Fluent in German, English and French and conversant in Spanish, Charlwood attended Southampton University on a scholarship before converting his part-time summer job as a tour guide into a full-fledged career in the travel industry. In 1966, Charlwood decided to come to Canada working for Western Airlines, quickly moving up management ranks to become Director of Consumer Affairs for CP Air. Charlwood wanted to go into business for himself and focused on selling residential real estate. From there, he was able to buy his own real estate company, fullfilling a lifelong dream.

In 1975 he and a partner bought the master franchise rights for CENTURY 21 Real Estate Canada.  Today, it is one of the largest real estate companies in the country, with more than 400 locations with more than 7,000 salespeople.  In 1980 Gary founded UNIGLOBE Travel and has guided the growth of the franchise travel organization to the point where today it has approximately more than 750 locations in more than 40 countries worldwide.  In 2003, Gary expanded CENTURY 21's reach into the Asia Pacific Theatre with offices in Taiwan, Hong Kong/Macao, Korea, Singapore, Thailand, Vietnam, Malaysia, The Philippines and Brunei.  There are now more than 400 offices in this Region.  Adding to his already successful real estate franchise business, Gary and his team created Centum Financial Group Inc., a mortgage brokerage network that is one of the fastest growing organizations in the Canadian mortgage industry today.

As founder of the family-owned Charlwood Pacific Group (CPG), Gary is joined in business by his sons, Martin and Christopher Charlwood.  Martin currently serves as President of UNIGLOBE Travel International LP, and Christopher is a Member of the Board of Directors and oversees the family's property development wing.  Daughter Bianca Maria is attending school.