Diane M. McDermott serves as the executive partner of Holland & Knight's Boston office. She is a Boston real estate attorney and co-chair of the firm's National Retail Development and Leasing Team. Ms. McDermott's practice focuses on numerous aspects of real estate law, including permitting and development, commercial and retail leasing, acquisitions and dispositions and financing. She represents clients in the hotel and hospitality and multifamily housing industries in connection with various aspects of those industry segments business.

Ms. McDermott is a part of the national leadership team for the industry segment team focusing on the Real Estate and Hospitality Industry.

Ms. McDermott's representative engagements include:

Relocation of Corporate Headquarters

  • Represented a client in the relocation of its corporate headquarters from Boston to Cambridge, including assistance in structuring the transaction, negotiating the lease with the landlord, as well as advising on the structuring and negotiation of the architect's contract, construction contracts and project management consultant contracts
  • Represented an international client, as a tenant, in its nationwide commercial office leasing requirements and the relocation of its North American headquarters

Institutional Commercial Property Owner

  • Represented a client in connection with a land acquisition and the financing, permitting and construction of a ground-up 425,000-square-foot commercial office building located on the South Shore of Boston
  • Represented a client in connection with the purchase of an existing 350,000-square-foot commercial office building and its substantial renovation and the construction of a garage facility for the building
  • Represented a client in connection with the sale of various parcels of land and negotiation regarding utilities, easements, repurchase right and related retained rights for a major park redevelopment of a former military base in the western suburbs of Boston
  • Represented a major institutional client in connection with its major expansion of office space in a downtown Boston tower

Retail Leasing

  • Represented a landlord/owner in connection with the leasing of multiple retail locations to commercial banking institutions and other retail users in a mixed-use project in Hartford, Conn.
  • Represented a landlord in connection with the leasing of retail locations on Newbury Street in Boston to a national retailer
  • Represented a national retailer in connection with its entry into the Boston market in connection with its tenant retail location on Newbury Street
  • Represented a tenant in connection with the national leasing of retail locations for its operations in the retail-clothing industry
  • Represented a national restaurant chain in connection with its national retail leasing
  • Represented landlord/owner in connection with the negotiation of a lease for a single-tenant retail user in the suburban Boston market
  • Represented a client in connection with the sale of a subsidiary entity, including 150 retail restaurant locations; presented an analysis of issues in the retail leases in connection with the transfer and negotiation with respective landlords on all locations

Multifamily Transactions

  • Represented a client in connection with the acquisition and financing of a 600-plus unit apartment complex in the Boston suburbs
  • Represented a client in connection with the acquisition and financing of a 300-plus unit apartment complex in Florida
  • Represented a client in connection with the acquisition of a 400-plus multifamily apartment complex in Santa Fe, N.M.


  • Represented a client/developer in multiple transactions involving land acquisition, permitting, financing and ground-up construction of hotel properties, as well as in the transactions regarding the sale of operating hotel properties
  • Represented a client in the ground lease with the Boston Redevelopment Authority d/b/a Boston Planning & Development Agency of a parcel of land in Boston and the related structuring, permitting and financing of a 300-plus hotel property.
  • Represented a client in connection with the acquisition and financing of an existing operating hotel located north of Boston
  • Represented client in connection with the acquisition, financing and permitting, including negotiation of the franchise agreement, of a full-service hotel in the Back Bay of Boston
  • Represented client in connection with the sale of a major hotel property located in the Seaport and transfer of all related permits and licenses


  • Suffolk University Law School, J.D., cum laude
  • Boston College, B.S., magna cum laude
Bar Admissions/Licenses
  • Massachusetts
  • American Bar Association
  • Massachusetts Bar Association, Real Property Section, Chair, 2007-2008
  • Boston Bar Association
  • Women's Lunch Place, Board of Directors, 2004-2017
  • Town of Holliston Affordable Housing Committee, 2010-present
  • Finance Council for Local Community Organization, 2009-present
  • American Foundation, Fellow, 2011-present
Honors & Awards
  • The Legal 500 USA, Real Estate, 2020
  • The Best Lawyers in America guide, Real Estate Law, 2008-2020
  • Massachusetts Super Lawyers magazine, 2005-2019