Chris Rapczynski has transformed Boston’s architectural landscape for thirty years through Sleeping Dog Properties, his award-winning design-build firm. Founded in 1993, the company quickly became a high-end residential and commercial construction leader throughout Greater Boston.
But in recent years, Rapczynski has strategically expanded his company’s footprint, bringing his signature blend of craftsmanship and innovation to new luxury markets across New England.
This expansion, particularly into Cape Cod and New Hampshire’s Lakes Region, represents a natural evolution for Sleeping Dog Properties. It also showcases Rapczynski’s client-centered approach to growth and his ability to maintain exceptional quality across multiple regions.
Following Clients to Their Second Homes
When asked about his decision to expand beyond Boston, Rapczynski’s answer reveals much about his business philosophy. “In the world of luxury, single-family residential builders, there’s a lot of competition. And for me it’s about the relationship of the clients,” he explained in a recent interview.
Rather than pursuing random growth opportunities, Sleeping Dog Properties has expanded by following existing clients to their vacation properties. “We are following our clients that are Boston primary. We’ve built those relationships of a successful team, and then they want us to go to these new communities where they vacation summer rental, summer or winter,” Rapczynski noted.
This client-driven approach to expansion differs markedly from traditional growth strategies. Instead of conducting market research to identify potential new territories, Sleeping Dog Properties has followed established relationships, allowing satisfied customers to pull the company into new regions.
The strategy makes sense, given Boston’s position as a center of wealth. “Boston’s a big epicenter of wealth, maybe the third largest in the United States, maybe even in the world,” Rapczynski observed. This concentration of affluent clients means many maintain multiple homes in vacation destinations throughout New England.
Interestingly, Rapczynski has received requests to build in far-flung locations like Aspen, San Diego, Hawaii, Stowe (Vermont), and Naples (Florida) – all places where his Boston clients maintain second homes. However, he has strategically chosen to focus on locations within a reasonable distance from Boston.
Strategic Selection of New Markets
Not every client request for expansion has been accepted. Rapczynski’s decision-making process reveals a thoughtful balance between business opportunity and practical constraints.
“It’s about my accessibility to the experience of that build. Can I get there?” he explained. This practical consideration has led him to limit expansion primarily to areas within a two-hour radius of Boston – specifically New Hampshire’s Lakes Region (about 90 minutes from his home in Andover) and Cape Cod (approximately two hours away).
This careful geographic selection allows Rapczynski to maintain personal oversight of projects while balancing family commitments. “I’m married, I got three kids, I’m not going to go build a house in Hawaii. I would love to build a house in Hawaii. It would be my dream, but I just don’t have that lifestyle,” he acknowledged.
Even promising nearby opportunities have sometimes been declined when practical challenges emerged. Rapczynski shared a story about turning down a $25 million project in Newport, Rhode Island, during the pandemic because COVID restrictions complicated transportation logistics.
“The only way that we could make it work was if we put everybody in a van to drive back and forth. We have our passenger vans, and they didn’t want to do that every day with COVID,” he explained. Despite the client’s insistence, Rapczynski declined the job because he couldn’t guarantee the company’s standards would be maintained.
This selective approach to expansion has allowed Sleeping Dog Properties to grow thoughtfully rather than rapidly, ensuring that each new project receives the same attention to detail as those in Boston.
Building Relationships in New Communities
Expanding into established vacation destinations presents unique challenges. Cape Cod and New Hampshire’s Lakes Region have their own building traditions, regulations, and quirks that differ from Boston’s urban environment.
Rapczynski has developed a systematic approach to entering these new markets. “Whenever I go into a new community, I start with the zoning code book. Usually, it’s a binder book, and I read it cover to cover,” he explained. This thorough research provides foundation knowledge about local regulations.
He then goes further, watching planning board meetings online to understand the community’s priorities and concerns. “You can find the tenor of what the valuable moments are in a community that they’re raising their flag to,” he noted.
This research is supplemented by building relationships with local professionals – surveyors and building department officials – who understand the nuances of the area. “I reach out to the building department and meet with the building inspector. Usually, there’s an administrative person who’s the most fluid in knowledge at the front desk because they’ve been there for 20 years,” Rapczynski said.
He also recognizes the value of local expertise when staffing projects outside Boston. “When we take on a project, we hire from the local employment base for the resources there, let’s say a site supervisor or a project manager,” he explained. While these local hires might not lead projects, they serve as “social liaisons” who help navigate community dynamics.
This methodical approach to entering new markets has allowed Sleeping Dog Properties to establish credibility in vacation communities while avoiding the pitfalls that often trap out-of-town builders.
Meeting Unique Regional Challenges
Each region presents distinct challenges that require adaptation. In Cape Cod, for instance, Rapczynski has encountered unique building regulations and environmental considerations that differ from Boston’s urban construction environment.
“Up in the Lakes region, one of the problems that they have is that they have an inconsistency in the number of bedrooms that gets measured for a septic tank,” Rapczynski explained, detailing how summer rentals can overwhelm systems designed for year-round residences. “The overflow of that water contaminates the lake, and the lake has a bloom of cyanobacteria, which can kill dogs and pets, give you rashes, and get you sick.”
Understanding these local concerns has helped Sleeping Dog Properties adapt designs and construction methods to meet regional needs. It’s also allowed the firm to advocate effectively for clients while respecting community priorities.
Navigating the “anecdotal mythology” of what’s required in seasonal communities presents another challenge. “Sometimes it’s just the way that they’ve done things,” Rapczynski noted, pointing out how construction practices in vacation areas sometimes rely more on tradition than formal code.
By balancing respect for local customs with professional standards, Sleeping Dog Properties has successfully integrated into these new communities while maintaining its reputation for excellence.
Maintaining Quality Across Multiple Regions
Perhaps the most impressive aspect of Chris Rapczynski’s expansion is his ability to maintain consistent quality across geographic boundaries. While many construction firms struggle to deliver consistent results within a single city, Sleeping Dog Properties has successfully exported its high standards to multiple regions.
This consistency stems from Rapczynski’s emphasis on what he calls the “three C’s” – cleanliness, communication, and competency. These core values travel with the company regardless of location.
“I feel like cleanliness is next to godliness,” Rapczynski explained in a recent interview. “My type A personality, I walk around and go, ‘That’s a mess. That’s a mess. That’s a mess. Let’s get the cleaners in here. We’ll start cleaning.'” This attention to job site organization creates confidence in clients, regardless of whether the project is in Boston, Cape Cod, or New Hampshire.
Communication remains equally vital across regions. While distance can complicate project oversight, Sleeping Dog Properties has developed systems to ensure clients remain informed and engaged. Technology plays a key role, with digital tools allowing remote monitoring and regular updates.
Competency – the third C – is ensured by bringing key team members from Boston and carefully selecting local talent. “We present the best candidates that there are on the market, and that’s costly and valuable to a project. But if something’s done incorrectly, that’s even more costly,” Rapczynski noted.
Long-Term Growth Strategy
While current expansion has focused on Cape Cod and New Hampshire, Rapczynski has broader ambitions for Sleeping Dog Properties’ future. He envisions controlled growth that preserves the company’s core values while allowing it to serve more clients.
“Ultimately, I think about legacy because I think about how long I can persist at doing the day-to-day that I do,” he explained. This forward-thinking mindset has led him to develop leadership within the company, who can eventually take ownership stakes.
“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,” Rapczynski said. “Most construction companies only survive a first generation of ownership.”
This succession planning suggests that Sleeping Dog Properties’ expansion beyond Boston represents the first phase of a longer-term vision. By establishing successful operations in multiple regions now, Rapczynski is creating opportunities for future growth under the next generation of leadership.
Interestingly, he even contemplates a different type of expansion in his own future. “With my wife, we joke about what my retirement would be, and my retirement, once my kids are off to college, it might be going to build fancy houses in all these communities. I’ll go to Aspen, I’ll go to Hawaii, I’ll go to these places where I’ve declined to build before and take on a project.”
Whether or not those far-flung projects materialize, Rapczynski’s thoughtful approach to expansion has positioned Sleeping Dog Properties for continued success throughout New England. By following clients, embracing local knowledge, and maintaining unwavering standards, he has successfully transported the company’s reputation for excellence beyond Boston while setting the stage for its next thirty years of growth.
