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  1. Subdivision Like Windermere
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212 1st Avenue
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Details for 212 1st Avenue, WINDERMERE, FL 34786
Single Family
  1. Price: $3,900,000.00
  2. Price sqft: $709.09 / sqft
  3. Days On Market: 16
  4. Bedrooms: 5
  5. Baths: 5
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 5500
  8. Acreage: 0.32 acres
  9. Pool: No
  10. Waterfront: Yes
  11. Wateraccess: Yes
  12. Waterfront Type: Lake Front,Lake Privileges
  13. Year Built: 1959
MLS#: S5148430
  1. County: ORANGE
  2. City: WINDERMERE
  3. Zipcode: 34786
  4. Subdivision: Windermere Town
  5. Elementary School: Windermere Elem
  6. Middle School: Gotha Middle
  7. High School: Olympia High
  8. Provided by: HOME WISE REALTY GROUP, INC.
  9. mfrmls
  10. DMCA Notice
Pre Construction. To be built. Positioned along the coveted Butler Chain of Lakes, this waterfront residence offers an exceptional opportunity to live in the Town of Windermere. Boasting approximately
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2 Chase Road
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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: 238
  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 Middle
  7. High School: Olympia High
  8. Provided by: REAL BROKER, LLC
  9. mfrmls
  10. DMCA Notice
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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105 Pine Street
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Details for 105 Pine Street, WINDERMERE, FL 34786
Single Family
  1. Price: $2,500,000.00
  2. Price sqft: $342.65 / sqft
  3. Days On Market: 6
  4. Bedrooms: 5
  5. Baths: 6
  6. Garage / Parking Spaces: 3
  7. Bldg sqft: 7296
  8. Acreage: 0.57 acres
  9. Pool: Yes
  10. Spa/HotTub: Yes
  11. Waterfront: No
  12. Year Built: 2015
MLS#: O6405163
  1. County: ORANGE
  2. City: WINDERMERE
  3. Zipcode: 34786
  4. Subdivision: Windermere
  5. Elementary School: Windermere Elem
  6. Middle School: Gotha Middle
  7. High School: Olympia High
  8. Provided by: ALIGN REAL ESTATE LLC
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Extraordinary multigenerational living opportunity in the Town of Windermere, where mature oak trees and a quiet, established setting create a true sense of place just moments from the Butler Chain of
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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: 57
  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 Privileges
  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 Middle
  7. High School: Olympia High
  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 with walkability to town, and a bike r
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505 Jennifer Lane
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Details for 505 Jennifer Lane, WINDERMERE, FL 34786
Single Family
  1. Price: $2,199,000.00
  2. Price sqft: $411.49 / sqft
  3. Previous Price: $2,250,000
  4. Last Price Change: 05/10/26
  5. Days On Market: 75
  6. Bedrooms: 4
  7. Baths: 4
  8. Garage / Parking Spaces: 3
  9. Bldg sqft: 5344
  10. Acreage: 1.00 acres
  11. Pool: Yes
  12. Spa/HotTub: Yes
  13. Waterfront: No
  14. Year Built: 1989
MLS#: O6384643
  1. County: ORANGE
  2. City: WINDERMERE
  3. Zipcode: 34786
  4. Subdivision: Windermere Oaks
  5. Elementary School: Windermere Elem
  6. Middle School: Chain of Lakes Middle
  7. High School: Olympia High
  8. Provided by: COMPASS FLORIDA LLC
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Villa Casablanca | Luxury Windermere Estate on 1 Acre. Some homes are built. this was transformed. Set on a rare private acre within one of Windermeres most privately held enclaves this estate makes
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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: 05/05/26
  5. Days On Market: 217
  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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713 Main Street
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Details for 713 Main Street, WINDERMERE, FL 34786
Single Family
  1. Price: $2,175,000.00
  2. Price sqft: $320.80 / sqft
  3. Previous Price: $2,235,000
  4. Last Price Change: 05/11/26
  5. Days On Market: 146
  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 Middle
  7. High School: Olympia High
  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 with exc
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12699 Hawkstone Drive
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Details for 12699 Hawkstone Drive, WINDERMERE, FL 34786
Single Family
  1. Price: $2,125,000.00
  2. Price sqft: $430.51 / sqft
  3. Days On Market: 20
  4. Bedrooms: 4
  5. Baths: 5
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 4936
  8. Acreage: 1.07 acres
  9. Pool: Yes
  10. Spa/HotTub: Yes
  11. Waterfront: Yes
  12. Wateraccess: Yes
  13. Waterfront Type: Lake Privileges
  14. Year Built: 2006
MLS#: O6401293
  1. County: ORANGE
  2. City: WINDERMERE
  3. Zipcode: 34786
  4. Subdivision: Lakes Windermere Ph 01 49 108
  5. Elementary School: Sunset Park Elem
  6. Middle School: Horizon West Middle School
  7. High School: Windermere High School
  8. Provided by: LAKEFIELD REALTY GROUP LLC
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Welcome to Chalet du Lac, set on the exclusive and private Lake Sawyer chain of lakes in Windermerewhere mornings are welcomed by sunrise over glistening waters dancing through a veil of Cypress trees
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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. Previous Price: $1,500,000
  3. Last Price Change: 04/10/26
  4. Days On Market: 34
  5. Acreage: 0.32 acres
  6. Pool: No
  7. Waterfront: Yes
  8. Wateraccess: Yes
  9. Waterfront Type: Lake Privileges
  10. 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 Middle
  7. High School: Olympia High
  8. Provided by: HOME WISE REALTY GROUP, INC.
  9. mfrmls
  10. DMCA Notice
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: 27
  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 Middle
  7. High School: Windermere High School
  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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