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CRE Conversions
October 29, 2025
The Union League ClubNew York, NY

Sam Cummings
Managing Partner at CWD Real Estate Investment
Speaker

Profile

A leading champion of the City of Grand Rapids, Sam Cummings has dedicated the last 30 years of his life to the preservation of Grand Rapids’ history and the enhancement of the community through the built environment.

Since forming CWD Real Estate Investment in 2008, Cummings and his partners have assembled, developed or renovated more than 2 and a half million square feet of retail and urban office real estate in West Michigan – making CWD one of the largest, locally-owned property management firms in the area. CWD’s investments in the community are focused on providing quality spaces that enrich people’s lives and strengthen the communities where they are located.

Prior to forming CWD, Cummings was founding principal and president of Second Story Properties. Under his leadership, Second Story developed and renovated more than 24 properties and 850,000 square feet of office, residential, and mixed use assets—most in downtown Grand Rapids and its near neighborhoods.

Sam is active in the local community and he and his family live in the Second Ward of Grand Rapids. When not in Grand Rapids, Sam enjoys skiing in northern Michigan and being on and near beautiful Lake Michigan in Saugatuck with his wife Janene and son Charlie.