Nearly 100 Years: What Four Generations Taught Us About Managing Property

November 5, 2026

From a Hamilton window shop in 1927 to more than 2,000 units today: four lessons from four generations of the Fraleigh family.

Historic photo looking down from the Hamilton Mountain over the city

In 2027, The Enfield Group marks its 100th year. Few property management firms in Ontario can say that, and fewer still are run by the same family that started them. As we head into our centennial, we looked back at what four generations of Fraleighs learned about building and managing property, and what those lessons mean for the boards and owners we serve today.


1927: A window shop on Beach Road

The story begins in 1927, when William John Fraleigh bought a struggling wood window manufacturer on Hamilton's Beach Road. Standard Sash & Door was one of the few businesses of its kind to survive the Depression. When builders ran out of money in the early 1930s, the company stepped in to finish their homes. It was the family's first taste of property development.


That work grew from single-family homes to apartment buildings. In 1949, William John built Fraleigh Apartments, a six-building complex at 775 Concession Street and the first multi-residential apartment buildings in the city. They still stand on the Mountain brow today.


Lesson one: service is the business

William John had a simple rule: "If we don't service you, someone else will." Nearly a century later, it is still how we work. A board should not have to chase its manager for a call back, a financial statement or a contractor who never showed up. Our 24/7 live support line, monthly financial statements and direct access to our President all come back to that rule.


The second generation: building for the long term

William Paul Fraleigh took over the family business in his mid-twenties and led it as Chairman from 1955 to 1999. He pioneered aluminum windows, built apartment buildings from Hamilton to Sarnia, including Patricia Apartments, and began the family's affordable housing work with buildings in Dundas, Stoney Creek and Waterdown under a Canada Mortgage and Housing Corporation program. The Enfield name itself comes from the window manufacturing business he bought on Enfield Road in Burlington in 1960.


In 1965 he built a small office building in downtown Hamilton that came with 50 parking spaces, and the family has operated downtown Hamilton parking ever since.


He also built some of the region's largest commercial buildings, including a one-million-square-foot warehouse for Firestone Canada in Stoney Creek and warehouses for The T. Eaton Company and G.W. Robinson. By 1970 he was operating three commercial parking lots in Hamilton's downtown core, and at one point the family managed more than 1,000 parking spaces. Every one of those properties had to be maintained, insured, financed and kept full, which taught the family to look at a building over its whole life, not just the next quarter.


Lesson two: owners think in decades

When you own buildings, you live with every decision for decades. A cheap repair that fails in five years is not a saving, and a reserve fund that is underfunded today becomes someone else's special assessment tomorrow. We bring that owner's view to every corporation we manage: realistic budgets, reserve fund planning that follows the study, and repairs done properly the first time.


The third generation: from parking lots to condominiums

Greg Fraleigh's first job was as an attendant on one of the family's parking lots. He joined the family firm in 1977 and bought the business in 1999. His move into condominium management started almost by accident: in 1993, a condominium owner asked him to help resolve a dispute between a board and its developer. Condominium management has been at the heart of the business ever since.


Greg also kept building. He developed McGivney Community Homes, a 53-unit non-profit housing community in Hamilton, luxury townhomes on Pearl and Elizabeth Streets in downtown Burlington, and The Madison at 174 Mountain Park Avenue, Hamilton's first luxury condominium: eleven storeys with just two units per floor. In 2012, The Enfield Group became ACMO 2000 certified.


Lesson three: know how buildings are put together

Because we have designed and built properties, we understand how roofs, windows, balconies and mechanical systems are put together and how they age. That helps our managers spot problems early, ask contractors the right questions and plan major repairs before they become emergencies. You can read more about our property development work.


The fourth generation, and lesson four: keep the basics

Today, a fourth generation of the family, including Vice President Liam Fraleigh, works in the business alongside Greg, and The Enfield Group manages more than 2,000 units across the Golden Horseshoe, from Toronto and Peel through Halton and Hamilton to Niagara. The tools have changed, but the basics have not. As Greg puts it, "It's standard, but so many forget the basics." Answer the phone. Explain the numbers. Supervise the work. Treat every corporation, large or small, as if it were your own building.


Looking ahead to our second century

2027 marks our 100th year, and we are proud to still be a family business that our clients can reach directly. Read the full story on our history page, see what our condominium management services include, or learn how we serve boards in Hamilton, where it all began. If your board is looking for a manager with nearly a century of experience behind it, call 905-689-7341 or request a proposal.



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Hi everyone! We will be closing the office early today so that our staff can attend the Canadian Condominium Institute - Grand River Chapter's conference at the Bingeman's Conference Centre at 425 Bingemans Centre Drive, Kitchener, Ontario. Our office will be closing at 11:00 a.m. Emergency calls will be responded to and we will be back in the office bright and early on Monday morning.
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