First Shaughnessy was created in the early 1900's by the Canadian Pacific Railway (CPR), then the largest real estate developer in Canada. CPR was granted Old Shaughnessy, north of King Edward Avenue, by the federal government as an enticement to extend the railway to the West Coast. From that initiative, Shaughnessy Heights was developed.  

Recognized architects Maclure & Fox, Parr & Fee, Sharp & Thompson, and Thomas Hooper designed many of the most beautiful homes in the area. Architectural themes reflect Tudor England, Colonial America and Dutch settlements. These standards were also evident in the large, private gardens and significant landscaping features built in the area. The Nichol House at 1402 McRae Avenue, the Frederick Kelly House at 1398 Crescent, the MacDonald House at 1388 Crescent, the Fleck House at 1296 Crescent,Hycroft Manor at 1489 McRae Avenue and Glen Brae (The Canuck House) at 1690 Mathews Street are all noted as for their striking architecture and distinct presence in the neighborhood.

Shaughnessy Crescent is home to some of Vancouver's most unusual trees, carried from the orient and eastern Canada, by shipping magnates and railway barons, including the Japanese snowbell tree, flowering ash, red horse chestnut, copper beech and others.

First Shaughnessy has an Official Development Plan that is intended to control and guide development in the area. There is also the First Shaughnessy Advisory Design Panel that advises City Council, the Development Permit Board, and the Director of Planning on development and design issues in First Shaughnessy, with a focus on preserving the area’s special character.  The advisory design panel also advises the City's Director of Planning concerning the implementation and effectiveness of the approved planning policies, regulations, and design guidelines for the First Shaughnessy District.

The First Shaughnessy Design Guidelines were adopted by City Council on May 11, 1982. These guidelines are intended to be used in conjunction with the First Shaughnessy Official Development Plan to assist in the preparation and review of all development in the First Shaughnessy District.