Cheshire Webb Headshot

Cheshire Webb

Senior Advisor


Cheshire joined Cresa in November of 2018, as Senior Advisor, specializing in corporate occupier representation and occupier services. His real estate career began in 2004, in New York City, where he worked on Wall Street in office development. Since returning to his hometown of Raleigh, NC in 2012, Cheshire worked early on with commercial developers and institutional and private buyers and sellers, and shortly thereafter turned his focus exclusively to corporate tenant representation.


223 S. West Street
Suite 900
Raleigh, NC 27603



Cheshire attended Episcopal High School in Alexandria VA and went on to attend the University of Alabama (Tuscaloosa) with a degree in Communications, minoring in General Business Administration. After graduating from the University of Alabama, Cheshire completed graduate studies in the real estate program at New York University in 2009.
  • Member of the Alexander YMCA
  • Member of The Juvenile Diabetes Research Foundation (JDRF), Eastern Carolinas chapter
  • Golden Corral
  • Fleet Feet
  • FMI
  • Globant
  • Cook Wealth Management
  • Lincoln Financial Group
  • Training Industry
  • Tiverton Advisors
  • Junior Diabetes Research Foundation, JDRF
  • Raymond James
  • Forestry Mutual Insurance Company
  • Mead & Hunt
  • Ameritrade
  • Chase
  • Balanced Scorecard Institute
  • Mutual of Omaha
  • QOL Medical
  • Progressive