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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: 258
  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 Middle
  7. High School: Olympia High
  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
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: 81
  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 Middle
  7. High School: Olympia High
  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
Details for 409 2nd Avenue, WINDERMERE, FL 34786
Single Family
  1. Price: $2,375,000.00
  2. Price sqft: $379.88 / sqft
  3. Previous Price: $2,399,000
  4. Last Price Change: 11/29/25
  5. Days On Market: 266
  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 Middle
  7. High School: Olympia High
  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 436 7th Avenue, WINDERMERE, FL 34786
Single Family
  1. Price: $2,375,000.00
  2. Price sqft: $466.79 / sqft
  3. Previous Price: $2,425,000
  4. Last Price Change: 11/30/25
  5. Days On Market: 60
  6. Bedrooms: 4
  7. Baths: 5
  8. Garage / Parking Spaces: 3
  9. Bldg sqft: 5088
  10. Acreage: 0.74 acres
  11. Pool: No
  12. Waterfront: No
  13. 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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Seller is Motivated and open to negotiate! Luxury new construction lakefront home in Windermere, newly completed. Situated on Lake Bessie, this modern custom residence delivers architectural elegance,
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: 11/08/25
  5. Days On Market: 356
  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 Middle
  7. High School: Olympia High
  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.
Details for 13048 Lake Roper Ct., WINDERMERE, FL 34786
Single Family
  1. Price: $1,999,000.00
  2. Price sqft: $355.82 / sqft
  3. Previous Price: $2,100,000
  4. Last Price Change: 11/20/25
  5. Days On Market: 86
  6. Bedrooms: 5
  7. Baths: 4
  8. Garage / Parking Spaces: 3
  9. Bldg sqft: 5618
  10. Acreage: 1.63 acres
  11. Pool: Yes
  12. Waterfront: Yes
  13. Wateraccess: Yes
  14. Waterfront Type: Lake Front
  15. Year Built: 2002
MLS#: O6342354
  1. County: ORANGE
  2. City: WINDERMERE
  3. Zipcode: 34786
  4. Subdivision: Windermere Pointe
  5. Provided by: WOODSTONE INVESTMENTS LLC
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Priced to sell fast. Unmatched Value! The only Windermere lakefront home with boat access available under $2M. Don't miss this opportunity. Enjoy the e evenings to a breathtaking sunset at your own pr
Details for 311 8th Avenue, WINDERMERE, FL 34786
Single Family
  1. Price: $1,660,000.00
  2. Price sqft: $436.27 / sqft
  3. Previous Price: $1,750,000
  4. Last Price Change: 11/22/25
  5. Days On Market: 122
  6. Bedrooms: 5
  7. Baths: 4
  8. Garage / Parking Spaces: 2
  9. Bldg sqft: 3805
  10. Acreage: 0.23 acres
  11. Pool: No
  12. Waterfront: Yes
  13. Wateraccess: Yes
  14. Waterfront Type: Lake Front
  15. 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 Middle
  7. High School: Olympia High
  8. Provided by: COLDWELL BANKER RESIDENTIAL RE
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Luxury Lakefront Living in Downtown Windermere | Fresh Opportunity on Lake Bessie. Welcome to your private slice of lakefront paradise on Lake Bessie, where luxury living meets laid back charm in the
Details for 2509 Ridgewind Way, WINDERMERE, FL 34786
Single Family
  1. Price: $1,545,000.00
  2. Price sqft: $284.95 / sqft
  3. Previous Price: $1,585,000
  4. Last Price Change: 12/05/25
  5. Days On Market: 34
  6. Bedrooms: 4
  7. Baths: 4
  8. Garage / Parking Spaces: 3
  9. Bldg sqft: 5422
  10. Acreage: 0.75 acres
  11. Pool: Yes
  12. Waterfront: No
  13. Year Built: 1998
MLS#: O6354737
  1. County: ORANGE
  2. City: WINDERMERE
  3. Zipcode: 34786
  4. Subdivision: Estates At Windermere
  5. Elementary School: Lake Whitney Elem
  6. Middle School: SunRidge Middle
  7. High School: West Orange High
  8. Provided by: COMPASS FLORIDA LLC
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If youve dreamed of a home that feels both timeless and tailor made for modern living, welcome to 2509 Ridgewind Way in the gated Estates at Windermere. Set on .75 acre this updated Southern estate co
Details for 101 Lee Street, WINDERMERE, FL 34786
Single Family
  1. Price: $1,485,000.00
  2. Price sqft: $256.43 / sqft
  3. Days On Market: 75
  4. Bedrooms: 5
  5. Baths: 4
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 5791
  8. Acreage: 0.42 acres
  9. Pool: Yes
  10. Waterfront: No
  11. Year Built: 1978
MLS#: O6344558
  1. County: ORANGE
  2. City: WINDERMERE
  3. Zipcode: 34786
  4. Subdivision: Windermere Town Rep
  5. Elementary School: Windermere Elem
  6. Middle School: Gotha Middle
  7. High School: Windermere High School
  8. Provided by: ISLEWORTH REALTY LLC
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A new long elegantly paved driveway leads up to this beautifully updated 5 bedroom, 4,200 sq. ft. home in the charming Town of Windermere. With lush views of established landscaping & surrounding tree
Details for 7135 Horizon Circle, WINDERMERE, FL 34786
Single Family
  1. Price: $1,449,000.00
  2. Price sqft: $323.87 / sqft
  3. Previous Price: $1,470,000
  4. Last Price Change: 12/03/25
  5. Days On Market: 145
  6. Bedrooms: 4
  7. Baths: 4
  8. Garage / Parking Spaces: 3
  9. Bldg sqft: 4474
  10. Acreage: 0.74 acres
  11. Pool: Yes
  12. Waterfront: No
  13. Year Built: 1993
MLS#: O6327225
  1. County: ORANGE
  2. City: WINDERMERE
  3. Zipcode: 34786
  4. Subdivision: Windermere Reserve
  5. Elementary School: Windermere Elem
  6. Middle School: Chain of Lakes Middle
  7. High School: Olympia High
  8. Provided by: THE BOSCH GROUP
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Today is the day reduced $96,000! Nestled in the true town of windermere is this absolutely stunning, meticulously maintained pool home with tall ceilings and lots of land surrounding on both sides! T