Nate Pickles

professional portrait of real estate agent Nate Pickles

Wainwright Real Estate

A local with an impressive knowledge of Hampton Roads, Nate Pickles is an award-winning agent people can trust.  Not only a whiz when it comes to anything technology-related, he excels at serving his clients with their real estate needs.  A unique find in this industry, he measures his success by the number of smiles he creates through his actions instead of a certain sales volume achieved.  And although Nate takes his profession seriously, he makes his clients feel at ease, and fun just naturally seems to follow.

Nate first learned about the importance of customer service in his role as a call center technician at a corporate real estate firm.  He’s also held positions in information technology (IT) and desktop engineering, where he researched to find solutions to complex issues.  Nate says, “In the IT world, people ask you questions on a daily basis; you need to be resourceful, and able to find accurate, truthfulanswers to those questions in a hurry.” 

Coming from a family where real estate is a preferred profession, Nate naturally gravitated towards this field.  But before making the jump, he bought a house and found out what can happen when a proficient real estate agent is not on the homebuyer’s side.  “I didn’t have any representation,” he adds, “I had such a bad experience my first time buying a house that is actually why I became a real estate agent.”  Now this not so distant memory guides Nate in making each of his transactions the best he can for his clients. 

He ensures his clients receive as much information as they need, so they’re equipped to make the most educated decisions.  When working with Nate, homebuyers get excellent customer service and access to valuable resources such as recommended home inspectors, termite companies, insurance providers and more.  He also employs a valuable assistant who helps makes sure everything goes smoothly throughout the entire process and communication is prompt. 

It’s really his clients that drive Nate to accomplish so much, even if that means being available throughout the wee hours and on holidays.  “I absolutely love working with people and answering their questions,” he continues, “There are no words to describe how great it feels when I’ve matched a family with their dream home.”  Some specialties include helping first-time buyers, new construction buyers and service members.  Living near the military culture his whole life gives Nate a better grasp of how to assist those who are buying or selling homes due to PCS moves.

“I know real estate increases in value.”  This member of the Tidewater Real Estate Investors Group actively invests in real estate, and uses his experience to guide others interested in doing the same.  “I tell every buyer that I work with, ‘You’re looking for a home you can live in; I’m looking for a home you can live in and that I can help you sell one day.’”  Being part of the team is a definite contributor to Nate’s momentum.  “I feel like I work with a family,” he continues, “They have a great training environment to make sure we’re constantly up-to-date on the real estate market.”

Nate offers homebuyers something special.  “I sit down with every buyer I work with, and give them anywhere from an hour to a three-hour long buyer consultation.”  Here he finds out exactly what his clients need and more.  “I basically give them a home buying crash course, explain the pros and the cons of all the different types of real estate that are out there and outline the entire process from start to finish.”  Although wanting to dive right in and begin touring homes may sound exciting, Nate takes the methodical approach- and it pays off. 

When Nate takes a break from real estate, he can usually be found in the great outdoors.  His tastes are on the adventurous side: snowboarding, skydiving, skateboarding and surfing.  Traveling to Nags Head is another favorite activity, but he also likes landscaping and gardening.  He enjoys spending time with his family, going camping and volunteering with his son’s scout troop.  God and helping people are his passions.  Nate resides in Chesapeake with his wife, two children and two dogs: a boxer and a pit bull/lab mix.


Nate Pickles was by far the most pleasant agent we have worked with. He was thorough in explaining everything to us about the whole process and was really good about hearing our concerns. Nate helped us find our dream home quickly which was so important, as time was of the essence with our relocation. He was both professional and prompt on all occasions and was excellent with communicating every step of the way during the entire process. At all times I felt like he was our advocate 100% and it really got our move here to Virginia off to a wonderful start. I would highly recommend him to work with to anyone who is looking for a knowledgeable agent. Thank you so much Nate for getting the job done; we are so excited about our new home and community. You made us feel welcomed! ~ Darren and Stacy E. Chesapeake, VA

"CLOSED!! We did it. We just became co-homeowners. AND we held onto my condo, so we're now landlords. It was a fast (but felt long) ride that took only 22 days from getting pre-approved to standing here closing in our new home. We owe it all to Nate Pickles Homes. We hit the ground running, and he ran with us every step of the way. Something tells me we've made a friend for life with him. He fought for us, encouraged us and gave up evenings with his family for us... Surprise! The Dominos are now your neighbors! So here we are toasting to our next venture as homeowners and landlords with the same flutes we drank from on our wedding night. What an awesome house buying experience thanks to Nate Pickles (who is always welcome at the Domino abode)!"

The Dominos