Top 10 Most Expensive Streets in Dunedin, FL

Crystal Circle is the 1st most expensive street in Dunedin. It has single-family homes built in 1989, with an average sale price of $790,000. It is home to the Waterford East subdivision.

Main Street is the 2nd most expensive street in Dunedin. It has condos, single-family homes, multi-units, and manufactured/mobiles built from 1920 to 2016, ranging in price from $180,000 to $1,150,000. It is home to the Victoria Place subdivision.

Santa Barbara Drive is the 3rd most expensive street in Dunedin. It has single-family homes and land built from 1951 to 1998, ranging in price from $440,000 to $7,000,000. It is home to the Dunedin Isles subdivision.

Paddock Circle is the 4th most expensive street in Dunedin. It has single-family homes built from 1969 to 1975, ranging in price from $1,060,000 to $1,250,000. It is home to the Spanish Trails subdivision.

Highland Woods Drive is the 5th most expensive street in Dunedin. It has single-family homes built from 2002 to 2003, ranging in price from $760,000 to $900,000. It is home to the Highland Woods subdivision.

Highland Avenue is the 6th most expensive street in Dunedin. It has single-family homes, townhouses, land, and multi-units built from 1921 to 2023, ranging in price from $495,000 to $1,240,000. It is home to the Gramercy Court and Highland Court subdivisions.

Bass Boulevard is the 7th most expensive street in Dunedin. It has single-family homes and multi-units built from 1940 to 2025, ranging in price from $372,600 to $1,235,000. It is home to the Lakeside Terrace subdivision.

Douglas Avenue is the 8th most expensive street in Dunedin. It has single-family homes and multi-units built from 1942 to 2021, ranging in price from $185,000 to $1,812,500. It is home to the Dunedin Isles Country Club, Dunedin Isles, and Highland Park subdivisions.

New York Avenue is the 9th most expensive street in Dunedin. It has condos, single-family homes, townhouses, and multi-units built from 1924 to 2022, ranging in price from $99,975 to $1,005,000. It is home to the Richland, Dexter Park, Grove Terrace, and Loch Lomond Estates subdivisions.

Paula Drive is the 10th most expensive street in Dunedin. It has condos and townhouses built from 1969 to 2001, ranging in price from $280,000 to $527,500. It is home to the Dolphin Pointe, Harbor Pointe Condominiums, Sea View at Honeymoon Island, Sun Ketch Townhomes at Dunedin Causeway, and Pipers Ten subdivisions.