"They're putting more obstacles in the road every day."
Brittons House Movers have bought both of Mr Gary's hydraulic trailers to continue using them.
Mr Gray has helped moved houses from as far as Auckland to Masterton, and has navigated some of the tricker routes such as the Saddle Rd to Castlepoint.
He's also helped move buildings over the Rimutaka Hill and the Waiohine River.
Over his time, Mr Gray has built up an extensive knowledge of the region and seen many changes in the industry - especially with technology.
A1 Homes Wairarapa have been using Mr Gray's company to move their houses for years.
Their showhome in Greytown was moved to Masterton on Monday, while Mr Gray was on site.
Paul Southey, of A1 Homes Wairarapa, said it will be a shame to see one of the best contractors in town shut up shop.
"They're just a wealth of knowledge and that's just because of time and experience," he said.