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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: 52
    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
    6. High School: Olympia
    7. Provided by: DOUGLAS ELLIMAN
    8. mfrmls
    9. DMCA Notice
    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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    11900 Lake Butler Boulevard
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    Details for 11900 Lake Butler Boulevard, WINDERMERE, FL 34786
    Single Family
    1. Price: $17,250,000.00
    2. Price sqft: $758.98 / sqft
    3. Previous Price: $18,500,000
    4. Last Price Change: 04/16/26
    5. Days On Market: 419
    6. Bedrooms: 7
    7. Baths: 9
    8. Garage / Parking Spaces: 6
    9. Bldg sqft: 22728
    10. Acreage: 3.75 acres
    11. Pool: Yes
    12. Spa/HotTub: Yes
    13. Waterfront: Yes
    14. Wateraccess: Yes
    15. Waterfront Type: Lake Front,Lake Privileges
    16. Year Built: 2014
    MLS#: O6275556
    1. County: ORANGE
    2. City: WINDERMERE
    3. Zipcode: 34786
    4. Subdivision: Metcalf Park Rep
    5. Elementary School: Windermere Elem
    6. Middle School: Chain of Lakes
    7. High School: Olympia
    8. Provided by: STOCKWORTH REALTY GROUP
    9. mfrmls
    10. DMCA Notice
    Presenting Sunset Isle: an iconic waterfront estate compound capturing timeless elegance on Windermeres largest and most prestigious Lake Butler, offering captivating unobstructed views from its 700 f
    Listing Details and 90 Additional Pictures
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    9323 Gladys Garden Court
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    Details for 9323 Gladys Garden Court, WINDERMERE, FL 34786
    Single Family
    1. Price: $12,500,000.00
    2. Price sqft: $999.20 / sqft
    3. Previous Price: $13,995,000
    4. Last Price Change: 04/04/26
    5. Days On Market: 84
    6. Bedrooms: 6
    7. Baths: 10
    8. Garage / Parking Spaces: 4
    9. Bldg sqft: 12510
    10. Acreage: 0.26 acres
    11. Pool: Yes
    12. Waterfront: No
    13. Year Built: 2026
    MLS#: O6381880
    1. County: ORANGE
    2. City: WINDERMERE
    3. Zipcode: 34786
    4. Subdivision: Isleworth
    5. Elementary School: Windermere Elem
    6. Middle School: Chain of Lakes
    7. High School: Olympia
    8. Provided by: CORCORAN PREMIER REALTY
    9. mfrmls
    10. DMCA Notice
    Brand new construction and fully furnished! Architecturally refined and intentionally designed by Ashley Martin Home, this custom estate is a masterclass in proportion, craftsmanship, and quiet luxury
    Listing Details and 83 Additional Pictures
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    4226 Downeast Lane
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    Details for 4226 Downeast Lane, WINDERMERE, FL 34786
    Single Family
    1. Price: $10,500,000.00
    2. Price sqft: $1,232.97 / sqft
    3. Previous Price: $11,800,000
    4. Last Price Change: 04/09/26
    5. Days On Market: 196
    6. Bedrooms: 5
    7. Baths: 3
    8. Garage / Parking Spaces: 4
    9. Bldg sqft: 8516
    10. Acreage: 9.03 acres
    11. Pool: Yes
    12. Waterfront: Yes
    13. Wateraccess: Yes
    14. Waterfront Type: Lake Front
    15. Year Built: 1980
    MLS#: O6355233
    1. County: ORANGE
    2. City: WINDERMERE
    3. Zipcode: 34786
    4. Elementary School: Windermere Elem
    5. Middle School: Chain of Lakes
    6. High School: Olympia
    7. Provided by: COLDWELL BANKER RESIDENTIAL RE
    8. mfrmls
    9. DMCA Notice
    Dramatic price improvement. Exceptional development opportunity, currently r ce zoning should allow for 3 luxury home sites discover over 5+acres of waterfront land with 300 feet of pristine shorelin
    Listing Details and 28 Additional Pictures
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    4226 Downeast Lane
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    Details for 4226 Downeast Lane, WINDERMERE, FL 34786
    Land
    1. Price: $10,500,000.00
    2. Previous Price: $11,800,000
    3. Last Price Change: 04/09/26
    4. Days On Market: 143
    5. Acreage: 9.03 acres
    6. Pool: No
    7. Waterfront: Yes
    8. Wateraccess: Yes
    9. Waterfront Type: Lake Privileges
    10. Year Built: Not Available
    MLS#: O6367852
    1. County: ORANGE
    2. City: WINDERMERE
    3. Zipcode: 34786
    4. Elementary School: Windermere Elem
    5. Middle School: Chain of Lakes
    6. High School: Olympia
    7. Provided by: COLDWELL BANKER RESIDENTIAL RE
    8. mfrmls
    9. DMCA Notice
    Dramatic price improvement. Exceptional development opportunity, currently r ce zoning should allow for 3 luxury home sites discover over 5+acres of waterfront land with 300 feet of pristine shoreline
    Listing Details and 27 Additional Pictures
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    5186 Vardon Drive
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    Details for 5186 Vardon Drive, WINDERMERE, FL 34786
    Single Family
    1. Price: $6,980,000.00
    2. Price sqft: $886.35 / sqft
    3. Previous Price: $4,960,000
    4. Last Price Change: 04/18/26
    5. Days On Market: 83
    6. Bedrooms: 4
    7. Baths: 5
    8. Garage / Parking Spaces: 3
    9. Bldg sqft: 7875
    10. Acreage: 1.01 acres
    11. Pool: Yes
    12. Waterfront: No
    13. Year Built: 1990
    MLS#: O6382040
    1. County: ORANGE
    2. City: WINDERMERE
    3. Zipcode: 34786
    4. Subdivision: Isleworth
    5. Elementary School: Windermere Elem
    6. Middle School: Chain of Lakes
    7. High School: Olympia
    8. Provided by: FLORIDA REALTY INVESTMENTS
    9. mfrmls
    10. DMCA Notice
    One or more photo(s) has been virtually staged. Fully reimagined golf front estate in the prestigious Isleworth community with sweeping views of the iconic 3rd hole. Situated on approximately 1 acre,
    Listing Details and 60 Additional Pictures
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    9725 Chestnut Ridge Drive
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    Details for 9725 Chestnut Ridge Drive, WINDERMERE, FL 34786
    Single Family
    1. Price: $6,000,000.00
    2. Price sqft: $502.01 / sqft
    3. Previous Price: $6,150,000
    4. Last Price Change: 05/02/26
    5. Days On Market: 126
    6. Bedrooms: 7
    7. Baths: 7
    8. Garage / Parking Spaces: 3
    9. Bldg sqft: 11952
    10. Acreage: 0.56 acres
    11. Pool: Yes
    12. Spa/HotTub: Yes
    13. Waterfront: Yes
    14. Wateraccess: Yes
    15. Waterfront Type: Pond
    16. Year Built: 1999
    MLS#: O6370294
    1. County: ORANGE
    2. City: WINDERMERE
    3. Zipcode: 34786
    4. Subdivision: Isleworth
    5. Elementary School: Windermere Elem
    6. Middle School: Chain of Lakes
    7. High School: Olympia
    8. Provided by: DOUGLAS ELLIMAN
    9. mfrmls
    10. DMCA Notice
    Newly renovated, this private Isleworth residence offers a rare balance of architectural authority, thoughtful design, and quiet indulgence. Spanning approximately 8,000 square feet, the home unfolds
    Listing Details and 60 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: 04/30/26
    5. Days On Market: 242
    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
    7. High School: Olympia
    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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    5138 Fairway Oaks Dr
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    Details for 5138 Fairway Oaks Dr, WINDERMERE, FL 34786
    Single Family
    1. Price: $5,500,000.00
    2. Price sqft: $930.47 / sqft
    3. Days On Market: 13
    4. Bedrooms: 4
    5. Baths: 5
    6. Garage / Parking Spaces: 3
    7. Bldg sqft: 5911
    8. Acreage: 0.50 acres
    9. Pool: Yes
    10. Spa/HotTub: Yes
    11. Waterfront: No
    12. Year Built: 1994
    MLS#: O6401757
    1. County: ORANGE
    2. City: WINDERMERE
    3. Zipcode: 34786
    4. Subdivision: Isleworth
    5. Elementary School: Windermere Elem
    6. Middle School: Chain of Lakes
    7. High School: Olympia
    8. Provided by: ISLEWORTH REALTY LLC
    9. mfrmls
    10. DMCA Notice
    Set along Isleworths signature 12th fairway, this fully reimagined estate captures the essence of refined golf course living within the renowned Isleworth Golf & Country Clubrecognized among the fines
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    5243 Isleworth Country Club Drive
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    Details for 5243 Isleworth Country Club Drive, WINDERMERE, FL 34786
    Single Family
    1. Price: $5,100,000.00
    2. Price sqft: $703.84 / sqft
    3. Previous Price: $5,325,000
    4. Last Price Change: 03/12/26
    5. Days On Market: 211
    6. Bedrooms: 4
    7. Baths: 6
    8. Garage / Parking Spaces: 3
    9. Bldg sqft: 7246
    10. Acreage: 0.51 acres
    11. Pool: Yes
    12. Waterfront: No
    13. Year Built: 1992
    MLS#: O6348067
    1. County: ORANGE
    2. City: WINDERMERE
    3. Zipcode: 34786
    4. Subdivision: Isleworth
    5. Elementary School: Windermere Elem
    6. Middle School: Chain of Lakes
    7. High School: Olympia
    8. Provided by: STOCKWORTH REALTY GROUP
    9. mfrmls
    10. DMCA Notice
    Presenting a magnificent Isleworth golf front estate with sweeping lake views, perched above holes #2 and #9 and Lake Chase, combining a completely reimagined interior with designer elegance and moder
    Listing Details and 64 Additional Pictures
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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.
    Display of MLS data is usually deemed reliable but is NOT guaranteed accurate.
    Datafeed Last updated on May 9, 2026 @ 12:00 am
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