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1003 Oakdale Street
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Details for 1003 Oakdale Street, Windermere, FL 34786
Single Family
  1. Price: $2,600,000.00
  2. Price sqft: $474.71 / sqft
  3. Days On Market: 11
  4. Bedrooms: 6
  5. Baths: 6
  6. Garage / Parking Spaces: 3
  7. Bldg sqft: 5477
  8. Acreage: 1.77 acres
  9. Pool: Yes
  10. Waterfront: Yes
  11. Wateraccess: Yes
  12. Waterfront Type: LakeFront,LakePrivileges
  13. Year Built: 2024
MLS#: O6332353
  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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Be the 1st to live in this completely remodeled and expanded luxurious lakefront home total of 6 bedrooms 5 full baths 1 pool or guest bath primary suite & guest suite on 1st floor 4 more be
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436 7th Avenue
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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: 20
  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: LakeFront,LakePrivileges
  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
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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: 27
  4. Bedrooms: 5
  5. Baths: 5
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 4863
  8. Acreage: 0.29 acres
  9. Pool: Yes
  10. Waterfront: No
  11. 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
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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: 08/05/25
  5. Days On Market: 239
  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
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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: 5
  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: LakeFront,LakePrivileges
  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
  7. High School: Olympia
  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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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: 32
  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
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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: 07/22/25
  5. Days On Market: 71
  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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