Direct: (919) 645-4305
For more than a decade and on a nationwide basis, Penn has advised clients in all aspects of complex real estate transactions. With a particular focus on multi-family (both traditional and student-housing) transactions, he has successfully represented clients in the development, purchase and sale of dozens of multi-family properties totaling more than $3 billion in value.
Penn also has substantial experience advising build-to-rent (BTR) and single-family-rental (SFR) housing sponsors and investors in the acquisition and development of residential subdivisions. Additionally, he routinely assists clients in the acquisition, financing, development, and sale of mixed-use, industrial, retail, and office projects and regularly prepares and negotiates joint venture agreements, development agreements, and management agreements. Furthermore, a substantial portion of Penn’s practice focuses on representing landlords and tenants in preparing and negotiating leases for industrial, retail, office, and medical office properties.
Penn has been named “Legal Elite” each year since 2019 by Business North Carolina magazine in the Real Estate and/or Young Guns category and has been annually listed as a Rising Star by North Carolina Super Lawyers since 2021. In 2024 and 2025, he and the firm were recognized in Chambers USA: Real Estate, Regional Spotlight North Carolina. Penn was honored by the Triangle Business Journal in 2024 with a 40 Under 40 Leadership Award, which “recognizes the top leaders under the age of 40 for their proven performance in their respective industries and communities” in the Triangle area.
Penn sits on the firm’s management committee and chairs its attorney recruiting committee. He has lectured on various commercial real estate topics to both law students at The University of North Carolina School of Law and MBA students at The University of North Carolina Kenan-Flagler Business School.
Prior to joining the firm, Penn practiced in the Charlotte and Raleigh offices of a large international law firm and served as temporary law clerk to the Honorable G. Steven Agee, United States Court of Appeals for the Fourth Circuit.
Penn lives in Raleigh with his wife and their two sons.
Practice Areas
Real Estate Acquisitions & Dispositions
Real Estate Leasing
Real Estate Finance & Capital Markets
Real Estate Investment & Development
Distinctions
Business North Carolina, Legal Elite, Real Estate and/or Young Guns, 2019-2025
Chambers USA: Real Estate, Regional Spotlight North Carolina, 2024-2025
North Carolina Super Lawyers, Rising Stars, Real Estate, 2021-2025
Triangle Business Journal, 40 Under 40 Leadership Award, 2024
Admissions
North Carolina
Memberships and Community Involvement
Board Member (2023-present), Aldert Root Elementary Educational Foundation
Board Member (2022-present), Washington & Lee University School of Law, Law Council
Board Member (2023-present), YMCA of the Triangle, Camp Sea Gull and Camp Seafarer Advisory Board
Board Member (2013-2016), University of North Carolina, Young Alumni Leadership Council
Member, White Memorial Presbyterian Church
Education
Washington and Lee University School of Law, J.D. (Martin P. Burks Scholar)
University of North Carolina at Chapel Hill, B.A. (with honors)
Representative Transactions
- Buyers and sellers in the acquisition and disposition of more than two dozen student housing apartment complexes totaling more than $3 billion across the country
- REIT in the $2.3 billion acquisition of a portfolio of 72 medical office buildings and development parcels over four serial closings
- REIT in the review of the real estate diligence, including leases, loan documents, title documents, and surveys, of the merging REIT related to the $5.7 billion merger of the two REITs
- Managing member in the negotiation of a $750 million platform joint venture and the subsequent acquisition of six (6) apartment complexes during a three-year period.
- SFR sponsor in the acquisition and development of numerous residential communities totaling more than $500 million
- Investment firm in the acquisition, sale, and development of numerous warehouse projects totaling more than $350 million
- National financial institution in dozens of sales of a variety of asset types totaling more than $100 million of owned real property acquired through foreclosure
- Buyer in the acquisition of a $120 million student housing apartment complex
- Landlords and tenants in commercial lease negotiations in tens of millions of rentable square feet
- REIT listed on the NYSE in the acquisition, sale, management, and leasing of real property
- International convenience store chain in the acquisition, development, sale, and leasing of real property
- Borrower in the $50 million refinancing of a portfolio of 7 shopping centers
- Pension fund in the acquisition of a $75 million mixed-use development
- Multi-family investment firm in the sale of a $47 million apartment complex
- Retail developer in the sale of a $32 million shopping center
- Buyer/borrower in the acquisition and financing of a $35 million apartment complex
- Retail developer in the land acquisition, financing, development, and leasing of a shopping center
- Multi-family investment firm in the acquisition of a $40 million apartment complex
- Investment firm in the $12 million acquisition of a historic office building
- Buyer/borrower in the $25 million acquisition of an apartment complex and related financing and joint venture
