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  1. School = Windermere Elem
Details for 4071 Isabella Circle, Windermere, FL 34786
Single Family
  1. Price: $3,200,000.00
  2. Price sqft: $280.31 / sqft
  3. Previous Price: $3,250,000
  4. Last Price Change: 06/16/25
  5. Days On Market: 61
  6. Bedrooms: 5
  7. Baths: 8
  8. Garage / Parking Spaces: 4
  9. Bldg sqft: 11416
  10. Acreage: 0.95 acres
  11. Pool: Yes
  12. Waterfront: No
  13. Year Built: 2017
MLS#: O6311409
  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: LA ROSA REALTY PREMIER LLC
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Welcome to Casabella at Windermere, a beautiful gated community where luxury and elegance converge. This stunning 6 bedroom, 5.5 bath estate sits on a sprawling one acre lot and showcases refined arch
Details for 1003 Oakdale Street, Windermere, FL 34786
Single Family
  1. Price: $2,650,000.00
  2. Price sqft: $483.84 / sqft
  3. Previous Price: $2,790,000
  4. Last Price Change: 06/15/25
  5. Days On Market: 231
  6. Bedrooms: 6
  7. Baths: 6
  8. Garage / Parking Spaces: 3
  9. Bldg sqft: 5477
  10. Acreage: 1.77 acres
  11. Pool: Yes
  12. Waterfront: Yes
  13. Wateraccess: Yes
  14. Waterfront Type: LakeFront,LakePrivileges
  15. Year Built: 2003
MLS#: O6261656
  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: VINTAGE REALTY GROUP LLC
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Never lived in since completely remodeled and expanded total of 6 bedrooms 5 full baths 1 pool or guest bath primary suite & guest suite on 1st floor 4 more bedrooms & 3 bathrooms on 2nd flo
Details for 409 2nd Avenue, Windermere, FL 34786
Single Family
  1. Price: $2,499,000.00
  2. Price sqft: $399.71 / sqft
  3. Days On Market: 127
  4. Bedrooms: 5
  5. Baths: 5
  6. Garage / Parking Spaces: 3
  7. Bldg sqft: 6252
  8. Acreage: 0.51 acres
  9. Pool: Yes
  10. Waterfront: No
  11. 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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Surrounded by glistening lakes and shaded by towering oaks, Windermere offers an unbeatable blend of natural beauty and small town charm. Friendly neighbors, golf cart friendly streets, and walkabilit
Details for 4108 Downeast Lane, Windermere, FL 34786
Land
  1. Price: $1,995,000.00
  2. Days On Market: 169
  3. Acreage: 3.31 acres
  4. Pool: No
  5. Waterfront: Yes
  6. Wateraccess: Yes
  7. Waterfront Type: Lake,LakePrivileges
  8. Year Built: Not Available
MLS#: O6276653
  1. County: ORANGE
  2. City: Windermere
  3. Zipcode: 34786
  4. Subdivision: Windermere
  5. Elementary School: Windermere Elem
  6. Middle School: Chain of Lakes
  7. High School: Olympia
  8. Provided by: KELLY PRICE & COMPANY LLC
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Now priced at $1,995,000, this expansive lakefront property presents an extraordinary value on the Butler Chain of Lakes. Whether youre seeking a private waterfront retreat, a renovation project, or a
Details for 4108 Downeast Lane, Windermere, FL 34786
Single Family
  1. Price: $1,995,000.00
  2. Price sqft: $351.60 / sqft
  3. Days On Market: 173
  4. Bedrooms: 4
  5. Baths: 3
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 5674
  8. Acreage: 3.31 acres
  9. Pool: No
  10. Waterfront: Yes
  11. Wateraccess: Yes
  12. Waterfront Type: Lake,LakePrivileges
  13. Year Built: 1979
MLS#: O6273954
  1. County: ORANGE
  2. City: Windermere
  3. Zipcode: 34786
  4. Subdivision: Windermere
  5. Elementary School: Windermere Elem
  6. Middle School: Chain of Lakes
  7. High School: Olympia
  8. Provided by: KELLY PRICE & COMPANY LLC
  9. Provided through
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Now priced at $1,995,000, this expansive lakefront property presents an extraordinary value on the Butler Chain of Lakes. Whether youre seeking a private waterfront retreat, a renovation project, or a
Details for 11721 Camden Park Drive, Windermere, FL 34786
Single Family
  1. Price: $1,429,000.00
  2. Price sqft: $341.95 / sqft
  3. Previous Price: $1,499,000
  4. Last Price Change: 06/16/25
  5. Days On Market: 53
  6. Bedrooms: 4
  7. Baths: 3
  8. Garage / Parking Spaces: 2
  9. Bldg sqft: 4179
  10. Acreage: 0.26 acres
  11. Pool: Yes
  12. Waterfront: No
  13. Year Built: 2005
MLS#: O6313389
  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: RE/MAX PRIME PROPERTIES
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Welcome to 11721 Camden Park Drive, a beautifully renovated executive home located in the prestigious guard gated community of Keenes Pointe in Windermere. This exquisite residence sits on a meticulou
Details for 109 12th Avenue, Windermere, FL 34786
Single Family
  1. Price: $1,300,000.00
  2. Price sqft: $392.87 / sqft
  3. Days On Market: 11
  4. Bedrooms: 4
  5. Baths: 4
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 3309
  8. Acreage: 0.29 acres
  9. Pool: Yes
  10. Waterfront: No
  11. Year Built: 1989
MLS#: O6326261
  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: EXECUTIVE PROPERTIES
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Modern upgrades meet timeless Windermere charm in this fully reimagined four bedroom, three and a half bath home, just steps from Lake Bessie. Set on a beautifully manicured corner lot with no HOA, th
Details for 8335 Lake Burden Circle, Windermere, FL 34786
Single Family
  1. Price: $1,198,000.00
  2. Price sqft: $294.64 / sqft
  3. Days On Market: 50
  4. Bedrooms: 4
  5. Baths: 3
  6. Garage / Parking Spaces: 3
  7. Bldg sqft: 4066
  8. Acreage: 0.29 acres
  9. Pool: Yes
  10. Waterfront: Yes
  11. Wateraccess: Yes
  12. Waterfront Type: LakePrivileges
  13. Year Built: 2000
MLS#: O6312684
  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: PREMIER SOTHEBY'S INTL. REALTY
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Welcome to this elegant Charleston style home, on a beautifully landscaped corner lot in a quiet cul de sac in the prestigious guard gated community of Keenes Pointe. Designed with comfort and functio
Details for 11031 Ledgement Lane, Windermere, FL 34786
Single Family
  1. Price: $899,900.00
  2. Price sqft: $237.07 / sqft
  3. Days On Market: 10
  4. Bedrooms: 5
  5. Baths: 4
  6. Garage / Parking Spaces: 3
  7. Bldg sqft: 3796
  8. Acreage: 0.45 acres
  9. Pool: Yes
  10. Waterfront: No
  11. Year Built: 2003
MLS#: O6325415
  1. County: ORANGE
  2. City: Windermere
  3. Zipcode: 34786
  4. Subdivision: Glenmuir Ut 02 51 42
  5. Elementary School: Windermere Elem
  6. Middle School: Bridgewater
  7. High School: Windermere
  8. Provided by: THE WILKINS WAY LLC
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Stunning waterfront executive pool home with 5 bedrooms 3. 5 bathrooms 3 car garage + 0. 45 acres! + conservation views in fully fenced in backyard with 2,750+ square feet of living space in the gated
Details for 4818 Breezy Palms Court, Windermere, FL 34786
Single Family
  1. Price: $539,900.00
  2. Price sqft: $209.51 / sqft
  3. Previous Price: $545,000
  4. Last Price Change: 07/21/25
  5. Days On Market: 173
  6. Bedrooms: 3
  7. Baths: 2
  8. Garage / Parking Spaces: 2
  9. Bldg sqft: 2577
  10. Acreage: 0.24 acres
  11. Pool: No
  12. Waterfront: No
  13. Year Built: 1986
MLS#: O6275406
  1. County: ORANGE
  2. City: Windermere
  3. Zipcode: 34786
  4. Subdivision: Silver Woods Ph 03
  5. Elementary School: Windermere Elem
  6. Middle School: Chain of Lakes
  7. High School: Olympia
  8. Provided by: KELLER WILLIAMS WINTER PARK
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PRICE REDUCED! PLUS $8000 BUYER CREDIT! Welcome home to Windermere! Dont miss this Silver Woods jewel box in the ideal location! Large corner lot on quiet cul de sac. Featuring a FANTASTIC 55x10 scr