The house builder will now have to pay the £1.3m it owes and the test case could see other firms facing a £65m bill.
HM Revenue and Customs challenged the “artificial and complex arrangements” made by Crest Nicholson to avoid paying SDLT on three purchases of development land near Rochester in Kent for a total of more than £32m.
The avoidance scheme tried to use the transfer of property between two sub-companies to avoid SDLT.
HMRC said the tribunal decision is likely to have an impact on more than 700 other cases, potentially protecting £65m of taxpayers’ money.
Crest Nicholson argued that HMRC didn’t have a legal right to make assessments of the tax due because it was out of time to do so, and that it had not carried out its assessments properly.
The judge disagreed with these arguments and found HMRC had acted correctly throughout.
HMRC’s Director General, Customer Compliance, Jennie Granger, said: “This decision makes it clear that setting up artificial and complex arrangements involving sub-companies to avoid paying tax doesn’t work.
“It’s another important success that’s protected taxpayers’ money. This win sends a clear message that tax avoidance is expensive and self-defeating.”