Like a mighty oak tree, Ann Brown embodies the strength to weather life’s storms. Affectionately known as “Annie Oak Tree” by her family, her journey is defined by resilience, adaptability, and a profound connection to the world around her—a fitting metaphor for a woman whose roots run deep and whose branches extend wide to support others.

Ann's first major storm came at just eleven years old when her father passed away, leaving her and her mother to navigate life together. “It was just my mom and me, and we had to figure things out,” she recalls. “I had to grow up quickly, but I always felt my dad’s presence through dreams and prayer—I could feel that he was always with me, guiding and comforting me in ways beyond the physical world.”

Despite the early challenge of losing her dad, Ann fondly remembers her childhood in Chicago’s Dunning neighborhood in the 1980s—a time filled with block parties, kids playing outside until dusk, and strong community ties. “My parents gave me a foundation built on hard work, faith, humility, and love,” Ann shares. “Those lessons shaped me into who I am today.”

The values instilled in Ann during her childhood were soon put to the test. As a young adult, she faced an abusive relationship that deeply affected her mental health. “It was a difficult period,” she shares, “but I learned the importance of self-worth and eventually found the strength to leave.” At the same time, she overcame addiction, a challenge that ultimately became a powerful catalyst for transformation. “I learned the importance of staying grounded no matter what life throws at you,” she says. 

Also, at just seventeen years old, Ann became a mother, adding both complexity and joy to her journey. “We faced our own set of struggles,” she says, “but those challenges deepened my commitment to being a supportive and present parent. They taught me invaluable lessons about resilience, perseverance, and the importance of seeking help when needed.”

After high school, Ann began a six-year career as a hairstylist in Chicago and Boca Raton, Florida, winning two national competitions in long-hair design. Living in Florida also introduced her to real estate when she started assisting her then mother-in-law, a seasoned broker. “Helping with marketing and backend tasks gave me my first glimpse into the industry,” Ann recalls.

Ann’s love for real estate deepened when she purchased her cabin in Wisconsin, sparking a passion for finding homes that feel truly special. Her career path also included a role as a real estate assistant for an attorney, where she gained invaluable insights into the industry. These experiences ultimately inspired her to pursue her real estate license.

Today, Ann is part of Chicago Properties, led by Sam Shaffer, where she thrives in their collaborative, supportive environment. “The most rewarding part of my business is working with Sam and our incredible team that feels like a second family,” she says. “I've always been comfortable in a supporting role, and it’s fulfilling to contribute to our collective success, helping to make the process as seamless and rewarding as possible for our clients.”

Of note, Ann is passionate about making the industry more environmentally friendly—looking at everything from using reclaimed materials and reducing waste to promoting energy-efficient and self-sufficient homes. She believes these changes can have a positive impact on the community in more ways than one: “I’d love to see homeownership become a reality for people from all backgrounds,” she shares. “There’s so much we can do to create affordable housing and preserve wild spaces.”

Ann dreams of stewarding land for vacation rentals and community living while continuing to grow her career. “It’s about finding ways to build smarter and be kinder to the Earth,” she says.

Outside of work, Ann’s life reflects her values. She’s an amateur homesteader who loves gardening, preserving food, and being in nature. “I love sleeping under the stars, and I’m obsessed with nature and trees,” she admits. “My family also calls me ‘the Tree Whisperer.’ She also enjoys practicing yoga, cooking, and spending quality time with her son, Daniel; her mother, Mary; her partner, Dan, who is also a REALTOR®; and Dan’s son, Adrian. Ann and Dan enjoy exploring nature and working on home improvement projects together.

Looking ahead, Ann envisions real estate as a way to foster stronger communities and sustainable living. “I want to help clients not just find homes, but to thrive in them,” she says.

Whether advocating for eco-friendly practices, supporting clients, or whispering to trees, Ann Brown’s journey reflects her steadfast resilience and deep commitment to leaving a positive impact. Like the oak tree she’s lovingly compared to, she stands tall and strong, her roots firmly planted in purpose, and her branches extended to uplift those around her.