Henry Farm was settled in 1806 by a native of County Monaghan, Irishman Henry Mullholland. The farm was sold but later reacquired in 1898 by his great grandson, George Stewart Henry who was also the tenth Premier of Ontario from 1930-1934. At the farm's peak, Henry was proud to hold ninety head of prized Holstein cattle. Henry sold the farm ten-days before his death in 1958 for two million dollars to the developers who transformed it into a housing subdivision in the 1960's. The original brick farmhouse that was the Henry family home, was known as Oriole Lodge, aptly-named because of the numerous orioles that nested there in the summer time. Oriole Lodge is still standing in its original location at 17 Manorpark Crescent and is still a private residence.
In the Henry Farm area, there is a large mix of Georgian and Tudor Revival style homes, as well as split-levels and bungalows. Many Henry Farm houses were built in the late 1950's and early 1960's with a large number of them sporting brick veneer on the ground floor and aluminum siding on the second-storey. The area's lawns are well-kept, landscaped and have nice gardens and sit on suburban sized lots with many of the homes backing onto the Don River Valley. Most of the neighbourhood is low-density suburban housing with townhouse developments along the northeast and southeast. There are two high-rise apartment buildings, Havenbrook Towers, at the southeast corner of the neighbourhood.
The Fairview Library and Theatre is located next to Fairview Mall and could be said to be the cultural and artistic hub of the neighbourhood. The theatre stages performances in both the evening and weekends by local theatre groups with yearly subscriptions available for all members of the family. Accessed off Havenbrook Boulevard, the East Don Valley Parkland trail passes through Moatfield Farm Park, where recently evidence of a former First Nations village was discovered that made the area its home approximately six hundred years ago.
Shaughnessy is a public school in the area and George S. Henry Academy and Georges Vanier are two public high schools. Residents of this area have organized Neighbourhood Watch and Block Parent Programmes and even publish a regular newsletter called the 'Henry Farmer,' that spreads the word about events and goings-on in the tight-knit community.