Jay Contessa

Jay Contessa

Licensed Real Estate Salesperson

Jay Contessa
  • M
470 Main Street
Ridgefield, CT 06877

About Me About Me

Delivering concierge level service to every client every day.

I am a third generation Ridgefield native currently living in Redding for over 25 years. I bring decades of local expertise on our awarded winning school systems and the distinct characteristics that make our communities so special. Our towns are graced with an abundance of scenic charm and family businesses with long held traditions of generosity and support. Fairfield County’s vast architecture of homes, proximity to NYC, the Vermont mountains, and to the shoreline, makes our communities the perfect choice to raise a family or for a weekend getaway.

I bring a strong proven track record of negotiation skills, marketing, financing and customer service from my prior successful years in corporate leadership. In addition, I have personal experience in home building and complex renovations including residential and commercial properties. As a realtor, my role will be to facilitate and educate my clients to make the best decisions in what could be a complicated process of buying and selling homes.

Today, you need a broker that knows the community's and has the professional resources and marketing tools to get the job done. I look forward to making that happen.

  • Born In Ridgefield, Ct
  • Lives In Redding, CT
  • Favorite Movie The Godfather
  • Inspiration Inches make Champions-Vince Lombardi

My Awards

  • Gold Award Winner
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My Listings and Sales

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Testimonials (14)

Jay Contessa was outstanding through all phases of our home selling process. His coaching, advise and guidance was always spot on and the results proved that. He and the full team at William Pitt / Sotheby's were truly a pleasure to work with. Michael Tusa
Jay Contessa has been the ultimate professional from start to finish and far exceeded our expectations for working with a realtor. His knowledge and expertise made him invaluable to the whole process. From market timing, to staging advice, to negotiating the best deal for us, Jay really helped alleviate much of the stress. We highly recommend Jay Contessa to anyone in the Ridgefield area. Pat and Mike Tusa Patricia Tusa
Jay Contessa was a fantastic realtor! He went over and above to support us in our process of buying a home, and made sure the home was ready for us to move in. It is a property that needed a bit of work beforehand, and Jay handled the tasks with true expertise, always making sure we were well informed. We felt comfortable the entire time. Thank you Jay for making our first home buying experience so seamless and special :) Jessi Brattengeier
Highly recommend! Our realtor, Jay Contessa, went above and beyond to help us find a home. He not only worked with us to find a home, but helped us connect with many in the community for the services we wanted to employ on our new home. Jay is fantastic and has become such a huge part of our buying experience. Meanwhile, my wife and I felt that Sotheby’s had our back and made the entire process smooth and low stress. This included not only the house, but the bank, lawyer, and the many inspectors needed during the buying process. Adoniram Weimer
We couldn't have been luckier when we were paired with Jay Contessa through his agency. Jay listened to all of our wants and needs and shared his thorough knowledge of the local communities and real estate market while showing us properties. He ensured that the purchase of our property went smoothly with the seller. Thank you, Jay! David and Amy
Jay is a true professional in his field. He constantly kept us in the loop with updates and feedback. He always went above and beyond in both buying and selling of our homes. Always responded in a very timely manner to any of our needs. Jay is both personable and professional in every way. Gloria Ogiela
Wonderful experience from start to finish! Thank you! Linda Kallner
We are so very happy that, now that the time has come to downsize, we entrusted the sale of our favorite home to Nick Davis (mgr) and Jay Contessa (our agent) at Sotheby's. The market information we received was spot on, and the preparation leading up to the listing of our home was insightful and thorough. Above all, we appreciate the personal interest, and the consideration of our feelings and needs through the entire process. Best real estate experience ever. Thank you! Rodrigo Escobar
Jay was the best real estate agent anyone could ask for. To say he went above and beyond is an understatement. He, of course, knew the market in our search radius very well and showed us any home that might be of interest while understanding the comps and relative pricing/value to advise us appropriately. But beyond that, he also scoped out open house volume, found and coordinated vendors for us, and really anything we needed (or didn’t even know we needed). Jay showed us what is possible and blew away all expectations we had for a real estate agent! Micah Spellman
Jay Contessa was exceptional and went above and beyond for myself and my family. He is honestly the epitome of what one would hope a real estate agent would be. We are beyond grateful for him and all he did for us. Leslie Lewis
In my opinion, Jay Contessa is a ten-star real estate agent and a person of absolute integrity. My experience with Jay was easy because he attended to every detail personally and took responsibility for on time performance throughout the process. My purchase was via a new LLC formation which is more involved than a usual purchase. Jay made sure all the banking, legal, inspection and accounting processes were knitted together as necessary, making the transaction as stress free as possible on my behalf. Jay is hard working, honest person who services his clients' interests. I whole heartedly recommend him to whomever is looking to buy or sell real estate. Leslie A Lewis III
Jay is awesome!! Jay is an agent who truly cares about his clients--not just a commission! He acts as your advocate, not one who is out there to collect a payday. He helped me with prompt research and strategy sessions for both renting a property and buying properties. A big thing that Jay does is finds the right home at the right price. Not just a home at whatever price. Those who I've referred him too were also delighted with his custom care and attention to detail in finding them their new homes! Sam Williams
Jay was the best real estate broker we have ever worked with ( and Have made 2 other house purchases in my life) . He went above and beyond for us and honestly gave great advice as well as being a great resource for services in the area. he was available 24/7 and was knowledgeable and professional. I would refer Jay to anyone I know looking for a house in Connecticut. Chris Hoffman
My husband and I are so thankful to have purchased our first home through Jay and William Pitt! Jay was so helpful in helping us learn about the different towns in the area and really helped us to understand where we were in relation to town landmarks and our jobs at each home we looked at. Searching for a home during the pandemic was not easy by any means, yet we still felt each offer we placed was fair thanks to Jay's guidance. Jay always knew all the houses on the market in our price range and tailored our search as much as he could given the circumstances! It was reassuring to tour houses with Jay because of his expertise - for example, he would always check the equipment in the basement, the heat, hot water, etc. to note the quality of them and if they'd likely need to be replaced soon. It was fantastic to work with a realtor like Jay who was quick to pick up on our personalities in addition to our housing "wants"! I'd absolutely recommend him to friends and family looking to purchase a home in the Ridgefield area! Lori , Buyer

Jay Contessa in the News

News Times

Letter: ‘A fun and successful breast cancer fundraiser’…

Hamlet Hub

William Pitt and Brasserie Saint Germain Celebrity Bartender Event on October 11…    

News Times

Danbury kids prepare for book event, Newtown church sets up craft fair, and more neighborhood…

The New York Times

Homes for Sale in Connecticut and New York: Easton Three-Bedroom…

Contact Me

  • Jay Contessa

    Jay Contessa

    Licensed Real Estate Salesperson
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