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  1. Subdivision Like Windermere
904 Main Street
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Details for 904 Main Street, WINDERMERE, FL 34786
Single Family
  1. Price: $4,100,000.00
  2. Price sqft: $607.77 / sqft
  3. Previous Price: $4,299,000
  4. Last Price Change: 03/10/25
  5. Days On Market: 183
  6. Bedrooms: 4
  7. Baths: 6
  8. Garage / Parking Spaces: 3
  9. Bldg sqft: 6746
  10. Acreage: 2.24 acres
  11. Pool: Yes
  12. Spa/HotTub: Yes
  13. Waterfront: Yes
  14. Wateraccess: Yes
  15. Waterfront Type: Lake
  16. Year Built: 2003
MLS#: O6241373
  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
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This property includes an incredibly rare air conditioned boathouse that is completely renovated with apartment, kitchen and bathroom. A custom platform boat lift with overhead garage door lends secur
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8441 Oakland Place
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Details for 8441 Oakland Place, ORLANDO, FL 32819
Single Family
  1. Price: $3,500,000.00
  2. Price sqft: $340.20 / sqft
  3. Days On Market: 284
  4. Bedrooms: 5
  5. Baths: 5
  6. Garage / Parking Spaces: 14
  7. Bldg sqft: 10288
  8. Acreage: 1.02 acres
  9. Pool: Yes
  10. Spa/HotTub: Yes
  11. Waterfront: No
  12. Year Built: 2018
MLS#: O6204737
  1. County: ORANGE
  2. City: ORLANDO
  3. Zipcode: 32819
  4. Subdivision: Windermere Heights Add 02
  5. Elementary School: Palm Lake Elem
  6. Middle School: Chain of Lakes Middle
  7. High School: Olympia High
  8. Provided by: MILLENIUM REALTY GROUP
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Experience the epitome of modern luxury living, where the fusion of location, style, innovation, and automotive excellence culminates in a masterpiece of architectural prowess. Nestled within the popu
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2 Chase Road
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Details for 2 Chase Road, WINDERMERE, FL 34786
Single Family
  1. Price: $3,168,000.00
  2. Price sqft: $574.33 / sqft
  3. Days On Market: 23
  4. Bedrooms: 4
  5. Baths: 5
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 5516
  8. Acreage: 0.44 acres
  9. Pool: Yes
  10. Waterfront: No
  11. Year Built: 2025
MLS#: O6282569
  1. County: ORANGE
  2. City: WINDERMERE
  3. Zipcode: 34786
  4. Subdivision: Windermere
  5. Provided by: PV LUXURY GROUP PA
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Pre construction. To be built. Pre construction | to be built | designed for unparalleled luxury discover an extraordinary opportunity to own a masterfully designed luxury residence in the prestigious
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325 Magnolia Street
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Details for 325 Magnolia Street, WINDERMERE, FL 34786
Single Family
  1. Price: $2,998,000.00
  2. Price sqft: $617.00 / sqft
  3. Previous Price: $3,049,900
  4. Last Price Change: 03/12/25
  5. Days On Market: 198
  6. Bedrooms: 4
  7. Baths: 3
  8. Garage / Parking Spaces: 2
  9. Bldg sqft: 4859
  10. Acreage: 2.97 acres
  11. Pool: Yes
  12. Waterfront: Yes
  13. Wateraccess: Yes
  14. Waterfront Type: Lake
  15. Year Built: 1954
MLS#: O6235395
  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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Boasting a prime location in the Town of Windermere on Lake Down with access to the Butler Chain of Lakes, enjoy the perks of town and lake living being in the heart of Windermere. Less than half a mi
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12428 Summerport Lane
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Details for 12428 Summerport Lane, WINDERMERE, FL 34786
Single Family
  1. Price: $2,995,000.00
  2. Price sqft: $638.87 / sqft
  3. Previous Price: $3,195,000
  4. Last Price Change: 03/01/25
  5. Days On Market: 198
  6. Bedrooms: 4
  7. Baths: 5
  8. Garage / Parking Spaces: 3
  9. Bldg sqft: 4688
  10. Acreage: 0.83 acres
  11. Pool: Yes
  12. Waterfront: Yes
  13. Wateraccess: Yes
  14. Waterfront Type: Lake
  15. Year Built: 2003
MLS#: O6236319
  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: COLDWELL BANKER RESIDENTIAL RE
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Awake to a breathtaking sunrise in this beautiful Key West Style custom designed house. ALMOST AN ACRE WITH 130 FEET DIRECT LAKEFRONT PROPERTY LOCATED ON PRESTIGE LAKE BUTLER, THE CHAIN OF LAKES! Enjo
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1003 Oakdale Street
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Details for 1003 Oakdale Street, WINDERMERE, FL 34786
Single Family
  1. Price: $2,900,000.00
  2. Price sqft: $529.49 / sqft
  3. Previous Price: $2,950,000
  4. Last Price Change: 03/10/25
  5. Days On Market: 102
  6. Bedrooms: 6
  7. Baths: 6
  8. Garage / Parking Spaces: 3
  9. Bldg sqft: 5477
  10. Acreage: 1.77 acres
  11. Pool: Yes
  12. Waterfront: Yes
  13. Wateraccess: Yes
  14. Waterfront Type: Lake
  15. Year Built: 2003
MLS#: O6261656
  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
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Never lived in since completely remodeled and expanded total of 6 bedrooms 5 full baths 1 pool or guest bath primary suite & guest suite on 1st floor 4 more bedrooms & 3 bathrooms on 2nd flo
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4108 Downeast Lane
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Details for 4108 Downeast Lane, WINDERMERE, FL 34786
Land
  1. Price: $2,675,000.00
  2. Previous Price: $3,300,000
  3. Last Price Change: 02/26/25
  4. Days On Market: 39
  5. Acreage: 3.31 acres
  6. Pool: No
  7. Waterfront: Yes
  8. Wateraccess: Yes
  9. Waterfront Type: Lake
  10. Year Built: Not Available
MLS#: O6276653
  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: KELLY PRICE & COMPANY LLC
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IMPROVED PRICE (Reduced $625,0000: The price adjustment is generating strong interest. Acting now ensures you dont miss out on this unique Butler Chain of Lakes opportunity.) Welcome to 4108 Downeast
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4108 Downeast Lane
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Details for 4108 Downeast Lane, WINDERMERE, FL 34786
Single Family
  1. Price: $2,675,000.00
  2. Price sqft: $471.45 / sqft
  3. Previous Price: $3,300,000
  4. Last Price Change: 02/26/25
  5. Days On Market: 44
  6. Bedrooms: 4
  7. Baths: 3
  8. Garage / Parking Spaces: 2
  9. Bldg sqft: 5674
  10. Acreage: 3.31 acres
  11. Pool: No
  12. Waterfront: Yes
  13. Wateraccess: Yes
  14. Waterfront Type: Lake
  15. Year Built: 1979
MLS#: O6273954
  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: KELLY PRICE & COMPANY LLC
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IMPROVED PRICE (Reduced $625,0000: The price adjustment is generating strong interest. Acting now ensures you dont miss out on this unique Butler Chain of Lakes opportunity.) Welcome to 4108 Downeast
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105 Pine Street
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Details for 105 Pine Street, WINDERMERE, FL 34786
Single Family
  1. Price: $2,495,000.00
  2. Price sqft: $341.97 / sqft
  3. Days On Market: 29
  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#: O6279246
  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 SOTHEBY'S INTL. REALTY
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On a serene over half acre lot in the heart of historic downtown Windermere this fabulous one of a kind multi generational home is a short distance from the charming boutiques, eateries, coffee shops,
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647 Ridgewood Drive
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Details for 647 Ridgewood Drive, WINDERMERE, FL 34786
Single Family
  1. Price: $2,359,000.00
  2. Price sqft: $666.20 / sqft
  3. Days On Market: 88
  4. Bedrooms: 3
  5. Baths: 3
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 3541
  8. Acreage: 1.43 acres
  9. Pool: No
  10. Waterfront: Yes
  11. Wateraccess: Yes
  12. Waterfront Type: Lake
  13. Year Built: 1974
MLS#: O6263552
  1. County: ORANGE
  2. City: WINDERMERE
  3. Zipcode: 34786
  4. Subdivision: Windermere Town Rep
  5. Elementary School: Windermere Elem
  6. Middle School: Gotha Middle
  7. High School: Olympia High
  8. Provided by: PREMIER SOTHEBYS INT'L REALTY
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One or more photo(s) has been virtually staged. Welcome to 647 Ridgewood Drive, an exquisitely remodeled three bedroom, three bathroom lakefront estate in the heart of Old Windermere. This exceptional
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Tropic Shores Realty - Crystal River
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Listing Data ©2025 Greater Fort Lauderdale REALTORS®
Listings provided courtesy of The Hernando County Association of Realtors MLS.
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Listing Data ©2025 Royal Palm Coast Realtor® Association
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Datafeed Last updated on March 15, 2025 @ 12:00 am
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