Top 10 Most Expensive Streets in Oakland, FL

Water Maple Drive is the 1st most expensive street in Oakland. It has single-family homes and land built in 2026, with an average sale price of $2,454,640. It is home to the Grove at the Harvest District subdivision.

Sarah Mathews Drive is the 2nd most expensive street in Oakland. It has single-family homes built in 2025, with an average sale price of $2,098,500.

Briley Avenue is the 3rd most expensive street in Oakland. It has single-family homes built from 1984 to 2026, ranging in price from $571,000 to $3,175,000. It is home to the Briley Farm subdivision.

Cheekwood Alley is the 4th most expensive street in Oakland. It has single-family homes built in 2022, with an average sale price of $1,835,000. It is home to the Oakland Park subdivision.

Oak Fort Lane is the 5th most expensive street in Oakland. It has single-family homes built in 2024, with an average sale price of $1,751,000.

Daniels St is the 6th most expensive street in Oakland. It has single-family homes built in 1953, with an average sale price of $1,696,482.

Johns Point Drive is the 7th most expensive street in Oakland. It has single-family homes built from 2006 to 2020, with an average sale price of $1,440,000. It is home to the John's Cove subdivision.

Tilden Oaks Trail is the 8th most expensive street in Oakland. It has single-family homes built in 2022, with an average sale price of $1,362,500. It is home to the Oakland Park subdivision.

Canyon Creek Trail is the 9th most expensive street in Oakland. It has single-family homes built in 2024, with an average sale price of $1,259,910.

Millholland Street is the 10th most expensive street in Oakland. It has single-family homes built from 2001 to 2015, ranging in price from $865,000 to $1,600,000.