Regular Expressions 101

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"
(?:\w+ ){0,2}Road\b
"
gm
Non-capturing group
(?:\w+ ){0,2}
{0,2} matches the previous token between 0 and 2 times, as many times as possible, giving back as needed (greedy)
\w
matches any word character (equivalent to [a-zA-Z0-9_])
+ matches the previous token between one and unlimited times, as many times as possible, giving back as needed (greedy)
matches the character with index 3210 (2016 or 408) literally (case sensitive)
Road
matches the characters Road literally (case sensitive)
\b assert position at a word boundary: (^\w|\w$|\W\w|\w\W)
Global pattern flags
g modifier: global. All matches (don't return after first match)
m modifier: multi line. Causes ^ and $ to match the begin/end of each line (not only begin/end of string)
Your regular expression does not match the subject string.

Regular Expression
No Match

r"
"
gm

Test String