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Meet The Benningtons

Bennington Properties is truly a family business. The founders of the company, Gene and Penny Bennington celebrated 41 years of marriage before Penny passed away in 2016. Penny’s sister, Carolyn, was an instrumental part of the company from its beginning until her passing in 2012 and Gene and Penny’s son Robert has been a part of the business since it beginning and became the company's CEO in 2010.

The Beginning

Gene Bennington was born and raised in Dayton, Ohio. After graduating from high school, Gene enlisted in the Marine Corp, where he served for four years. The Marines took him to the Kaneohe Marine base in Honolulu, Hawaii, where after his service he graduated from the University of Hawaii with a degree in Zoology.

Penny was born and raised on the Hawaiian Island of Kauai and after high school moved to Oahu where she graduated from the University of Hawaii with a degree in Medical Technology. After college, Penny and Gene married and eventually gave birth to their only son, Robert. After Robert’s birth, the Benningtons moved to Tualatin, Oregon where they spent the next 15 years. Gene worked in Real Estate and Penny worked as a medical administrator for Kaiser Permanente until she obtained her Masters degree in Business and joined Gene as a licensed Realtor.

In 1997, Robert was off to college and Gene and Penny decided it was time to move to beautiful Sunriver, Oregon. In 1998, Gene and Penny started Bennington Properties, LLC with only 1 vacation home.

Robert graduated from Oregon State University with a degree in Zoology (the apple doesn’t fall too far from the tree). While in school Robert met Holly, who was in the Spanish Masters Program at the University of Oregon.  Learn more about Robert.

Bennington Kids

The Bennington family welcomed the birth of Robert and Holly's first, second, and third child (triplets) in 2009. Born 3 months early the Bennington triplets spent the first 3 months of life in the Neonatal Intensive Care Unit (NICU) at St. Charles Hospital in Bend. Audrey, Oliver, and Grace are all doing great now and have become the delight and joy of the Bennington Family. In 2012 the Bennington's welcomed their fourth child, Abigail, to the family and in 2015 they welcome their fifth child, Henry Eugene Scott, to the family.

Dog Lovers

One notable thing about the Benningtons is their love for dogs.  The founding dogs, Molly (yellow lab) and Kai (Chesapeake Bay Retriever) have both gone onto heaven, but the Bennington's welcomed a Golden Retriever, Ohana, into their family in 2014.  Learn more about Ohana.

Family Photos


Founders, Gene and Penny Bennington (Penny passed away in 2016)


Bennington Family ~ early days (Gene, Penny, and baby Robert)

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