Top 10 Most Expensive Streets in Oakland, FL

is the 1st most expensive street in Oakland. It has single-family homes built from 2001 to 2025, with an average sale price of $1,783,268. It is home to the Johns Landing subdivision.

Oak Fort Lane is the 2nd 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 3rd 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 4th most expensive street in Oakland. It has single-family homes built from 2001 to 2020, ranging in price from $1,440,000 to $1,610,000. It is home to the John's Cove subdivision.

Riverway Drive is the 5th most expensive street in Oakland. It has single-family homes built from 2024 to 2025, ranging in price from $1,017,951 to $1,587,269.

Tilden Oaks Trail is the 6th 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.

Millholland Street is the 7th most expensive street in Oakland. It has single-family homes built from 2001 to 2015, ranging in price from $1,100,000 to $1,600,000.

Canyon Creek Trail is the 8th most expensive street in Oakland. It has single-family homes built in 2024, with an average sale price of $1,259,910.

Oak Fort Lane is the 9th most expensive street in Oakland. It has single-family homes built in 2025, with an average sale price of $1,057,482.

Allendale Lane is the 10th most expensive street in Oakland. It has single-family homes built in 2023, with an average sale price of $1,031,701.