Top 10 Most Expensive Streets in Rosemary District, Sarasota, FL

Whittier Drive is the 1st most expensive street in Sarasota. It has single-family homes built in 2023, with an average sale price of $13,950,000.

Hillview Drive is the 2nd most expensive street in Sarasota. It has single-family homes built from 1952 to 2025, ranging in price from $5,965,000 to $20,000,000. It is home to the Harbor Acres subdivision.

Owl Drive is the 3rd most expensive street in Sarasota. It has land and single-family homes built from 2003 to 2025, ranging in price from $9,750,000 to $11,250,000. It is home to the Bird Key subdivision.

Southwest Drive is the 4th most expensive street in Sarasota. It has single-family homes built in 2003, with an average sale price of $9,400,000. It is home to the Cherokee Park subdivision.

Cedar Park Circle is the 5th most expensive street in Sarasota. It has single-family homes built from 1998 to 2009, ranging in price from $7,700,000 to $10,350,000. It is home to the Cocoanut Bayou subdivision.

Bryant Drive is the 6th most expensive street in Sarasota. It has single-family homes built in 1998, with an average sale price of $8,995,000.

Sanderling Road is the 7th most expensive street in Sarasota. It has single-family homes built from 1952 to 1989, ranging in price from $6,500,000 to $14,500,000. It is home to the Sanderling Club subdivision.

Tangier Way is the 8th most expensive street in Sarasota. It has single-family homes built from 2008 to 2024, ranging in price from $8,250,000 to $8,450,000. It is home to the San Remo Estates subdivision.

Point Crisp Road is the 9th most expensive street in Sarasota. It has single-family homes built from 1971 to 2001, with an average sale price of $8,100,000. It is home to the Point Crisp subdivision.

Jungle Plum Road is the 10th most expensive street in Sarasota. It has single-family homes built from 2001 to 2012, ranging in price from $6,000,000 to $9,330,000. It is home to the Hidden Harbor subdivision.