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  1. Subdivision Like Windermere Town
904 Main Street
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Details for 904 Main Street, WINDERMERE, FL 34786
Single Family
  1. Price: $4,100,000.00
  2. Price sqft: $607.77 / sqft
  3. Previous Price: $4,299,000
  4. Last Price Change: 03/10/25
  5. Days On Market: 183
  6. Bedrooms: 4
  7. Baths: 6
  8. Garage / Parking Spaces: 3
  9. Bldg sqft: 6746
  10. Acreage: 2.24 acres
  11. Pool: Yes
  12. Spa/HotTub: Yes
  13. Waterfront: Yes
  14. Wateraccess: Yes
  15. Waterfront Type: Lake
  16. Year Built: 2003
MLS#: O6241373
  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: VINTAGE REALTY GROUP LLC
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This property includes an incredibly rare air conditioned boathouse that is completely renovated with apartment, kitchen and bathroom. A custom platform boat lift with overhead garage door lends secur
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325 Magnolia Street
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Details for 325 Magnolia Street, WINDERMERE, FL 34786
Single Family
  1. Price: $2,998,000.00
  2. Price sqft: $617.00 / sqft
  3. Previous Price: $3,049,900
  4. Last Price Change: 03/12/25
  5. Days On Market: 198
  6. Bedrooms: 4
  7. Baths: 3
  8. Garage / Parking Spaces: 2
  9. Bldg sqft: 4859
  10. Acreage: 2.97 acres
  11. Pool: Yes
  12. Waterfront: Yes
  13. Wateraccess: Yes
  14. Waterfront Type: Lake
  15. Year Built: 1954
MLS#: O6235395
  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: REVEL REALTY LLC
  9. mfrmls
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Boasting a prime location in the Town of Windermere on Lake Down with access to the Butler Chain of Lakes, enjoy the perks of town and lake living being in the heart of Windermere. Less than half a mi
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1003 Oakdale Street
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Details for 1003 Oakdale Street, WINDERMERE, FL 34786
Single Family
  1. Price: $2,900,000.00
  2. Price sqft: $529.49 / sqft
  3. Previous Price: $2,950,000
  4. Last Price Change: 03/10/25
  5. Days On Market: 102
  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
  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 Middle
  7. High School: Olympia High
  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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647 Ridgewood Drive
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Details for 647 Ridgewood Drive, WINDERMERE, FL 34786
Single Family
  1. Price: $2,359,000.00
  2. Price sqft: $666.20 / sqft
  3. Days On Market: 88
  4. Bedrooms: 3
  5. Baths: 3
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 3541
  8. Acreage: 1.43 acres
  9. Pool: No
  10. Waterfront: Yes
  11. Wateraccess: Yes
  12. Waterfront Type: Lake
  13. 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. Welcome to 647 Ridgewood Drive, an exquisitely remodeled three bedroom, three bathroom lakefront estate in the heart of Old Windermere. This exceptional
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729 Main Street
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Details for 729 Main Street, WINDERMERE, FL 34786
Single Family
  1. Price: $2,295,000.00
  2. Price sqft: $311.91 / sqft
  3. Days On Market: 102
  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 Middle
  7. High School: Olympia High
  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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98 E 10th Ave
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Details for 98 E 10th Ave, WINDERMERE, FL 34786
Single Family
  1. Price: $2,280,000.00
  2. Price sqft: $471.56 / sqft
  3. Previous Price: $2,300,000
  4. Last Price Change: 03/11/25
  5. Days On Market: 123
  6. Bedrooms: 4
  7. Baths: 4
  8. Garage / Parking Spaces: 2
  9. Bldg sqft: 4835
  10. Acreage: 0.29 acres
  11. Pool: Yes
  12. Spa/HotTub: Yes
  13. Waterfront: No
  14. Year Built: 2024
MLS#: S5115380
  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: WATSON REALTY CORP.
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Stunning, thoughtfully designed, contemporary pool home, NEW (completed in 2024). Bright, open floor plan boasting 4 spacious bedrooms, two with en suite bathrooms, and an office or 5th bedroom. Step
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830 Oakdale Street
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Details for 830 Oakdale Street, WINDERMERE, FL 34786
Single Family
  1. Price: $1,950,000.00
  2. Price sqft: $392.83 / sqft
  3. Days On Market: 145
  4. Bedrooms: 4
  5. Baths: 5
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 4964
  8. Acreage: 0.29 acres
  9. Pool: Yes
  10. Spa/HotTub: Yes
  11. Waterfront: No
  12. 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 Middle
  7. High School: Olympia High
  8. Provided by: CORCORAN PREMIER REALTY
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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: $1,394,000.00
  2. Price sqft: $421.28 / sqft
  3. Previous Price: $1,395,000
  4. Last Price Change: 02/19/25
  5. Days On Market: 90
  6. Bedrooms: 4
  7. Baths: 4
  8. Garage / Parking Spaces: 2
  9. Bldg sqft: 3309
  10. Acreage: 0.29 acres
  11. Pool: Yes
  12. Waterfront: No
  13. Year Built: 1989
MLS#: O6264634
  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: EXECUTIVE PROPERTIES
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Welcome to this fully renovated four bedroom, three and a half bath home in the heart of Windermere, just steps from Lake Bessie and surrounded by lush, mature landscaping on a spacious corner lot wit
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116 Main Street
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Details for 116 Main Street, WINDERMERE, FL 34786
Land
  1. Price: $695,000.00
  2. Days On Market: 12
  3. Acreage: 0.38 acres
  4. Pool: No
  5. Waterfront: No
  6. Year Built: Not Available
MLS#: O6285957
  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: METROPOLIS R.E. SOLUTIONS, LLC
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Welcome to a rare opportunity in the heart of Windermere! Located at 116 Main Street, this property represents one of the most coveted locations in Central Florida's premier community. Situated on Mai
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116 Main Street
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Details for 116 Main Street, WINDERMERE, FL 34786
Single Family
  1. Price: $695,000.00
  2. Price sqft: $194.84 / sqft
  3. Days On Market: 73
  4. Bedrooms: 3
  5. Baths: 2
  6. Garage / Parking Spaces: 3
  7. Bldg sqft: 3567
  8. Acreage: 0.38 acres
  9. Pool: No
  10. Waterfront: No
  11. Year Built: 1958
MLS#: O6267443
  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: METROPOLIS R.E. SOLUTIONS, LLC
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Welcome to a rare opportunity in the heart of Windermere! Located at 116 Main Street, this property represents one of the most coveted locations in Central Florida's premier community. Situated on Mai
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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.
Listing Data ©2025 REALTOR® Association of Citrus County
Listing Data ©2025 Royal Palm Coast Realtor® Association
The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.
Display of MLS data is usually deemed reliable but is NOT guaranteed accurate.
Datafeed Last updated on March 15, 2025 @ 12:00 am
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