Brian Montgomery

Brian Montgomery Large Format Image

Brian Montgomery
(p): 857.383.3118
(e): [email protected]

In order to get a better grasp of the real estate market in Boston, Brian has lived in just about every neighborhood– South Boston, North End, Back Bay, Kenmore Square, and Brighton/Allston.  A graduate of Tabor Academy in Massachusetts and of Gettysburg College in Pennsylvania, Brian is a native son of Vermont, having grown up in the ski town of Killington, where he not only skied and snowboarded but also played hockey and baseball.  While at college, he continued his sports endeavors. He was also awarded the Anderson Entrepreneurial Student award for all four years at Gettysburg and was named to the Dean’s Honor List.   After working for Vermont’s Senior Senator, he interned for a semester at the Heritage Foundation during his foreign policy studies at American University in DC.

After graduating from college, Brian worked in the Financial Services field as a financial planner, with expertise in insurance instruments, long-term care plans, small business retirement plans and investment planning.  Now working in the leasing and sales division, Brian firmly believes that real estate should be an integral part of a well-balanced and diversified investment portfolio.  He looks forward to gaining further experience in the investment and commercial divisions of Charlesgate Realty Group.

Brian enjoys taking advantage of all Boston has to offer and is an avid fan of any team playing any sport, whether at Fenway, Gillette, or the Garden.  Brian enjoys international travel, playing hockey, golf, and spending time on the coast of Maine.  He has an engaging energy, a quick wit, and looks forward to working with clients in all phases of their real estate needs, both now and into the future.


Blog Articles

Want to make sure Rufus can live in your Boston condo? Read this.



“Brian Montgomery was the epitome of a professional throughout my search as a first-time home buyer. I had been searching for a 2BR / 2BA home since January of 2008. At first I had another broker from a different firm who was dishonest regarding the entire process and ended up costing me a $1,000 deposit by not explaining all of the steps in the offer-P&S-closing process. This deception was difficult to overcome, but I was recommended to Charlesgate realty by a friend.

Immediately, Brian and a coworker set up a meeting at their office to go over my goals, timing, and financial situation. They walked me through each step in the process and made it very clear at which times various financial commitments would likely be needed. This was Summer 2008.

Over the following year, Brian showed me more than 20-25 different places in person, while also offering his opinion on countless others. Every discussion was honest and at no time did I feel pressured to make a quick decision. Brian, helped me narrow my search to South Boston and specifically worked with me to identify Single-Family homes. His rapport with other brokers was instrumental in always getting me into showings later in the evening and as places were listed on the market.

In April, I received a notice through Brian’s daily emails of a new listing and immediately called Brian to set up a showing that day. He quickly called the agent and was able to set up the first showing which put us in the advantageous spot of being able to place an offer immediately. Brian was excellent in negotiating on my behalf and his firm stance on timing likely enabled me to get a property under contract below listing price that would otherwise have gone for at least listing price.

This is only a short summary of the work Brian did for me. He readily fielded emails, phone calls, and voice-mails in a responsive manner. He negotiated three different offers on my behalf and made me trust him. While one of them we lost because of an already accepted offer, the other he was upfront in telling me the value wasn’t there to increase the offer.

Now, a year since we started working together I am putting the finishing touch’s on my new home. Brian was instrumental throughout the entire process and in 5-6 years when I am looking to move the suburbs, Brian will be the first person I call.” Sherwin P.


“Brian Montgomery was an absolute pleasure to work with in my attempt to purchase a condo in South Boston. He was able to put all the resources of Charlesgate Realty Group at my fingertips allowing me to search and set up showings all from my computer. If I had any questions, he was always available and very accommodating when it came to scheduling showings of properties. During the closing process he was always on top of all dates and “to do’s” to make sure everything was done in a timely manner and correct. Also his ability to use his network of business associates when applicable to answer any questions or concerns I may bring up to get me accurate and up date answers which occurred frequently with the housing market climate changing almost on a daily basis. I would recommend Brian and Charlesgate Realty Group to anyone of my friends and I plan to continue using them in the future.” Antonio B.