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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: 73
  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 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
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325 Magnolia Street
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Details for 325 Magnolia Street, WINDERMERE, FL 34786
Single Family
  1. Price: $2,881,000.00
  2. Price sqft: $592.92 / sqft
  3. Previous Price: $2,998,000
  4. Last Price Change: 04/08/25
  5. Days On Market: 280
  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 Front
  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
  10. DMCA Notice
PRICED BELOW APPRAISAL VALUE. 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 W
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1003 Oakdale Street
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Details for 1003 Oakdale Street, WINDERMERE, FL 34786
Single Family
  1. Price: $2,790,000.00
  2. Price sqft: $509.40 / sqft
  3. Previous Price: $2,800,000
  4. Last Price Change: 06/01/25
  5. Days On Market: 184
  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 Middle
  7. High School: Olympia High
  8. Provided by: VINTAGE REALTY GROUP LLC
  9. mfrmls
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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. Previous Price: $2,599,000
  4. Last Price Change: 06/01/25
  5. Days On Market: 80
  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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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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647 Ridgewood Drive
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Details for 647 Ridgewood Drive, WINDERMERE, FL 34786
Single Family
  1. Price: $2,339,000.00
  2. Price sqft: $660.55 / sqft
  3. Previous Price: $2,359,000
  4. Last Price Change: 05/31/25
  5. Days On Market: 171
  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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  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.
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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. Previous Price: $2,150,000
  4. Last Price Change: 05/27/25
  5. Days On Market: 185
  6. Bedrooms: 5
  7. Baths: 4
  8. Garage / Parking Spaces: 4
  9. Bldg sqft: 7358
  10. Acreage: 0.37 acres
  11. Pool: Yes
  12. Waterfront: No
  13. 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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830 Oakdale Street
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Details for 830 Oakdale Street, WINDERMERE, FL 34786
Single Family
  1. Price: $1,895,000.00
  2. Price sqft: $381.75 / sqft
  3. Previous Price: $1,950,000
  4. Last Price Change: 05/17/25
  5. Days On Market: 228
  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 Middle
  7. High School: Olympia High
  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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111 Main Street
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Details for 111 Main Street, Windermere, FL 34786
Single Family
  1. Price: $1,089,000.00
  2. Price sqft: $398.61 / sqft
  3. Days On Market: 3
  4. Bedrooms: 3
  5. Baths: 2
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 2732
  8. Acreage: 0.39 acres
  9. Pool: No
  10. Waterfront: No
  11. Year Built: 1984
MLS#: O6313903
  1. County: ORANGE
  2. City: Windermere
  3. Zipcode: 34786
  4. Subdivision: Windermere Town
  5. Provided by: SUNDIAL REAL ESTATE LLC
  6. Provided through
  7. DMCA Notice
Prime Windermere Location! Fully Renovated and Move In Ready! Dont miss this beautifully updated 3 bedroom, 2 bath home nestled in the heart of Windermere. Situated on an oversized, fully fenced lot,
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111 Main Street
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Details for 111 Main Street, WINDERMERE, FL 34786
Single Family
  1. Price: $1,089,000.00
  2. Price sqft: $398.61 / sqft
  3. Days On Market: 3
  4. Bedrooms: 3
  5. Baths: 2
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 2732
  8. Acreage: 0.39 acres
  9. Pool: No
  10. Waterfront: No
  11. Year Built: 1984
MLS#: O6313903
  1. County: ORANGE
  2. City: WINDERMERE
  3. Zipcode: 34786
  4. Subdivision: Windermere Town
  5. Provided by: SUNDIAL REAL ESTATE LLC
  6. mfrmls
  7. DMCA Notice
Prime Windermere Location! Fully Renovated and Move In Ready! Dont miss this beautifully updated 3 bedroom, 2 bath home nestled in the heart of Windermere. Situated on an oversized, fully fenced lot,
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235 Oakdale Street
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Details for 235 Oakdale Street, WINDERMERE, FL 34786
Single Family
  1. Price: $950,000.00
  2. Price sqft: $302.16 / sqft
  3. Previous Price: $975,000
  4. Last Price Change: 06/04/25
  5. Days On Market: 245
  6. Bedrooms: 3
  7. Baths: 2
  8. Garage / Parking Spaces: 2
  9. Bldg sqft: 3144
  10. Acreage: 0.31 acres
  11. Pool: Yes
  12. Waterfront: No
  13. Year Built: 1971
MLS#: O6247080
  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: THE SIMON SIMAAN GROUP
  9. mfrmls
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Best priced home within the town! Here is your opportunity to own a single story fully remodeled pool home on a corner lot in the desirable downtown Windermere with NO HOA on county water! At first gl
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