Isleworth - Windermere

Located in the heart of Windermere, almost entirely surrounded by bodies of water, is the prestigious and exclusive community of Isleworth. Athletes, CEO's, Medical professionals, and entertainers call the area home. Multi-million dollar estate homes adorn this 600-acre gated community of nearly 900 residents. The world class Isleworth Golf & Country Club boasts the finest of country club experiences. Isleworth real estate is some of the most highly coveted land in all of Florida.

Isleworth Homes for Sale

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New
5199 Latrobe Drive, WINDERMERE

$5,494,000

5199 Latrobe Drive, WINDERMERE

5 Beds 7 Baths 4,665 SqFt Residential MLS® # O6315618
New Pending
9743 Chestnut Ridge Drive, WINDERMERE

$3,250,000

9743 Chestnut Ridge Drive, WINDERMERE

5 Beds 7 Baths 6,328 SqFt Residential MLS® # O6314871
5157 Latrobe Drive, WINDERMERE

$4,777,000

5157 Latrobe Drive, WINDERMERE

6 Beds 9 Baths 5,721 SqFt Residential MLS® # O6312420
9724 Chestnut Ridge Dr, WINDERMERE

$4,800,000

9724 Chestnut Ridge Dr, WINDERMERE

5 Beds 6 Baths 5,557 SqFt Residential MLS® # O6310606
5525 Isleworth Country Club Dr, WINDERMERE

$14,250,000

5525 Isleworth Country Club Dr, WINDERMERE

5 Beds 6 Baths 9,511 SqFt Residential MLS® # O6304800
5067 Latrobe Drive, WINDERMERE

$2,850,000

↓ $47,000

5067 Latrobe Drive, WINDERMERE

5 Beds 8 Baths 6,219 SqFt Residential MLS® # O6292882
6120 Payne Stewart Dr, WINDERMERE

$2,799,000

↓ $100,000

6120 Payne Stewart Dr, WINDERMERE

4 Beds 5 Baths 3,636 SqFt Residential MLS® # O6288273
5138 Fairway Oaks Drive, WINDERMERE

$3,200,000

5138 Fairway Oaks Drive, WINDERMERE

4 Beds 5 Baths 4,330 SqFt Residential MLS® # O6282470
5271 Isleworth Country Club Drive, WINDERMERE

$8,775,000

5271 Isleworth Country Club Drive, WINDERMERE

7 Beds 13 Baths 11,403 SqFt Residential MLS® # O6267644
5126 Fairway Oaks Dr, WINDERMERE

$4,495,000

↓ $295,000

5126 Fairway Oaks Dr, WINDERMERE

5 Beds 5 Baths 5,565 SqFt Residential MLS® # S5113369
Pending
5121 Latrobe Drive, WINDERMERE

$5,250,000

↓ $650,000

5121 Latrobe Drive, WINDERMERE

6 Beds 7 Baths 8,178 SqFt Residential MLS® # O6249529
Pending
5174 Vardon Drive, WINDERMERE

$5,250,000

↓ $250,000

5174 Vardon Drive, WINDERMERE

6 Beds 9 Baths 10,701 SqFt Residential MLS® # O6246894
9832 Laurel Valley Drive, WINDERMERE

$9,490,000

↓ $410,000

9832 Laurel Valley Drive, WINDERMERE

6 Beds 10 Baths 11,100 SqFt Residential MLS® # O6211352
5507 Worsham Court, WINDERMERE

$7,500,000

↓ $350,000

5507 Worsham Court, WINDERMERE

5 Beds 11 Baths 10,200 SqFt Residential MLS® # O6180706
9844 Laurel Valley Drive, WINDERMERE

$4,700,000

↓ $250,000

9844 Laurel Valley Drive, WINDERMERE

5 Beds 6 Baths 5,613 SqFt Residential MLS® # O6173216
Isleworth

Windermere Communities

Isleworth Real Estate Market Statistics

Average Price $5.8M
Lowest Price $2.8M
Highest Price $14.3M
Total Listings 15
Avg. Days On Market 166
Avg. Price/SQFT $800
List to Sell Price Percentage 93 %

Property Types (active listings)


The History of Isleworth | Windermere, Florida

The Windermere, FL community of Isleworth namesake comes from its roots in Florida's citrus production.  The "Isle of Worth" refers to the bountiful land that brothers, Sydney and Joshua Chase, used to develop their citrus company, Chase and Co., formed in 1884.  The Chase brothers drove their horse and buggy to an island by Lake Tibet-Butler, searching for fruit to supplement the scarce supply in Sanford, due to a severe frost.  They discovered the land now known as Isleworth.  While many other growers were leaving the Florida area, the Chase brothers had the foresight to stay in Florida and to expand their land holdings.

Sydney Chase built a cypress bungalow on Lake Louis in 1913, and in 1931, his younger son Frank W. Chase, Sr. went to Windermere to oversee company's activities.  In 1935 Frank and his new wife Helen moved into the beautiful Lake Louise home and lived there until his death in 1986.

After flying over Isleworth, PGA Golf legend Arnold Palmer purchased the land in 1984 with the brilliant idea of creating luxury real estate with a residential community surrounding a world class golf course.  Before anything else, Palmer, along with his development partner The Concord Corporation of San Antonio, planned out the majestic 18-hole golf course exactly to Palmer's grand vision.

In 1993, Palmer sold the 600-acre community of real estate to Aviva Land Holdings.  Working under the motto "Only The Best," the company has redeveloped the land to feature estate homes and luxury living, that has made Isleworth one of Florida's most beloved and desirable upscale communities.

Additional Isleworth Real Estate Information: Isleworth Real Estate


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