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Haddad's grandfather opened the business on East Street in 1932.
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Haddad Auto Marks 90 Years

By Sabrina DammsiBerkshires Staff
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PITTSFIELD, Mass. — Over the last 90 years, Haddad Auto has withstood many changes but one thing has remained the same: its commitment to its staff and community. 
 
Even after all these years, the dealership remains a family business, run by third-generation owner George L. Haddad.
 
The dealership has gone on to win awards in service excellence, and customer satisfaction. The Toyota stores have earned the President's Award for 16 years in a row, Haddad said. 
 
There are a few things that make a legacy–the employees and the community, Haddad said. 
 
These are the things that his grandfather, George A. Haddad, established when he opened the business on East Street in 1932.
 
Haddad’s grandfather moved to North Adam from Lebanon in eighth grade and immediately started working in grocery stores to help support his family. 
 
Haddad said from the beginning, his grandfather was a hard worker.
 
"He was a pretty sharp guy to come over with an eighth-grade education. He knew what he was doing and ran successful businesses," Haddad said. 
 
Haddad said he started working for the dealership at the age of 12, cleaning cars. Before he could even drive, he started selling cars. At the age of 15, he sold his first car, a 1975 Pontiac. 
 
"I sold five [cars] in a week, and I had to sit in the backseat because I couldn't drive," Haddad said. 
 
The dealership has undergone a variety of changes. Starting as a Pontiac dealership, it expanded into Toyota, Jeep, Buick, Hyundai, Ford, Subaru, and Chevy among others.
 
Today the dealership operates three car brands, Subaru, Toyota, and Hyundai, in addition to offering everything automotive-related including a collision center, rental services, and an on-site insurance company. 
 
"[Success] doesn't get handed to you. I'm blessed in one sense that I was handed an opportunity, but I still had to take advantage of the opportunity. I still had to grow that opportunity," Haddad said. "So, you have to take advantage of an opportunity, work, find opportunities, find different things, and work hard to make it work."
 
The road to success was not always clear. The family had to adjust to markets and economic changes. 
 
When General Electric cut its workforce in half, Pittsfield went through a recession which created challenges for the dealership.
 
"I was almost broke," Haddad said. 
 
Toyota sent one of its employees, John Brown, to help steer Haddad back in the right direction. 
 
Recalling his interaction with Brown, Haddad said Brown asked him two questions: "Do you really know what the problem is with the dealership and do you know what the solution is?"
 
At the time Haddad was unsure what the answer was, assuming it was a bunch of little things he was doing wrong. 
 
Brown led Haddad to his office bathroom and had him look in the mirror and asked: "what do you see?"  
 
"So, I say 'me.' He says, 'That's your problem and that's your solution. You're the problem, and you can be the solution.' He said, 'If you want to be the solution and fix things, I'll be glad to sit with you. We'll go through everything and we'll figure it out.'" Haddad said. 
 
And that is exactly what they did. 
 
Haddad said they sat down, rebalanced the books, and had to lay off 10 employees to adjust to the economic change. 
 
They started to make money again the following month. 
 
Like his grandfather, Haddad has donated time and money to various organizations including Rites of Passage and Empowerment, Berkshire Humane Society,  Strong Little Souls, and more. 
 
"I think if you do well enough you've got to help out. There's places that need help," Haddad said.
 
He has mentored youth with the Big Brother program which has since left the area but continues the work with the Boys and Girls Club. 
 
"I just believe in helping the youth that want to help themselves as best you can," Haddad said.
 
This sense of hard work passed down by his grandfather has always been with Haddad. He said nothing was just given to him, and he noted that in college he worked as a waiter for Friendly's.
 
He learned to treat customers nicely, even when the restaurant was busy because that encouraged them to come back, tip better, and request to sit in his section. 
 
During his time there he also had to deal with a "crotchety" manager who was mean to the employees. 
 
Haddad said these lessons guide him as a business owner and manager to this day.
 
"I learned from it. You don't need to treat people that way," he said.  
 
He hopes this legacy of hard work continues with his children. Working to achieve your goals is something he has tried to instill in his son, Ben, and daughter, Julia. At the age of 14, they both started to work at the restaurant Mazzeo's. 
 
Both his children are in college now and have expressed an interest in continuing the family business but he will be happy even if they choose not to.
 
"I am very proud of both of them. They are both great kids," Haddad said. 
 
More information here: https://www.haddadauto.com/
 
 
 
If you would like to contribute information on this article, contact us at info@iberkshires.com.

Friday Front Porch Feature: This Luxury Home Has Plenty of Amenities

By Breanna SteeleiBerkshires Staff

LENOX, Mass. — Are you looking for a big house to enjoy your days with a big movie theater, a sauna, and more? Then this is the house for you.

Built in 2004, this seven-bedroom, and nine-bathroom home is 7,073 square feet on more than an acre. The home comes with an elevator to the lower level to access a theater, sauna, gym, wine cellar, massage room, and its very own soda fountain. 

The home also has a guest house with a saltwater pool. A multi-car garage greets you with heated floors.

The this home is listed for $4,950,000 and is located in the 125-acre, gated Pinecroft compound.

We spoke to Leslie Chesloff, the listing agent with William Pitt Sotheby's.

What do you think makes this property stand out in the current market?

Chesloff: This gated Berkshire stone estate truly redefines luxury living in the Berkshires. What sets it apart is the rare combination of resort-style amenities and complete privacy. The property offers Canyon Ranch-level wellness living with a full spa experience at home — including a sauna, massage room, and gym — plus an eight-seat hi-def theater with wine cellar for entertaining. The heated, gunite saltwater pool and spa are complemented by a fully equipped pool house with a guest suite and complete kitchen, perfect for extended family or guests.

What was your first impression when you walked into the home?

The moment you step inside, you're struck by the quality and craftsmanship — those 300-year-old reclaimed timber floors set an immediate tone of authenticity and warmth. The scale is impressive but never overwhelming; this is a home designed for gracious living, not just show. The natural light, cathedral ceilings, and thoughtful flow between spaces create an inviting atmosphere that balances grandeur with genuine comfort.

How would you describe the feel or atmosphere of this home?

This home feels like a private wellness retreat meets sophisticated family estate. There's a serene, spa-like quality throughout — enhanced by features like the sauna, steam shower, and massage room — but it never feels clinical or cold. The Berkshire stone exterior and reclaimed timber floors ground the home in a sense of place and permanence. It's designed for people who appreciate the finer things but want to actually live well — whether that's screening a film in the eight-seat theater with wine from your own cellar, hosting poolside gatherings, or simply unwinding in your own spa sanctuary.

What kind of buyer would this home be ideal for?

This is perfect for the discerning buyer who values wellness, privacy, and culture in equal measure. I envision someone who spends their days hiking or exploring the Berkshires, then comes home to unwind in the sauna or pool. They might entertain guests in the theater wine room, host multi-generational gatherings with family staying in the pool house guest suite (which has a full kitchen), and appreciate being minutes from Tanglewood, world-class dining, and Berkshire arts.

This could be an executive looking for a primary residence with work-from-home flexibility (there's an office/bedroom suite), a wellness-focused family, or empty nesters who want to host adult children and grandchildren in style and comfort.

What would you say to a buyer trying to imagine their life in this space?

Picture Saturday morning: you're sipping coffee on the terrace overlooking your heated saltwater pool, planning a day at Tanglewood. Your guests are making breakfast in the pool house kitchen — they have their own private retreat but are steps away when you're ready to gather. Evening arrives, and you screen a favorite film in your eight-seat theater, selecting a perfect bottle from your wine cellar. This isn't just a home; it's a lifestyle that brings resort-level wellness, entertainment, and hospitality to your doorstep — all within a secure, maintenance-free compound where nature meets luxury.

Are there any standout design features or recent renovations?

Absolutely. The home includes an elevator for multilevel accessibility, which is both practical and forward-thinking. The lower level is exceptionally well-conceived — a true entertainment and wellness wing featuring the eight-seat hi-def theater, wine cellar, sauna, gym, massage room, and even a charming soda fountain. The gourmet kitchen has been recently updated, customized wet bar, while outdoor living is elevated with the heated gunite saltwater pool/spa, firepit, and that incredible pool house with guest suite and full kitchen. Also, new HVAC system and heated driveway.

Thoughtful details like cedar closets, steam showers, central vacuum, and backup generator show this home was built to the highest standards.

You can find out more about this house on its listing here.

*Front Porch Feature brings you an exclusive to some of the houses listed on our real estate page every week. Here we take a bit of a deeper dive into a certain house for sale and ask questions so you don't have to.

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