Originally from Washington, D.C., Penelope first worked in the high-profile world of entertainment for over 10 years. After her role in public relations at the American Film Institute at the Kennedy Center, she was business manager at a noted talent agency in NYC where she negotiated contracts, and prior to that, interpreted the working code at Screen Actors Guild for actors and producers. This initial career move made complete sense, as her upbringing was steeped in fine arts. After all, Penelope's grandfather was a national Living Treasure of Japan for woodblock printing, and her father was a screen writer who mentored under director John Ford as well as a writer/editor with NASA developing projects for the Apollo space program. In 1989, Penelope redirected her artistic sensibilities and turned her deep love of buildings, design and architecture into a new career in commercial real estate running a successful midtown executive suite called Corporate Executive Offices. She also handled all facets of sales and marketing for Executive Systems International as executive director. She worked with The Lawrence Group, LLC and as a tenant broker, moved a wide variety of tenants ranging from creative companies to law firms into office and loft space from 65th Street to the Battery. As a Landlord's Agent, she handled buildings in Soho and the Flatiron district. Visiting Shelter Island for the first time in 1995, Penelope immediately fell in love with its simplicity and tranquility, and bought a house there. Two years later, she began selling residential real estate there, and after the events of 9/11 moved out East full time. . Penelope also handled two transactions that were each the highest sale on Shelter Island in its history.