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About Terri
As a Connecticut native, I wanted to explore another part of the country. Before moving to Crossville, I ran a solo real estate agency, DCK Realty and Design, which I opened in 2016. Before that, I held administrative and managerial roles in the medical, pharmaceutical, retail, and non-profit sectors.
In 2018, when my twin daughters were in their final year of college and my son was beginning life as an adult, I realized there was nothing keeping me in Connecticut. At the time, my parents, brothers, sister, and most nieces and nephews were in Connecticut and Rhode Island, yet the pull to explore was deep.
After visiting in 2018, I decided on Crossville, TN, and quietly settled in Fairfield Glade with my golden retriever. I became a real estate broker associate and created my business down here. My main focus was first-time homebuyers, and I thoroughly enjoyed educating them about the mortgage, inspection, and homebuying process. For over two years, life was good until late 2020, when the real estate market began to change rapidly as COVID took hold and reshaped the industry. Sellers were selling, cash was king, and it was challenging to run a business representing first-time home buyers. At the same time, my Dad was diagnosed with early dementia, and I felt it was important to return to Connect to help my family.
I decided to rent my home in TN and move back to CT to help my family with my Dad. For the next four years, I worked as an office manager for a Financial Advisor, a role I enjoyed because I could interact with clients and support them in achieving their financial objectives. After taking care of my Dad, who passed the day before St. Patrick's Day in 2024, and then my Mom, who passed in October 2025, I moved back to TN. The last two years of my parents' lives were spent in and out of hospitals, doctors' offices, and nursing care facilities. I received an unwanted but necessary education in our healthcare system and realized the importance of having an advocate who speaks up and intervenes when required. I also learned about the complexities of the Medicare system and how it affects hospital and physician care.
My family is incredibly important to me. My twin daughters, one a Physician Assistant in Seattle, WA, and the other a Systems and Industrial Engineer at a manufacturing company in Hutchinson, MN, and married to a wonderful man from Morocco. My son, also an engineer, is in Connecticut and works as a Medicare advisor. Recently, I visited my daughter in Seattle, where we hiked through 3 national parks in Washington (the above photo was taken while hiking in Canada) and explored Vancouver and Victoria. Spending time with my other daughter and her husband in Minnesota, exploring Minneapolis and Duluth, MN, on Lake Superior, was a delight. And I make a semi-annual trip back to CT to connect with my son, friends, and family.
In 2025, I turned 65 and needed to make important healthcare decisions. It didn’t take long for me to recognize how challenging and complicated Medicare is, and I saw how many older folks might need help navigating its complexities.
Recently, I was offered the opportunity to pursue a new career as a Medicare Advisor. After exploring, I found that my listening skills, combined with a passion for educating my clients and a desire to bring value and service to my community and its older population, felt like a purpose-filled calling.
Today, as an independent broker, I'm dedicated to putting my clients—whether friends or new connections—in the best possible position, regardless of age or health. I'm not just another insurance broker; my mission is to educate, empower, and guide my clients toward informed decisions for their health and financial future.
My goal is simple: to help anyone eligible for Medicare understand their options, choose with knowledge and confidence, and do so without pressure.


Terri O'Brien
Your Local
Medicare Advisor
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