Meet the Team

About Dennis & Eileen Montgomery: 

The Hilton Head Lowcountry became our home after years of vacationing and working in the area.  We moved to the Hilton Head area in 2001 and have truly enjoyed the location, the opportunities, and most of all the people.  We searched across the country doing our due diligence from Hawaii to Las Vegas, Arizona, Texas, and Florida and finally back to Hilton Head like 'homing pigeons' we returned to the place where we love to live and now work.  Our experience is extensive as you can peruse on our web page.  We believe with our varied backgrounds we can serve you and represent your best interest at all times. 

Meet Dennis

J. Dennis Montgomery in 2001 relocated to the Hilton Head area and has become affiliated with Gateway Realty specializing in the acquisition and sale of both residential and commercial opportunities.

Prior to relocating, Mr. Montgomery was the president and chief operating officer of the Illinois League of Financial Institutions, Springfield, IL. He assumed that position October 1, 1985.

The Illinois League of Financial Institutions is the statewide trade association serving the state’s 160 savings and loan associations and savings banks with assets in excess of $60 billion.

As the League’s chief administrator, Mr. Montgomery was responsible for implementing all policies and programs of the 160 member trade group. He directed and controlled the League’s daily activities.

Prior to becoming president of the Illinois League, he served as president of the Iowa Credit Union League, and president of the Society of Association Executives and Controllers Society.

Mr. Montgomery holds the rank of Major General (Retired-Iowa) in the Iowa Air National Guard and has received numerous military honors. Because of his combined civilian and military experience, he was assigned complete responsibility for the events and activities surrounding the Iowa gubernatorial inaugurations and all operations relating to the Des Moines visit of Pope John Paul II in 1979.

Mr. Montgomery's wife, Eileen, has been a professional speaker and president of her own company as well as Public Relations Consultant with Lincoln Land Development Company, a commercial real estate developer.

Meet Eileen 

Eileen M. Montgomery relocated to the Hilton Head area with her husband Dennis, and has become affiliated with Gateway Realty using her special expertise of working with people to assist them to achieve their real estate goals.

Eileen is the founder and continues to serve as president of her public relations consulting business.  In this capacity she has worked with a variety of clients in the commercial development area including shopping centers, strip malls, stand alone boutiques, and other cooperative business developments.  She has designed many training programs in the area of communications for the corporate world.  Eileen was a national presenter for Dun & Bradstreet.  Eileen traveled to 42 states and made eight hour presentations for audiences ranging from 10 to 500 people. Among her many clients were various state agencies, universities and Fortune 500 companies. 

Eileen managed the Rail Golf Course for 5 years ago, which is the second oldest tour stop on the LPGA tour.

Eileen has served in a variety of public service activities including president of Rotary in Illinois, board member of a college foundation, board member of a muscular dystrophy association and board member of her college.