Top 10 Most Expensive Streets in Main Street Merchants, Sarasota, FL

Palm Avenue is the 1st most expensive street in Sarasota. It has condos and single-family homes built from 1928 to 2026, ranging in price from $350,000 to $6,500,000. It is home to the Tessera, Embassy House, Palm Place, The DeMarcay, Palm Avenue Villas, Sarabande, Azure on Palm, The Savoy on Palm, Frances Carlton, and Mira Mar subdivisions.

Commonwealth Place is the 2nd most expensive street in Sarasota. It has single-family homes built in 1973, with an average sale price of $1,667,500. It is home to the Siestas Bayside Waterside East subdivision.

Mckinley Drive is the 3rd most expensive street in Sarasota. It has single-family homes built from 1956 to 2022, ranging in price from $2,750,000 to $4,830,000.

Freeling Drive is the 4th most expensive street in Sarasota. It has single-family homes and land built from 1950 to 2026, ranging in price from $1,300,000 to $9,250,000. It is home to the Bay Island Shores and Bay Island subdivisions.

Flamingo Avenue is the 5th most expensive street in Sarasota. It has single-family homes and land ranging in price from $1,800,000 to $4,500,000. It is home to the Bay Island, Bay Island Park, and Bay Island Shores subdivisions.

Golden Gate Point is the 6th most expensive street in Sarasota. It has condos built from 1962 to 2026, ranging in price from $775,000 to $8,100,000. It is home to the Bay Point, Evolution, Vista Bay Point, En Pointe, Aqua, Marina View, Harbor View, Harbor House South, Harbor House West, La Bellasara, Grande Riviera, Harbor House, Golden Bay, Majestic Bay, Alta Mer, Town House, and Peninsula Sarasota subdivisions.

Antiquity Way is the 7th most expensive street in Sarasota. It has single-family homes built from 2015 to 2019, ranging in price from $1,280,000 to $1,300,000. It is home to the Vilano subdivision.

Osprey Avenue is the 8th most expensive street in Sarasota. It has single-family homes, condos, townhouses, and multi-units built from 1921 to 2025, ranging in price from $82,000 to $2,950,000. It is home to the Oasis on Osprey, Newtown Park, Central Park, Plaza Gardens, Mcclellan Park, Inwood Park, Avondale, and Newtown subdivisions.

Tamiami Trail is the 9th most expensive street in Sarasota. It has condos and land built from 1959 to 2025, ranging in price from $95,000 to $7,000,000. It is home to the Alinari at Rosemary Place, The Strand, Central Park II, Broadway Promenade, Edgewater, Sarasota Cay Club, BLVD Sarasota, Renaissance, and Akoya subdivisions.

Stillwater Way is the 10th most expensive street in Sarasota. It has single-family homes built in 1966, with an average sale price of $691,000. It is home to the Gulf Gate subdivision.