The Top 10 Most Expensive Residential Real Estate Listings in Windermere on the Market Right Now

Windermere is one of the most desirable addresses in Central Florida and features some of the most luxurious homes in the most exclusive neighborhoods. Here is a fun peak into ten of the most expensive residential real estate listings in Windermere that are currently on the market.

Top 10 Most Expensive Listings in Windermere

5603 Marleon Drive, Windermere $27,000,000

A rare legacy estate of extraordinary scale and architectural significance, this magnificent lakefront compound spans over 22,000 square feet across more than 11 private ...

7 Beds
10 Baths
Na SubDv.
34786 Zip Code

6119 Grosvenor Shore Drive, Windermere image

6119 Grosvenor Shore Drive, Windermere $15,900,000

Experience luxury lakefront living on a grand scale in this exquisite estate on Lake Tibet, part of the pristine Butler Chain of Lakes in Windermere. This custom-built ma...

8 Beds
11 Baths
Keenes Point SubDv.
34786 Zip Code

12488 Park Avenue, Windermere $15,500,000

Commanding a rare 2.75-acre lakefront setting on the coveted Butler Chain of Lakes, this extraordinary Windermere estate is a true work of art. Recently completed after a...

10 Beds
17 Baths
Chaine Du Lac SubDv.
34786 Zip Code

3057 Porto Lago Court, Windermere $13,995,000

BRAND NEW ESTATE. A truly exceptional one-of-one on the shores of Lake Down, boasting over 12,000SF, 6BR's, 6/5BA's, and unmatched multigenerational flexibility. Designed...

6 Beds
11 Baths
Lake Down Pointe 50 42 SubDv.
34786 Zip Code

9312 Blanche Cove Dr, Windermere $12,350,000

Set along beautiful Lake Blanche within the gates of Isleworth, this extraordinary modern estate is a grand haven of remarkable scale and design. Spanning more than 11,00...

7 Beds
10 Baths
Isleworth 5th Amd SubDv.
34786 Zip Code

9323 Gladys Garden Court, Windermere image

9323 Gladys Garden Court, Windermere $11,900,000 ▼

Brand new construction and fully furnished! Architecturally refined and intentionally designed by Ashley Martin Home, this custom estate is a masterclass in proportion, c...

6 Beds
10 Baths
Isleworth SubDv.
34786 Zip Code

9832 Laurel Valley Drive, Windermere image

9832 Laurel Valley Drive, Windermere $11,750,000 ▼

Virtually Staged. A true Lake Butler trophy estate. Set within the world-famous gates of Isleworth and commanding panoramic western sunset water views of Lake Butler from...

6 Beds
10 Baths
Isleworth SubDv.
34786 Zip Code

728 Forest Street, Windermere $10,200,000

An extraordinary brand-new contemporary lakefront estate on prestigious LAKE BUTLER, part of the renowned Butler Chain of Lakes, offering an exceptional blend of architec...

6 Beds
9 Baths
Windermere Town SubDv.
34786 Zip Code

4226 Downeast Lane, Windermere $9,750,000 ▼

DRAMATIC PRICE IMPROVEMENT on this exceptional 5+ acre LAKE DOWN development opportunity, offering 300 feet of pristine shoreline on the coveted BUTLER CHAIN of Lakes and...

5 Beds
3 Baths
Na SubDv.
34786 Zip Code

9343 Tibet Pointe Circle, Windermere image

9343 Tibet Pointe Circle, Windermere $7,695,000 ▼

PRICE Improvenent!! Perfectly sited on pristine Lake Tibet in Keene's Pointe Country Club, this stunning lakefront Stonebridge custom home has been completely updated. ...

7 Beds
10 Baths
Keenes Pointe Unit 03 46/104 SubDv.
34786 Zip Code

The Top 10 Most Expensive Residential Real Estate Listings in Windermere on the Market Right Now

Top 10 Most Expensive Listings in Windermere

Address Search

Windermere Neighborhoods

Windermere Interactive Map Search

Popular Windermere Searches

Windermere FYI

Ziro in on Windermere