

Gavin Pickles
Real Estate Professional
- (757) 720-2522
- gavin@trustworthyagents.com
- Search for Homes
- DPOR: 0225273283
Social Links
About Gavin Pickles
A Third-Generation Realtor with a Passion for Service
For Gavin, Real Estate was never just a career choice—it’s in his DNA. As a third-generation real estate professional, he proudly follows in the footsteps of his father and grandfather, who partnered to form the Trustworthy Agents Group in 2009. With his mother, grandmother, aunt, and uncle also deeply rooted in the industry, it's no exaggeration that real estate has always been a family affair. Some of his earliest lessons in negotiation and market strategy came from gathering around the dinner table at cherished family events, listening as the elders in his life told inevitable stories of helping their clients overcome varying challenges—often accompanied by an always interesting game of Monopoly. And when you’re playing Monopoly with the CEOs of two highly successful real estate companies, you learn to think strategically fast!
Before launching his real estate career, Gavin honed his skills in the service industry, where he quickly earned recognition for his initiative, attention to detail, and ability to intuitively anticipate the needs of others. His experience in fast-paced, customer-focused environments sharpened his ability to provide exceptional client service—always going the extra mile to ensure satisfaction. Business owners took notice, promoting him quickly as a result of his strong work ethic and natural leadership. Those same qualities now define his approach to real estate, where he strives to pursue the custom solutions each unique family needs to make their real estate experience both successful and genuinely enjoyable.
As a proud lifelong resident of the Hampton Roads community, Gavin brings an insider’s knowledge of the area’s neighborhoods, schools, market trends, and vibrant culture. His deep roots here give him a unique ability to connect clients with not just the perfect home, but also the lifestyle and resources that make Hampton Roads such an amazing place to work and live.
Beyond real estate, Gavin is a true history buff at heart, always pursuing some fascinating or little known fact about our past, and the culture of humanity as a whole. He resides in Chesapeake with his family, their two sweet Boxers, Wally and Eva and their vigilante cat, Benji.
With a strong and deeply rooted family foundation in the real estate industry, a heart for service, and an unshakable work ethic, Gavin is ready to provide the professional council you deserve to purchase your next home with confidence, sell your current home for top dollar, or build your investment portfolio with ease! Give him a call today to get started!