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Steepleview Realty, Berkshire Elder Law Mark 25 Years
By Tammy Daniels, iBerkshires Staff
05:48PM / Wednesday, April 19, 2023
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Jennifer Segala, holding a proclamation from the mayor, and the team at Steepleview Realty celebrating 25 years in business.

Mayor Jennifer Macksey speaks at last Thursday's open house celebration for Steepleview Realty and Berkshire Elder Law at the Berkshire Plaza.

The mayor with Steepleview broker-owners Jennifer Segala and Deb Trzcinski.



Attorney James Sisto speaks after receiving a proclamation on Berkshire Elder Law's 25th anniversary from Mayor Jennifer Macksey. 
NORTH ADAMS, Mass. — Two local businesses have celebrated their 25th anniversaries — and their founders' quarter-century of friendship.
 
Jennifer Segala of Steepleview Realty and attorney James Sisto of Berkshire Elder Law marked their anniversaries last week with an open house and music at the Berkshire Plaza on Main Street, where both have offices. 
 
"Twenty-five years ago this nerdy attorney with a full head of hair walks into my office and says, 'I just opened a new practice we're going to be best friends,'" Segala joked. "And 25 years later, we are."
 
Each was presented with a proclamation from Mayor Jennifer Macksey recognizing their years in business and service to their clients.
 
Steepleview was established in 1998 with its first and main office in Adams, later opening offices in North Adams and Pittsfield. 
 
"Steepleview Realty has provided high quality, professional sales and support to the residents of North Adams for so many years, investing countless hours ensuring that their clients are making sound investments," said Macksey.
 
The firm has brokered more than $600 million in real estate sales in Massachusetts, New York, Vermont and the state of Florida. Segala, a graduate of Massachusetts College of Liberal Arts, has been in the real estate business for more than three decades and operates two real estate schools.
 
She was joined as broker-owner in 2015 by Deb Trzcinski, who has been with Steepleview since it opened. 
 
"If you would have asked me 25 years ago, this young lady, with I guess a lot of moxie, who decided to go out on her own, if I would be here today, I would never have guessed in a million years," Segala said. "I have a powerful team of strong women that are dedicated to the business. And I'm amazed, I'm amazed that we've sold over $600 million over the 25 years ... I guess we're up to McDonald's standards."
 
Segala said she and her team believe in North Adams and that Scarafoni & Associates has been a "wonderful partner ... making sure we always had a beautiful presence downtown." Steepleview had been located at 53 Main before moving to 33 Main, both owned by Scarafoni. 
 
Sisto, an elder law and real estate attorney, came to the Berkshires in 1990 after working in the World Trade Center as a tax consultant. 
 
"He promised he would only practice in the areas he enjoyed and enhance the quality of life for all of us in Berkshire County," said Macksey, who pointed to his founding membership in the National Alliance of Attorneys for Alzheimer's Training, his speaking engagements explaining the many aspects of elder law and financial planning, and his informative reports.
 
"He provides free newsletters to help others make sound decisions, and his work and responsiveness to the city of North Adams is remarkable," she said. 
 
Sisto said the cost of buying a home in New York City led to him to the "country" as his then wife was from the Berkshires.
 
"I love it, I love the fact that it's not congested and the people are so nice," he said. "It has been my honor to serve the people of North Adams with real estate and estate planning, especially my elder clients, that's a passion of mine. 
 
"Berkshire County has welcomed me with open arms. I consider myself a resident now."
 
Macksey described both as good friends, telling how Segala had helped her through the difficulties in buying her house on Hospital Avenue — which suffered squirrel damage — and how Sisto had arrived at the closing for the seller and gave her — a squirrel. 
 
"We've been good friends and we survived it. So if anybody has any squirrels, you can send them to Jim Sisto," she said to laughter.
 
As dozens of friends, colleagues and clients mingled in the Steepleview offices, Segala was already thinking about the next 25 years. 
 
"We'll be here for a while longer," she laughed. "We'll be selling everybody's great-grandchildren's houses."
 
Correction: Jennifer Segala's name was originally given incorrectly in this article. iBerkshires regrets the error. 
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