The following are the Top 10 most expensive streets in Winston. The average price for homes on these streets range from $475,000 to $988,000.
Pool Road is the 1st most expensive street in Winston. It has single-family homes built from 1966 to 2008, ranging in price from $440,000 to $1,964,000.
Kraft Drive is the 2nd most expensive street in Winston. It has single-family homes built in 2008, with an average sale price of $960,000.
Shell Road is the 3rd most expensive street in Winston. It has single-family homes built in 2017, with an average sale price of $750,000.
Cool Springs Road is the 4th most expensive street in Winston. It has single-family homes built from 1985 to 2025, ranging in price from $625,000 to $831,225.
Post Road is the 5th most expensive street in Winston. It has single-family homes built in 2024, with an average sale price of $669,900.
Diamond Court is the 6th most expensive street in Winston. It has single-family homes built in 2001, with an average sale price of $595,000. It is home to the Grande Pointe at Fairplay subdivision.
Carroll Road is the 7th most expensive street in Winston. It has single-family homes and land ranging in price from $322,000 to $775,000. It is home to the Fairplay subdivision.
Watkins Mill Road is the 8th most expensive street in Winston. It has single-family homes and land built from 1946 to 2005, ranging in price from $110,000 to $875,000.
Daniel Mill Road is the 9th most expensive street in Winston. It has single-family homes built in 2015, with an average sale price of $490,000.
South Baggett Road is the 10th most expensive street in Winston. It has single-family homes built in 2020, with an average sale price of $475,000.