The Wynn family is well-known in Canada for their real estate business and philanthropic efforts. The family’s story begins with David Weinzweig, a Polish immigrant who chose Toronto as the best place to build a new life. He started in the furniture industry, but his son Philip (later known as Phil Wynn) expanded the family business into property rentals and management. More on torontonka.
The next generation—Paul, Jeffrey, and Leslie—carried on the legacy, founding The Wynn Group of Companies and Gold Wynn. These companies became major players in the real estate markets of Toronto and other parts of Canada. The Wynn family is also renowned for its philanthropy, supporting various organizations, including Birthright Israel and the Jewish National Fund.
Origins and Founding of the Weinzweig (Wynn) Family
It’s worth noting that the family’s original surname was Weinzweig. One family member, Alex, later changed it to Wynn, a name that others, including Philip, eventually adopted. Officially, however, the family is known as Wynn, especially in business and public records.
The family emigrated from Poland to Canada in the mid-1920s. David Weinzweig established the family in Toronto, moving to the city to provide better opportunities for his children. David started out in the furniture business and later opened his own upholstery workshop. His hard work and entrepreneurial spirit laid the groundwork for the future of the family business.
David’s children, Alex and Philip, grew up in Toronto and joined the family business at a young age. Beyond their business ventures, the family was known for being very close-knit. As an adult, Philip focused not only on work but also on family harmony, raising his three children: Paul, Jeffrey, and Leslie.
The family’s personal life was always intertwined with their business; values of hard work, education, and mutual support became the foundation of their strategy and eventual success. This blend of family tradition and entrepreneurial drive helped the Weinzweig/Wynn family establish themselves in Canada and build a lasting business that would grow into a large-scale real estate enterprise.
Business Development
As mentioned, it all began with David’s work in the furniture industry. His sons followed in his footsteps, and in 1958, Philip founded his own company, National Furniture. He also began renting apartments, furnishing them with his own products, and leasing them out. This marked the family’s pivot into the real estate sector.
In 1961, Philip purchased his first apartment building on Spencer Avenue for approximately $400,000. Over the next decade, he amassed a portfolio of about 1,500 units across several properties, becoming one of the largest landlords in Toronto’s west end. The primary company for these operations was Pajelle Investments, a name created by combining the first letters of his children’s names: Paul, Jeffrey, and Leslie.
The family began managing the business together in 1984, although Leslie officially joined in 1991. By the late 1990s, Philip had retired, and Jeffrey took over the day-to-day operations of the family’s real estate portfolio, which had grown to 3,400 units in 22 buildings. By the end of the 2010s, they controlled approximately 4,500 residential units and 3 million square feet of commercial real estate.
In April 2018, the Wynn Group sold the majority of its Toronto portfolio to Timbercreek Asset Management for $1 billion USD, shifting its focus more toward international development.
International Expansion and Business Initiatives
After achieving success in Canada, the Wynn family began exploring new opportunities abroad. Their strategy involved investing in real estate and other sectors in various countries around the world.
- The Caribbean
In 2014, the family acquired the historic Gold Blossom Estate in Nassau, Bahamas. The site was developed into the luxurious Goldwynn Residences, which opened in 2023. This project became part of their international Gold Wynn brand. In 2019, they also opened the Presidential Suites at the Lifestyle Holidays resort in Puerto Plata, Dominican Republic. In 2022, the family announced their main corporate headquarters would be relocated from Toronto to Nassau, Bahamas.
- United States
Between 2014 and 2015, the Wynn family invested $27 million USD in Tulsa, Oklahoma real estate, acquiring 900 residential units. This move expanded their footprint in the U.S. market and led to the opening of a local office.
- United Kingdom
In the UK, the family began building a rental property portfolio, acquiring the former Northern and Shell Tower in London and the Station House building in Milton Keynes. These properties were redeveloped for residential and commercial use. In 2023, the Wynn family became the majority shareholder in Blue Shield Capital, a London-based short-term lending company.
- Israel
In Israel, the family held interests in the Tel Aviv area. They acquired several apartment buildings and a stake in Reality Investment Funds, which manages the Arena shopping centre in Herzliya.
- United Arab Emirates
In 2025, the brothers announced real estate investments in the United Arab Emirates, specifically in the emirate of Ras Al Khaimah. They plan to build the luxurious Wynn Al Marjan Island resort, slated to open in 2027. The project will feature the first casino in the UAE and is expected to have a major impact on the local real estate market.
Philanthropy
The Wynn family are active supporters of the Taglit-Birthright Israel program, which offers young Jewish adults a free trip to Israel to learn more about their cultural heritage. They believe the program helps young people from around the world connect with the Jewish community and support Israel. The Wynn Family Foundation is a key supporter of this initiative, fostering Jewish identity among youth.
The family also provides funding to Canadian medical institutions, including Mount Sinai and Toronto Western hospitals. Their contributions help improve medical services and advance research at these facilities. While specific donation amounts are not public, their support in this sector is significant.
In partnership with the Tel Aviv Foundation, they also helped fund the construction of the Cees and Phil Wynn Beach Sports Community Center on the Tel Aviv coast. The centre provides residents with access to open public spaces, sports fields, and a café, promoting water sports and active lifestyles. This project was made possible through a generous donation from Paul Wynn.
Their contributions don’t stop there. Through a partnership with the Jerusalem Foundation, the prominent Toronto family donated to the Phil and Cees Wynn Business Centre at Canada House in Jerusalem. It serves as a dynamic community hub that fosters business and cultural initiatives reflecting Jerusalem’s multicultural identity.
They also actively support the Jewish National Fund (JNF), an organization focused on land development and environmental initiatives in Israel, and the Canadian Jewish Political Affairs Committee (CJPAC), which works to advance the interests of the Jewish community in Canada.
Through their many contributions, the renowned entrepreneurial family significantly advances a wide range of initiatives spanning medicine, culture, sports, environmentalism, and political affairs. Overall, their philanthropy highlights a deep commitment to supporting individuals, communities, and those in need.