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    9508 Windy Ridge Road
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    Details for 9508 Windy Ridge Road, WINDERMERE, FL 34786
    Single Family
    1. Price: $30,000,000.00
    2. Price sqft: $639.85 / sqft
    3. Days On Market: 53
    4. Bedrooms: 7
    5. Baths: 14
    6. Garage / Parking Spaces: 12
    7. Bldg sqft: 46886
    8. Acreage: 18.16 acres
    9. Pool: Yes
    10. Spa/HotTub: Yes
    11. Waterfront: Yes
    12. Wateraccess: Yes
    13. Waterfront Type: Lake Front,Lake Privileges
    14. Year Built: 2011
    MLS#: O6388674
    1. County: ORANGE
    2. City: WINDERMERE
    3. Zipcode: 34786
    4. Elementary School: Thornebrooke Elem
    5. Middle School: Gotha Middle
    6. High School: Olympia High
    7. Provided by: DOUGLAS ELLIMAN
    8. mfrmls
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    Presenting Windy Ridge Estate on 18 gated acres with 614 feet of pristine frontage on Lake Down, Butler Chain of Lakes. Manicured grounds, panoramic water views, and over 50,000 SF across multiple str
    Listing Details and 40 Additional Pictures
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    9639 Westover Roberts Road
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    Details for 9639 Westover Roberts Road, WINDERMERE, FL 34786
    Single Family
    1. Price: $5,900,000.00
    2. Price sqft: $299.40 / sqft
    3. Previous Price: $6,395,000
    4. Last Price Change: 04/29/26
    5. Days On Market: 244
    6. Bedrooms: 5
    7. Baths: 9
    8. Garage / Parking Spaces: 7
    9. Bldg sqft: 19706
    10. Acreage: 4.43 acres
    11. Pool: Yes
    12. Spa/HotTub: Yes
    13. Waterfront: Yes
    14. Wateraccess: Yes
    15. Waterfront Type: Lake Front
    16. Year Built: 2017
    MLS#: O6341883
    1. County: ORANGE
    2. City: WINDERMERE
    3. Zipcode: 34786
    4. Subdivision: Gotha Town
    5. Elementary School: Thornebrooke Elem
    6. Middle School: Gotha Middle
    7. High School: Olympia High
    8. Provided by: STOCKWORTH REALTY GROUP
    9. mfrmls
    10. DMCA Notice
    Welcome to a residence that transcends even the highest expectations of luxury living! This is a once in a lifetime estate where architecture, scale, and location combine to create an experience that
    Listing Details and 77 Additional Pictures
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    9575 Westover Roberts Road
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    Details for 9575 Westover Roberts Road, WINDERMERE, FL 34786
    Single Family
    1. Price: $4,925,000.00
    2. Price sqft: $352.37 / sqft
    3. Days On Market: 180
    4. Bedrooms: 7
    5. Baths: 8
    6. Garage / Parking Spaces: 6
    7. Bldg sqft: 13977
    8. Acreage: 5.44 acres
    9. Pool: Yes
    10. Spa/HotTub: Yes
    11. Waterfront: Yes
    12. Wateraccess: Yes
    13. Waterfront Type: Lake Front
    14. Year Built: 2008
    MLS#: O6357873
    1. County: ORANGE
    2. City: WINDERMERE
    3. Zipcode: 34786
    4. Subdivision: Gotha Town
    5. Elementary School: Thornebrooke Elem
    6. Middle School: Gotha Middle
    7. High School: Olympia High
    8. Provided by: STOCKWORTH REALTY GROUP
    9. mfrmls
    10. DMCA Notice
    Discover Bella Olivia: a grand mediterranean estate perched high above Lake Olivia showcasing sweeping lake views, private gates, and an expansive luxury residence spanning over 8,900 square feet of l
    Listing Details and 94 Additional Pictures
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    3026 Porto Lago Court
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    Details for 3026 Porto Lago Court, WINDERMERE, FL 34786
    Single Family
    1. Price: $4,500,000.00
    2. Price sqft: $376.85 / sqft
    3. Days On Market: 73
    4. Bedrooms: 5
    5. Baths: 9
    6. Garage / Parking Spaces: 3
    7. Bldg sqft: 11941
    8. Acreage: 2.17 acres
    9. Pool: Yes
    10. Spa/HotTub: Yes
    11. Waterfront: Yes
    12. Wateraccess: Yes
    13. Waterfront Type: Lake Front,Lake Privileges
    14. Year Built: 2003
    MLS#: O6381606
    1. County: ORANGE
    2. City: WINDERMERE
    3. Zipcode: 34786
    4. Subdivision: Lake Down Pointe 50 42
    5. Elementary School: Thornebrooke Elem
    6. Middle School: Gotha Middle
    7. High School: Olympia High
    8. Provided by: SERHANT
    9. mfrmls
    10. DMCA Notice
    Welcome to an extraordinary 8700+ SQ FT estate located within the GATED COMMUNITY of Marbella in Windemere. This estate offers 40 feet of frontage on Lake Down complete with a private dock and boat li
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    11002 Lake Butler Boulevard
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    Details for 11002 Lake Butler Boulevard, WINDERMERE, FL 34786
    Single Family
    1. Price: $3,999,999.00
    2. Price sqft: $438.26 / sqft
    3. Previous Price: $4,200,000
    4. Last Price Change: 03/20/26
    5. Days On Market: 398
    6. Bedrooms: 5
    7. Baths: 8
    8. Garage / Parking Spaces: 10
    9. Bldg sqft: 9127
    10. Acreage: 1.15 acres
    11. Pool: Yes
    12. Waterfront: Yes
    13. Wateraccess: Yes
    14. Waterfront Type: Lake Privileges
    15. Year Built: 1954
    MLS#: O6284922
    1. County: ORANGE
    2. City: WINDERMERE
    3. Zipcode: 34786
    4. Subdivision: Metcalf Park Rep
    5. Elementary School: Windermere Elem
    6. Middle School: Gotha Middle
    7. High School: Olympia High
    8. Provided by: SERENDIPITY REALTY LLC
    9. mfrmls
    10. DMCA Notice
    Price Adjustment! Lakefront Living in the Heart of Windermere A Rare Opportunity for Multigenerational Luxury Situated along the tranquil, open waters of Wauseon Baypart of the world renowned
    Listing Details and 70 Additional Pictures
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    801 2nd Avenue
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    Details for 801 2nd Avenue, WINDERMERE, FL 34786
    Single Family
    1. Price: $3,995,000.00
    2. Price sqft: $543.09 / sqft
    3. Previous Price: $4,150,000
    4. Last Price Change: 05/02/26
    5. Days On Market: 108
    6. Bedrooms: 5
    7. Baths: 7
    8. Garage / Parking Spaces: 3
    9. Bldg sqft: 7356
    10. Acreage: 0.45 acres
    11. Pool: Yes
    12. Spa/HotTub: Yes
    13. Waterfront: Yes
    14. Wateraccess: Yes
    15. Waterfront Type: Lake Front,Lake Privileges
    16. Year Built: 2008
    MLS#: O6375693
    1. County: ORANGE
    2. City: WINDERMERE
    3. Zipcode: 34786
    4. Subdivision: Aladar On Lake Butler
    5. Elementary School: Windermere Elem
    6. Middle School: Gotha Middle
    7. High School: Olympia High
    8. Provided by: PREMIER SOTHEBY'S INTL. REALTY
    9. mfrmls
    10. DMCA Notice
    Priced below appraised value, this extraordinary Windermere estate presents a rare opportunity to enjoy refined lakefront living on the Butler Chain of Lakes. Set along one of the areas most desirable
    Listing Details and 43 Additional Pictures
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    1206 Sutter Avenue
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    Listing Details for 1206 Sutter Avenue, GOTHA, FL 34734
    Single Family
    1. Price: $3,795,000.00
    2. Price sqft: $419.06 / sqft
    3. Previous Price: $3,995,000
    4. Last Price Change: 05/05/26
    5. Days On Market: 124
    6. Bedrooms: 5
    7. Baths: 6
    8. Garage / Parking Spaces: 4
    9. Bldg sqft: 9056
    10. Acreage: 0.78 acres
    11. Pool: Yes
    12. Waterfront: No
    13. Year Built: 2024
    MLS#: O6371168
    1. County: ORANGE
    2. City: GOTHA
    3. Zipcode: 34734
    4. Subdivision: Gotha Town
    5. Elementary School: Thornebrooke Elem
    6. Middle School: Gotha Middle
    7. High School: Olympia High
    8. Provided by: DOUGLAS ELLIMAN
    9. mfrmls
    10. DMCA Notice
    One or more photo(s) has been virtually staged. Welcome to 1206 Sutter Avenue, a truly exceptional estate and the crown jewel of Gotha, Floridawhere refined luxury meets modern innovation. This 2025 b
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    43 Main Street
    New Construction
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    Listing Details for 43 Main Street, WINDERMERE, FL 34786
    Single Family
    1. Price: $3,500,000.00
    2. Price sqft: $817.76 / sqft
    3. Days On Market: 66
    4. Bedrooms: 4
    5. Baths: 4
    6. Garage / Parking Spaces: 2
    7. Bldg sqft: 4280
    8. Acreage: 0.37 acres
    9. Pool: No
    10. Waterfront: Yes
    11. Wateraccess: Yes
    12. Waterfront Type: Canal - Freshwater
    13. Year Built: 2026
    MLS#: O6387626
    1. County: ORANGE
    2. City: WINDERMERE
    3. Zipcode: 34786
    4. Subdivision: Davis Shores
    5. Elementary School: Windermere Elem
    6. Middle School: Gotha Middle
    7. High School: Olympia High
    8. Provided by: GOLDEN GROUP REALTY LLC
    9. mfrmls
    10. DMCA Notice
    Under Construction. Modern New Construction on the Butler Chain Canal Downtown Windermere Experience bright, modern waterfront living in the heart of the Town of Windermere. This brand new construct
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    10577 Down Lakeview Circle
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    Details for 10577 Down Lakeview Circle, WINDERMERE, FL 34786
    Single Family
    1. Price: $3,450,000.00
    2. Price sqft: $467.92 / sqft
    3. Previous Price: $3,475,000
    4. Last Price Change: 05/07/26
    5. Days On Market: 102
    6. Bedrooms: 4
    7. Baths: 4
    8. Garage / Parking Spaces: 3
    9. Bldg sqft: 7373
    10. Acreage: 2.97 acres
    11. Pool: Yes
    12. Spa/HotTub: Yes
    13. Waterfront: Yes
    14. Wateraccess: Yes
    15. Waterfront Type: Lake Front,Lake Privileges
    16. Year Built: 1986
    MLS#: O6377244
    1. County: ORANGE
    2. City: WINDERMERE
    3. Zipcode: 34786
    4. Subdivision: Lakes
    5. Elementary School: Thornebrooke Elem
    6. Middle School: Gotha Middle
    7. High School: Olympia High
    8. Provided by: THE SIMON SIMAAN GROUP
    9. mfrmls
    10. DMCA Notice
    Experience true lakefront living on the famed Butler Chain of Lakes. This exceptional custom home offers 137 feet of pristine shoreline and sits on nearly one acre of high, dry land with sweeping pano
    Listing Details and 99 Additional Pictures
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    19 Main Street
    New Construction
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    Listing Details for 19 Main Street, WINDERMERE, FL 34786
    Single Family
    1. Price: $3,000,000.00
    2. Price sqft: $721.15 / sqft
    3. Days On Market: 80
    4. Bedrooms: 5
    5. Baths: 5
    6. Garage / Parking Spaces: 2
    7. Bldg sqft: 4160
    8. Acreage: 0.40 acres
    9. Pool: No
    10. Waterfront: Yes
    11. Wateraccess: Yes
    12. Waterfront Type: Canal - Freshwater
    13. Year Built: 2026
    MLS#: O6383837
    1. County: ORANGE
    2. City: WINDERMERE
    3. Zipcode: 34786
    4. Subdivision: Davis Shores
    5. Elementary School: Windermere Elem
    6. Middle School: Gotha Middle
    7. High School: Olympia High
    8. Provided by: GOLDEN GROUP REALTY LLC
    9. mfrmls
    10. DMCA Notice
    Under Construction. New Construction in Downtown Windermere Waterfront on the Butler Chain of Lakes! Experience modern lakefront living in the heart of the golf cartfriendly Town of Windermere. This
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    Equal Housing Opportunity
    Listings provided courtesy of The Hernando County Association of Realtors MLS.
    Listing Data ©2026 REALTOR® Association of Citrus County
    The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.
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    Datafeed Last updated on May 10, 2026 @ 12:00 am
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