Gladys Montgomery

I love my work as a realtor and take pride in maintaining the highest standards of client service. This means having a thorough knowledge of the real estate market and surpassing the expectations of my buyers and sellers by listening to them, understanding their needs, being responsive, communicating effectively, providing sound advice, negotiating successfully, and handling transactions seamlessly and perfectly. It’s gratifying to know that my skills and experience are being used to the fullest in helping others. I experience that satisfaction every day as a realtor in Berkshire County and contiguous areas of Massachusetts, New York State, and Connecticut.

My forte is representing architecturally distinctive properties and pairing buyers with the right home---a Contemporary or an Antique, a fixer-upper, or one that offers every 21st-century amenity. My recent sales have ranged from under $45,000 for a building lot, to $209,000 for a place that first-time buyers now call home, to $3,500,000 for a 90-acre estate. Whether it's a cottage on a lake, a cabin in the woods, a comfortable in-town home, or a significant estate, luxury really does come in every price range.

One of six agents selected to launch Sotheby's Berkshire brokerage in 2013, I have been instrumental in building our business to a #1 market share position in Berkshire County. I am currently #1 in sales (dollar volume) and am consistently among the top-selling realtors in the County. In 2017, I founded The Shire Group with Maggie Barry and Leslie Chesloff. We are now the top-selling realtor team in Berkshire County.

Before becoming a realtor in 2007, I had a 25-year career in international strategic marketing and as a writer, editor, and author specializing in architecture and design. I’ve penned more than 300 home-focused magazine feature articles and was the founding editor of Berkshire Living Home + Garden. I’ve also authored several books about historic buildings. Having supervised countless photo shoots, I learned, from some of the nation’s foremost architectural photographers, how to present a home to its best advantage. This background, and my experience with renovating/restoring antique houses, taught me to evaluate homes in terms of light, flow, and quality, and to articulate these in a meaningful way, which is of tremendous help to my buyers and sellers.

Like many people choosing a primary or second home here, I made the transition to the Berkshires in 2004, attracted by the region’s unparalleled quality of life. I’ve lived in many places: the North Shore of Long Island, Washington D.C., New York’s Upper West Side, a Boston suburb, and, for eight years, as an expat in the Philippines and Japan. So, I know first-hand what a truly extraordinary community the Berkshires is and why this sophisticated rural area attracts people from all over the country and the world. It's rewarding to help new arrivals make a successful transition.

 I look forward to speaking with you about how my team and I can help you achieve your real estate goals.