He inherited the bulk of his family's property and, after the War of 1812, purchased and acquired land through marriage around what is now the Kensington Market neighborhood of Toronto.

At the end of his life, he held 556 acres (2.25 km2) in York and was one of the wealthiest landowners in Canada West.

[4][5] He married four times and fathered thirteen children; he wed Esther Borden Lippincott (daughter of Richard Lippincott) in 1806, Maria Taylor in 1828, Elizabeth Eleanor Caldwell in 1835, and Mary Priscilla Coates in 1850.

In 1815, he built an estate named Belle Vue (including an orchard and farm) on the south side of Russell Creek, which followed the style of Georgian architecture.

His grandson George Taylor Denison III was an officer in the army of the new Dominion of Canada and later served as a Toronto city councillor.