About

Wintergreen Home Watch has been providing boutique property management services since 2011.  Wintergreen is a special and beautiful spot, and our company is committed to treating your property the way we would treat our own.

Chris DesBarres

Prior to Wintergreen Home Watch, I was running another company that we own, Help Unlimited.  Help Unlimited assists senior citizens with managing their personal financial chores: very nitty-grity tasks like paying bills, understanding medical insurance and processing medical claims, organizing important documents for taxes and estate planning, and coordinating services with our clients’ attorneys, wealth advisers, care managers, and accountants.  This is a family company that was largely started by my mother-in-law, Roberta, back in the early 90s.  We bought the company from her in 2010.  Amanda now runs Help Unlimited while I focus on Wintergreen Home Watch.

Before going into business, I was a counterintelligence officer with the Defense Intelligence Agency, where I ran a program identifying and neutralizing terrorist groups’ intelligence networks.  I deployed to Iraq in 2004-2005 in support of the Joint Special Operations Command.  In 2006, I deployed to Afghanistan in support of some of our human intelligence operations.  In 2007, I was selected for a two-year rotation as a Duty Officer in the White House Situation Room — basically, I waited for bad things to happen and then told the President about it!  I was very fortunate to work under both President Bush and President Obama.

I earned my undergraduate degree from the University of Notre Dame, and my MBA from Wake Forest University.  I have been accused of being a Notre Dame “fanatic,” but I think my passion is entirely reasonable. I serve on the St. Thomas Aquinas Parish Council in Charlottesville and as a Den Leader for Pack 17 at Charlottesville Catholic School.

Amanda DesBarres

Amanda has been a Daily Money Manager, working for — and now in charge of! — Help Unlimited since 2001.  She is also an accomplished opera singer whose appearances includeThe Academy of Music and the Kennedy Center.  She obtained her bachelor’s degree from Catholic University of America and her master’s degree from The Curtis Institute of Music. 

Chris and Amanda actually met at one of her performances: Chris' friends dragged him to an opera at the Austrian Embassy, where he sat pouting until a certain soprano walked on stage.  He perked up, said “Hey, this opera stuff isn’t bad after all,” met her after the show, and the rest is history.

Chris have four great kids, Jack (7), Annie (5), Emma (2), and Carolyn (1).  The family enjoys spending time together hiking, skiing, and cooking.