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  1. Subdivision Like Windermere Town
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: 129
  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
  9. mfrmls
  10. DMCA Notice
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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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: 240
  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
  9. mfrmls
  10. DMCA Notice
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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436 7th Avenue
New Construction
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Details for 436 7th Avenue, WINDERMERE, FL 34786
Single Family
  1. Price: $2,599,900.00
  2. Price sqft: $510.99 / sqft
  3. Days On Market: 7
  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: Yes
  11. Wateraccess: Yes
  12. Waterfront Type: Lake Front
  13. Year Built: 2025
MLS#: TB8403295
  1. County: ORANGE
  2. City: WINDERMERE
  3. Zipcode: 34786
  4. Subdivision: Town Of Windermere
  5. Elementary School: Windermere Elem
  6. Middle School: Gotha
  7. High School: Olympia
  8. Provided by: TALENT REALTY SOLUTIONS
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Under Construction. Luxury new construction lakefront home in Windermere, newly completed. Situated on Lake Bessie, this modern custom residence delivers architectural elegance, premium finishes, and
Listing Details and 75 Additional Pictures
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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: 136
  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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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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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: 136
  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 Middle
  7. High School: Olympia High
  8. Provided by: UPSIDE REAL ESTATE INC
  9. Provided through
  10. DMCA Notice
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
Listing Details and 54 Additional Pictures
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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: 227
  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
  9. mfrmls
  10. DMCA Notice
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.
Listing Details and 38 Additional Pictures
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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: 227
  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
  9. Provided through
  10. DMCA Notice
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.
Listing Details and 38 Additional Pictures
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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: 15
  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
  9. mfrmls
  10. DMCA Notice
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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830 Oakdale Street
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Details for 830 Oakdale Street, WINDERMERE, FL 34786
Single Family
  1. Price: $1,875,000.00
  2. Price sqft: $377.72 / sqft
  3. Previous Price: $1,895,000
  4. Last Price Change: 06/11/25
  5. Days On Market: 284
  6. Bedrooms: 4
  7. Baths: 5
  8. Garage / Parking Spaces: 2
  9. Bldg sqft: 4964
  10. Acreage: 0.29 acres
  11. Pool: Yes
  12. Spa/HotTub: Yes
  13. Waterfront: No
  14. Year Built: 2019
MLS#: O6250631
  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: CORCORAN PREMIER REALTY
  9. mfrmls
  10. DMCA Notice
RARE FIND IN DOWNTOWN WINDERMERE!! This immaculate home defines where luxury meets contemporary, nestled in the heart of downtown Windermere. Pull up into your drive of Italian laced pavers and enter
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109 12th Avenue
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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: 20
  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
  9. mfrmls
  10. DMCA Notice
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
Listing Details and 63 Additional Pictures
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Tropic Shores Realty - Crystal River
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Listing Data ©2025 Greater Fort Lauderdale REALTORS®
Listings provided courtesy of The Hernando County Association of Realtors MLS.
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Listing Data ©2025 Royal Palm Coast Realtor® Association
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Display of MLS data is usually deemed reliable but is NOT guaranteed accurate.
Datafeed Last updated on July 31, 2025 @ 12:00 am
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