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436 7th Avenue
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Details for 436 7th Avenue, WINDERMERE, FL 34786
Single Family
  1. Price: $2,175,000.00
  2. Price sqft: $427.48 / sqft
  3. Previous Price: $2,275,000
  4. Last Price Change: 01/25/26
  5. Days On Market: 114
  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: 11/22/25
  5. Days On Market: 176
  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 Middle
  7. High School: Olympia High
  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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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: 43
  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 Middle
  7. High School: Olympia High
  8. Provided by: THE AGENCY FL
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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: $1,100,000.00
  2. Price sqft: $509.02 / sqft
  3. Previous Price: $1,199,999
  4. Last Price Change: 01/17/26
  5. Days On Market: 33
  6. Bedrooms: 4
  7. Baths: 2
  8. Garage / Parking Spaces: 2
  9. Bldg sqft: 2161
  10. Acreage: 0.37 acres
  11. Pool: Yes
  12. Waterfront: No
  13. 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 Middle
  7. High School: Olympia High
  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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416 Magnolia Street
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Details for 416 Magnolia Street, WINDERMERE, FL 34786
Single Family
  1. Price: $885,000.00
  2. Price sqft: $305.91 / sqft
  3. Days On Market: 70
  4. Bedrooms: 2
  5. Baths: 2
  6. Garage / Parking Spaces: 3
  7. Bldg sqft: 2893
  8. Acreage: 0.38 acres
  9. Pool: No
  10. Waterfront: No
  11. Year Built: 1915
MLS#: O6362356
  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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Back on the Market. Buyer unable to secure financing. Step into a storybook cottage tucked in the heart of Windermere, where history whispers through every room and morning light dances across origi
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311 8th Avenue
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Details for 311 8th Avenue, WINDERMERE, FL 34786
Rental
  1. Price: $6,500.00
  2. Price sqft: $1.32 / sqft
  3. Previous Price: $6,750
  4. Last Price Change: 01/14/26
  5. Days On Market: 60
  6. Bedrooms: 5
  7. Baths: 4
  8. Garage / Parking Spaces: 2
  9. Bldg sqft: 4928
  10. Acreage: 0.23 acres
  11. Pool: No
  12. Waterfront: No
  13. 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 Middle
  7. High School: Olympia High
  8. Provided by: COLDWELL BANKER RESIDENTIAL RE
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One or more photo(s) has been virtually staged. Luxury Lakefront Executive Rental | Downtown Windermere | Lake Bessie. Now offered at an exceptional value, this rare luxury lakefront rental in Downt
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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: 367
  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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Available for lease, this refined single story pool residence is located in the Town of Windermere, just moments from Main Street and the downtown districts dining, shopping, and community amenities.
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805 Oakdale Street
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Details for 805 Oakdale Street, WINDERMERE, FL 34786
Rental
  1. Price: $2,600.00
  2. Price sqft: $1.14 / sqft
  3. Previous Price: $2,800
  4. Last Price Change: 01/15/26
  5. Days On Market: 87
  6. Bedrooms: 3
  7. Baths: 2
  8. Garage / Parking Spaces: 2
  9. Bldg sqft: 2286
  10. Acreage: 0.34 acres
  11. Pool: No
  12. Waterfront: No
  13. 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 Middle
  7. High School: Olympia High
  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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