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Jeff Cummings



"We are very interested in what our clients have to say. We listen then we ask insightful questions. And when we have all the information that we need, we work diligently until we come up with the best legal solutions for their real estate, tax, estate planning, and business issues."

Jeffrey Cummings believes that no one works harder for their clients than CCSB – and they have the referrals and reputation to back it up. From starting work early to answering client emails late at night, Jeff is diligent and dedicated to adding strategic insight and value to every deal that he is involved in.

Over his 40-plus-year career, Jeff has represented clients in all aspects of land development, leasing and commercial real estate. He has acted on many U.S. business acquisitions and has supervised a number of major real estate acquisitions for Canadian purchasers in various U.S. states including: California, Florida, Maryland, New York, New Jersey, Oregon, Utah, Tennessee, Virginia, Washington (D.C.), and Washington.

He has also been a partner at a large downtown Toronto full-service law firm where he directed the Private Entrepreneurial Practice Group, was a member of its Management Committee, a leader in its Real Estate and Leasing Sections, and established and managed its Ottawa and North York branch offices.

Jeff is now a founding partner of CCSB where he continues to provide top-notch legal advice and service in an environment that is more personal, responsive, and accessible to his clients. 


He is a member of the Canadian Bar Association, the Law Society of Upper Canada, the American Bar Association, the Real Property, Probate and Trust Law Section, A.B.A., and the General Practice, Solo and Small Firm Section, A.B.A.

Jeff has been a guest speaker and writer for the American Bar Association Section of Real Property, Probate and Trust Law (including his article on "Canadian Investment in U.S. Real Estate"). 


Jeff received his Bachelor of Commerce Degree from the University of Toronto in 1970 and his law degree (J.D.) from the University of Toronto Law School in 1974. He has practiced commercial real estate since he was called to the Bar of Ontario in 1976.

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