Florida Neighborhood Realty
  • Sell Your Florida Home
  • Buy A Florida Home
  • Advanced Home Search
Login
407.801.3286

Sign in to your account

Need to reset your phone number?

Don't have an account with us?

Click here to sign up.
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

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
5192 Vardon Drive, Windermere image
5192 Vardon Drive, Windermere $19,500,000

Timeless elegance and extraordinary privacy define this magnificent lakefront estate within the renowned Isleworth Golf & Country Club. Gracefully positioned on Lake Bla...

  • 6 Beds
  • 10 Baths
  • Isleworth Amd 03 SubDv.
  • 34786 Zip Code
5036 Latrobe Drive, Windermere image
5036 Latrobe Drive, Windermere $18,750,000

Virtually Staged. Pre-Construction. To be built. Poised on a remarkable .69-acre homesite along the shores of Lake Bessie, this exceptional new residence offers a rare op...

  • 6 Beds
  • 9 Baths
  • Isleworth 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 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
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
4226 Downeast Lane, Windermere image
4226 Downeast Lane, Windermere $9,250,000 ▼

NEW 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...

  • 5 Beds
  • 3 Baths
  • Na SubDv.
  • 34786 Zip Code
5092 Isleworth Country Club Drive, Windermere image
5092 Isleworth Country Club Drive, Windermere $8,500,000

Set along the front nine of Isleworth championship golf course with breathtaking views of Hole 6, this grand estate occupies an oversized lot along Isleworth’s main drive...

  • 4 Beds
  • 5 Baths
  • Isleworth SubDv.
  • 34786 Zip Code
9343 Tibet Pointe Circle, Windermere image
9343 Tibet Pointe Circle, Windermere $7,450,000

Located directly on Lake Tibet within the guard-gated community of Keene’s Pointe, this extensively updated Stonebridge custom residence blends Mediterranean-inspired arc...

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

Address Search

Realtor David MyersDavid Myers
Your Windermere Neighborhood Expert
Call/Text: 407.801.3286
Windermere Home Buyers Guide

Windermere Neighborhoods

  • Arlington Bay
  • Ashlin Park
  • Balmoral
  • Bellaria
  • Bella Vita
  • Belmere Village
  • Berkshire Park
  • Butler Ridge
  • Carrington
  • Casa Del Lago
  • Casabella
  • Chaine Du Lac
  • Courtleigh Park
  • Crescent Lake Estates
  • Cypress Chase
  • Cypress Isle
  • Eden Isle
  • Enclave Wndrmr Lndng
  • Estancia Windermere
  • Estates at Lake Clarice
  • Estates at Windermere
  • Glenmuir
  • Grande Pines
  • Harbor Isle
  • Havencrest
  • Isleworth
  • Keenes Pointe
  • Lake Burden
  • Lake Butler Estates
  • Lake Butler Sound
  • Lake Buynak Estates
  • Lake Cawood Cove
  • Lake Cawood Estates
  • Lake Crescent Reserve
  • Lake Cypress Cove
  • Lake Down Cove
  • Lake Down Crest
  • Lake Down Estates
  • Lake Down Reserve
  • Lake Down Shores
  • Lake Mabel Shores
  • Lake Olivia Reserve
  • Lake Reams Townhomes
  • Lake Sawyer
  • Lake Sheen Reserve
  • Lakes at Lake Down
  • Lakes of Windermere
  • Lakeside
  • Lakeside Village
  • Legado
  • Les Terraces
  • Mabel Bridge
  • Magnolia Park
  • Manors at Butler Bay
  • Marina Bay Estates
  • Merrick Landing
  • Newbury Park
  • Oasis Cove
  • Oxford Moor
  • Palms at Windermere
  • Peachtree Park
  • Prsrve Lks Windermere
  • Preston Square
  • Providence
  • Providence Lake Sheen
  • Reserve at Belmere
  • Reserve at Windermere
  • Roberts Landing
  • Royal Cypress Preserve
  • Royal Estates
  • Royal Ranch Estates
  • Sawyer Sound
  • Silver Woods
  • Southbridge Village
  • Southern Acres
  • Summerport
  • Sunset Bay
  • Thornhill
  • Tildens Grove
  • Tuscany Ridge
  • Vineyards
  • Waterford Pointe
  • Waterstone
  • Weatherstone
  • West Lake Butler Estates
  • Westminster Landing
  • Westover Club
  • Westover Reserve
  • Westside Village
  • Wickham Park
  • Willows at Lake Rhea
  • Windermere Club
  • Windermere Downs
  • Windermere Grande
  • Windermere Isle
  • Windermere Landing
  • Windermere Oaks
  • Windermere Pointe
  • Windermere Reserve
  • Windermere Ridge
  • Windermere Sound
  • Windermere Terrace
  • Windermere Town
  • Windermere Trails
  • Windsor Hill
  • Windstone
  • Woods of Windermere
  • Worthington Park

Windermere Interactive Map Search

Windermere Interactive Real Estate Map Search

Popular Windermere Searches

  • Active Adult
  • Commercial
  • Condos
  • Foreclosures
  • Gated Homes
  • Golf Front Homes
  • Land
  • Luxury Homes
  • New Construction
  • No HOA Homes
  • One Story Homes
  • Pool Homes
  • Townhomes
  • Waterfront Homes

Realtor David Myers - Florida Neighborhood Realty

Windermere FYI

  • About Windermere
  • Butler Chain of Lakes
  • Windermere Insider
  • Community Contacts
  • Arts & Culture
  • Fun Things to Do
  • Health & Wellness
  • Home Builders
  • Parks & Recreation
  • Restaurants & Dining
  • Schools & Education
  • Shopping Guide
  • Sports & Athletics
  • Where is Windermere

About Florida Neighborhood Realty powered by Ziro Realty

Ziro in on Windermere

  • Buy a Windermere Home
  • Sell Your Windermere Home
  • Windermere Home Valuation
  • Windermere Market Report
  • Get a Mortgage
  • Visit Our Other Sites:
  • NonaOrlandoProperties.com
  • MyOrlandoVacationHome.com

David Myers - Broker Associate
Florida Neighborhood Realty Team
Ziro Realty, LLC
549B Water Street
Celebration, FL 34747
Phone/Text: 407.801.3286
Web: FloridaNeighborhoodRealty.com
Stay Updated: Subscribe to Our Blog RSS Feed

Realtor, MLS, and Equal Housing Opportunity logos

© Florida Neighborhood Realty LLC - All Rights Reserved

Site Support

  • About Us
  • Facebook
  • Terms of Use
  • Contact Us
  • Instagram
  • Privacy Policy
  • Office Listings
  • Neighborhood Blog
  • AI & Data Disclaimer
IDX Real Estate Websites by
• Accessibility • Terms • Privacy
80402