Of Counsel
(617) 233-4897
Jump to:
BiographyPractice AreasRepresentative ExperienceProfessional and Community InvolvementPublications and Mentions

About Rob


Boston College Law School, Juris Doctor, Magna Cum Laude
Boston College, Bachelor of Arts, Political Science, Cum Laude

Bar Admissions

United States District Court, District of Massachusetts
First Circuit Court of Appeals


Rob Brennan brings to Smolak & Vaughan over 25 years of land use, development and environmental law experience that includes lead client and matter responsibilities at leading national, regional and boutique law firms; and more than 10 years of experience as an award-winning developer of innovative neighborhoods and work-force housing. Rob’s involvement and advocacy on behalf of the home building industry includes ongoing leadership at the local, state, and national levels within the National Association of Home Builders; recognition as a thought-leader on housing production and economic development throughout the Cape & Islands; and relationships built across private industry, government, and non-profit communities. Rob’s unique combination of experience provides Smolak & Vaughan clients with insightful, precise and effective counsel and advocacy, whether in the board room, on the job site, before local and state authorities, or in the courtroom.

an icon of an arrow

Practice Areas

  • Local zoning and wetlands permitting
  • Sustainable development – bridging increased housing production with climate resilient design and reduced carbon emission construction
  • Permitting under 40B, 40R and local housing incentive bylaws
  • Development of Regional Impact (DRI) review by Cape Cod and Martha’s Vineyard Commissions
  • Land use litigation and regulatory appeals
  • Brownfields redevelopment, regulatory proceedings and litigation under 21E
  • Federal, state and local economic development incentives
  • Public-private development partnerships
an icon of an arrow

Representative Experience

  • As developer of Heritage Sands in Dennis Port, Massachusetts, Rob worked collaboratively with the Town of Dennis to draft the Town’s Seasonal Resort Community bylaw allowing for the “as of right” construction of 63 new homes; successfully defended against abutter challenges filed before Dennis Zoning Board of Appeals and Land Court; exempted the eight-acre waterfront neighborhood from Cape Cod Commission review. Heritage Sands was recognized as the 2017 “Community of the Year” by the National Association of Home Builders.
  • Rob served as counsel for New Seabury Properties in Mashpee, Massachusetts, for more than a decade, and represented Carl Icahn’s real estate group in permitting, litigation, condominium and home owner association creation, and the sale of over 275 individual properties.
  • Representing The Flatley Company, Rob negotiated Chapter 91 and Designated Port Area permitting for the Company’s extensive holdings in Charlestown, Massachusetts.  
an icon of an arrow

Professional and Community Involvement

National Association of Home Builders

  • Leadership Council, Delegate
  • State & Local Government Affairs Committee, Member 
  • Build-PAC, Trustee

Home Builders & Remodelers Association of Massachusetts

  • Executive Committee, Member
  • Government Affairs Committee, Chair
  • Net Zero Building Code Study Committee, Chair

Massachusetts Development Finance Agency

  • Transformative Development Initiative District Stakeholder Group, Member

Barnstable County

  • Economic Development Council, Vice-Chair
  • Cape & Islands License Plate Grant Committee, Chair

Housing for the Preservation of Cape Cod

  • Board of Directors, Member

Cape Cod Climate Change Collaborative

  • Board of Directors, Member

Hyannis Main Street Business Improvement District

  • Board of Directors, Member

Town of Barnstable

  • Economic Development Task Force (2019 – 2020)

Friends or Relatives with Autism & Related Disabilities

  • Board of Trustees, Vice-President Building Committee, Chair (2016 – 2022)

National Marine Life Center

  • Board of Trustees (2002 – 2009)
an icon of an arrow

Publications and Mentions

  • Commonwealth Magazine, June 7, 2022 “Don’t Pit Housing Crisis Against Climate Crisis”
  • Bay State Builder Magazine, Cover Stories:
  • Fall 2020
  • Winter 2021
  • Spring 2021
  • Winter 2022
  • Modern Builder + Design, Summer 2015 “Heritage Sands Captures Cape Cod Community Fabric”