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About Matt Diamond

Sales Associate - Old Saybrook Office
33 Main Street, Old Saybrook, CT 06475
Cell: 860.391.9461

Life is a Journey, Real Estate is a Destination :)

Professional Association

Just elected in 2020

Old Saybrook Board Of Assessment Appeals

Connecticut Association of Realtors

New Haven MiddShore Board of Realtors

Old Saybrook Republican Town Committee

Saybrook Ram Boosters Club

Pine Crest Athletic Hall of Fame


Pine Crest Preparatory - Fort Lauderdale, Florida
University of Miami - BBA MKT 1992


Chairman's Club

Professional Specialty

Buyers, Sellers and Investors

Bilingual Talents

Some Espanol....


Hello and thank you for visiting my page. I have been a licensed realtor since 2002 and really enjoy this business. It was after buying and selling four houses of my own and transacting with some great realtors that I felt it was something I wanted to do.

My business background in Marketing from University of Miami in Coral Gables, FL has added immensely to my career path. It all started growing up in New England and working in My Father's Company, Astro Chemicals. I experienced every facet of that business prior to even going to college. Sales is my forte and onward I went always asking for the order and building confidence that I could stake my claim in a business environment. Upon transfer of Astro Chemicals to My Brothers and I at Dad's passing, I knew I wanted to be back to Florida. I negotiated the sale of my shares and we structured a deal to be able to have my shares kept in the family.

In Florida I was hired and licensed by Raymond James and Associates be a financial advisor. This was a perfect fit as I had made many alliances with the mutual fund industry. Then one day in 1995 a friend came to me with an idea to start a company on a new thing called the "internet". It was at that time the entrepreneurial spirit of my father awoke in me.

My business partner on this new company was involved with the Triple Crown winning thoroughbred Secretariat and our winning combination created a revolutionary new way to buy cars. AutobyInternet was born and helped make purchases of autos more fair to everyone. There came a time when this business grew and we sold it to AutoNation, a Fortune 200 Company.

Having had these successes and now desiring to move out of corporate life I got my license to broker real estate transactions as an agent. Within my first two years I reached Chairman's Club Designation. That happened a Preferred Properties, Inc. the premier boutique firm in Greenwich Connecticut. Chairman's Club is given to agents surpassing $10,000,000 in sales annually.

My clients have encompassed the entire spectrum; from helping regular 'guys" to financial moguls and even Ambassadors to the United Nations.

For me it's all about everyone being treated equitably and honestly. When you purchase a home one thing is true, it does not have to come with an agent. For me I always strive to be so valuable to the equation that my clients return the next time need to make a move!

My personal life is simple. I am a single dad of five great kids from 12-29. I show up for everything that is scheduled and I get to the end of the line what I begin. I enjoy golfing and Oceans are my serenity. Christ is my Savior.


Licensed Realtor since 2002

Areas Covered

All of Connecticut

Niche Marketing

Shoreline Homes - Flood Zone Expert - Horse Properties
Investor/Builder Flips targeting minimum $50K Net Profit
First time buyers
Short sales, Fannie Mae, HUD, Freddie Mac, Hubzu
203K Loans
Rent backs
Land Sales
Mobile Homes

  • Matt was relentless in his effort to sell my beach house and found no task too small. He did several open houses and paid for newspaper advertising almost every weekend. In addition, he created email newsletters that were sent to potential buyers. If it snowed, Matt shoveled. He fixed a running to... Lincoln Tedeschi (Westbrook, CT)

  • TO WHOM IT MAY CONCERN: The purpose of this communication is to share with William Raveis and all who may come into real estate contact with Sales Executive Matt Diamond whose Services Office is located at 33 Main Street in Old Saybrook, Connecticut 06475 Mr. Diamond rendered me exemplary serv... Shirley Hill Witt (Guilford, CT)

  • Our agent, Matt Diamond, epitomizes professionalism. I felt we had an advocate by our side the entire home-buying process. As first-time buyers, we went into the search a bit nervous-- we left it thrilled with our purchase, and equally thrilled with the service Matt provided. Marc Kilstein (NEW HAVEN, CT)

  • This is the 2nd home I have bought with Matt, he is a nice person and works hard. Knows his business. He always has my interests and needs first. Rasim Feratovic (Old Saybrook, CT)

  • Matt was a delight to work with from beginning to end. I would not hesitate to recommend him to others. Kim Minor (Killingworth, CT)

  • Looking for a house was almost a hobby for me during this time. I was glued to and Matt was always willing to set up a showing when I found something. Kim Minor (East Hampton, CT)

  • Matt went above and beyond to get our home sold. At all times he kept us updated and when the offer came he negotiated an amazing deal. We are so thankful. Maureen and Larry Larry Burridge and Maureen Cianci (WESTBROOK, CT)

  • Matt went out of his way on several occasions, hosted several open houses, worked with us on listing descriptions and revisions, updated photos, and worked hard up to closing to ensure we got the house sold. CT Rental Ventures (WESTBROOK, CT)

  • It was fun working with Matt and his tremendous knowledge base/negotiations ability helped get us the best deal. Teressa Sonski (WESTBROOK, CT)

  • One month, one open house, three showings and done - our home was sold! Matt Diamond and William Raveis helped us find our perfect new home with all the charm and character we had in mind. From pricing and marketing our home to supporting us through the buying and selling process, our expectations... Susan Carpenter (WESTBROOK, CT)

  • Excellent services, a quick closing, all questions answered. Carol Ann Cote (BRANFORD, CT)

  • Matt is trustworthy Realtor. He empathetic and concentrated on our needs so we found just the right house. The whole search and buying process was made simple by him. We had fun doing it. Thank you. Omar and Silvia Michael Hurlburt (Old Saybrook, CT)

  • Matt is a great agent and I would recommend him to anyone. He is thorough and he is dedicated to helping you find your home. He is knowledgeable of the area and is well connected to people and services who can help further. Delwin Harvey (Evanston, IL)

  • Our sale was not an easy one, but Matt was tireless to get it done. He was kind and empathetic to our difficult situation; leaving our farm after 20 years. We have bought a new home with him and that purchase went well also. Thank you. Michael Pisani Jr. (Haddam, CT)

More Testimonials ›


Your Insurance Rep.

Katherine Gauthier
Insurance NPN#
Office - 860.838.3024
Fax - 860.838.3024

Email Insurance Rep. › Insurance Quote ›

Your Loan Officer

Robert Bradley
NMLS Mortgage Loan Originator ID 431493
Cell - 860.391.1099

Email Loan Officer › Loan Quote ›