Top 10 Most Expensive Streets in Downtown Dade City, Dade City, FL

Trailing Moss Drive is the 1st most expensive street in Dade City. It has single-family homes built from 2007 to 2022, ranging in price from $490,000 to $835,000.

Tradition Drive is the 2nd most expensive street in Dade City. It has land and single-family homes built in 2003, with an average sale price of $655,000.

Rowntree Drive is the 3rd most expensive street in Dade City. It has single-family homes, land, and manufactured/mobiles built in 2016, ranging in price from $72,500 to $1,475,000.

Wineberry Drive is the 4th most expensive street in Dade City. It has single-family homes built from 2022 to 2023, ranging in price from $328,000 to $499,000. It is home to the Heritage Hills subdivision.

Eastpointe Drive is the 5th most expensive street in Dade City. It has single-family homes built from 2018 to 2020, ranging in price from $369,000 to $422,000.

Spruce Knob Court is the 6th most expensive street in Dade City. It has single-family homes built from 2023 to 2025, ranging in price from $311,500 to $329,990. It is home to the Summit View subdivision.

Thimbleberry Drive is the 7th most expensive street in Dade City. It has single-family homes built from 2022 to 2023, with an average sale price of $310,000. It is home to the Heritage Hills subdivision.

Florida Avenue is the 8th most expensive street in Dade City. It has single-family homes and multi-units built from 1945 to 2025, ranging in price from $98,000 to $350,500.

Us Hwy 301 is the 9th most expensive street in Dade City. It has land and single-family homes built from 1955 to 1958, ranging in price from $135,000 to $300,000.

Preakness Stakes Way is the 10th most expensive street in Dade City. It has land with an average sale price of $205,000. It is home to the Farmington Hills subdivision.