Stephen R. Pleines founded Eastern Land Company in 2018. Stephen's exposure to the commercial real estate field began at an early age in the 1990's.

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In 2006 Stephen enrolled at the University of Colorado at Boulder, where he was a four-year athlete for the Snowboard Team. In 2011 Stephen was hired as the Assistant Coach for the University of Colorado Snowboard Team, leading them to the USCSA Nationals in Sun Valley, ID.

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In 2012 Stephen began his career at Boston Properties, where he was part of a team responsible for the management of the retail portfolio at The Prudential Center. In 2013 Stephen joined The Dartmouth Company where he specialized in Landlord and Tenant representation in the Boston-Metro Market. Throughout his time at The Dartmouth Company, Stephen represented clients such as Emerson College, Boston Public Library, Oxford Properties, Union Investment, Carpenter & Co., PGIM, GID, BioMed Realty Trust, Federal Realty Investment Trust, Pebblebrook Hotel Trust, and National Amusements.

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Stephen completed Harvard Business School's Negotiation Mastery and Leadership Principals courses in 2019 and 2021, respectively. Stephen is an active member of the International Council of Shopping Centers, the Urban Land Institute, and the Massachusetts Audubon Society. Stephen is a recipient of CoStar's 2017 Power Broker Award for Top Retail Brokers in the City of Boston.