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Searching on:
  1. Subdivision Like Windermere
  2. Listing Status = Active
Details for 724 W 2nd Avenue, WINDERMERE, FL 34786
Single Family
  1. Price: $7,500,000.00
  2. Price sqft: $722.13 / sqft
  3. Days On Market: 111
  4. Bedrooms: 6
  5. Baths: 8
  6. Garage / Parking Spaces: 4
  7. Bldg sqft: 10386
  8. Acreage: 1.10 acres
  9. Pool: Yes
  10. Spa/HotTub: Yes
  11. Waterfront: Yes
  12. Wateraccess: Yes
  13. Waterfront Type: Lake Front,Lake Privileges
  14. Year Built: 2024
MLS#: O6426995
  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 SIMON SIMAAN GROUP
  9. mfrmls
  10. DMCA Notice
Under contract accepting backup offers. Welcome to an extraordinary lakefront estate on the prestigious shores of Lake Butler with 182 feet of water frontage, where timeless architecture, exceptional
Details for 703 E 6th Avenue, WINDERMERE, FL 34786
Single Family
  1. Price: $3,450,000.00
  2. Price sqft: $456.47 / sqft
  3. Days On Market: 11
  4. Bedrooms: 4
  5. Baths: 5
  6. Garage / Parking Spaces: 3
  7. Bldg sqft: 7558
  8. Acreage: 3.75 acres
  9. Pool: Yes
  10. Spa/HotTub: Yes
  11. Waterfront: Yes
  12. Wateraccess: Yes
  13. Waterfront Type: Lake Privileges
  14. Year Built: 2005
MLS#: O6453037
  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: PREMIER SOTHEBYS INT'L REALTY
  9. mfrmls
  10. DMCA Notice
Exceptional waterfront living on the prestigious Butler Chain of Lakes. Discover an extraordinary expression of waterfront luxury in the charming Town of Windermere, where timeless Tuscan and Mediterr
Details for 515 W 2nd Avenue, WINDERMERE, FL 34786
Single Family
  1. Price: $3,300,000.00
  2. Price sqft: $556.40 / sqft
  3. Days On Market: 64
  4. Bedrooms: 4
  5. Baths: 6
  6. Garage / Parking Spaces: 4
  7. Bldg sqft: 5931
  8. Acreage: 0.66 acres
  9. Pool: Yes
  10. Spa/HotTub: Yes
  11. Waterfront: Yes
  12. Wateraccess: Yes
  13. Waterfront Type: Lake Front,Lake Privileges
  14. Year Built: 2000
MLS#: O6439554
  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: VINTAGE REALTY GROUP LLC
  9. mfrmls
  10. DMCA Notice
Experience the extraordinary lifestyle of waterfront living in the heart of historic Windermere. Set on approximately 2/3rd of an acre with an impressive 100 feet of frontage on the renowned Butler Ch
Details for 105 Forest Street, WINDERMERE, FL 34786
Single Family
  1. Price: $2,700,000.00
  2. Price sqft: $452.94 / sqft
  3. Days On Market: 10
  4. Bedrooms: 5
  5. Baths: 6
  6. Garage / Parking Spaces: 3
  7. Bldg sqft: 5961
  8. Acreage: 0.38 acres
  9. Pool: Yes
  10. Waterfront: No
  11. Year Built: 2027
MLS#: O6450227
  1. County: ORANGE
  2. City: WINDERMERE
  3. Zipcode: 34786
  4. Subdivision: Windermere Town
  5. Provided by: ALIGN REAL ESTATE LLC
  6. mfrmls
  7. DMCA Notice
Virtually Staged. Pre Construction. To be built. Experience bespoke living without the guesswork. Perfectly positioned on an expansive ~0.38 acre corner homesite in the heart of historic downtown Wind
Details for 2 Chase Road, WINDERMERE, FL 34786
Single Family
  1. Price: $2,200,000.00
  2. Price sqft: $565.70 / sqft
  3. Previous Price: $3,200,000
  4. Last Price Change: 08/27/26
  5. Days On Market: 418
  6. Bedrooms: 4
  7. Baths: 5
  8. Garage / Parking Spaces: 2
  9. Bldg sqft: 3889
  10. Acreage: 0.44 acres
  11. Pool: Yes
  12. Waterfront: No
  13. 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
Under contract accepting backup offers. Pre construction. To be built. Pre construction. To be built. Pre construction | to be built | designed for unparalleled luxury discover an extraordinary opport
Details for 713 Main Street, WINDERMERE, FL 34786
Single Family
  1. Price: $1,999,000.00
  2. Price sqft: $294.84 / sqft
  3. Previous Price: $2,099,000
  4. Last Price Change: 11/05/26
  5. Days On Market: 326
  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
  9. mfrmls
  10. DMCA Notice
SIGNIFICANT PRICE IMPROVEMENT! Come experience the character and charm of Historic Olde Windermere in a home that simply cannot be duplicated. Thoughtfully custom built, this one owner Transitional Cr
Details for 930 East Boulevard, WINDERMERE, FL 34786
Single Family
  1. Price: $1,895,000.00
  2. Price sqft: $542.82 / sqft
  3. Days On Market: 74
  4. Bedrooms: 4
  5. Baths: 5
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 3491
  8. Acreage: 1.43 acres
  9. Pool: Yes
  10. Spa/HotTub: Yes
  11. Waterfront: Yes
  12. Wateraccess: Yes
  13. Waterfront Type: Lake Front
  14. Year Built: 2024
MLS#: O6437093
  1. County: ORANGE
  2. City: WINDERMERE
  3. Zipcode: 34786
  4. Subdivision: Windermere Town
  5. Elementary School: Windermere Elem
  6. Middle School: Chain of Lakes Middle
  7. High School: Olympia High
  8. Provided by: CORCORAN PREMIER REALTY
  9. mfrmls
  10. DMCA Notice
Set along the shores of Lake Bessie in the heart of Downtown Windermere, this contemporary lakefront residence pairs clean architectural design with effortless single story living. Completed in 2024,
Details for 4282 Mckinnon Road, WINDERMERE, FL 34786
Single Family
  1. Price: $1,845,000.00
  2. Price sqft: $248.38 / sqft
  3. Previous Price: $1,895,000
  4. Last Price Change: 10/25/26
  5. Days On Market: 89
  6. Bedrooms: 6
  7. Baths: 6
  8. Garage / Parking Spaces: 3
  9. Bldg sqft: 7428
  10. Acreage: 1.15 acres
  11. Pool: Yes
  12. Waterfront: No
  13. Year Built: 2002
MLS#: O6432910
  1. County: ORANGE
  2. City: WINDERMERE
  3. Zipcode: 34786
  4. Subdivision: Windermere
  5. Elementary School: Windermere Elem
  6. Middle School: Bridgewater Middle
  7. High School: Windermere High School
  8. Provided by: COMPASS FLORIDA LLC
  9. mfrmls
  10. DMCA Notice
A rare opportunity in Windermere for the buyer who values space, privacy and flexibility. Set on approximately 1.15 acres with no HOA, 4282 McKinnon Road offers nearly 5,900 square feet, six bedroo
Details for 212 W 1st Avenue, WINDERMERE, FL 34786
Single Family
  1. Price: $1,388,000.00
  2. Price sqft: $356.63 / sqft
  3. Previous Price: $1,488,000
  4. Last Price Change: 11/03/26
  5. Days On Market: 91
  6. Bedrooms: 4
  7. Baths: 2
  8. Garage / Parking Spaces: 2
  9. Bldg sqft: 3892
  10. Acreage: 0.32 acres
  11. Pool: No
  12. Waterfront: Yes
  13. Wateraccess: Yes
  14. Waterfront Type: Lake Privileges
  15. Year Built: 1959
MLS#: S5155372
  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
Virtually Staged. Owner/developer is swamped with other projects currently... BOAT INCLUDED IN PURCHASE PRICE: Recent appraisal $1.6M. Although the value is heavily weighted towards the land this home
Details for 101 Lee Street, WINDERMERE, FL 34786
Single Family
  1. Price: $1,300,000.00
  2. Price sqft: $224.49 / sqft
  3. Previous Price: $1,395,000
  4. Last Price Change: 11/03/26
  5. Days On Market: 69
  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#: O6437573
  1. County: ORANGE
  2. City: WINDERMERE
  3. Zipcode: 34786
  4. Subdivision: Town Of Windermere
  5. Elementary School: Windermere Elem
  6. Middle School: Gotha Middle
  7. High School: Olympia High
  8. Provided by: STOCKWORTH REALTY GROUP
  9. mfrmls
  10. DMCA Notice
Virtually Staged. Nestled in the heart of Windermere, and featuring more than $300,000 in recent improvements including a brand new roof September 2026, this character rich home offers nearly 4,200 sq