The Wrong Roof, Eastern Point, Gloucester, MA
The Highlands (now Highlands Historical Society), 7001 Sheaff Ln, Fort Washington, PA 19034
The Woodlands, 4000 Woodland Ave, Philadelphia, PA 19104
Caroline Sidney Sinkler (April 23, 1860 - May 5, 1949) was born on the Belvidere Plantation in Orange County, South Carolina.
Sinkler purchased The Highlands from the Sheaff family in 1917. She resided year-round at the estate and made many improvements to it. She then sold the estate to her niece Emily Wharton Sinkler Roosevelt (1884-1970) in 1941. In 1916, Emily had married Nicholas Guy Roosevelt (1883-1965), third cousin to President Theodore Roosevelt. Emily Roosevelt later donated the property to the Commonwealth of Pennsylvania in 1957, retaining the right to occupy the property until her death. The state took over ownership after her death in 1970. The Highlands is now administered by The Highlands Historical Society.
Caroline Sidney Sinkler owned The Wrong Roof, the house between Beauport and The Red Roof, respectively Henry Davis Sleeper and A. Piatt Andrew's houses in Eastern Point, Gloucester. She was a good friends of Cecilia Beaux (1853-1942), who also lived at Eastern Point.