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While it apparently does work under Windows 7, 8, and 8.1, it was only officially supported under Windows XP and Vista. In terms of support it appears to be abandoned and no longer available in digital or physical (box) form. The last patch was released in November 2007.
The associated studio, Ubisoft Bucharest (Romania) were responsible for both the 10th edition (2004) and the Grandmaster edition, aka XI edition (2007), but since then Ubisoft Bucharest have been involved in a number of large blockbuster titles which would make Chessmaster far less of a priority because of reduced sales volume in comparison.
I also don't know of the chess engine, The King being updated, which has historically been done by its creator Johan de Koning (used since Chessmaster 4000) up to the Grandmaster edition, which would be a potential motivation for releasing a new version of the game. Additionally, the version included with the Grandmaster edition was tested on dual-core processors, but not multi-core (more than two) processor systems, and some users have had issues with it on > 2 core systems. So this is one issue that would have to be resolved given the increased popularity in quad and higher core processors in personal systems.
Experienced chess players (rated or tournament level) have largely moved to Chessbase (database) and/or Fritz (engine) for serious analysis and human-computer play. Though Chessmaster is still the most desirable chess system for children and novices of any age; this divides Ubisoft's Chessmaster potential market even further.