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  1. Subdivision Like Windermere Town
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: 87
  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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  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
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: 198
  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
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: 94
  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
Details for 647 Ridgewood Drive, WINDERMERE, FL 34786
Single Family
  1. Price: $2,339,000.00
  2. Price sqft: $660.55 / sqft
  3. Days On Market: 185
  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 Privileges
  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
  7. High School: Olympia
  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.
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: 199
  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
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: 242
  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
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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
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: 17
  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
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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,
Details for 235 Oakdale Street, WINDERMERE, FL 34786
Single Family
  1. Price: $950,000.00
  2. Price sqft: $302.16 / sqft
  3. Days On Market: 259
  4. Bedrooms: 3
  5. Baths: 2
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 3144
  8. Acreage: 0.31 acres
  9. Pool: Yes
  10. Waterfront: No
  11. 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
  7. High School: Olympia
  8. Provided by: THE SIMON SIMAAN GROUP
  9. mfrmls
  10. DMCA Notice
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
Details for 311 8th Avenue, WINDERMERE, FL 34786
Rental
  1. Price: $6,750.00
  2. Price sqft: $1.93 / sqft
  3. Previous Price: $7,500
  4. Last Price Change: 06/17/25
  5. Days On Market: 49
  6. Bedrooms: 5
  7. Baths: 4
  8. Garage / Parking Spaces: 2
  9. Bldg sqft: 3502
  10. Acreage: 0.23 acres
  11. Pool: No
  12. Waterfront: Yes
  13. Wateraccess: Yes
  14. Waterfront Type: Lake Front
  15. Year Built: 1913
MLS#: O6302814
  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
  9. mfrmls
  10. DMCA Notice
Price Reduced! Lakefront Living in the Heart of Windermere Don't miss this rare opportunity to lease a beautifully renovated lakefront home on the pristine shores of Lake Bessienow available at a
Details for 307 4th Avenue, WINDERMERE, FL 34786
Rental
  1. Price: $6,450.00
  2. Price sqft: $2.02 / sqft
  3. Days On Market: 142
  4. Bedrooms: 4
  5. Baths: 3
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 3190
  8. Acreage: 0.38 acres
  9. Pool: Yes
  10. Waterfront: No
  11. Year Built: 1968
MLS#: O6275058
  1. County: ORANGE
  2. City: WINDERMERE
  3. Zipcode: 34786
  4. Subdivision: Windermere Town
  5. Provided by: MAINFRAME REAL ESTATE
  6. mfrmls
  7. DMCA Notice
Executive rental pool home located in the charming town of Windermere! The location is just two block from Main st and all that downtown Windermere has to offer! This single story, 4 bedroom (2 primar
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