Robert M. Pickles Jr.
Local: 757-694-2979
Toll Free: 877-704-7604

Robert M. Pickles Jr. is the epitome of focus and professionalism in his role as a real estate agent. Originally from Florida, this 35-plus year resident of Hampton Roads knows the area, the market and the industry. The devotion to his clients and commitment to giving superior service resulted in him earning a number of awards including the coveted regional Five-Star Award for client satisfaction every year since becoming an agent. His high energy level and responsive nature makes Robert someone both sellers and buyers can count on when they need to accomplish particular goals.

Serving eight years in the U.S. Navy as a programmer analyst first showed Robert how harnessing the power of technology could open doors. After acquiring extensive training in information technology (IT) and sales, he started his own consultancy business. Soon, he began providing consulting services to several Fortune 100 companies across the country. “Technical consulting, like real estate, is about problem-solving,” Robert adds, “I know how to actively listen to learn what my clients’ needs are, and carefully help them prioritize so that they have an informed and productive shopping experience.”

He decided to take his vast knowledge and apply it in the real estate arena. “Technology’s redefined real estate.” This active member of the Real Estate Information Network (REIN) user group says, “I typically know about the technology changes that are coming down the road four to six months in advance; that means I’m highly proficient at using that technology for my clients.” One of the things Robert likes about this field is being able to look at someone’s specific needs and come up with a creative solution. “I enjoy solving problems and love serving people.”

Embracing his fiduciary responsibilities is something Robert does well. “I become my clients’ consultant, and put their needs above my own.” So whether it’s helping military families successfully PCS into the area, assisting first-time buyers or helping sellers maximize the profit on the sale of their homes, Robert stays the course. His caring approach sometimes goes beyond that of a typical agent, as evidenced when a recent client without family nearby required emergency surgery upon arriving into the area. Robert became somewhat of a surrogate brother, even visiting his newfound friend in the hospital several times.  “It’s these kinds of experiences that are hugely rewarding. I become friends with many of my clients, but this one became like part of my own family!”

Robert founded Team Homedog to offer the most efficient service to buyers, sellers and those interested in building new homes. Robert’s also developed a niche for helping clients get custom homes built. “I’m extremely adept at helping customers locate land, interview and select a builder and help them through the building process.” This motivated agent stays on top of his game because he never loses his zeal for both those he works for and the business itself.

Tearing himself away from real estate can be a challenge, as Robert is so passionate about what he does. But when this avid outdoorsman does take time for himself, he enjoys hunting, fishing and boating. He stays in shape by walking his dog, loves animals and appreciates country living. Robert makes his home in Chesapeake with his wife and Team Homedog’s mascot, Mr. Kodi.


"Thank you for the prayers, I really do need them. I really do appreciate you and Heather for all your hard work. I've heard a lot of horror stories about realtors and I know it was indeed divine intervention on my behalf, it wasn't by accident that I found SimonHouses website. I thank God for all you do for military families and helping us with our dreams. I will see you soon and I can't wait to see the pictures of the house. I wish I was a little closer so I could visit and take pictures from start to finish. Thank you again..." Nora M.