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  1. Subdivision Like Windermere
Details for 1003 Oakdale Street, Windermere, FL 34786
Single Family
  1. Price: $2,800,000.00
  2. Price sqft: $511.23 / sqft
  3. Previous Price: $2,900,000
  4. Last Price Change: 04/01/25
  5. Days On Market: 151
  6. Bedrooms: 6
  7. Baths: 6
  8. Garage / Parking Spaces: 3
  9. Bldg sqft: 5477
  10. Acreage: 1.77 acres
  11. Pool: Yes
  12. Waterfront: Yes
  13. Wateraccess: Yes
  14. Waterfront Type: LakeFront,LakePrivileges
  15. Year Built: 2003
MLS#: O6261656
  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
  9. Provided through
  10. DMCA Notice
Never lived in since completely remodeled and expanded total of 6 bedrooms 5 full baths 1 pool or guest bath primary suite & guest suite on 1st floor 4 more bedrooms & 3 bathrooms on 2nd flo
Details for 409 2nd Avenue, Windermere, FL 34786
Single Family
  1. Price: $2,599,000.00
  2. Price sqft: $415.71 / sqft
  3. Previous Price: $2,650,000
  4. Last Price Change: 03/30/25
  5. Days On Market: 47
  6. Bedrooms: 5
  7. Baths: 5
  8. Garage / Parking Spaces: 3
  9. Bldg sqft: 6252
  10. Acreage: 0.51 acres
  11. Pool: Yes
  12. Waterfront: No
  13. 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
  7. High School: Olympia
  8. Provided by: UPSIDE REAL ESTATE INC
  9. Provided through
  10. DMCA Notice
Welcome to Second Avenue, a serene peninsula in the heart of Old Windermere. This modern masterpiece offers 5 bedrooms, 4.5 baths, including a detached poolside Guest House, seamlessly blending sleek
Details for 109 12th Avenue, Windermere, FL 34786
Single Family
  1. Price: $1,300,000.00
  2. Price sqft: $392.87 / sqft
  3. Previous Price: $1,394,000
  4. Last Price Change: 02/20/25
  5. Days On Market: 140
  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#: O6264634
  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
  9. Provided through
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Welcome to this fully renovated four bedroom, three and a half bath home in the heart of Windermere, just steps from Lake Bessie and surrounded by lush, mature landscaping on a spacious corner lot wit
Details for 8478 Elba Isle Court, Windermere, FL 34786
Single Family
  1. Price: $1,300,000.00
  2. Price sqft: $233.48 / sqft
  3. Days On Market: 2
  4. Bedrooms: 5
  5. Baths: 5
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 5568
  8. Acreage: 0.39 acres
  9. Pool: Yes
  10. Community Pool: Yes
  11. Waterfront: No
  12. Year Built: 2018
MLS#: O6304507
  1. County: ORANGE
  2. City: Windermere
  3. Zipcode: 34786
  4. Subdivision: Windermere Isle Phase 2
  5. Elementary School: Castleview
  6. Middle School: Horizon West
  7. High School: Horizon
  8. Provided by: THE ROSENBLOOM TEAM
  9. Provided through
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THE Best Lot in Windermere IsleA Designers Dream with Unmatched Privacy and a Chefs Kitchen That Redefines Luxury Welcome to a rare offering in Windermere Isleset on the most private homesite in th
Details for 12002 Angle Pond Avenue, Windermere, FL 34786
Single Family
  1. Price: $1,200,000.00
  2. Price sqft: $207.58 / sqft
  3. Days On Market: 41
  4. Bedrooms: 6
  5. Baths: 5
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 5781
  8. Acreage: 0.21 acres
  9. Pool: Yes
  10. Community Pool: Yes
  11. Waterfront: No
  12. Year Built: 2013
MLS#: O6292566
  1. County: ORANGE
  2. City: Windermere
  3. Zipcode: 34786
  4. Subdivision: Windermere Trails Phase 1b
  5. Elementary School: Bay Lake
  6. Middle School: Horizon West
  7. High School: Windermere
  8. Provided by: ORLANDO ADVANTAGE REALTY INC
  9. Provided through
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Discover the elegance of this spacious residence situated on a premium corner lot within the highly sought after Windermere Trails community. This exquisite home features a formal living room and dini
Details for 9149 Outlook Rock Trail, Windermere, FL 34786
Single Family
  1. Price: $1,185,000.00
  2. Price sqft: $198.66 / sqft
  3. Previous Price: $1,225,000
  4. Last Price Change: 03/12/25
  5. Days On Market: 497
  6. Bedrooms: 6
  7. Baths: 5
  8. Garage / Parking Spaces: 3
  9. Bldg sqft: 5965
  10. Acreage: 0.18 acres
  11. Pool: Yes
  12. Waterfront: No
  13. Year Built: 2015
MLS#: O6165489
  1. County: ORANGE
  2. City: Windermere
  3. Zipcode: 34786
  4. Subdivision: Windermere Trls Ph 5b
  5. Elementary School: Castleview
  6. Middle School: Horizon West
  7. High School: Windermere
  8. Provided by: DE PAULA REALTY USA INC.
  9. Provided through
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Stunning property located in WINDERMERE Florida. The grand entrance opens to an expansive great room, perfect for entertaining or relaxing with family. With 6 bedrooms, 4.5 bathrooms, and a bonus room
Details for 13525 Gorgona Isle Drive, Windermere, FL 34786
Single Family
  1. Price: $1,159,990.00
  2. Price sqft: $204.66 / sqft
  3. Days On Market: 3
  4. Bedrooms: 5
  5. Baths: 5
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 5668
  8. Acreage: 0.19 acres
  9. Pool: Yes
  10. Waterfront: No
  11. Year Built: 2018
MLS#: TB8378196
  1. County: ORANGE
  2. City: Windermere
  3. Zipcode: 34786
  4. Subdivision: Windermere Isle
  5. Elementary School: Castleview
  6. Middle School: Horizon West
  7. High School: Horizon
  8. Provided by: LISTED SIMPLY
  9. Provided through
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Luxury Custom Home Minutes from Disney 5 Bed | 4,625 Sq Ft Live just minutes from the magic in this beautifully upgraded 5 bedroom, 4,625 sq ft luxury home, ideally located, 6 minutes to Magic Ki
Details for 8352 Lookout Pointe Drive, Windermere, FL 34786
Single Family
  1. Price: $1,100,000.00
  2. Price sqft: $190.94 / sqft
  3. Days On Market: 16
  4. Bedrooms: 6
  5. Baths: 5
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 5761
  8. Acreage: 0.17 acres
  9. Pool: Yes
  10. Community Pool: Yes
  11. Waterfront: No
  12. Year Built: 2016
MLS#: S5124888
  1. County: ORANGE
  2. City: Windermere
  3. Zipcode: 34786
  4. Subdivision: Windermere Trls Ph 3b
  5. Elementary School: Bay Lake
  6. Middle School: Horizon West
  7. High School: Windermere
  8. Provided by: SIX STAR REALTY GROUP LLC
  9. Provided through
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Sitting directly on LAKE REAMS with a serene lake view, this impeccably upgraded residence is nestled in the heart of the highly sought after Windermere Trails community and offers an exceptional comb
Details for 9676 Wild Oak Drive, Windermere, FL 34786
Single Family
  1. Price: $925,000.00
  2. Price sqft: $243.10 / sqft
  3. Days On Market: 29
  4. Bedrooms: 4
  5. Baths: 3
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 3805
  8. Acreage: 0.50 acres
  9. Pool: Yes
  10. Waterfront: No
  11. Year Built: 1977
MLS#: O6292764
  1. County: ORANGE
  2. City: Windermere
  3. Zipcode: 34786
  4. Subdivision: Windermere Downs
  5. Elementary School: Thornebrooke Elem
  6. Middle School: Gotha
  7. High School: Olympia
  8. Provided by: BHHS FLORIDA REALTY
  9. Provided through
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Welcome to Windermere Downs. Nestled in one of the most sought after neighborhoods in Windermere, this 70s modern gem sits on a half acre lot. The U shaped layout of the house wraps around a generous
Details for 9227 Outlook Rock Trail, Windermere, FL 34786
Single Family
  1. Price: $825,000.00
  2. Price sqft: $199.90 / sqft
  3. Days On Market: 24
  4. Bedrooms: 4
  5. Baths: 4
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 4127
  8. Acreage: 0.17 acres
  9. Pool: No
  10. Waterfront: No
  11. Year Built: 2016
MLS#: O6297463
  1. County: ORANGE
  2. City: Windermere
  3. Zipcode: 34786
  4. Subdivision: Windermere Trls Ph 4a
  5. Elementary School: Bay Lake
  6. Middle School: Horizon West
  7. High School: Windermere
  8. Provided by: CORCORAN PREMIER REALTY
  9. Provided through
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Beautiful home in Windermere Trails, where luxury and convenience come together in the heart of one of Central Florida's most desirable communities. This stunning 4 bedroom, 4 bathroom home is ideally