One of Rye’s best-known landmarks is The Osborn, a continuing care retirement community that has undergone significant changes since it was founded more than one hundred years ago.

By Paul Hicks

One of Rye’s best-known landmarks is The Osborn, a continuing care retirement community that has undergone significant changes since it was founded more than one hundred years ago. The introduction to its centennial history begins: “In 1908, one woman’s dream that had become one man’s passion became a reality when the Miriam Osborn Memorial Home opened.” The book includes a valuable historical record and some priceless photographs of its early days during a period when Rye evolved from a rural to a suburban community.

Although the original name has been abbreviated to reflect the current broader mission, the centennial history honors the vision of Miriam Osborn, who had both the dream and the fortune to found The Osborn. It also emphasizes, however, the important role played by John W. Sterling, whose passion and professional skills turned her dream into reality.

A founder of the prominent law firm of Shearman & Sterling, he was renowned for his success in organizing numerous railroads and other corporations. Yet his clients also included a number of wealthy individuals like Mrs. Osborn, who was the widow of a prosperous stockbroker and yachtsman. Following the death of Mrs. Osborn in 1891, her will, prepared by Sterling, created a trust of $500,000 to establish and endow a home for “respectable indigent women in the State” (multiply all numbers by about twenty for current dollar values).

An additional $500,000 was left in trust to pay income for life to her son, Howell Osborn, a notorious playboy and spendthrift. Sterling included in the will a provision that at Howell’s death the trust principal would go to his issue, so long as they were by a wife “who had not acted, sung or danced professionally.” Howell did marry a well-known actress, Fay Templeton, but he died without issue, so the trust principal and residue of his mother’s estate were added to the endowment established for the Miriam Osborn Memorial Home.

While continuing to manage his growing law firm, Sterling devoted countless hours to planning and acquiring land for the Osborn Home and its spacious grounds on what was known as Theall’s Hill. Much of the acquired property was farmland that had belonged to some of the oldest Rye families. Photos in the book of the Mead farmhouse, built in 1681, and a Purdy House that dated to around 1740 (both of which had to be demolished), should make us realize how fortunate we are to have the Square House and the Knapp House still standing.

A 1910 map of the Village of Rye shows numerous parcels of land, aggregating more than 200 acres, held in the name of John W. Sterling between what is now Osborn Road and North Street. These included Mead Pond, which was renamed Lake Miriam for a while. The properties extended east to the Old Post Road and west across the current Theodore Fremd Avenue (where a trolley line ran).

To the west of the railroad tracks there was a 37-acre parcel adjoining Greenwood Union Cemetery. According to the centennial history, “John Sterling thought that the hillside west of the railroad was perfect for the dairy he planned. Beaver Swamp Brook that flowed through it had sufficient water for eight Guernsey cows, seven calves and one award-winning Holstein bull he purchased.”

Sterling continued his purchases of farmland in Westchester, including nearly 600 acres off North Street in Harrison in what is now known as Sterling Ridge. A lifelong bachelor, his estate, following his death in 1918, was valued at more than $20 million, of which $18 million was left to Yale University, his alma mater. Included in that gift, according to The New York Times, were 568 acres in Harrison and 11 parcels in Rye.

His will required that Yale use part of his estate to fund “at least one enduring, useful and architecturally beautiful building, which will constitute a fitting memorial of my gratitude to and affection for my Alma Mater.”

It turned out that was enough money for four buildings: Sterling Memorial Library, the Sterling Law Building, the Hall of Graduate Studies and the Sterling Hall of Medicine. There were even enough funds left over to endow a number of Sterling professorships, the highest honor for members of the Yale faculty.

Also included in his will was a bequest of $1.5 million to the Miriam Osborn Memorial Home Association plus another $100,000, which he said was the amount Mrs. Osborn had bequeathed to him in a hand written codicil to her will. To those gifts were added funds to build a wing in memory of his mother, Catherine Sterling, as well as 25 acres of land in Rye and 32 acres in Harrison. It is fitting that the newest additions to The Osborn’s campus are the apartments and garden homes for independent living within what is called Sterling Park. The centennial history of The Osborn by Mark R. Zwerger, Janet M. Malang, and Andrew F. Horn is available for purchase from Arcade Books, Rye’s only independent bookstore.