The first notable estate and mansion on the escarpment was Davenport, which was located just west of modern Wells Hill Avenue and north of Austin Terrace. The first owner of lot 25, in the second concession from the Bay, was John McGill, an ensign with the Queen',s Rangers. He probably built his home in 1797 and named it after Major Davenport, another officer at Fort York. Davenport Road, called the Plank Road for many years, was a curving portage trail from the Don to the Humber, which had been used by generations of Native people.
The second owner of lot 25 was Colonel Joseph Wells who distinguished himself during the Napoleonic Wars under the Duke of Wellington. In 1813, he accepted the post of inspector of the militia in Upper Canada. He purchased Davenport in 1821, for L750, from McGill’s widow, built a much larger home on the original site and planted orchards and fields. Colonel Wells sat on both the Legislative and Executive Councils of Upper Canada, and was on the first board of directors of the Bank of Upper Canada. He died in 1853. The Davenport property was divided into three strips that ran from Bloor up to St. Clair, going to three of his sons. The eastern portion, with the house, went to his fourth son, Frederick. By 1862, the area south of Wells Street had been subdivided and the land between Wells Street and Dupont followed. Frederick’s daughter, Nina, returned in 1894 to live in Davenport for ten years. Davenport was sold in 1913, demolished and the remaining property subdivided. (For more about Davenport and its owners, see "The Estates of Old Toronto" by Liz Lundell).
The south end of lot 25 was sudivided into lots that are now the west part of The Annex.