About Me

I moved to the Berkshires in 2004, having grown up on the north shore of Long Island and lived in Washington, D.C., New York’s Upper West Side, the Boston area, and as an expat in Asia. I love this area for its natural beauty, wealth of cultural activities, organic farms and markets, food scene, and recreational amenities. I love its tradition of independent thought and its diversity – it was the first place that American colonists rebelled against the British, it was the birthplace of W.E.B. Du Bois, and for over a century it has been a haven for artists, so if you had talent, no matter what your race or background – you are welcome here. This is an idyllic rural place and an incredibly sophisticated one. And, people who are drawn to it, and move here, are genuinely interested in contributing to the community. It’s an extraordinary place, a place where one can truly be oneself.

The place one chooses to live says a lot about the person. So, though I seem to have been describing the place I live, I’ve already told you a lot about me and my values. I recently came across a thought from the creative director of the couturier Valentino that luxury isn’t just a certain lifestyle, but a “community of people who share values.”  I have that feeling here.

Now for the basics: I graduated Syracuse University, having focused on American Studies and Journalism, worked in the arts and in government, transitioned to research, then consulting, then to public policy work in the corporate world. I married, and as a trailing spouse in Asia, began travel writing, authored my first book, created a social responsibility project for Mobil Philippines, and did PR for Northern Telecom Asia Pacific. Returning to a Boston suburb with an infant daughter, I served on the historical commission, restored two antique houses, and began writing for home magazines. Fast forward 11 years: my daughter and I moved to the Berkshires, an intuitive choice for me and the right one. I started writing for Berkshire Living, then founded its annual Home + Garden magazine, then authored a few more books. In 2007, I earned my Massachusetts real estate sales license, followed by licenses in New York and Connecticut. In 2013, I was one of six agents chosen to launch William Pitt Sotheby’s Berkshire Brokerage. Consistently one of the area’s top-producing realtors, I ranked #1 in 2018 Berkshire County dollar volume sales.

I’m passionate about travel, and wherever I travel, I indulge my passion for the arts, architecture and design, architectural history, and local experiences that enrich my understanding of other people and other cultures.

Gladys Montgomery

Realtor | Writer | Explorer

I live in the Berkshires, which, to me, is like an expatriate community, open, friendly, sophisticated, well-traveled, endlessly interesting.