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Bennington Real Estate Team

Bennington Properties is a family business in heart and in structure. When you work with Bennington Properties to buy or sell your home you will have full access to our real estate and vacation rental teams.  Our team combines experience in real estate investing, property management, vacation home rentals and resort properties.

Before you spend your time looking through hundreds of homes for sale in Central Oregon, let us build you a profile that will track every home in our area that meets your specific needs. When a new home or condo comes on the market that matches the specific things you are interested in, our system sends you an email alert.

Meet the Team

Gene Bennington, Owner & Principal Broker
541.948.6209


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. After college, Gene married Mary Margaret Wallis (Penny) and they eventually had their only son, Robert.  After Robert’s birth, the Benningtons moved from the Big Island, Hawaii to Tualatin, Oregon where they spent the next 15 years. 

John D. Watkins, Principal Broker
541.390.3600

I am a born and raised Oregonian and have lived in Central Oregon for almost 15 years. I spent 30 years as a CPA and Chief Financial Officer of both public and private companies prior to becoming a real estate broker.  I have been with Bennington Properties for 10 years and exclusively sell in Sunriver.  I am consistently in the top 3 brokers in Sunriver year after year.  If you are looking for a primary home or a vacation home, let me help get the most for your money. I have many years of experience evaluating rental and income property and want to make sure you understand the full cost of ownership before you buy.

Shannon Gleasman, Reservation Sales Manager, Real Estate Broker
855.272.2725


As a native Oregonian, graduate of the University of Oregon and 4th generation broker, Shannon has a genuine passion for this area and the people here. While a desire for new experiences and connections brought her around the world; a Rotary Youth Exchange in Denmark, semester abroad in Chile and travel with her husband in Central America, there is no place quite like home. Shannon's love of the mountains and priority to be near family made the move to Central Oregon in 2011 a perfect fit. Her background in hospitality services across Oregon and experience in client relationships, revenue management and marketing of vacation homes gained through Bennington Properties gives her an in-depth knowledge of Sunriver and the vacation rental home market. Shannon's heartfelt approach to her interactions with each individual ensures you will experience personalized care and attention to detail when buying, selling, or renting your home.

Learn more about Shannon

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