Gladys Montgomery

Gladys Montgomery

Real Estate Salesperson

Great Barrington

306 Main Street
Great Barrington, MA 01230

Lenox

34 Church Street
Lenox, MA 01240
  • Born In:
    Huntington, Long Island, New York
  • Live In:
    The Berkshires
  • Favorite Movie:
    On the Waterfront
  • Passion:
    Living Life Creatively and to the Fullest
  • Interests:
    International Travel, Architecture, Architectural History, Garden Design, Food, Textiles, Art, Politics
  • Favorite Lyric:
    "I'm a soul in wonder." Van Morrison.
  • Can’t Live Without:
    A positive attitude
  • Inspiration:
    Diverse cultures, Family & friends, Nature, A clear night sky spangled with stars

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 architecturally distinctive properties and pairing buyers with the right home---a contemporary or 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.

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...

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 architecturally distinctive properties and pairing buyers with the right home---a contemporary or 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.

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.

One of the six agents who founded the Berkshire brokerage in 2013, I have been instrumental in helping my firm become a leader in market share here. Consistently a top producer, I founded The Shire Group in the Berkshire brokerage in 2017, with Maggie Merelle and Maggie Barry. Our goal is simple: to provide the best client service in the business.

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

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 architecturally distinctive properties and pairing buyers with the right home---a contemporary or 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.

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.

One of the six agents who founded the Berkshire brokerage in 2013, I have been instrumental in helping my firm become a leader in market share here. Consistently a top producer, I founded The Shire Group in the Berkshire brokerage in 2017, with Maggie Merelle and Maggie Barry. Our goal is simple: to provide the best client service in the business.

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

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  • Awards
    • Top Office Producer, Dollars & Units, 2015
    • Platinum Award
    • Top Office Producer, 2014, Bronze Award
    • Top Office Producer Dollars & Units, 2013
    • Silver Award
    • Adirondack Writing Center - Nonfiction Award for An Elegant Wilderness
    • Victorian Society of New York Book Award for An Elegant Wilderness
    • City and Regional Magazine Award for Berkshire Living Home + Garden
  • Specialities
    • Architecturally Distinctive Properties
    • Antique Homes

My Listings

390&399 Under Mountain Rd $3,650,000 link

390&399 Under Mountain Rd

Lenox, MA 01240 | Berkshire County
$3,650,000
7 Beds 7/2 Baths 10,629 Sqft 106 Acres

''High Wick Farm,'' a magnificent, superbly located 106-Acre estate––a once-in-a-lifetime opportunity. At its centerpiece is a baronial Tudor mansion...

7
bed
7/2
bath
10,629
sqft
79 Hawthorne St $2,750,000 link

79 Hawthorne St

Stockbridge, MA 01262 | Berkshire County
$2,750,000
4 Beds 4/3 Baths 5,952 Sqft 36.4 Acres

Spectacular 36-acre estate steps from Tanglewood's Hawthorne Gate. Enjoy the relaxed elegance of the impeccable New Traditional brick manor house, which combines 21st-century...

4
bed
4/3
bath
5,952
sqft
165 Kemble St #14 $2,300,000 link

165 Kemble St #14

Lenox, MA 01240 | Berkshire County
$2,300,000
2 Beds 2/1 Baths 1,790 Sqft

Now you can live in luxury at Canyon Ranch® in Lenox, Massachusetts, and enhance your life with greater health and vigor and longevity. There are only 19 beautifully appointed...

2
bed
2/1
bath
1,790
sqft

My Sales

3 & 7 Dellea Rd $3,525,000 link

3 & 7 Dellea Rd

Alford, MA 01266 | Berkshire County
$3,525,000
8 Beds 6/1 Baths 7,492 Sqft 91 Acres

Contemporary 5 BR estate home, reno'd 2014, pool, pool hse, & 3BR guest quarters over carriage barn. Incl. is 7 Dellea, a 2 bedroom ranch, 1,292 sf + finished basement rms. Pastoral...

8
bed
6/1
bath
7,492
sqft
151 East Rd $1,700,000 link

151 East Rd

Alford, MA 01266 | Berkshire County
$1,700,000
5 Beds 3/2 Baths 3,750 Sqft 18.79 Acres

A long driveway leads to this magnificently simple contemporary farmhouse with protected views in all directions. For stylishly casual country living: an airy, light-filled plan,...

5
bed
3/2
bath
3,750
sqft
121 Top Of Dean Hill Rd $1,070,000 link

121 Top Of Dean Hill Rd

Canaan, NY 12029
$1,070,000
3 Beds 3 Baths 3,181 Sqft 16.85 Acres

Stunning, private, sophisticated Contemporary, combining the Taliesin West & Usonian styles pioneered by Frank Lloyd Wright, interpreted here by two of his prominent disciples....

3
bed
3
bath
3,181
sqft