Skip to Main Content
  1. Home
  2. Search Listings
  3. Search Results
Searching on:
  1. School = Olympia High
  2. Listing Status = Active
9508 Windy Ridge Road
Virtual Tour
Green Listing
More Like This
Active
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: 37
  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
  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
Request more information about this listing.
11900 Lake Butler Boulevard
Virtual Tour
More Like This
Active
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: 04/15/26
  5. Days On Market: 404
  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 Middle
  7. High School: Olympia High
  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
Request more information about this listing.
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: 69
  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.
4226 Downeast Lane
Virtual Tour
More Like This
Active
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: 128
  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 Middle
  6. High School: Olympia High
  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
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. Previous Price: $4,960,000
  3. Last Price Change: 04/18/26
  4. Days On Market: 69
  5. Bedrooms: 4
  6. Baths: 5
  7. Garage / Parking Spaces: 3
  8. Bldg sqft: 7875
  9. Acreage: 1.01 acres
  10. Pool: Yes
  11. Waterfront: No
  12. 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.
11 Main Street
New Construction
More Like This
Active
Details for 11 Main Street, WINDERMERE, FL 34786
Single Family
  1. Price: $6,700,000.00
  2. Price sqft: $1,095.85 / sqft
  3. Days On Market: 50
  4. Bedrooms: 5
  5. Baths: 5
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 6114
  8. Acreage: 0.41 acres
  9. Pool: No
  10. Waterfront: Yes
  11. Wateraccess: Yes
  12. Waterfront Type: Canal - Freshwater
  13. Year Built: 2026
MLS#: O6387596
  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. Brand New Construction in the Heart of Downtown Windermere Currently Under Construction! Walking distance to downtown events, the farmers market, food trucks, and the local bre
Listing Details and 3 Additional Pictures
Request more information about this listing.
9639 Westover Roberts Road
Virtual Tour
More Like This
Active
Details for 9639 Westover Roberts Road, WINDERMERE, FL 34786
Single Family
  1. Price: $6,395,000.00
  2. Price sqft: $324.52 / sqft
  3. Days On Market: 227
  4. Bedrooms: 5
  5. Baths: 9
  6. Garage / Parking Spaces: 7
  7. Bldg sqft: 19706
  8. Acreage: 4.43 acres
  9. Pool: Yes
  10. Spa/HotTub: Yes
  11. Waterfront: Yes
  12. Wateraccess: Yes
  13. Waterfront Type: Lake Front
  14. 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 64 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: $6,150,000.00
  2. Price sqft: $514.56 / sqft
  3. Previous Price: $6,950,000
  4. Last Price Change: 04/15/26
  5. Days On Market: 112
  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 56 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: 196
  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.
9575 Westover Roberts Road
Virtual Tour
More Like This
Active
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: 163
  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
Request more information about this listing.
Refine Search
No Properties Found
Tropic Shores Realty - Spring Hill
#cq1021318
Disclaimer: All information provided is deemed to be reliable but not guaranteed.
Equal Housing Opportunity
Listing Data ©2026 Greater Fort Lauderdale REALTORS®
Listings provided courtesy of The Hernando County Association of Realtors MLS.
Listing Data ©2026 REALTOR® Association of Citrus County
Listing Data ©2026 Royal Palm Coast Realtor® Association
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 April 24, 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