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: 138
  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: 46
  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: 117
  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: 10/09/25
  5. Days On Market: 143
  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: 179
  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 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: 17
  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 11472 Park Avenue Ne, WINDERMERE, FL 34786
Single Family
  1. Price: $1,320,000.00
  2. Price sqft: $295.96 / sqft
  3. Previous Price: $1,400,000
  4. Last Price Change: 01/29/26
  5. Days On Market: 20
  6. Bedrooms: 5
  7. Baths: 4
  8. Garage / Parking Spaces: 2
  9. Bldg sqft: 4460
  10. Acreage: 0.96 acres
  11. Pool: No
  12. Waterfront: No
  13. 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
Details for 8162 Oak Park Road, ORLANDO, FL 32819
Single Family
  1. Price: $1,249,000.00
  2. Price sqft: $166.78 / sqft
  3. Days On Market: 56
  4. Bedrooms: 4
  5. Baths: 4
  6. Garage / Parking Spaces: 4
  7. Bldg sqft: 7489
  8. Acreage: 1.00 acres
  9. Pool: Yes
  10. Waterfront: No
  11. Year Built: 1986
MLS#: O6365197
  1. County: ORANGE
  2. City: ORLANDO
  3. Zipcode: 32819
  4. Subdivision: Windermere Heights Sec 03
  5. Elementary School: Palm Lake Elem
  6. Middle School: Chain of Lakes
  7. High School: Olympia
  8. Provided by: COLDWELL BANKER REALTY
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Looking for land and no hoa, but want to be close to everything and have excellent schools and easy access to all major highways? This one is for you!! Set on 1 acre of prime property in coveted dr. P
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: 46
  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 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
Details for 6146 Golden Dewdrop Trail, WINDERMERE, FL 34786
Single Family
  1. Price: $1,200,000.00
  2. Price sqft: $223.42 / sqft
  3. Previous Price: $1,225,000
  4. Last Price Change: 01/13/26
  5. Days On Market: 44
  6. Bedrooms: 7
  7. Baths: 5
  8. Garage / Parking Spaces: 2
  9. Bldg sqft: 5371
  10. Acreage: 0.20 acres
  11. Pool: Yes
  12. Community Pool: Yes
  13. Spa/HotTub: Yes
  14. Waterfront: Yes
  15. Wateraccess: Yes
  16. Waterfront Type: Pond
  17. Year Built: 2012
MLS#: O6368142
  1. County: ORANGE
  2. City: WINDERMERE
  3. Zipcode: 34786
  4. Subdivision: Windermere Lndgs Fd1
  5. Elementary School: SunRidge
  6. Middle School: Horizon West
  7. High School: Windermere
  8. Provided by: KELLER WILLIAMS CLASSIC
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Move in ready and thoughtfully upgraded, this spacious residence is located in the established windermere landing community and offers serene pond views, energy efficient construction, and a flexible