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About Terri

A native of Connecticut, I wanted to explore another area of the country. Before moving to Crossville, I was a solo real estate broker with my own agency, DCK Realty and Design, which I opened in 2016.

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 had 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 business was first-time homebuyers, and I thoroughly enjoyed educating them as to 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 was able to 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 received an education on the complexities of the Medicare system and how it impacts 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 is married to a wonderful man from Morocco. My son, who is also an engineer, is in Connecticut and is exploring two different career paths. 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. 

In 2025, I turned 65 and needed to make important decisions about my healthcare. It didn’t take long for me to recognize how challenging and complicated Medicare is, and I saw how many seniors might need help navigating its complexities.

 

Recently, I was offered the opportunity to pursue a new career as a Medicare Advisor. My skills in listening, combined with a passion to educate 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. 
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Terri O'Brien
Your Local
Medicare Advisor

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 1-203-231-4484

P.O. Box xxxx, Fairfield Glade, TN 38558

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O'Brien Senior Benefits is not connected with or endorsed by the United States government or the federal Medicare program.​

We do not offer every plan available in your area. 

Please contact Medicare.gov, 1-800-MEDICARE, or your local State Health Insurance Program to get information on all your options.

© 2026 by O'Brien Senior Benefits 

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