Michael Gilbert

With over 20 years of experience and more than $350 million in personal sales, Michael is a seasoned real estate professional whose extensive career spans single-family homes, condominiums, property management, investment properties, vacation homes, off-market transactions, leasing and short-term rental consulting. In today’s market, where multiple offers drive bids beyond the asking price, it’s essential to have an experienced agent to strategically craft a winning offer that secures the property without overpaying.

A consistent recipient of the prestigious Boston Magazine Top Producer award, Michael has represented buyers and sellers in hundreds of transactions across 28 towns, from Provincetown to the Berkshires, where he has owned vacation homes and operated a thriving short-term rental business. In 2022, Boston Common Magazine featured Michael as a Power Player in the Greater Boston Real Estate market. His market expertise was recently featured in The Wall Street Journal, where he provided commentary on Boston’s real estate landscape. As a member of the Greater Boston Association of Realtors, National Association of Realtors, and the exclusive Top Agent Network—a private platform for Boston’s elite agents—Michael remains at the forefront of the industry. 

A lifelong Boston-area resident, Michael has lived in Jamaica Plain, Norwood, Back Bay, South End, Newton and now resides in Winchester with his wife, Molly, their one-year-old son, Griffin, their four-year-old German Shorthaired Pointer, Barrington and a baby boy due in August! An avid CrossFit enthusiast for over 12 years, Michael brings the same discipline and energy to his real estate practice, ensuring every client receives exceptional service and results.

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Alexander

Michael helped my wife and I buy our first home late in 2024. I honestly don't think we would be in our house now if it was not for his expertise, commitment, and his unwavering support throughout our home buying experience. Not once did we feel rushed or confused about any of the process. We can't thank him enough and you would be lucky to work with him on any of your home purchase needs!

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Cynthia

It was such a pleasure to work with Michael to buy our first home. I can truly say that I do not know how my husband and I would have navigated the process without Michael's unwavering commitment to supporting us. He answered every question we had and many that we didn't even think to ask) and worked tirelessly within our constraints to ensure that we ended up in a home that we loved. We...

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Christine

I've had the pleasure of working with Michael multiple times now, both for buying and selling in some of the most sought-after neighborhoods in the Boston area. His deep knowledge of local markets, properties, and various selling strategies is unmatched. What truly sets him apart is his dedication to making the entire process not only seamless but also enjoyable. Michael's extensive network...

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Michelle

Amazing experience with Michael! He managed the listing of our Charlestown condo. Michael made the entire process so easy for us. He handled all aspects of the listing from start to finish with minimal involvement from us. He leveraged his years of experience and extensive knowledge of the market to sell our unit within days of when the listing went live. We received an over asking offer...

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Pat

My son and I had the pleasure of working with Michael on two properties. While the first deal fell through, it had nothing to do with Michael's efforts. I mention it because Michael was incredibly diligent in helping us find the perfect place in a timely manner. I had specific criteria to meet, including staying within a certain price range and finding a property with few, if any, stairs - both of which can be...

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We work with a wide range of clients—from first-time buyers and seasoned sellers to landlords, tenants, and developers. Our experience spans all kinds of properties, including single-family homes, luxury high-rises, historic brownstones, multi-family investments, and new development projects.