How Hard Work Led Jami Winchester to Become a Top Illinois Realtor

By Vivienne Benitz Vivienne Benitz has been verified by Muck Rack's editorial team
Published on December 12, 2023

People often perceive real estate as one of the most opaque industries. How do you launch a career amid a sea of competitors and few resources behind you? Winning this uphill battle can create some of the most unique individuals in the space.

Yet with modest beginnings, Jami Winchester was recently named a top 10 agent in Illinois. As a Partner at The Real Estate Group, she is now a regional luminary, providing lessons for her contemporaries and immense value for her clients.

Jami’s journey demonstrates the extraordinary heights one can reach through tireless work and a life that embodies the American dream. Now, she reveals everything about a career that has become a treasure trove for potential property buyers and sellers.


From rags to realty

The story begins in the heart of Springfield, Illinois, a place the Realtor lovingly calls home. Her foray into real estate in 1998 wasn’t a grandiose affair; Jami embarked on her real estate career with nothing but determination and a few invaluable life lessons she learned growing up.

Continual learning was a cornerstone of her ascent in the real estate industry. A list of certifications and designations, including a broker’s license, Certified Residential Specialist status, and graduation from the Realtor Institute, speaks to her pursuit of knowledge and professional development. It’s a resounding lesson for all aspiring real estate enthusiasts: in this ever-evolving field, the thirst for knowledge can be a compass.


Curating client connection

Jami attributes much of her success to her ability to forge genuine connections with her clients: “I’m a down-to-earth Realtor, and I care about my clients.”

A personalized touch, coupled with swift responsiveness and near-constant availability, creates a foundation of trust beyond the ordinary transactional relationship. Pivotal life decisions are at stake daily in real estate, and trust is invaluable. The Partner’s ethos drives home the message that in addition to contracts and negotiations, the human connection is the heart and soul of any real estate journey.

“My success has been the ability to connect with clients and make them feel comfortable through what can be a stressful but exciting time in their lives,” she offers. “As a result, the largest bulk of my business comes from repeat clients and referrals.”

It’s not just a matter of attracting new clients; it’s about tending to and maintaining relationships with existing ones. After all, the real estate experience isn’t just a one-time transaction—it’s a lifelong partnership.


Local market leadership

It’s no secret that regional insight is at the top of most buyers’ and sellers’ lists when looking for a realtor. But Jami’s familiarity with Springfield is lifelong, bestowing an innate understanding of the local market and offering insights only someone ingrained in a community can provide. Collaborating with a locally-informed realtor is essential for anyone contemplating a property transaction.

Awards and accolades inevitably came with Jami’s rise to the top, including being named ‘Best Realtor’ by Illinois Times in 2013, 2014, and 2017, and most recently tying for the top spot in 2023. Her team, the Winchester Sales Team, also secured recognition as the ‘Best Team in Real Estate’ in 2023.


Balancing business and family

Through all of the Realtor’s professional accolades, one accomplishment stays in her heart: “My most personal achievement is being the mom of my two children.” Her ability to balance a thriving career with her family life underscores the idea that success transcends the workplace and extends to all facets of life.

Jami Winchester’s journey offers reassurance in a real estate world that often seems bewildering. Her story is a poignant reminder that diligence, commitment, and a pursuit of excellence can bring success within reach, regardless of your background. 

It’s not about where you start but the path your determination and dedication can carve. Having shattered real estate’s glass ceiling, Jami became an example of how hard work can create prosperity in any aspect of life.

By Vivienne Benitz Vivienne Benitz has been verified by Muck Rack's editorial team

Vivienne Benitz is a featured columnist at Grit Daily. She is originally from Germany and is a publicist at an international PR agency based in the United States.

Read more

More GD News