Top 10 Most Expensive Streets in Maitland, FL

Eastwind Lane is the 1st most expensive street in Maitland. It has single-family homes built in 2024, with an average sale price of $3,950,000.

Bentley Ln Lane is the 2nd most expensive street in Maitland. It has single-family homes built in 1995, with an average sale price of $3,150,000.

Old Horatio Avenue is the 3rd most expensive street in Maitland. It has single-family homes built in 2025, with an average sale price of $2,850,000.

Manor Road is the 4th most expensive street in Maitland. It has single-family homes built in 1981, ranging in price from $1,725,000 to $3,385,000.

Lake Sybelia Drive is the 5th most expensive street in Maitland. It has single-family homes built from 1951 to 2024, ranging in price from $1,520,000 to $3,193,000. It is home to the Maitland Club and Poors subdivisions.

Whitecaps Circle is the 6th most expensive street in Maitland. It has single-family homes and land built from 1956 to 2026, ranging in price from $605,000 to $6,000,000. It is home to the Hollieanna Shores subdivision.

Terra Place is the 7th most expensive street in Maitland. It has single-family homes built in 2025, with an average sale price of $2,250,000. It is home to the Terra Place subdivision.

Adams Drive is the 8th most expensive street in Maitland. It has single-family homes and land built from 1953 to 1991, ranging in price from $840,000 to $3,500,000. It is home to the Adams Grove and Kings Row subdivisions.

Northwind Road is the 9th most expensive street in Maitland. It has single-family homes built from 1955 to 2019, with an average sale price of $2,150,000.

Bentley Lane is the 10th most expensive street in Maitland. It has single-family homes built from 2003 to 2024, ranging in price from $1,300,000 to $2,650,000. It is home to the Maitland Forest subdivision.