Sleeping Dog Properties and Chris Rapczynski Honored in General Contractors Magazine

By Exec Edge Editorial Staff

The Boston area is a challenging place to be a general contractor. It’s home to innovative modern structures as well as colonial architecture that requires the highest level of construction knowledge to service. Not only that, but at 400 years old, the market is established and highly competitive.

But that hasn’t stopped Sleeping Dog Properties and Chris Rapczynski, its founder and president, from becoming one of most successful construction firms in New England in just under 30 years. Sleeping Dog Properties’ meteoric rise is the result of pioneering strategies that boost efficiency in construction project delivery and a client-first service model.


Recently, Sleeping Dog Properties was honored in General Contractors Magazine as one of the best general contracting firms in Cambridge, Massachusetts. Over the past three decades, the firm has managed over $500 million in construction projects, specializing in luxury residential, bespoke commercial, and unique hospitality projects. And its growth is accelerating. Sleeping Dog Properties is expanding its services into Massachusetts’ Cape Cod area and the Lakes Region of New Hampshire.

And if Rapczynski’s got anything to say about it, SDP will be flourishing for years to come.

“Life is humbling,” he says. “And as you age and gain a few pounds or slow in your step, whatever the dynamic might be, you start to think about where the company will be. I think for the next generation is where my mindset is right now because I have to be forward-thinking about the long planning that it takes to get a company into a position where it can have a second generation. Most construction companies only survive a first generation of ownership. I think that our company serves by empowering our leadership to take on the responsibilities in an ownership type of capacity.”

Sleeping Dog Properties has managed over $500 million in construction projects in the Boston area. Some notable custom real estate projects include a high-rise apartment in Boston’s Millennium Tower, a high-end steak house in Andover, Massachusetts, and a 4,000-square-foot children’s medical facility in Wellesley, Massachusetts. The company also undertakes remodeling and repair projects of all types, such as kitchen, bathroom, and office remodeling.

Introducing Innovation to an Entrenched Market

Chris Rapczynski has been a respected member of the construction community in Boston for 25 years. But when he founded Sleeping Dog Properties 30 years ago, he was on his own. He was a creative type who saw construction as an act of creativity, and he began flipping condos as a way to fulfill his passion. “I’ve always believed that if you do what you love, then the rest will follow,” he says.

And it did. Soon after, demand for his work grew, prompting him to start his contracting firm, Sleeping Dog Properties. Rapczynski brought his unique perspective and values to his company: integrity, service, compassion, and discipline. In an industry fraught with dishonesty, fraud, and poor customer service, Sleeping Dog Properties’ people-first business model was a strong differentiator.

Raqpczynski has been a member of the Boston construction community for 25 years, and he’s a member of the Association of General Contractors and the American Institute of Architects.


Chris Rapczynski has been recognized throughout his career for his work and leadership, earning multiple awards from the Boston Society of Architects, the Small Business Association of New England, and the Commonwealth of Massachusetts. In his free time, Rapczynski volunteers as a coach for the Andover Soccer Association in his hometown. He also actively engages in philanthropic giving, supporting charities such as Build Health International, Music Drives Us, and Pan-Mass Challenge.

Breaking Away From Competitors

Sleeping Dog Properties snowballed by building lasting relationships with clients, employees, and contractors. Customers who had grown to expect unreliable service and no-shows from contractors were easily won over by SDP’s reliability, fair pricing, and overall demeanor. Rapczynski even talks of taking break-even jobs and providing assistance to customers who fell on financial hard times.

“We might not make a profit in that job or this item, but we’re happy, we have good lives,” he says. “Those are the important balances that I focus on and I think that resonates with the clients.”

SDP’s employees are treated with the same dignity. Rapczynski pays his team above-average wages, incentivizing higher quality output — and it works. “The human stock of our company is held in the highest regard,” he says — although he laments that headhunters are constantly at his employees’ heels.

Rapczynski has also mentored disadvantaged and career-path-challenged individuals aspiring to become future Boston contractors. By building bridges within the contracting ecosystem, Sleeping Dog Properties has gained access to suppliers, materials, and subcontractors that even more established competitors can’t match.

All of this is backed by a discipline of service and quality built into the foundation of Sleeping Dog Properties. Rapczynski cites this discipline as the company’s most important competitive advantage. Developing a process that guarantees a standard of quality and implementing it companywide (otherwise known as good management) is something sorely lacking in the construction industry today.

Overcoming Industry Challenges

Chris Rapczynski is no stranger to the unexpected challenges that come with each contracting job. “Our zone is a zone of chaos,” he says. Sleeping Dog Properties confronted some of its most formidable challenges during the COVID-19 pandemic.

Rapczynski admits that supply chain issues and inflation put a strain on his employees, subcontractor partners, and customers. “I don’t know one person who’s not felt the pain of the pandemic,” he says. Luckily, SDP’s depth of suppliers and skilled tradespeople allows for a high degree of flexibility. If one material isn’t available, a substitute can be found. If a team cannot perform a specific task, they find an alternative method to get the job done. In the words of Rapczynski, “We have to be creative.” And nobody in the Boston construction community seems to outdo Rapczynski when it comes to creativity.

Despite the insecurity brought by supply chain issues and inflation, Sleeping Dog Properties has flourished during the pandemic. Tight budgets have led to fewer projects industrywide, which has expanded SDP’s access to subcontractors. And a rise in mortgage rates has spurred demand for luxury residential projects as affluent residents opt to renovate their homes instead of buying real estate.

Recognized for Excellence

Sleeping Dog Properties is not only the choice general contractor among customers in the Boston area. It’s also been recognized for excellence in construction, design, and contracting by various institutions and publications over the years. A few notable awards and features include: Boston Society Architecture Access Award; four Best of Houzz Awards for service and design; Boston Society of Architects Design Award; Commonwealth of Massachusetts Department of Public Safety Architectural Access Board Honor Award for Accessible Design; a cover feature in Interiors magazine; a feature in The Boston Globe; and many more.

Recently, Sleeping Dog Properties was named one of the best general contractors in Cambridge by General Contractors Magazine. Eight general contractors were honored (out of 40-plus firms in the Boston area) for their excellence in construction services and their contributions to the iconic real estate landscape of Cambridge. Sleeping Dog Properties was selected for its unwavering customer service standards and its continued dedication to innovation going 30 years strong.



Exec Edge