Cheshire Webb

Vice President




Cheshire Webb joins Foundry Commercial as Vice President, with a focus on the corporate services business and tenant representation. Cheshire is a corporate real estate strategist, consultant and broker, licensed in North Carolina and New York State with over 15 years’ experience, representing both public and private companies throughout multiple industries. He will continue to focus on occupier services and growing the tenant representation platform in Foundry’s Raleigh office.

Cheshire has an extensive background in real estate that began in NYC, where he worked on Wall Street, Long Island, and in the Tri State Region. Alongside brokerage, his business experience includes strategic consulting, asset repositioning, site selection, acquisition, disposition, real estate administration, and portfolio management. Through his diverse background and well-established business relationships, Cheshire has acquired a unique and broad-based client following. A sophisticated approach to the business allows him to better position clients towards long-term solutions instead of simply finding space and negotiating a lease from a one-off perspective.

Cheshire grew up in Raleigh’s Hayes Barton neighborhood and attended Broughton High School locally and Episcopal High School in Alexandria, Virginia. He graduated from the University of Alabama (Tuscaloosa) and later completed graduate studies in the real estate program at New York University. Cheshire is married to Ashley Vermillion Webb, a leading Triangle high-end women’s boutique owner for over 15 years, and together they are raising three daughters.

Key Assignments

  • Golden Corral
  • Fleet Feet
  • CRB Consulting
  • 3D Systems
  • Vermillion
  • Triple Crown Consulting
  • Reinforced Earth
  • RealPage
  • CHG Weatherby
  • Pruitt Health
  • North Star Financial
  • SilverPeak Systems
  • Samet Corp.
  • Ashton Woods Homes
  • Meritage Homes
  • Peter Millar
  • First Heritage Mortgage
  • FMI Corporation
  • Mark Spain Real Estate
  • Greystone Affordable Housing
  • Cook Wealth Management
  • Lincoln Financial
  • Training Industry
  • Triverton Advisors
  • JDRF International
  • Raymond James Financial
  • Forestry Mutual
  • Mead & Hunt
  • Balanced Scorecard Institute
  • Dickenson, Logan, Todd & Barber
  • TD Ameritrade
  • Chase Bank
  • UMT Consulting
  • Kennedy Johnson
  • Infrastructure Consulting and Engineering, of the Carolinas
  • QOL Medical – One Patient Services
  • Saratoga Capital
  • Specialist Marketing
  • Progressive Insurance
  • Savin Engineers
  • Sorenson Communications
  • Skidmore Owings Merrill
  • E.G. Bowman Co. Inc.
  • Gucciardo Law Firm
  • Harris Rothenberg Int’l.
  • Laila Rowe
  • Gwinnett College – The Medical Arts School
  • Mutual of Omaha

Community Involvement

  • Christ Church, Member
  • Alexander YMCA, Member
  • Juvenile Diabetes Research Foundation (JDRF), Eastern Carolinas Chapter


  • University of Alabama (Tuscaloosa)
  • New York University Graduate Studies – Real Estate Program