Top 10 Most Expensive Streets in Maitland, FL

Lake Catherine Drive is the 1st most expensive street in Maitland. It has single-family homes built from 1970 to 2019, ranging in price from $840,000 to $2,150,000.

Stone Hill Drive is the 2nd most expensive street in Maitland. It has single-family homes built from 1992 to 2004, ranging in price from $1,025,000 to $1,880,000.

Big Bend Trail is the 3rd most expensive street in Maitland. It has single-family homes built in 1967, with an average sale price of $775,000.

Orlando Avenue is the 4th most expensive street in Maitland. It has condos built from 1964 to 1973, ranging in price from $199,900 to $500,000.

Manor Road is the 5th most expensive street in Maitland. It has single-family homes built from 1981 to 1996, ranging in price from $1,725,000 to $10,300,000.

Terra Place is the 6th most expensive street in Maitland. It has single-family homes built from 1984 to 2025, ranging in price from $958,000 to $2,250,000.

Whitecaps Circle is the 7th most expensive street in Maitland. It has single-family homes and land built from 1956 to 2004, ranging in price from $605,000 to $6,000,000.

Windgrove Trail is the 8th most expensive street in Maitland. It has single-family homes built in 2024, with an average sale price of $950,000. It is home to the Windgrove subdivision.

Old Horatio Avenue is the 9th most expensive street in Maitland. It has single-family homes built in 2025, with an average sale price of $2,850,000.

East Boulevard is the 10th most expensive street in Maitland. It has single-family homes built in 1969, with an average sale price of $525,000. It is home to the Northgate subdivision.