Jackie Flanagan

Agent

Jackie Flanagan

Meet Jackie Flanagan—a corporate leader turned powerhouse real estate advisor, combining data-driven strategy with a heart for connection. After years leading global teams in the corporate world, Jackie traded in boardrooms for open houses—and never looked back. Now, she brings her executive-level negotiation, communication, and leadership skills to the Triangle’s fast-moving real estate market, helping clients confidently buy and sell in Cary, Morrisville, Apex, North Raleigh, and surrounding communities. With an MBA, a broker’s license, and a deep understanding of market trends, Jackie approaches every deal with insight, precision, and professionalism. Whether she’s helping sellers price to win, guiding buyers through a competitive market, or navigating complex timelines, she shows up as a calm, strategic partner who knows how to get results. But it’s not just about the numbers. For Jackie, it’s personal. Her clients become family—and she treats each transaction with the care, communication, and transparency they deserve. Her education-first, relationship-based approach ensures every buyer or seller feels empowered, supported, and never rushed.

She’s also deeply committed to creating an inclusive and welcoming experience, helping people from all backgrounds feel confident and seen throughout their journey. She’s proud to give back through her involvement in the National Charity League and loves helping others find not just a house—but a place they truly belong. When she’s not showing homes or analyzing market data, Jackie is cheering on her three kids at sports and competitions, relaxing on the porch with her husband, or hitting the greenway for a run or Pure Barre session. She believes real estate should be exciting—not stressful—and that a trusted advisor makes all the difference. With Jackie Flanagan, you get a rare blend of corporate savvy, community connection, and client-first care—the kind of agent who makes you feel like you’re the only one that matters.

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What my clients say!

"Choosing to work with Jackie Flanagan and the Caul Group was the best decision I could have made! As Read More Read Less
"Jody Doran is an absolute dream to work with! From our very first meeting, I knew that she would be Read More Read Less
"Trevor and his team are amazing! He was there with me through each step of my "complicated" situatio Read More Read Less
"We just purchased our first home with the help of Cassandra Baier-Pyszczynski from Caul Group Reside Read More Read Less
"My spouse and I have worked with Minda C. at The Caul Group several times now, and each time she has Read More Read Less
"Working with Jackie Flanagan was a great experience. She really listened to what I was looking for a Read More Read Less
"Sarah, Ashley, and the team at Caul Group are exceptional! They were able to expertly navigate a fe Read More Read Less
"Stefano worked hard to ensure my partner and I got the best home that we could in our journey to hom Read More Read Less
"I recently had the pleasure of working with Nakia Totten from Caul Group Residential to buy my first Read More Read Less
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