Deborah Benjamin

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AboutDeborah Benjamin

After over 20 years of teaching business education, personal finance, and marketing in Waterbury, I decided it was time for a new chapter. Real estate has always been a lifelong passion of mine, and with my strong relationship-building skills, extensive business and marketing experience, and genuine desire to help others, I knew this was the perfect path where I could truly make a difference.
In January 2021, I joined Showcase Realty, which turned out to be a perfect fit. Having lived my entire life in this area, I bring extensive knowledge of local communities, neighborhoods, and amenities, along with many personal and professional connections. Showcase and I share the same values—professionalism, integrity, attention to detail, skilled negotiation, and unwavering dedication to our clients.
Over the past four and a half years, I’ve been humbled by how much I’ve grown and by the many clients I’ve had the privilege to serve. My clients consistently rate me five stars and leave glowing reviews, which motivates me to continue exceeding expectations. I have sold over $24 million dollars of real estate!

I’m proud to have received multiple awards recognizing my hard work and success, including:

Top Producer and Quarterly Best Agents – 2022, 2023, 2024, 2025
Five to Ten Million Dollar Sales Club – 2023, 2024
Million Dollar Sales Club – 2024
Rookie of the Year – Highest Sales by a New Agent, 2021
Ranked 5th Overall in Sales – Showcase Realty, 2022
Ranked 8th Overall in Sales – Showcase Realty, 2023
Ranked 7th Overall in Sales – Showcase Realty, 2024
Agent of the Month – Several times

In my free time, I enjoy spending time with my family, babysitting my five grandchildren and attending all their school, sports and dance events, spending time at my Rhode Island home and travelling whenever I can.

Whether you’re a first-time homebuyer, selling your current home, searching for your dream property, flipping houses, or purchasing an investment, my goal is to guide you every step of the way with dedication and expert care.

If you’re looking for an agent who will get the job done and close deals in your favor – I AM YOUR AGENT! Contact me today—I look forward to working with you!

Contact Deborah

203.228.4269

Debbie(at)ShowcaseCT(dotted)com

216 Davis Street , Oakville CT 06779

Testimonials AboutDeborah

More Reviews

Debbie is the consummate professional while being one of the kindest, most thoughtful people you will ever meet. She knows the market, she knows precisely how to gauge the timing and presentation of the properties she represents. I count myself fortunate to have been given the privilege of working with her. She waded into the midst of a difficult situation and made magic happen! I can honestly say that her dedication to selling my home changed my life in the best possible way, and I am forever grateful. If you require the Best of the Best, turn to Debbie. You will NOT be disappointed.

- Heather Kay Tracy
Debbie did it all! She contacted me immediately to talk to me about the potential to sell. Then waited until I was ready. She gave me the advise I needed. She was creative in her marketing, having multiple open houses. She communicated with me throughout the process. The home sold and Both the Buyer and Seller are very happy.

- Sheila
Getting paired with Debbie was completely random and a complete act of god - she is nothing short of amazing. She makes the entire process of buying and/or selling so seamless, she’s on your team 100% and she is so very approachable. Not to mention completely knowledgeable about all things real-estate. She also has all the hook- ups, i.e. the best home inspector ever. Debbie takes care of her clients and she’s genuine. She’ll even take care of your baby while you’re signing the closing documents. I think I would sell and buy another home just to work with her again soon! We love you Debbie!

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Debbie is an excellent woman - great communication!! Very brave in her work! Very disciplined - it was a pleasure to work with her !!

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Debbie made buying my first house such a breeze! I was new to home buying, and have heard horror stories from friends and family about terrible agents. Debbie was so professional and personal! She never made me feel uncomfortable and helped me every step of the way! Debbie was very good at explaining everything in a way that was easy to understand from making the offer, to working with the mortgage broker. This made it really easy to move into Wolcott in less than 3 months. I highly recommend Debbie Benjamin.

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She was absolutely great. I got the complete package with her. She had all the connections you needed for buying a new home. Lawyers, inspectors, mortgage brokers, etc. She is very professional, responsible and, very important to me, very on time. When she tells you we will meet at 3:45 she will be there at that time or early. Always available. Always gives you all the pertinent information about the house/apartment/condo before you get inside the place. Always positive. For me it was a great experience having her as my realtor. Absolutely the BEST.

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Debbie is an amazing agent and very professional. She was very helpful and walked us through every step of the way- if there were any concerns she made things clear for us to understand. Thank you Debbie for being so genuine and most of all a friend.

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Debbie is the BEST AGENT! Friendly, patient and knowledgeable! She always stays on top of things and takes the time to ensure you have a full understanding of any questions. Loved working with her! I highly recommend Debbie - she is your choice if you are looking for an agent!

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Very pleased to work with Debbie. She is very honest, very knowledgeable and a very skilled realtor agent. I would refer her name to all of my friends.

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She is very nice, kind, and professional. She helped a lot from the beginning to end and treats every client as her family member. I am very fortunate to have her as my realtor.

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We want to thank you for all your fantastic work you've done for us. Thank you for going the extra mile for us on every step of our home buying journey! We could not have done this without you, and are so grateful for your assistance, patience, and expertise. Thank you again for everything. We are very grateful to have worked with you as our agent.

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It was a Godsend when I met you. You were instrumental in helping me achieve what some thought would be unachievable in this market. You helped me to close on my first home for my new family. You will forever hold a special place in my heart. Thank you for helping a dream to come true.

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Debbie Benjamin is absolutely the best. It was a great experience working with her to find my own place. Always available and very positive

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Deborah Benjamin is a delight to work with! She is knowledgeable, always stays on top of things and takes the time to ensure you have a full understanding of any questions. She was by our side throughout the entire process. As first time homebuyers, we were so blessed to have her with us. If you are looking for a realtor that treats you like a family or a friend, I highly recommend Deborah Benjamin!

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Deborah was always immensely helpful with every question or problem that came up with the stressful job of selling my condo. She was very professional; very easy to communicate with and made the whole process a lot easier to handle. Anyone would be lucky to have her as their realtor.

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She is exceptional, always calls back and answers my concerns, she knows what I want. The Best realtor I have ever had and I sold and bought two houses . None of the others had the experience to get you your dream house. 5 Stars

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From the first day we met Debbie Benjamin, our connection was instant and we knew we were in excellent hands. She is an absolute bulldog in her field offering extraordinary knowledge and patience with a bit of Sass!!! She went above and beyond our expectations! She provided invaluable advice and coordinated every stage of our showings and closing with such professionalism ensuring every detail was perfect with timely updates. We highly 💯 recommend Debbie not only because of her kindness and high credentials but the fact that she has become a true friend and “soul sister” We love you Debbie - 💖🤗 R&D Xoxo

- Roula Vithoulkas
Debbie is a skilled, congenial professional who marketed our home expertly and found a buyer within one week! She sold our home for well over the going rate for similar homes in the area. We couldn't be happier with her expertise! Debbie is both a skilled professional and a congenial, ethical person whose passion for helping clients obtain just the right home for them has provided us with great contentment.

- Dianne Frost & Al Mayer
Give this woman a raise, she always went above and beyond for everything and anything my family and I needed. She is top tier in her field and an even better human being. It was an honor and a pleasure to have her on my side. I love her very much and would do anything I can to help her and her family.

- Peter Crocilla