About Me

     Having lived in the Berkshires since 2004, I decided in 2021 to add a New York City home and focus. With an apartment in my old neighborhood on the Upper West Side, I now have one foot I the country and one in the city. As many of my real estate clients know, the two complement each other perfectly. A realtor affiliated with William Pitt Sotheby's International Realty in the Berkshires since 2012, I added an affiliation with Sotheby's Upper East Side Manhattan brokerage in 2021, so I can serve clients in both markets.

     They have a lot in common: authenticity and sophistication, thriving food scenes, myriad performing arts venues and museums, a strong sense of community, and an open and welcoming attitude are just a few of the things I love about both places. And, importantly, both the Berkshires and New York City are places where one can truly be oneself.

     Though I seem to have been describing places I live, I’ve already told you a lot about me, my interests and 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 couldn't agree more. 

     Now for the basics: I grew up on the north shore of Long Island and have also lived in Washington, D.C., the Boston area, and as an expat in Asia. 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. The average home sale price in Berkshire County has run in the three-and-four-hundred thousands: my average sale is a million plus. Many of my clients in this range hail from New York, so professionally, my dual Sotheby's International Realty affiliations make sense.

     Wherever I am based, or traveling, 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.

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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.