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 $5,200,000 to $15,000,000.

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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. Lake Louise Drive

Lake Louise Drive is the 2nd most expensive street in Windermere. It has single-family homes built in 2012, with an average sale price of $11,100,000. It is home to the Isleworth subdivision.

Average Price: $11,100,000
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3. Laurel Valley Drive

Laurel Valley Drive is the 3rd most expensive street in Windermere. It has single-family homes built in 2004, with an average sale price of $9,000,000. It is home to the Isleworth subdivision.

Average Price: $9,000,000
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4. Kirkstone Lane

Kirkstone Lane is the 4th most expensive street in Windermere. It has single-family homes built in 2002, with an average sale price of $6,800,000. It is home to the Reserve at Lake Butler Sound subdivision.

Average Price: $6,800,000
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5. Worsham Court

Worsham Court is the 5th most expensive street in Windermere. It has single-family homes built in 2003, with an average sale price of $6,175,000. It is home to the Isleworth subdivision.

Average Price: $6,175,000
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6. Isleworth Country Club Drive

Isleworth Country Club Drive is the 6th most expensive street in Windermere. It has single-family homes and land ranging in price from $3,500,000 to $8,500,000. It is home to the Isleworth subdivision.

Average Price: $6,000,000
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7. Park Avenue

Park Avenue is the 7th most expensive street in Windermere. It has single-family homes and land built from 1985 to 1996, ranging in price from $835,000 to $8,000,000. It is home to the Chaine Du Lac and Wauseon Ridge subdivisions.

Average Price: $5,611,666.67
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8. Deacon Circle

Deacon Circle is the 8th most expensive street in Windermere. It has single-family homes built from 1989 to 1991, ranging in price from $4,250,000 to $6,750,000. It is home to the Isleworth subdivision.

Average Price: $5,500,000
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9. Down Reserve Court

Down Reserve Court is the 9th most expensive street in Windermere. It has single-family homes built from 2021 to 2025, ranging in price from $4,500,000 to $6,000,000. It is home to the Lake Down Reserve subdivision.

Average Price: $5,250,000
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10. Vardon Drive

Vardon Drive is the 10th most expensive street in Windermere. It has single-family homes built from 1990 to 2008, with an average sale price of $5,200,000. It is home to the Isleworth subdivision.

Average Price: $5,200,000
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