Top 10 Most Expensive Streets in South Pasadena, FL

1st Avenue is the 1st most expensive street in South Pasadena. It has townhouses built in 2025, with an average sale price of $799,000.

Sailboat Key Boulevard is the 2nd most expensive street in South Pasadena. It has condos built from 1981 to 1992, ranging in price from $275,000 to $1,020,000. It is home to the Harbourside Condominiums subdivision.

Lighthouse Terrace is the 3rd most expensive street in South Pasadena. It has townhouses built in 1985, ranging in price from $451,000 to $500,000. It is home to the Lighthouse Harbor Marina subdivision.

Shore Drive is the 4th most expensive street in South Pasadena. It has single-family homes built in 1958, with an average sale price of $475,000. It is home to the Pasadena Isle subdivision.

Grevilla Avenue is the 5th most expensive street in South Pasadena. It has townhouses, single-family homes, and multi-units built from 1952 to 2016, ranging in price from $207,000 to $705,000.

Sailboat Key Blvd S is the 6th most expensive street in South Pasadena. It has condos built in 1981, with an average sale price of $425,000. It is home to the Harbourside Condominiums subdivision.

Oleander Way is the 7th most expensive street in South Pasadena. It has single-family homes built in 1953, with an average sale price of $410,000.

Gulfport Boulevard is the 8th most expensive street in South Pasadena. It has single-family homes built from 1953 to 1957, ranging in price from $275,000 to $485,000. It is home to the Pasadena Golf Club Estates subdivision.

Pasadena Avenue is the 9th most expensive street in South Pasadena. It has condos and single-family homes built from 1983 to 2016, ranging in price from $220,000 to $612,500. It is home to the Pasadena Cove Condominiums subdivision.

Shore Drive is the 10th most expensive street in South Pasadena. It has condos, single-family homes, and land built from 1959 to 1979, ranging in price from $108,000 to $1,620,000. It is home to the Casa Prima, Shore View, Shore Towers, Shore Plaza, Shore Crest, Shore Manor, The Hemingway, and Pasadena Isle subdivisions.