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A Legacy of Building in MetroWest.
Founded on the principles of structural integrity and enduring design, O'Leary Homes is a boutique development firm rooted in Holliston, Massachusetts. For two generations, we have bridged the gap between traditional New England craftsmanship and modern residential planning.
Stephen O'Leary, Sr. Founder & President
Credentials:
MA Unrestricted Construction Supervisor
Technical Studies, Wentworth Institute of Technology
With over 40 years of development experience, Stephen is the visionary behind the O'Leary standard. His deep knowledge of construction is rooted in grit and discipline; he launched the company after five years of hands-on field experience, simultaneously completing technical night classes at the Wentworth Institute of Technology.
Stephen transformed his specialized framing outfit into one of Massachusetts’ premier boutique home builders, overseeing landmark projects across MetroWest and Cape Cod. His reputation is built on an uncompromising work ethic and a granular understanding of structural engineering.
Stephen O'Leary, Jr. Principal & Director of Operations
Credentials:
MBA, Entrepreneurship & Finance (Babson College)
B.S. Business Management (University of Rhode Island)
MA Unrestricted Construction Supervisor
Licensed Real Estate Broker (MA)
Stephen brings a modern, data-driven approach to residential development. Holding a Master of Business Administration (MBA) with distinction from Babson College, he bridges the gap between field operations and market trends.
As a Licensed Real Estate Broker and Construction Supervisor, Stephen manages the full project lifecycle—from land acquisition and financial planning to final closing. He ensures every O'Leary community is delivered on schedule, on budget, and to the highest standard of quality.
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