Roy Macdowell

Roy S. MacDowell, Jr. is a Greater Boston real estate developer with more than 30 years in real estate investment, development, and management. Over his career he has personally developed and/or permitted more than 2 million square feet of commercial space and more than 3,500 dwelling units. He founded The MacDowell Company, Inc., a New England landscape architecture and construction firm, where he served as president, and he has also served as a director of Sterling Bank, which grew from roughly $250 million to more than $1 billion in assets before its sale to Fleet Bank. He earned his undergraduate degree from Babson College, where he studied entrepreneurial studies and real estate.

Since 2009, MacDowell has directed the vision and strategic planning for Baystone Development, a Weston, Massachusetts–based real estate development and investment company. In that role he sets the firm's overall strategy, leads the evaluation of new opportunities, and oversees project management and execution. Baystone works across the full development lifecycle — acquisition, master planning, design, landscape architecture, permitting, construction management, ground-up development, and adaptive reuse — and describes itself as a regional leader whose projects have won multiple awards and been used as case studies by the Harvard Graduate School of Design.

MacDowell's earlier work earned recognition including a Massachusetts Historical Commission award for the restoration of the Associates Block in Arlington, MA, and a 2000 Design Excellence in Housing award from the Boston Society of Architects for Cronin's Landing in Waltham. Once regarded as one of Greater Boston's most successful developers, he was hit hard by the real estate downturn of the late 2000s, which affected his personal holdings (including the reported listing of a large Wayland-area residence); he has since remained active through his leadership at Baystone.

He is also known for extensive civic and philanthropic involvement: he served as President of the Board of Trustees of The Rivers School in Weston, MA, as a Trustee of the Boston Children's Hospital Trust Board and of Babson College, as a past board member of the Massachusetts Chapter of NAIOP, and as an overseer of the Anti-Defamation League of New England. In 2002 he invested $8.5 million to preserve the former Deaconess-Waltham Hospital — where he was born — before it transferred to Boston Children's Hospital.

• Invests as a real estate developer/principal, deploying capital into projects rather than into operating companies or startups.
• Focus on distinctive, community-oriented development that creates lasting value — Baystone's stated aim is "distinctive properties of lasting beauty" with "significant value creation."
• Works across mixed-use, residential/multifamily, healthcare, downtown revitalization, and open-space preservation projects.
• Full-lifecycle approach: acquisition, master planning, design, permitting, and construction management — with a track record spanning adaptive reuse and large master-planned communities.
• Emphasis on community input and sustainability (e.g., low-impact development goals at Legacy Farms), suggesting projects that align local/municipal buy-in with long-horizon value are favored.
• Geographically concentrated in New England / Greater Boston, where he has decades of relationships and permitting experience.