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Sydney Watkins Phillips

Sydney Watkins Phillips passed away peacefully at home in the early hours of November 15, 2022 in the company of her two children, Nancy Osborne Almquist and Richard Watkins Osborne.

Sydney was born in Elmira, NY, the third of three children to parents Alida Wilbur Watkins and Julian Lewis Watkins and spent her childhood years in Westport, CT and Weston, MA where she attended the public elementary school and then the Winsor School in Boston. Following her graduation from Winsor, she moved to New York City where she worked at the magazine Women’s Home Companion and shared an apartment with two friends from the Boston area. She met her first husband Maurice Machado Osborne Jr. who was attending the Columbia College of Surgeons and Physicians as a Navy recruit. After their marriage in 1947, they lived in Boston, Bethesda MD, and a year in Naples Italy before returning to the U.S. in 1953. After residing in Cambridge  and Brookline, she moved to Atherton, CA in 1960 where her husband served as a physician and then Director of the Student Health Services of Stanford University. In 1967 she returned to Boston where her husband had taken a new job at Tufts University. Purchasing and tastefully renovating a five-story town house at 126 Marlboro Street just two blocks from the Public Gardens was an early indication of her subsequent affinity for real estate and smart investments. Following divorce in 1974 and the sale of the Marlboro Street house, she purchased a three-unit house in the Bay Village neighborhood of Boston where she lived while re-entering the work force. In the warmer months, she lived in Ipswich in a newly built house on land given to her and her ex-husband by her mother-law-law Francis Cabot Osborne. This modest house on a five-acre glacial moraine in the Great Marsh then became her primary residence in 1976. Meanwhile, she became a successful real estate agent and broker on the North Shore with Vernon Martin during a time of unprecedented growth. She took special pride in the further development of her Ipswich property – “Syd’s Site by The Sea” as it was affectionately called. An excellent cook and gracious hostess, she greatly enjoyed hosting family and friends for visits both brief and long.

In 1997, she married Christopher H. Phillips of Essex, who she had met through mutual friends. They enjoyed a decade together before his death in 2008, travelling regularly to Arizona to ride horses at a favorite ranch resort and to Dorset, VT often spending winters in D.C. where Chris maintained numerous friendships from a long career in politics and diplomatic service. In her last two decades, she focused on home and friends and family. She was also actively interested in her local community and was a generous donor to local causes and charities especially the Ipswich Y, The Trustees of Reservations, and Ascension Church. She was also a member of the Chilton Club of Boston for many years where she enjoyed taking family and friends to lunch and hosting family gatherings.

Sydney is survived by her daughter Nancy Osborne Almquist and husband Eric of Belmont;  her son Dr. Richard Watkins Osborne and his wife Sara E. of Schuylerville, NY; five grandchildren Adam Almquist and his wife Jennifer Marie of Santa Rosa, CA, Adrian Almquist and his wife Dalila M. of Painfield,  Nicholas Almquist and his wife Clementtine Jang of Oakland, CA, Gillian Osborne and her husband Brian Petit of Santa Barbara, CA and Nathaniel Osborne of Bronx, NY and four great grandchildren: Julian and Shepherd Almquist and Quin and Remi Pettit. She was the brother of the late Wilbur Watkins formerly of  Napa, CA and Tedrowe Watkins formerly of Big Fork, MT and Palm Springs, CA

A Memorial Service for family and friends will be held 11 am Wednesday, November 30  in the Ascension Memorial Church. Arrangements are under the direction of the Whittier-Porter Funeral Home of Ipswich.  In lieu of flowers memorial contributions in her name may be made to: Ascension Memorial Church, 31, County St. Ipswich, MA 01938, Ipswich YMCA, 110 County St., Ipswich, MA 01938 and or the Trustees of the Reservation, development@thetrustees.org.


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