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Home › Windermere › 10 Most Expensive Listings

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

9508 Windy Ridge Road, Windermere image
9508 Windy Ridge Road, Windermere $30,000,000

Showcasing Central Florida’s most iconic lakefront estate: an 18-acre compound with 614 feet of pristine frontage on Lake Down on The Butler Chain of Lakes. The Windy Rid...

  • 7 Beds
  • 14 Baths
  • N/A SubDv.
  • 34786 Zip Code
5603 Marleon Drive, Windermere image
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
11900 Lake Butler Boulevard, Windermere image
11900 Lake Butler Boulevard, Windermere $17,250,000 ▼

Presenting Sunset Isle: an iconic waterfront estate compound capturing timeless elegance on Windermere’s largest and most prestigious Lake Butler, offering captivating un...

  • 7 Beds
  • 9 Baths
  • Metcalf Park Rep 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...

  • 7 Beds
  • 9 Baths
  • Keene's Point SubDv.
  • 34786 Zip Code
12488 Park Avenue, Windermere image
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 image
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
9621 Windy Ridge Road, Windermere image
9621 Windy Ridge Road, Windermere $12,999,999 ▼

Under Construction. Under Construction. Experience unmatched privacy, prestige, and personalization with this brand-new mansion on 2.5 pristine acres in the heart of Wind...

  • 9 Beds
  • 16 Baths
  • Windsor Hill SubDv.
  • 34786 Zip Code
9832 Laurel Valley Drive, Windermere image
9832 Laurel Valley Drive, Windermere $12,750,000 ▼

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
9312 Blanche Cove Dr, Windermere image
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
728 Forest Street, Windermere image
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
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Realtor David MyersDavid Myers
Your Windermere Neighborhood Expert
Call/Text: 407.801.3286
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Windermere Neighborhoods

  • Arlington Bay
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