Jessica Penley

Partner | Vaughan


Portrait of Jessica Penley


Jessie Penley brings a thoughtful and business-minded approach to her commercial real estate practice. Focusing on acquisitions, dispositions, financing and leasing of commercial properties, including multi-family residential, office, mixed-use and self-storage buildings, she works with sophisticated clients to manage complex transactions in a practical way and get deals done efficiently.

Jessie’s acquisition and disposition work includes significant single-asset transactions, large portfolio transactions and private and public M&A transactions in which she works closely with teams that can comprise clients, multiple law firms and other professional advisors on issues such as deal structure, formation of transaction parties (including corporations, limited partnerships and co-ownerships), third-party consents and financing considerations.

In her financing and refinancing work, Jessie regularly acts for borrowers on mortgage transactions as well as having experience in more complex credit agreements for portfolio deals.

Jessie acts for both landlords and tenants in commercial leasing matters involving office, retail and industrial premises.

Before joining Miller Thomson, Jessie articled and practised as an associate at another national firm as well as a highly regarded real estate boutique firm in Toronto.

Professional achievements & leadership

  • The Best Lawyers in Canada - Real Estate Law, 2021-2024
  • The Canadian Legal Lexpert Directory - Property Leasing, 2022-2023; Property Development, 2023

Notable matters

  • Acted on a joint venture acquisition of a 50% interest in a 1.1 million sf commercial complex in Mississauga.
  • Acted on the sale by affiliates of Starlight Investments Ltd. of a national portfolio of multi-family residential properties to Northern Property REIT ($535 million).
  • Acted on a joint venture acquisition of 840,000 sf commercial complex in west Toronto.
  • Acted on True North Apartment REIT's acquisition of 127 multi-family residential and commercial properties in St. Laurent, Quebec ($121 million).
  • Acted on the acquisition by affiliates of Starlight Investments Ltd. of a national portfolio of multi-family residential properties as part of the $2.3 billion privatization of Transglobe Apartment REIT.
  • Acted as borrower's counsel on refinancing of a portfolio of owned and leased self-storage properties across three provinces.
  • Acted as senior landlord’s counsel on lease of urban premises in Toronto to national grocery chain.
  • Acted as tenant's counsel in lease of 195,000 square feet industrial premises.
  • Acted as senior landlord's counsel in lease of various office and retail premises to Class A tenants.
  • Acted for affiliates of Starlight Investments Ltd. on the acquisition of multi-family properties from TransGlobe Apartment Real Estate Investment Trust in connection with the approximately $2.0 billion privatization of TransGlobe REIT.

Bar admissions & education

  • Ontario, 2006
  • LL.B., Queen’s University, 2005
  • B.A. (Hons.), Queen’s University, 2002