Searching on:
  1. Subdivision Like Windermere
  2. Listing Status = Active
Details for 2 Chase Road, WINDERMERE, FL 34786
Single Family
  1. Price: $3,200,000.00
  2. Price sqft: $822.83 / sqft
  3. Days On Market: 134
  4. Bedrooms: 4
  5. Baths: 5
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 3889
  8. Acreage: 0.44 acres
  9. Pool: Yes
  10. Waterfront: No
  11. Year Built: 2026
MLS#: O6345197
  1. County: ORANGE
  2. City: WINDERMERE
  3. Zipcode: 34786
  4. Subdivision: Windermere
  5. Elementary School: Windermere Elem
  6. Middle School: Chain of Lakes
  7. High School: Olympia
  8. Provided by: REAL BROKER, LLC
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Pre construction. To be built. Pre construction. To be built. Pre construction | to be built | designed for unparalleled luxury discover an extraordinary opportunity to own a masterfully designed luxu
Details for 713 Main Street, WINDERMERE, FL 34786
Single Family
  1. Price: $2,285,000.00
  2. Price sqft: $337.02 / sqft
  3. Days On Market: 42
  4. Bedrooms: 6
  5. Baths: 6
  6. Garage / Parking Spaces: 3
  7. Bldg sqft: 6780
  8. Acreage: 0.37 acres
  9. Pool: No
  10. Waterfront: No
  11. Year Built: 2013
MLS#: O6368185
  1. County: ORANGE
  2. City: WINDERMERE
  3. Zipcode: 34786
  4. Subdivision: Windermere
  5. Elementary School: Windermere Elem
  6. Middle School: Gotha
  7. High School: Olympia
  8. Provided by: THE REAL ESTATE COLLECTION LLC
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Architecturally refined and thoughtfully designed, this custom built Transitional Craftsman residence blends timeless craftsmanship with modern luxury in the heart of Historic Olde Windermere. Rich wo
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: 113
  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,
Details for 13048 Lake Roper Ct., WINDERMERE, FL 34786
Single Family
  1. Price: $1,999,000.00
  2. Price sqft: $355.82 / sqft
  3. Previous Price: $2,100,000
  4. Last Price Change: 01/24/26
  5. Days On Market: 139
  6. Bedrooms: 5
  7. Baths: 4
  8. Garage / Parking Spaces: 3
  9. Bldg sqft: 5618
  10. Acreage: 1.63 acres
  11. Pool: Yes
  12. Waterfront: Yes
  13. Wateraccess: Yes
  14. Waterfront Type: Lake Front
  15. Year Built: 2002
MLS#: O6342354
  1. County: ORANGE
  2. City: WINDERMERE
  3. Zipcode: 34786
  4. Subdivision: Windermere Pointe
  5. Provided by: WOODSTONE INVESTMENTS LLC
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Back on the market. Buyer's contingency fell through. Unmatched Value! The only Windermere lakefront home with boat access available under $2M. Don't miss this opportunity. Enjoy the e evenings to a b
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: 175
  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
Details for 2509 Ridgewind Way, WINDERMERE, FL 34786
Single Family
  1. Price: $1,545,000.00
  2. Price sqft: $284.95 / sqft
  3. Previous Price: $1,585,000
  4. Last Price Change: 12/02/25
  5. Days On Market: 86
  6. Bedrooms: 4
  7. Baths: 4
  8. Garage / Parking Spaces: 3
  9. Bldg sqft: 5422
  10. Acreage: 0.75 acres
  11. Pool: Yes
  12. Waterfront: No
  13. Year Built: 1998
MLS#: O6354737
  1. County: ORANGE
  2. City: WINDERMERE
  3. Zipcode: 34786
  4. Subdivision: Estates At Windermere
  5. Elementary School: Lake Whitney Elem
  6. Middle School: SunRidge
  7. High School: West Orange
  8. Provided by: COMPASS FLORIDA LLC
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If youve dreamed of a home that feels both timeless and tailor made for modern living, welcome to 2509 Ridgewind Way in the gated Estates at Windermere. Set on .75 acre this updated Southern estate co
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: 128
  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
Details for 13596 Gorgona Isle Drive, WINDERMERE, FL 34786
Single Family
  1. Price: $1,452,000.00
  2. Price sqft: $357.81 / sqft
  3. Days On Market: 13
  4. Bedrooms: 6
  5. Baths: 5
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 4058
  8. Acreage: 0.20 acres
  9. Pool: Yes
  10. Waterfront: No
  11. Year Built: 2017
MLS#: O6374555
  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: WRA BUSINESS & REAL ESTATE
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Stunning Two Story Pool Home in Prime Windermere Location Welcome to this exceptional two story residence located in the highly desirable Windermere area, offering the perfect blend of luxury, space,
Details for 7135 Horizon Circle, WINDERMERE, FL 34786
Single Family
  1. Price: $1,399,000.00
  2. Price sqft: $312.70 / sqft
  3. Previous Price: $1,449,000
  4. Last Price Change: 01/08/26
  5. Days On Market: 198
  6. Bedrooms: 4
  7. Baths: 4
  8. Garage / Parking Spaces: 3
  9. Bldg sqft: 4474
  10. Acreage: 0.74 acres
  11. Pool: Yes
  12. Waterfront: No
  13. Year Built: 1993
MLS#: O6327225
  1. County: ORANGE
  2. City: WINDERMERE
  3. Zipcode: 34786
  4. Subdivision: Windermere Reserve
  5. Elementary School: Windermere Elem
  6. Middle School: Chain of Lakes
  7. High School: Olympia
  8. Provided by: THE BOSCH GROUP
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New price, new year! Nestled in the true town of windermere is this absolutely stunning, meticulously maintained pool home with tall ceilings and lots of land surrounding on both sides! This hidden ge
Details for 11472 Park Avenue Ne, WINDERMERE, FL 34786
Single Family
  1. Price: $1,320,000.00
  2. Price sqft: $295.96 / sqft
  3. Days On Market: 16
  4. Bedrooms: 5
  5. Baths: 4
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 4460
  8. Acreage: 0.96 acres
  9. Pool: No
  10. Waterfront: No
  11. Year Built: 1985
MLS#: G5105731
  1. County: ORANGE
  2. City: WINDERMERE
  3. Zipcode: 34786
  4. Subdivision: Windermere
  5. Elementary School: Windermere Elem
  6. Middle School: Gotha
  7. High School: Windermere
  8. Provided by: WEICHERT, REALTORS-HALLMARK PR
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Approximately 3,000 sq ft home in a desirable Windermere location within FEMA Flood Zone X. The residence offers a flexible layout with multiple living areas and is fully livable, presenting an excell