Email: | Brokerage: HR Moon Homes
    1. Home
    2. Search Listings
    3. Search Results
    Searching on:
    1. Subdivision Like Isleworth
    2. Listing Status = Active
    9323 Gladys Garden Court
    Virtual Tour
    New Construction
    More Like This
    Active
    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: 04/03/26
    5. Days On Market: 85
    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 Middle
    7. High School: Olympia High
    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
    Request more information about this listing.
    5074 Isleworth Country Club Drive
    More Like This
    Active
    Details for 5074 Isleworth Country Club Drive, WINDERMERE, FL 34786
    Single Family
    1. Price: $7,595,000.00
    2. Price sqft: $847.56 / sqft
    3. Days On Market: 115
    4. Bedrooms: 5
    5. Baths: 7
    6. Garage / Parking Spaces: 3
    7. Bldg sqft: 8961
    8. Acreage: 0.54 acres
    9. Pool: Yes
    10. Waterfront: No
    11. Year Built: 1988
    MLS#: O6373191
    1. County: ORANGE
    2. City: WINDERMERE
    3. Zipcode: 34786
    4. Subdivision: Isleworth
    5. Provided by: MEMARPOURI REALTY LLC
    6. mfrmls
    7. DMCA Notice
    A masterfully reimagined golf front estate, this residence offers an unparalleled standard of luxury within the acclaimed guard gated community of Isleworth. Completely reimagined and expanded, the re
    Listing Details and 79 Additional Pictures
    Request more information about this listing.
    5186 Vardon Drive
    Virtual Tour
    More Like This
    Active
    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: $698,000
    4. Last Price Change: 04/20/26
    5. Days On Market: 85
    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 Middle
    7. High School: Olympia High
    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
    Request more information about this listing.
    9725 Chestnut Ridge Drive
    Virtual Tour
    More Like This
    Active
    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: 128
    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 Middle
    7. High School: Olympia High
    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
    Request more information about this listing.
    5138 Fairway Oaks Dr
    Virtual Tour
    More Like This
    Active
    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: 14
    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 Middle
    7. High School: Olympia High
    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
    Listing Details and 50 Additional Pictures
    Request more information about this listing.
    6117 Louise Cove Drive
    Virtual Tour
    Reduced
    More Like This
    Active
    Details for 6117 Louise Cove Drive, WINDERMERE, FL 34786
    Single Family
    1. Price: $5,250,000.00
    2. Price sqft: $675.50 / sqft
    3. Previous Price: $5,400,000
    4. Last Price Change: 05/05/26
    5. Days On Market: 120
    6. Bedrooms: 4
    7. Baths: 5
    8. Garage / Parking Spaces: 3
    9. Bldg sqft: 7772
    10. Acreage: 0.79 acres
    11. Pool: Yes
    12. Waterfront: Yes
    13. Wateraccess: Yes
    14. Waterfront Type: Lake Privileges
    15. Year Built: 2002
    MLS#: O6372197
    1. County: ORANGE
    2. City: WINDERMERE
    3. Zipcode: 34786
    4. Subdivision: Isleworth West
    5. Elementary School: Windermere Elem
    6. Middle School: Bridgewater Middle
    7. High School: Windermere High School
    8. Provided by: ISLEWORTH REALTY LLC
    9. mfrmls
    10. DMCA Notice
    Nestled along the shores of Lake Louise within Isleworth West, this exceptional two story estate represents the finest in lakefront living. Offering four bedrooms, four and a half baths, and more than
    Listing Details and 57 Additional Pictures
    Request more information about this listing.
    5243 Isleworth Country Club Drive
    Virtual Tour
    More Like This
    Active
    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: 03/11/26
    5. Days On Market: 212
    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 Middle
    7. High School: Olympia High
    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
    Request more information about this listing.
    5151 Latrobe Dr
    Virtual Tour
    Reduced
    More Like This
    Active
    Details for 5151 Latrobe Dr, WINDERMERE, FL 34786
    Single Family
    1. Price: $3,900,000.00
    2. Price sqft: $543.78 / sqft
    3. Previous Price: $4,100,000
    4. Last Price Change: 05/05/26
    5. Days On Market: 50
    6. Bedrooms: 4
    7. Baths: 5
    8. Garage / Parking Spaces: 3
    9. Bldg sqft: 7172
    10. Acreage: 0.51 acres
    11. Pool: Yes
    12. Waterfront: No
    13. Year Built: 2000
    MLS#: O6392380
    1. County: ORANGE
    2. City: WINDERMERE
    3. Zipcode: 34786
    4. Subdivision: Isleworth
    5. Provided by: ISLEWORTH REALTY LLC
    6. mfrmls
    7. DMCA Notice
    Positioned along the stunning 4th fairway of the renowned Isleworth Golf & Country Club, this exceptional single story estate offers four bedrooms and more than 5,300 square feet of meticulously craft
    Listing Details and 56 Additional Pictures
    Request more information about this listing.
    9648 Mccormick Place
    Virtual Tour
    More Like This
    Active
    Details for 9648 Mccormick Place, WINDERMERE, FL 34786
    Single Family
    1. Price: $3,800,000.00
    2. Price sqft: $529.99 / sqft
    3. Days On Market: 225
    4. Bedrooms: 3
    5. Baths: 4
    6. Garage / Parking Spaces: 3
    7. Bldg sqft: 7170
    8. Acreage: 0.54 acres
    9. Pool: Yes
    10. Spa/HotTub: Yes
    11. Waterfront: No
    12. Year Built: 1988
    MLS#: O6346918
    1. County: ORANGE
    2. City: WINDERMERE
    3. Zipcode: 34786
    4. Subdivision: Isleworth
    5. Elementary School: Windermere Elem
    6. Middle School: Chain of Lakes Middle
    7. High School: Olympia High
    8. Provided by: ISLEWORTH REALTY LLC
    9. mfrmls
    10. DMCA Notice
    Stunning golf and lake views and beautifully updated grounds are hallmarks of this elegant Isleworth estate. Nestled along the front nine overlooking Isleworths 2nd fairway and beautiful Lake Chase, t
    Listing Details and 60 Additional Pictures
    Request more information about this listing.
    4812 Alexandra Garden Court
    Virtual Tour
    More Like This
    Active
    Details for 4812 Alexandra Garden Court, WINDERMERE, FL 34786
    Single Family
    1. Price: $3,699,000.00
    2. Price sqft: $495.38 / sqft
    3. Days On Market: 248
    4. Bedrooms: 3
    5. Baths: 5
    6. Garage / Parking Spaces: 2
    7. Bldg sqft: 7467
    8. Acreage: 0.26 acres
    9. Pool: Yes
    10. Spa/HotTub: Yes
    11. Waterfront: No
    12. Year Built: 2007
    MLS#: O6339134
    1. County: ORANGE
    2. City: WINDERMERE
    3. Zipcode: 34786
    4. Subdivision: Isleworth
    5. Elementary School: Windermere Elem
    6. Middle School: Chain of Lakes Middle
    7. High School: Olympia High
    8. Provided by: STOCKWORTH REALTY GROUP
    9. mfrmls
    10. DMCA Notice
    Luxury villa living within the exclusive Gardens of Isleworth, part of the Isleworth Golf & Country Club. This exceptional Southpoint built residence boasts a captivating courtyard floor plan that pro
    Listing Details and 65 Additional Pictures
    Request more information about this listing.
    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 10, 2026 @ 12:00 am
    ©2006-2026 brokerIDXsites.com - https://brokerIDXsites.com
    We believe in accessibility for all
    Your Privacy Is Important
    XML Sitemap
    Manage Your Account