Top 10 Most Expensive Streets in Sheboygan, WI

The following are the Top 10 most expensive streets in Sheboygan. The average price for homes on these streets range from $700,000 to $1,490,000.

1. Dennwood Dr

Dennwood Dr is the 1st most expensive street in Sheboygan. It has single-family homes built in 1995, with an average sale price of $1,490,000.

Average Price: $1,490,000
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2. Baronwood Way

Baronwood Way is the 2nd most expensive street in Sheboygan. It has land and single-family homes built from 2002 to 2003, ranging in price from $224,900 to $2,000,000.

Average Price: $1,034,966.67
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3. Oak Tree Rd

Oak Tree Rd is the 3rd most expensive street in Sheboygan. It has single-family homes built from 1961 to 1969, with an average sale price of $909,900.

Average Price: $909,900
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4. Bender Ct

Bender Ct is the 4th most expensive street in Sheboygan. It has single-family homes built in 1998, with an average sale price of $900,000.

Average Price: $900,000
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5. Blackstock Rd

Blackstock Rd is the 5th most expensive street in Sheboygan. It has single-family homes built in 1991, with an average sale price of $865,000.

Average Price: $865,000
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6. Birch Tree Rd

Birch Tree Rd is the 6th most expensive street in Sheboygan. It has single-family homes built from 1965 to 1969, ranging in price from $449,000 to $1,150,000.

Average Price: $799,500
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7. Ridgemor Dr

Ridgemor Dr is the 7th most expensive street in Sheboygan. It has single-family homes built in 2014, with an average sale price of $720,000.

Average Price: $720,000
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8. County Road Y -

County Road Y - is the 8th most expensive street in Sheboygan. It has land with an average sale price of $706,090.

Average Price: $706,090
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9. Business Dr

Business Dr is the 9th most expensive street in Sheboygan. It has land and townhouses built in 2025, with an average sale price of $700,000.

Average Price: $700,000
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10. Playbird Rd

Playbird Rd is the 10th most expensive street in Sheboygan. It has land with an average sale price of $700,000.

Average Price: $700,000
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