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436 7th Avenue
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Details for 436 7th Avenue, WINDERMERE, FL 34786
Single Family
  1. Price: $2,275,000.00
  2. Price sqft: $447.13 / sqft
  3. Previous Price: $2,375,000
  4. Last Price Change: 12/15/25
  5. Days On Market: 94
  6. Bedrooms: 4
  7. Baths: 5
  8. Garage / Parking Spaces: 3
  9. Bldg sqft: 5088
  10. Acreage: 0.74 acres
  11. Pool: No
  12. Waterfront: No
  13. Year Built: 2025
MLS#: O6350454
  1. County: ORANGE
  2. City: WINDERMERE
  3. Zipcode: 34786
  4. Subdivision: Windermere Town Rep
  5. Provided by: TALENT REALTY SOLUTIONS
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Seller is Motivated and open to negotiate! Luxury new construction lakefront home in Windermere, newly completed. Situated on Lake Bessie, this modern custom residence delivers architectural elegance,
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311 8th Avenue
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Details for 311 8th Avenue, WINDERMERE, FL 34786
Single Family
  1. Price: $1,660,000.00
  2. Price sqft: $436.27 / sqft
  3. Previous Price: $1,750,000
  4. Last Price Change: 10/21/25
  5. Days On Market: 156
  6. Bedrooms: 5
  7. Baths: 4
  8. Garage / Parking Spaces: 2
  9. Bldg sqft: 3805
  10. Acreage: 0.23 acres
  11. Pool: No
  12. Waterfront: Yes
  13. Wateraccess: Yes
  14. Waterfront Type: Lake Front
  15. 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 | Fresh Opportunity on Lake Bessie. Welcome to your private slice of lakefront paradise on Lake Bessie, where luxury living meets laid back charm in the
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101 Lee Street
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Details for 101 Lee Street, WINDERMERE, FL 34786
Single Family
  1. Price: $1,485,000.00
  2. Price sqft: $256.43 / sqft
  3. Previous Price: $1,550,000
  4. Last Price Change: 12/08/25
  5. Days On Market: 109
  6. Bedrooms: 5
  7. Baths: 4
  8. Garage / Parking Spaces: 2
  9. Bldg sqft: 5791
  10. Acreage: 0.42 acres
  11. Pool: Yes
  12. Waterfront: No
  13. 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: Gotha
  7. High School: Windermere
  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: $1,224,000.00
  2. Price sqft: $369.90 / sqft
  3. Days On Market: 23
  4. Bedrooms: 4
  5. Baths: 4
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 3309
  8. Acreage: 0.29 acres
  9. Pool: Yes
  10. Spa/HotTub: Yes
  11. Waterfront: No
  12. Year Built: 1989
MLS#: O6368253
  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 AGENCY ORLANDO
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Modern sophistication and timeless Windermere charm come together in this fully reimagined residence located just steps from Lake Bessie and the heart of Windermere Town. Set on a beautifully landscap
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106 Butler Street
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Details for 106 Butler Street, WINDERMERE, FL 34786
Single Family
  1. Price: $1,199,999.00
  2. Price sqft: $555.30 / sqft
  3. Days On Market: 13
  4. Bedrooms: 4
  5. Baths: 2
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 2161
  8. Acreage: 0.37 acres
  9. Pool: Yes
  10. Waterfront: No
  11. Year Built: 1969
MLS#: O6369696
  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: STOCKWORTH REALTY GROUP
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Located within the coveted town limits of Windermere, this completely updated four bedroom, two bath residence offers a rare combination of modern comfort, outdoor living, and the timeless character t
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101 Lee Street
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Details for 101 Lee Street, WINDERMERE, FL 34786
Rental
  1. Price: $7,500.00
  2. Price sqft: $1.30 / sqft
  3. Previous Price: $8,000
  4. Last Price Change: 12/08/25
  5. Days On Market: 44
  6. Bedrooms: 5
  7. Baths: 4
  8. Garage / Parking Spaces: 2
  9. Bldg sqft: 5791
  10. Acreage: 0.42 acres
  11. Pool: Yes
  12. Waterfront: No
  13. Year Built: 1978
MLS#: O6363362
  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: Windermere
  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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311 8th Avenue
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Details for 311 8th Avenue, WINDERMERE, FL 34786
Rental
  1. Price: $6,750.00
  2. Price sqft: $1.37 / sqft
  3. Days On Market: 40
  4. Bedrooms: 5
  5. Baths: 4
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 4928
  8. Acreage: 0.23 acres
  9. Pool: No
  10. Waterfront: No
  11. Year Built: 1913
MLS#: O6364016
  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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One or more photo(s) has been virtually staged. Luxury Lakefront Living in Downtown Windermere Executive Rental Opportunity. Discover the ultimate Florida lifestyle with this rare lakefront rental i
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307 4th Avenue
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Details for 307 4th Avenue, WINDERMERE, FL 34786
Rental
  1. Price: $5,900.00
  2. Price sqft: $1.85 / sqft
  3. Previous Price: $6,000
  4. Last Price Change: 10/23/25
  5. Days On Market: 347
  6. Bedrooms: 4
  7. Baths: 3
  8. Garage / Parking Spaces: 2
  9. Bldg sqft: 3190
  10. Acreage: 0.38 acres
  11. Pool: Yes
  12. Waterfront: No
  13. Year Built: 1968
MLS#: O6275058
  1. County: ORANGE
  2. City: WINDERMERE
  3. Zipcode: 34786
  4. Subdivision: Windermere Town
  5. Provided by: MAINFRAME REAL ESTATE
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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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805 Oakdale Street
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Details for 805 Oakdale Street, WINDERMERE, FL 34786
Rental
  1. Price: $2,800.00
  2. Price sqft: $1.22 / sqft
  3. Days On Market: 67
  4. Bedrooms: 3
  5. Baths: 2
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 2286
  8. Acreage: 0.34 acres
  9. Pool: No
  10. Waterfront: No
  11. Year Built: 1968
MLS#: O6357829
  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: PREMIER MANAGEMENT GROUP INC
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Live amongst the oaks in this 3BD/2BA large corner lot home in the heart of Olde Windermere. Just a short walk to the historic downtown of Windermere. Stainless steel appliances, granite countertops
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