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2 Chase Road
New Construction
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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: 214
  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
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325 Magnolia Street
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Details for 325 Magnolia Street, WINDERMERE, FL 34786
Single Family
  1. Price: $2,475,000.00
  2. Price sqft: $509.36 / sqft
  3. Days On Market: 34
  4. Bedrooms: 4
  5. Baths: 3
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 4859
  8. Acreage: 2.97 acres
  9. Pool: Yes
  10. Waterfront: Yes
  11. Wateraccess: Yes
  12. Waterfront Type: Lake Front
  13. Year Built: 1954
MLS#: O6391047
  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: REVEL REALTY LLC
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Location Location Location. Set along the shores of Lake Down, part of the Butler Chain of Lakes, this Windermere home offers a rare mix of laid back lake living and walkability to town. The Town of W
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713 Main Street
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Details for 713 Main Street, WINDERMERE, FL 34786
Single Family
  1. Price: $2,235,000.00
  2. Price sqft: $329.65 / sqft
  3. Previous Price: $2,285,000
  4. Last Price Change: 02/28/26
  5. Days On Market: 123
  6. Bedrooms: 6
  7. Baths: 6
  8. Garage / Parking Spaces: 3
  9. Bldg sqft: 6780
  10. Acreage: 0.37 acres
  11. Pool: No
  12. Waterfront: No
  13. 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
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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: 01/13/26
  5. Days On Market: 193
  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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13048 Lake Roper Ct.
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Details for 13048 Lake Roper Ct., WINDERMERE, FL 34786
Single Family
  1. Price: $1,950,000.00
  2. Price sqft: $347.10 / sqft
  3. Previous Price: $1,999,000
  4. Last Price Change: 02/08/26
  5. Days On Market: 219
  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. Unmatched Value! The only Windermere lakefront home with boat access available under $2M. Don't miss this opportunity. Enjoy the e evenings to a breathtaking sunset at your own pri
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212 1st Avenue
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Details for 212 1st Avenue, WINDERMERE, FL 34786
Land
  1. Price: $1,600,000.00
  2. Days On Market: 10
  3. Acreage: 0.32 acres
  4. Pool: No
  5. Waterfront: Yes
  6. Wateraccess: Yes
  7. Waterfront Type: Lake Privileges
  8. Year Built: Not Available
MLS#: S5147532
  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: HOME WISE REALTY GROUP, INC.
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Positioned along the coveted Butler Chain of Lakes, this waterfront residence offers an exceptional opportunity in the Town of Windermere. Boasting approximately 65 feet of private frontage and a dedi
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12718 Windermere Isles Place
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Details for 12718 Windermere Isles Place, Windermere, FL 34786
Single Family
  1. Price: $1,490,000.00
  2. Price sqft: $328.99 / sqft
  3. Days On Market: 3
  4. Bedrooms: 4
  5. Baths: 4
  6. Garage / Parking Spaces: 3
  7. Bldg sqft: 4529
  8. Acreage: 0.93 acres
  9. Pool: Yes
  10. Waterfront: No
  11. Year Built: 1997
MLS#: O6399958
  1. County: ORANGE
  2. City: Windermere
  3. Zipcode: 34786
  4. Subdivision: Isles Windermere
  5. Elementary School: Windermere Elem
  6. Middle School: Bridgewater
  7. High School: Windermere
  8. Provided by: CHARLES RUTENBERG REALTY ORLANDO
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Welcome to 12718 Windermere Isles Place, a spectacular residence tucked away on a quiet cul de sac in the heart of Windermere. Situated on a sprawling nearly one acre lot, this beautifully remodeled h
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12718 Windermere Isles Place
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Details for 12718 Windermere Isles Place, WINDERMERE, FL 34786
Single Family
  1. Price: $1,490,000.00
  2. Price sqft: $328.99 / sqft
  3. Days On Market: 3
  4. Bedrooms: 4
  5. Baths: 4
  6. Garage / Parking Spaces: 3
  7. Bldg sqft: 4529
  8. Acreage: 0.93 acres
  9. Pool: Yes
  10. Spa/HotTub: Yes
  11. Waterfront: No
  12. Year Built: 1997
MLS#: O6399958
  1. County: ORANGE
  2. City: WINDERMERE
  3. Zipcode: 34786
  4. Subdivision: Isles Windermere
  5. Elementary School: Windermere Elem
  6. Middle School: Bridgewater
  7. High School: Windermere
  8. Provided by: CHARLES RUTENBERG REALTY ORLANDO
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Welcome to 12718 Windermere Isles Place, a spectacular residence tucked away on a quiet cul de sac in the heart of Windermere. Situated on a sprawling nearly one acre lot, this beautifully remodeled h
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13596 Gorgona Isle Drive
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Details for 13596 Gorgona Isle Drive, WINDERMERE, FL 34786
Single Family
  1. Price: $1,396,000.00
  2. Price sqft: $344.01 / sqft
  3. Previous Price: $1,452,000
  4. Last Price Change: 03/07/26
  5. Days On Market: 93
  6. Bedrooms: 6
  7. Baths: 5
  8. Garage / Parking Spaces: 2
  9. Bldg sqft: 4058
  10. Acreage: 0.20 acres
  11. Pool: Yes
  12. Waterfront: No
  13. 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,
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2219 Ridgewind Way
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Details for 2219 Ridgewind Way, Windermere, FL 34786
Single Family
  1. Price: $1,349,000.00
  2. Price sqft: $277.69 / sqft
  3. Days On Market: 1
  4. Bedrooms: 6
  5. Baths: 4
  6. Garage / Parking Spaces: 3
  7. Bldg sqft: 4858
  8. Acreage: 0.63 acres
  9. Pool: Yes
  10. Waterfront: No
  11. Year Built: 1997
MLS#: O6400508
  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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Set behind the gates of The Estates at Windermerean intimate enclave of just 67 homes2219 Ridgewind Way is the kind of property that stops you mid scroll. A true Victorian inspired residence, its a
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