Jon Stroud

As the author of the Great Game of Real Estate, Jon is known not only for his real estate expertise, but for his passion, leadership, and heart for service.

jon-stroud

With more than two decades of experience in Charleston’s dynamic real estate market, Jon Stroud is known not only for his real estate expertise, but for his passion, leadership, and heart for service. Licensed since 2004 and the founder of The Stroud Team at The Boulevard Company, Jon has helped hundreds of clients—from first-time buyers to seasoned investors—navigate real estate with strategy, clarity, and confidence.

Jon holds several respected designations including Certified Luxury Home Marketing Specialist, Historic Properties Specialist, ePro, and At Home With Diversity. His areas of specialty range from luxury homes and waterfront properties to investment portfolios, new construction, and relocation. With a unique ability to connect deeply with clients and teach through the process, Jon makes complex transactions feel approachable and even enjoyable.

He is also a well-known leader in the Realtor® community. Jon served on the Charleston Trident Association of Realtors® (CTAR) Board of Directors for four years, including as President in 2022, and is actively involved at both the local and state level through committee leadership and advocacy. Throughout his career, he’s trained and mentored dozens of agents and is known for his generosity in sharing what he’s learned along the way.

In 2025, Jon published 'The Great Game of Real Estate', a one-of-a-kind eBook designed to help buyers, sellers, and investors approach real estate with emotional intelligence, long-term vision, and a game plan. The book captures his coaching spirit and his belief that real estate should be both strategic and deeply human.

When he’s not working, Jon enjoys boating on his 41’ Maxum motor yacht, restoring his two 1965 Mustang convertibles, or playing music. He’s been married to his wife Wendy for over 34 years, and together they’ve raised two daughters and a pack of beloved pups. Whether you’re buying your first home or your dream estate, Jon’s mission is simple: to leave every client—and every community—better than he found them.

The Great Game of Real Estate

Real Estate Is a Journey. Why Not Make It a Game Worth Winning?

Welcome to The Great Game of Real Estate by Jon Stroud: a new way to navigate buying, selling, or investing, while ...

  • Replacing stress with strategy,
  • Turning uncertainty into clarity, and
  • Enjoying the process instead of just enduring it.

Real People. Real Success.

Jon Turned a Stressful Move Into a Lifestyle - Aligned Win

"Jon was able to sell our house in a short amount of time as we were moving to another state. He listened to us and got a good neighbor for our children who lived across the street. He showed our home many times and worked hard for us. I thank God for him.”

- Leanne Russell, Client


More Than a Home—A Better Life for Our Family

"We are loving this area. The neighborhood could not have been a better fit for us. Our son already has a best friend across the street who is the exact same age (2 weeks apart). We are very, very happy here. Thank you so much for all your help and patience while finding us our home”

- Emily W, Client

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We Want to Hear From You!

Whether you have questions, need guidance, or are just beginning to explore your real estate journey, we’re here to help.

Reach out anytime; we can’t wait to connect!

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