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  1. Michelle Hill, ABR,AHWD,PA,PSA,REALTOR ®,SFR
  2. Tropic Shores Realty
  3. Mobile: 352.247.2177
  4. 229.834.4988
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  1. Subdivision Like Windermere Town
  2. Listing Status = Active
436 7th Avenue
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New Construction
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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: 01/13/26
  5. Days On Market: 154
  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
  6. mfrmls
  7. DMCA Notice
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: $1,549,000.00
  2. Price sqft: $407.10 / sqft
  3. Previous Price: $1,660,000
  4. Last Price Change: 02/24/26
  5. Days On Market: 216
  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
  9. mfrmls
  10. DMCA Notice
Luxury Lakefront Home in Downtown Windermere. New Price No HOA Private Lake Bessie. Now offered at a newly adjusted price, this exceptional luxury lakefront home in Windermere, Florida presents o
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109 12th Avenue
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Reduced
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Details for 109 12th Avenue, WINDERMERE, FL 34786
Single Family
  1. Price: $1,170,000.00
  2. Price sqft: $353.58 / sqft
  3. Previous Price: $1,219,000
  4. Last Price Change: 03/06/26
  5. Days On Market: 83
  6. Bedrooms: 4
  7. Baths: 4
  8. Garage / Parking Spaces: 2
  9. Bldg sqft: 3309
  10. Acreage: 0.29 acres
  11. Pool: Yes
  12. Spa/HotTub: Yes
  13. Waterfront: No
  14. 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 FL
  9. mfrmls
  10. DMCA Notice
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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735 Oakdale Street
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Details for 735 Oakdale Street, WINDERMERE, FL 34786
Single Family
  1. Price: $975,000.00
  2. Price sqft: $384.01 / sqft
  3. Days On Market: 9
  4. Bedrooms: 3
  5. Baths: 3
  6. Bldg sqft: 2539
  7. Acreage: 0.38 acres
  8. Pool: Yes
  9. Waterfront: No
  10. Year Built: 1986
MLS#: S5144907
  1. County: ORANGE
  2. City: WINDERMERE
  3. Zipcode: 34786
  4. Subdivision: Windermere Town
  5. Elementary School: Windermere Elem
  6. Middle School: Gotha
  7. Provided by: ALTIS REALTY
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Fully Renovated Windermere Home. Move In Ready! Discover 735 Oakdale St, a beautifully updated 3 bedroom, 2.5 bathroom home in the heart of Windermere Town. Over the past four years, no detail has be
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4 Chase Road
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Details for 4 Chase Road, WINDERMERE, FL 34786
Single Family
  1. Price: $900,000.00
  2. Price sqft: $377.20 / sqft
  3. Days On Market: 19
  4. Bedrooms: 3
  5. Baths: 2
  6. Garage / Parking Spaces: 1
  7. Bldg sqft: 2386
  8. Acreage: 0.29 acres
  9. Pool: No
  10. Waterfront: No
  11. Year Built: 1971
MLS#: O6384257
  1. County: ORANGE
  2. City: WINDERMERE
  3. Zipcode: 34786
  4. Subdivision: Windermere Town
  5. Provided by: REAL BROKER, LLC
  6. mfrmls
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FULLY RENOVATED DREAM HOME. This home is located right in the heart of the Town of Windermere. Welcome to 4 Chase Rd, Windermere a refined expression of luxury living where elevated design, privacy,
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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: 01/13/26
  5. Days On Market: 100
  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
  7. High School: Olympia
  8. Provided by: COLDWELL BANKER RESIDENTIAL RE
  9. mfrmls
  10. DMCA Notice
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: $5,475.00
  2. Price sqft: $1.72 / sqft
  3. Previous Price: $5,900
  4. Last Price Change: 02/28/26
  5. Days On Market: 407
  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
  6. mfrmls
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One or more photo(s) has been virtually staged. Available for lease, this refined single story pool residence is located in the Town of Windermere, just moments from Main Street and the downtown distr
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721 Magnolia Street
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Details for 721 Magnolia Street, WINDERMERE, FL 34786
Rental
  1. Price: $2,250.00
  2. Price sqft: $2.53 / sqft
  3. Days On Market: 11
  4. Bedrooms: 2
  5. Baths: 1
  6. Bldg sqft: 891
  7. Acreage: 0.38 acres
  8. Pool: No
  9. Waterfront: No
  10. Year Built: 1913
MLS#: S5144805
  1. County: ORANGE
  2. City: WINDERMERE
  3. Zipcode: 34786
  4. Subdivision: Windermere Town
  5. Provided by: EXP REALTY LLC
  6. mfrmls
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This Charming Fully Renovated Home is available for rent in the Heart of Downtown Windermere Welcome to this beautifully remodeled 2 bedroom, 1 bathroom gem, ideally located within short distance to t
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