. High School: Olympia
  8. Provided by: UPSIDE REAL ESTATE INC
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Step inside this beautifully updated home where clean lines, soaring ceilings, and two story windows fill every corner with natural light. A floating staircase makes a stunning first impression, while
Details for 6252 Blakeford Dr, WINDERMERE, FL 34786
Single Family
  1. Price: $2,390,000.00
  2. Price sqft: $427.09 / sqft
  3. Days On Market: 4
  4. Bedrooms: 5
  5. Baths: 4
  6. Garage / Parking Spaces: 3
  7. Bldg sqft: 5596
  8. Acreage: 0.44 acres
  9. Pool: Yes
  10. Waterfront: No
  11. Year Built: 1999
MLS#: O6356056
  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: COLDWELL BANKER RESIDENTIAL RE
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Now its your turn to live on the 18th hole of the Golden Bear Club golf course in a fully updated custom home, located on one of the most desirable streets in Keenes Pointe. This house with a timeles
Details for 6134 Keenes Pointe Drive, WINDERMERE, FL 34786
Single Family
  1. Price: $2,375,000.00
  2. Price sqft: $385.62 / sqft
  3. Previous Price: $2,395,000
  4. Last Price Change: 10/23/25
  5. Days On Market: 45
  6. Bedrooms: 4
  7. Baths: 4
  8. Garage / Parking Spaces: 3
  9. Bldg sqft: 6159
  10. Acreage: 0.43 acres
  11. Pool: Yes
  12. Spa/HotTub: Yes
  13. Waterfront: No
  14. Year Built: 2002
MLS#: O6345101
  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: WRA BUSINESS & REAL ESTATE
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Welcome to a rare fully furnished opportunity in the heart of Keenes Pointe, Windermeres most acclaimed community. This renovated residence, with over 4,400 square feet of living space, has been re