$re = '/^\s*(?:(?:(?<A_Addition_to_address_1>.*?),\s*)?(?:No\.\s*)?(?<A_House_number_1>\p{N}+[a-zA-Z]?(?:\s*[-\/\p{P}]\s*\p{N}+[a-zA-Z]?)*)\s*,?\s*(?<A_Street_name_1>(?:[a-zA-Z]\s*|\p{N}\p{L}{2,}\s\p{L})\S[^,#]*?(?<!\s))\s*(?:(?:[,\/]|(?=#))\s*(?!\s*No\.)(?<A_Addition_to_address_2>(?!\s).*?))?|(?:(?<B_Addition_to_address_1>.*?),\s*(?=.*[,\/]))?(?!\s*No\.)(?<B_Street_name>\S\s*\S(?:[^,#](?!\b\p{N}+\s))*?(?<!\s))\s*[\/,]?\s*(?:\sNo\.)?\s+(?<B_House_number>\p{N}+\s*-?[a-zA-Z]?(?:\s*[-\/\p{P}]?\s*\p{N}+(?:\s*[-a-zA-Z])?)*|[IVXLCDM]+(?!.*\b\p{N}+\b))(?<!\s)\s*(?:(?:[,\/]|(?=#)|\s)\s*(?!\s*No\.)\s*(?<B_Addition_to_address_2>(?!\s).*?))?)\s*$/mu';
$str = '109 - 111 Wharfside Street
40-42 Parkway
25b-26 Sun Street
43a Garden Walk
6/7 Marine Road
10 - 12 Acacia Ave
4513 3RD STREET CIRCLE WEST
0 1/2 Fifth Avenue
194-03 1/2 50th Avenue';
preg_match_all($re, $str, $matches, PREG_SET_ORDER, 0);
// Print the entire match result
var_dump($matches);
Please keep in mind that these code samples are automatically generated and are not guaranteed to work. If you find any syntax errors, feel free to submit a bug report. For a full regex reference for PHP, please visit: http://php.net/manual/en/ref.pcre.php