Many of my life experiences—personal, professional, and everything in between—have come together in this new chapter where I use it all to help people through one of life’s biggest transitions.
I’m a third-generation Ridgefield native and have been residing in Redding for over 30 years. These communities have played a major role in shaping who I am. Growing up here taught me the value of strong relationships, being involved, and showing up for others. I was raised in a tight-knit family, surrounded by people who looked out for each other, and that extended into the community around us. Whether it was through school, sports, or neighborhood events, there was always a sense of connection that stayed with me.
Over the years, those relationships only grew stronger, and the value of connection became an even bigger part of my life as I moved into my professional career. Right after college, a friend and I decided to apply to Chesebrough-Pond's, inspired by a neighbor who seemed to genuinely enjoy his work in the consumer products industry. He traveled often, had great stories, and carried himself in a way people were drawn to. We both got hired, and I was sent to Seattle. That marked the beginning of a career that would span nearly 40 years.
What made the work meaningful was the people. Throughout my career, I lived and worked in different parts of the country before eventually returning to Connecticut. No matter where I was, relationships were always at the core of what I did. The nature of the work also gave me the flexibility to stay active in my family’s life and be involved in the community like coaching football, serving as a member of the Redding Boys and Girls Club for 25 years, and supporting local events.
After retiring from my career, I still wanted to do something. It is just in my nature to enjoy solving problems and helping people. Initially, I worked a startup in Baltimore called Hex Performance, alongside my daughter who did the marketing. But with time, I was ready for a more local job.
That’s when real estate came into view. A friend who managed the local Sotheby’s office suggested I get my license. It made sense. I knew the area well, had strong relationships, and enjoyed working with people. I jumped in just before the pandemic hit. The timing felt uncertain, but as people began leaving the city, the local market surged and I quickly found my footing.
Not relying on real estate for income was a huge advantage early on. I could focus entirely on doing things the right way from the start. I have operated with my clients’ best interests in mind and never had to compromise on that. I’m in real estate because I genuinely love the challenges, the people, and the fact that no two days are alike.
My background in business taught me that whether you're selling a house or a household product, it's about understanding what people need and guiding them to a solution. Real estate is personal. Every transaction is tied to major life moments, and I approach each one with the same care, no matter the price point. My local knowledge helps buyers find the right fit for their lifestyle, and I often connect them with trusted local businesses that have served this area for generations. Having raised my own kids here, I know what families need to feel confident when making the move.
The greatest compliment is having a past client refer their friends and family to me, helping me organically grow a referral-based business I’m proud of. It feels full circle to use everything I have learned throughout my life, from relationship-building and problem-solving to prioritizing family and community, to guide others as they put down roots in the community that has always been home for me.
My wife, Denise, and I have been married for over 40 years, and have two kids and two grandkids. When I’m not working, I like being outside, staying active, and spending time with family!
One of the most important things I do for my clients is provide hands-on guidance every step of the way. For sellers, I help identify smart, cost-effective improvements that can boost value and make the home more market ready. I connect clients with reliable local vendors, some of which my family has used for generations, including builders, contractors, painters, stagers, and cleaners. Buyers benefit from the same level of attention. I help them evaluate homes with a practical eye, offer honest feedback, and share insights they may not have considered. I enjoy being the go-to person for all things related to homeownership. When your furnace goes out, you're looking for a great landscaper, or you simply have questions about the market, I am always here to help!
Every transaction gets the same focus, regardless of the home value. With a background in negotiating deals worth millions of dollars, I bring a high level of preparation, strategic thinking, and skill to every transaction.
At the same time, I stay focused on the emotional side of the process because for most people, this isn’t just a financial move, it’s a major life transition. My job is to keep things steady, help clients make informed decisions, and make sure they always feel supported along the way.
Sincerely,
Jay Contessa
REALTOR®
Direct Call/Text 203.461.3880