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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: 196
  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 Privileges
  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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409 2nd Avenue
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Details for 409 2nd Avenue, WINDERMERE, FL 34786
Single Family
  1. Price: $2,425,000.00
  2. Price sqft: $387.88 / sqft
  3. Previous Price: $2,450,000
  4. Last Price Change: 09/28/25
  5. Days On Market: 203
  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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Step inside this beautifully updated home where clean lines, soaring ceilings, and two story windows fill every corner with natural light. A floating staircase makes a stunning first impression, while
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1020 Oakdale Street
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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: 81
  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 Middle
  7. High School: Olympia High
  8. Provided by: COMPASS FLORIDA LLC
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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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647 Ridgewood Drive
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Details for 647 Ridgewood Drive, WINDERMERE, FL 34786
Single Family
  1. Price: $2,150,000.00
  2. Price sqft: $607.17 / sqft
  3. Previous Price: $2,269,500
  4. Last Price Change: 08/27/25
  5. Days On Market: 294
  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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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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311 8th Avenue
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Details for 311 8th Avenue, WINDERMERE, FL 34786
Single Family
  1. Price: $1,750,000.00
  2. Price sqft: $459.92 / sqft
  3. Days On Market: 60
  4. Bedrooms: 5
  5. Baths: 4
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 3805
  8. Acreage: 0.23 acres
  9. Pool: No
  10. Waterfront: Yes
  11. Wateraccess: Yes
  12. Waterfront Type: Lake Front
  13. Year Built: 1913
MLS#: O6333319
  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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Luxury Lakefront Living in Downtown Windermere. Dont miss this rare opportunity to live on the pristine shores of Lake Bessie, just moments from charming Downtown Windermere. Perfectly positioned in
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101 Lee Street
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Details for 101 Lee Street, WINDERMERE, FL 34786
Single Family
  1. Price: $1,650,000.00
  2. Price sqft: $284.93 / sqft
  3. Days On Market: 13
  4. Bedrooms: 5
  5. Baths: 4
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 5791
  8. Acreage: 0.42 acres
  9. Pool: Yes
  10. Waterfront: No
  11. Year Built: 1978
MLS#: O6344558
  1. County: ORANGE
  2. City: WINDERMERE
  3. Zipcode: 34786
  4. Subdivision: Windermere Town Rep
  5. Elementary School: Windermere Elem
  6. Middle School: Horizon West Middle School
  7. High School: Windermere High School
  8. Provided by: ISLEWORTH REALTY LLC
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A new long elegantly paved driveway leads up to this beautifully updated 5 bedroom, 4,200 sq. ft. home in the charming Town of Windermere. With lush views of established landscaping & surrounding tree
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109 12th Avenue
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Details for 109 12th Avenue, WINDERMERE, FL 34786
Single Family
  1. Price: $1,294,000.00
  2. Price sqft: $391.06 / sqft
  3. Previous Price: $1,296,000
  4. Last Price Change: 09/28/25
  5. Days On Market: 87
  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#: O6326261
  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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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
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111 Main Street
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Details for 111 Main Street, WINDERMERE, FL 34786
Single Family
  1. Price: $979,000.00
  2. Price sqft: $358.35 / sqft
  3. Previous Price: $999,000
  4. Last Price Change: 09/27/25
  5. Days On Market: 126
  6. Bedrooms: 3
  7. Baths: 2
  8. Garage / Parking Spaces: 2
  9. Bldg sqft: 2732
  10. Acreage: 0.39 acres
  11. Pool: No
  12. Waterfront: No
  13. 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,
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720 Main Street
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Details for 720 Main Street, WINDERMERE, FL 34786
Single Family
  1. Price: $925,000.00
  2. Price sqft: $250.34 / sqft
  3. Days On Market: 4
  4. Bedrooms: 3
  5. Baths: 2
  6. Bldg sqft: 3695
  7. Acreage: 0.41 acres
  8. Pool: Yes
  9. Waterfront: No
  10. Year Built: 1980
MLS#: O6340062
  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 Home to this beautiful ONE STORY Pool Home in Downtown Windermere! Don't miss this RARE OPPORTUNITY to live among Majestic Oaks with a small town Lifestyle. The setting is Old Florida at it's
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720 Main Street
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Details for 720 Main Street, Windermere, FL 34786
Single Family
  1. Price: $925,000.00
  2. Price sqft: $250.34 / sqft
  3. Days On Market: 4
  4. Bedrooms: 3
  5. Baths: 2
  6. Bldg sqft: 3695
  7. Acreage: 0.41 acres
  8. Pool: Yes
  9. Waterfront: No
  10. Year Built: 1980
MLS#: O6340062
  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 Home to this beautiful ONE STORY Pool Home in Downtown Windermere! Don't miss this RARE OPPORTUNITY to live among Majestic Oaks with a small town Lifestyle. The setting is Old Florida at it's
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