History of the Weston Roads Trust
The Weston Roads Trust was established to maintain the private roads within a unique and historically significant area of Weston, Massachusetts—an area originally shaped by the Winsor Estate and its development in the early 20th century.
Robert Winsor, a prominent financier and partner at Kidder, Peabody & Co., began acquiring land in Weston in 1884. By 1919, he owned over 488 acres, including what is now the Weston Golf Club and large portions of Wellesley Street and Meadowbrook Road. Winsor retained 16 acres and his personal residence at 68 Winsor Way, donated 50 acres to form the Weston Golf Club, and placed the remaining 422 acres into the Weston Real Estate Trust—the predecessor to today’s Weston Roads Trust.
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n an effort to attract young families to the area, Winsor sponsored an architectural competition offering a prize for the best home design that could be expanded over time. As a result, six notable homes were built along Wellesley Street between 1920 and 1926—at numbers 40, 44, 56, 60, 64, and 70—contributing to the distinctive character of the neighborhood.
The legacy of Winsor’s planning remains central to the Roads Trust’s purpose: maintaining safe, functional roadways to support this private residential community. Today, the Trust maintains 17 private roads and operates solely as a utility focused on road integrity and safety.
For a deeper dive into the history, explore these resources: