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  1. Subdivision Like Windermere
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: 93
  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
  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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2937 Butler Bay Drive N
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Details for 2937 Butler Bay Drive N, WINDERMERE, FL 34786
Single Family
  1. Price: $3,200,000.00
  2. Price sqft: $419.40 / sqft
  3. Days On Market: 6
  4. Bedrooms: 6
  5. Baths: 6
  6. Garage / Parking Spaces: 3
  7. Bldg sqft: 7630
  8. Acreage: 0.80 acres
  9. Pool: Yes
  10. Spa/HotTub: Yes
  11. Waterfront: Yes
  12. Wateraccess: Yes
  13. Waterfront Type: Lake Front
  14. Year Built: 1990
MLS#: O6319132
  1. County: ORANGE
  2. City: WINDERMERE
  3. Zipcode: 34786
  4. Subdivision: Windermere Clubbutler Bay
  5. Elementary School: Windermere Elem
  6. Middle School: Bridgewater
  7. High School: Windermere
  8. Provided by: KELLER WILLIAMS ELITE PARTNERS III REALTY
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**Video tour and 3D floorplan experience available.** Indulge in ultimate luxury at this gated Lake Crescent retreat. Enjoy water skiing on a private lake, fishing from your private boat dock, and mar
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1003 Oakdale Street
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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: 06/16/25
  5. Days On Market: 204
  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: Lake Front
  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
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409 2nd Avenue
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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: 100
  4. Bedrooms: 5
  5. Baths: 5
  6. Garage / Parking Spaces: 3
  7. Bldg sqft: 6252
  8. Acreage: 0.51 acres
  9. Pool: Yes
  10. Spa/HotTub: Yes
  11. Waterfront: No
  12. 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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Welcome to Second Avenue, a serene peninsula in the heart of Old Windermere. This recently remodeled home offers 5 bedrooms, 4.5 baths, including a detached poolside Guest House, seamlessly blending s
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409 2nd Avenue
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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: 100
  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
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4108 Downeast Lane
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Details for 4108 Downeast Lane, WINDERMERE, FL 34786
Single Family
  1. Price: $2,295,000.00
  2. Price sqft: $404.48 / sqft
  3. Days On Market: 147
  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 Privileges
  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
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IMPROVED PRICE (Reduced $625,0000: The price adjustment is generating strong interest. Acting now ensures you dont miss out on this unique Butler Chain of Lakes opportunity.) Welcome to 4108 Downeast
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4108 Downeast Lane
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Details for 4108 Downeast Lane, WINDERMERE, FL 34786
Land
  1. Price: $2,295,000.00
  2. Days On Market: 142
  3. Acreage: 3.31 acres
  4. Pool: No
  5. Waterfront: Yes
  6. Wateraccess: Yes
  7. Waterfront Type: Lake Privileges
  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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IMPROVED PRICE (Reduced $625,0000: The price adjustment is generating strong interest. Acting now ensures you dont miss out on this unique Butler Chain of Lakes opportunity.) Welcome to 4108 Downeast
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647 Ridgewood Drive
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Details for 647 Ridgewood Drive, WINDERMERE, FL 34786
Single Family
  1. Price: $2,269,500.00
  2. Price sqft: $640.92 / sqft
  3. Previous Price: $2,339,000
  4. Last Price Change: 06/20/25
  5. Days On Market: 191
  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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647 Ridgewood Drive
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Details for 647 Ridgewood Drive, Windermere, FL 34786
Single Family
  1. Price: $2,269,500.00
  2. Price sqft: $640.92 / sqft
  3. Previous Price: $2,339,000
  4. Last Price Change: 05/31/25
  5. Days On Market: 191
  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
  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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729 Main Street
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Details for 729 Main Street, WINDERMERE, FL 34786
Single Family
  1. Price: $2,100,000.00
  2. Price sqft: $285.40 / sqft
  3. Days On Market: 205
  4. Bedrooms: 5
  5. Baths: 4
  6. Garage / Parking Spaces: 4
  7. Bldg sqft: 7358
  8. Acreage: 0.37 acres
  9. Pool: Yes
  10. Waterfront: No
  11. Year Built: 2015
MLS#: S5116063
  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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This custom home is truly a gem, blending luxury, craftsmanship, and the charm of small town windermere living. The attention to detail in every featurefrom the stunning architectural design to the th
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Tropic Shores Realty - Crystal River
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Listings provided courtesy of The Hernando County Association of Realtors MLS.
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Datafeed Last updated on June 26, 2025 @ 12:00 am
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