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Georgian architecture with elements of Classical Revival style, built in the late 1830s. The owner, J.B. Caldwell, sympathized with the rebellion of 1837 thus explaining the building's name.
© OpenStreetMap contributors
Built in 1883, this two-storey buff brick building was designed in the Italianate style, with a projecting frontispiece, a crested central square bell-tower, tall narrow windows and a heavily bracketed cornice.
a.k.a. Walter Playter House
Built in circa 1880, this 2½-storey picturesque Italianate villa house is very fanciful.
Newmarket Post Office
Italianate style with bell tower constructed 1914-15. The building is now the Postmark Hotel.
Constructed in 1883-1884.
formerly King George School
This square, 2-storey brick building has entrances on both corner streets. Built 1912-1913, this was Newmarket's oldest functioning elementary public school. Today, the building serves as a condominium.
The house built in 1861 has a medium-pitch gable roof. It belonged to Robert Simpson who later opened a large department store at Yonge & Queen in Toronto.