Top 10 Most Expensive Streets in Windermere, FL

The following are the Top 10 most expensive streets in Windermere. The average price for homes on these streets range from $5,500,000 to $15,000,000.

1. Champions Point

Champions Point is the 1st most expensive street in Windermere. It has land with an average sale price of $15,000,000. It is home to the Isleworth subdivision.

Average Price: $15,000,000
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2. Blanche Cove Drive

Blanche Cove Drive is the 2nd most expensive street in Windermere. It has single-family homes built in 2022, with an average sale price of $13,000,000. It is home to the Isleworth subdivision.

Average Price: $13,000,000
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3. Isleworth Country Club Dr Drive

Isleworth Country Club Dr Drive is the 3rd most expensive street in Windermere. It has single-family homes built in 2003, with an average sale price of $7,000,000. It is home to the Isleworth subdivision.

Average Price: $7,000,000
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4. Grosvenor Shore Drive

Grosvenor Shore Drive is the 4th most expensive street in Windermere. It has single-family homes and land with an average sale price of $6,500,000. It is home to the Keenes Pointe subdivision.

Average Price: $6,500,000
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5. Grosvenor Shore Dr

Grosvenor Shore Dr is the 5th most expensive street in Windermere. It has single-family homes built from 2009 to 2013, with an average sale price of $6,000,000. It is home to the Keenes Pointe subdivision.

Average Price: $6,000,000
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6. Green Island Cove

Green Island Cove is the 6th most expensive street in Windermere. It has single-family homes built in 1986, with an average sale price of $5,990,000. It is home to the Isleworth subdivision.

Average Price: $5,990,000
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7. Worsham Court Court

Worsham Court Court is the 7th most expensive street in Windermere. It has single-family homes built in 2008, with an average sale price of $5,719,050. It is home to the Isleworth subdivision.

Average Price: $5,719,050
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8. Rosella Court

Rosella Court is the 8th most expensive street in Windermere. It has single-family homes built from 2007 to 2008, ranging in price from $5,475,000 to $5,900,000. It is home to the Keenes Pointe subdivision.

Average Price: $5,687,500
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9. Kelso Boulevard

Kelso Boulevard is the 9th most expensive street in Windermere. It has single-family homes built from 1977 to 2008, with an average sale price of $5,600,000. It is home to the Kelso on Lake Butler subdivision.

Average Price: $5,600,000
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10. Laurel Valley Drive

Laurel Valley Drive is the 10th most expensive street in Windermere. It has single-family homes built from 1987 to 2004, with an average sale price of $5,500,000. It is home to the Isleworth subdivision.

Average Price: $5,500,000
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