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  1. Subdivision Like Windermere Town
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515 W 2nd Avenue
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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
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105 Forest Street
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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
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930 East Boulevard
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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,
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212 W 1st Avenue
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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
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101 Lee Street
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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
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104 E 1st Avenue
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Details for 104 E 1st Avenue, WINDERMERE, FL 34786
Single Family
  1. Price: $1,280,000.00
  2. Price sqft: $388.00 / sqft
  3. Days On Market: 52
  4. Bedrooms: 4
  5. Baths: 3
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 3299
  8. Acreage: 0.45 acres
  9. Pool: Yes
  10. Waterfront: No
  11. Year Built: 1985
MLS#: O6442932
  1. County: ORANGE
  2. City: WINDERMERE
  3. Zipcode: 34786
  4. Subdivision: Windermere Town
  5. Elementary School: Windermere Elem
  6. Middle School: Bridgewater Middle
  7. High School: Olympia High
  8. Provided by: NOVA REAL ESTATE SERVICES INC
  9. mfrmls
  10. DMCA Notice
Experience the charm of Old Windermere at 104 E 1st Ave, ideally situated in the heart of one of Central Floridas most sought after communities. Set on an oversized 0.45 acre corner lot surrounded by
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1221 Oakdale Street
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Details for 1221 Oakdale Street, WINDERMERE, FL 34786
Land
  1. Price: $1,250,000.00
  2. Days On Market: 39
  3. Acreage: 1.00 acres
  4. Pool: No
  5. Waterfront: Yes
  6. Wateraccess: Yes
  7. Waterfront Type: Lake Front
  8. Year Built: Not Available
MLS#: O6446547
  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: THE SIMON SIMAAN GROUP
  9. mfrmls
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Under contract accepting backup offers. Build Your Dream Lakefront Home in the Town of Windermere! Opportunity is knocking in one of Central Floridas most desirable areas! This exceptional one acre la
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715 Magnolia Street
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Details for 715 Magnolia Street, WINDERMERE, FL 34786
Single Family
  1. Price: $1,089,000.00
  2. Price sqft: $257.14 / sqft
  3. Previous Price: $1,099,000
  4. Last Price Change: 09/25/26
  5. Days On Market: 212
  6. Bedrooms: 4
  7. Baths: 3
  8. Garage / Parking Spaces: 3
  9. Bldg sqft: 4235
  10. Acreage: 0.38 acres
  11. Pool: No
  12. Waterfront: No
  13. Year Built: 1999
MLS#: S5147648
  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: IRIS INTERNATIONAL
  9. mfrmls
  10. DMCA Notice
A beautiful home in the heart of downtown Windermere, this property offers four bedrooms and three bathrooms with a perfect blend of comfort, style, and convenience. The main residence features hardwo
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105 Forest Street
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Details for 105 Forest Street, WINDERMERE, FL 34786
Land
  1. Price: $900,000.00
  2. Days On Market: 10
  3. Acreage: 0.38 acres
  4. Pool: No
  5. Waterfront: No
  6. Year Built: Not Available
MLS#: O6451242
  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
Build Your Dream Home in the Heart of Downtown Windermere! An incredible opportunity awaits on this desirable 0.38 acre corner lot with NO HOA, perfectly situated in the charming heart of Downtown Wi
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104 E 11th Avenue
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Listing Details for 104 E 11th Avenue, WINDERMERE, FL 34786
Single Family
  1. Price: $862,500.00
  2. Price sqft: $339.03 / sqft
  3. Days On Market: 2
  4. Bedrooms: 3
  5. Baths: 2
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 2544
  8. Acreage: 0.29 acres
  9. Pool: No
  10. Waterfront: No
  11. Year Built: 1980
MLS#: O6455790
  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: ZIRO REALTY
  9. mfrmls
  10. DMCA Notice
Photos coming soon! Welcome to your new home in the historic, golf cart friendly Town of Windermere! Nestled on a 0.29 acre corner lot shaded by mature trees, this charming 1 story block home offer
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