Our History 

Berkshire Real Estate traces its long history back to 1969 when the first office opened. Jump forward to 1991 where our very own Broker/Owner Steve Ray began his full-time real estate career under one of his early mentors, Donald Ruffer at Ruffer Real Estate. At the time Donald Ruffer had built a large real estate office that not only included residential sales but also had a strong presence in the local commercial real estate market. Ruffer passed his company on to his sales manager Peter Arms with Steve Ray serving as the Broker and continues now as its successor in Berkshire Real Estate. Over 50 years later and we still serve both residential and local commercial real estate from our large Downtown Pittsfield Office 

With over currently 125 years of real estate sales experience in Berkshire County by agents that serve a broad range of the market. No office in Berkshire County is better prepared to serve your real estate needs. 


Our Broker/Owner 

Steve Ray throughout his 30-year career has been known as Berkshire County’s most innovative real estate broker. In 1993 he was one of the state's first exclusive buyers agents. He is a pioneer in buyer representation and has developed many of the practices we see used today.  

In 2003 he was one of the state's first discount real estate brokers offering new options for the consumer never seen in the local market place.  

Holding High Esteems such as: 

Past President of Berkshire Multiple Listing Service (2017) 

MAR state political coordinator  

Past President of the Berkshire County Boards of Realtors (2015) 

Berkshire County Board of Realtors Realtor of the Year (2015) 


Having trained with Real Estate Success Trainer Verl Workman he now teaches as a Real Estate Success Coach. Devoting much of his time passing on his knowledge and leading his team of veteran and well experienced agents to further success. 

Our Core Values


At Berkshire Real Estate Associates, we provide honest counsel and objective strategy based on decades of successful experience, a wealth of professional knowledge and a position of leadership in the community. After nearly 30 years in the Berkshire real estate market, we not only know the business, we know the neighborhood. It’s just one reason why we help our clients buy or sell over so many properties every year. Like the weather in the Berkshires, Berkshire Real Estate is ever changing and adapting. 


Every real estate agent likes to think they’re innovative. But what does that really mean? At Berkshire Real Estate Associates, it means a great deal – not only to us but especially to you. It means state-of-the-art systems, industry-leading technology and world-class marketing tactics. More importantly, it also means a progressive attitude and unique aptitude for anticipating possibilities, assessing opportunities and delivering desired results. 


One of the things we hear about most from our clients is our willingness to tell them what they may not want to hear. The truth is our brand of honest communication may not be for everyone. But the way we see it, a relationship based on anything else will never really benefit anyone. So, we look at things objectively, look you in the eye and tell you all you need to make the best possible decision. 

This commitment to collaboration and custom-tailored feedback not only keeps you engaged, but provides a competitive advantage that allows you to move forward with complete confidence.