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225 Magnolia Street
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Details for 225 Magnolia Street, WINDERMERE, FL 34786
Single Family
  1. Price: $4,899,000.00
  2. Price sqft: $504.53 / sqft
  3. Days On Market: 201
  4. Bedrooms: 7
  5. Baths: 11
  6. Garage / Parking Spaces: 3
  7. Bldg sqft: 9710
  8. Acreage: 1.09 acres
  9. Pool: Yes
  10. Spa/HotTub: Yes
  11. Waterfront: Yes
  12. Wateraccess: Yes
  13. Waterfront Type: Beach Front,Lake Privileges
  14. Year Built: 2019
MLS#: O6292745
  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: COMPASS FLORIDA LLC
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LAKEFRONT GRANDEUR IN WINDERMERE | A MASTERPIECE ON LAKE DOWN Unveiling a rare opportunity to own an architectural masterpiece on the famed Butler Chain of Lakesa residence that redefines lakefront l
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2 Chase Road
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Details for 2 Chase Road, WINDERMERE, FL 34786
Single Family
  1. Price: $3,200,000.00
  2. Price sqft: $822.83 / sqft
  3. Days On Market: 24
  4. Bedrooms: 4
  5. Baths: 5
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 3889
  8. Acreage: 0.44 acres
  9. Pool: Yes
  10. Waterfront: No
  11. Year Built: 2026
MLS#: O6345197
  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: REAL BROKER, LLC
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Pre construction. To be built. Pre construction. To be built. Pre construction | to be built | designed for unparalleled luxury discover an extraordinary opportunity to own a masterfully designed luxu
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409 2nd Avenue
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Details for 409 2nd Avenue, WINDERMERE, FL 34786
Single Family
  1. Price: $2,425,000.00
  2. Price sqft: $387.88 / sqft
  3. Previous Price: $2,450,000
  4. Last Price Change: 09/22/25
  5. Days On Market: 208
  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
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436 7th Avenue
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Details for 436 7th Avenue, Windermere, FL 34786
Single Family
  1. Price: $2,425,000.00
  2. Price sqft: $476.61 / sqft
  3. Days On Market: 3
  4. Bedrooms: 4
  5. Baths: 5
  6. Garage / Parking Spaces: 3
  7. Bldg sqft: 5088
  8. Acreage: 0.74 acres
  9. Pool: No
  10. Waterfront: No
  11. Year Built: 2025
MLS#: O6350454
  1. County: ORANGE
  2. City: Windermere
  3. Zipcode: 34786
  4. Subdivision: Windermere Town Rep
  5. Provided by: TALENT REALTY SOLUTIONS
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Luxury new construction lakefront home in Windermere, newly completed. Situated on Lake Bessie, this modern custom residence delivers architectural elegance, premium finishes, and a prime location jus
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436 7th Avenue
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Details for 436 7th Avenue, WINDERMERE, FL 34786
Single Family
  1. Price: $2,425,000.00
  2. Price sqft: $476.61 / sqft
  3. Days On Market: 3
  4. Bedrooms: 4
  5. Baths: 5
  6. Garage / Parking Spaces: 3
  7. Bldg sqft: 5088
  8. Acreage: 0.74 acres
  9. Pool: No
  10. Waterfront: No
  11. Year Built: 2025
MLS#: O6350454
  1. County: ORANGE
  2. City: WINDERMERE
  3. Zipcode: 34786
  4. Subdivision: Windermere Town Rep
  5. Provided by: TALENT REALTY SOLUTIONS
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Luxury new construction lakefront home in Windermere, newly completed. Situated on Lake Bessie, this modern custom residence delivers architectural elegance, premium finishes, and a prime location jus
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1020 Oakdale Street
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New Construction
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Details for 1020 Oakdale Street, WINDERMERE, FL 34786
Single Family
  1. Price: $2,200,000.00
  2. Price sqft: $452.40 / sqft
  3. Days On Market: 86
  4. Bedrooms: 5
  5. Baths: 5
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 4863
  8. Acreage: 0.29 acres
  9. Pool: Yes
  10. Spa/HotTub: Yes
  11. Waterfront: No
  12. Year Built: 2025
MLS#: O6322270
  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: COMPASS FLORIDA LLC
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Under Construction. Extraordinary new construction estate by renowned builder Davila Homes, nestled in the heart of Downtown Windermere. Meticulously designed and artfully executed, this five bedroom,
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647 Ridgewood Drive
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Details for 647 Ridgewood Drive, WINDERMERE, FL 34786
Single Family
  1. Price: $2,150,000.00
  2. Price sqft: $607.17 / sqft
  3. Previous Price: $2,269,500
  4. Last Price Change: 08/07/25
  5. Days On Market: 299
  6. Bedrooms: 3
  7. Baths: 3
  8. Garage / Parking Spaces: 2
  9. Bldg sqft: 3541
  10. Acreage: 1.43 acres
  11. Pool: No
  12. Waterfront: Yes
  13. Wateraccess: Yes
  14. Waterfront Type: Lake Privileges
  15. Year Built: 1974
MLS#: O6263552
  1. County: ORANGE
  2. City: WINDERMERE
  3. Zipcode: 34786
  4. Subdivision: Windermere Town Rep
  5. Elementary School: Windermere Elem
  6. Middle School: Gotha
  7. High School: Olympia
  8. Provided by: PREMIER SOTHEBYS INT'L REALTY
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One or more photo(s) has been virtually staged. Back on market buyers home sale contingency did not clear. Inspection and appraisal were completed satisfactorily, no fault of the seller or property.
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12663 Hawkstone Drive
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Details for 12663 Hawkstone Drive, WINDERMERE, FL 34786
Single Family
  1. Price: $1,750,000.00
  2. Price sqft: $326.80 / sqft
  3. Previous Price: $1,770,000
  4. Last Price Change: 10/02/25
  5. Days On Market: 121
  6. Bedrooms: 5
  7. Baths: 4
  8. Garage / Parking Spaces: 3
  9. Bldg sqft: 5355
  10. Acreage: 1.89 acres
  11. Pool: Yes
  12. Community Pool: Yes
  13. Waterfront: Yes
  14. Wateraccess: Yes
  15. Waterfront Type: Lake Front
  16. Year Built: 2006
MLS#: O6316774
  1. County: ORANGE
  2. City: WINDERMERE
  3. Zipcode: 34786
  4. Subdivision: Lakes Windermere Ph 01 49 108
  5. Elementary School: Sunset Park Elem
  6. Middle School: Horizon West
  7. High School: Windermere
  8. Provided by: KELLER WILLIAMS CLASSIC
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Discover the only single story lakefront home available under $2 million on the prestigious Lake Sawyer. This rare opportunity offers unmatched privacy, breathtaking views, and true single level luxur
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311 8th Avenue
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Details for 311 8th Avenue, WINDERMERE, FL 34786
Single Family
  1. Price: $1,750,000.00
  2. Price sqft: $459.92 / sqft
  3. Days On Market: 65
  4. Bedrooms: 5
  5. Baths: 4
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 3805
  8. Acreage: 0.23 acres
  9. Pool: No
  10. Waterfront: Yes
  11. Wateraccess: Yes
  12. Waterfront Type: Lake Front
  13. Year Built: 1913
MLS#: O6333319
  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: COLDWELL BANKER RESIDENTIAL RE
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Luxury Lakefront Living in Downtown Windermere. Dont miss this rare opportunity to live on the pristine shores of Lake Bessie, just moments from charming Downtown Windermere. Perfectly positioned in
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12663 Hawkstone Drive
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Details for 12663 Hawkstone Drive, Windermere, FL 34786
Single Family
  1. Price: $1,700,000.00
  2. Price sqft: $317.46 / sqft
  3. Previous Price: $1,750,000
  4. Last Price Change: 10/05/25
  5. Days On Market: 121
  6. Bedrooms: 5
  7. Baths: 4
  8. Garage / Parking Spaces: 3
  9. Bldg sqft: 5355
  10. Acreage: 1.89 acres
  11. Pool: Yes
  12. Community Pool: Yes
  13. Waterfront: Yes
  14. Wateraccess: Yes
  15. Waterfront Type: LakeFront,LakePrivileges
  16. Year Built: 2006
MLS#: O6316774
  1. County: ORANGE
  2. City: Windermere
  3. Zipcode: 34786
  4. Subdivision: Lakes Windermere Ph 01 49 108
  5. Elementary School: Sunset Park Elem
  6. Middle School: Horizon West
  7. High School: Windermere
  8. Provided by: KELLER WILLIAMS CLASSIC
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Discover the only single story lakefront home available under $2 million on the prestigious Lake Sawyer. This rare opportunity offers unmatched privacy, breathtaking views, and true single level luxur
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