Gladys Montgomery

Real Estate Salesperson

Gladys Montgomery

Gladys Montgomery

Real Estate Salesperson

Great Barrington

306 Main Street
Great Barrington, MA 01230

Lenox

34 Church Street
Lenox, MA 01240
Visit my website

It’s gratifying to know that your 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.

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...

It’s gratifying to know that your 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.

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 both my buyers and my 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 it is a magnet for people from all over the country and the world. It's rewarding to help new arrivals discover this sophisticated, rural region and make a successful transition to the area.

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.

I take great pleasure in representing architecturally distinctive properties and to pairing buyers with the right home, whether it’s 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 large contemporary estate. Quality properties do come in every price range!


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

It’s gratifying to know that your 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.

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 both my buyers and my 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 it is a magnet for people from all over the country and the world. It's rewarding to help new arrivals discover this sophisticated, rural region and make a successful transition to the area.

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.

I take great pleasure in representing architecturally distinctive properties and to pairing buyers with the right home, whether it’s 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 large contemporary estate. Quality properties do come in every price range!


 I look forward to speaking with you about how 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
  • Specialities
    • Architecturally Distinctive Properties
    • Antique Homes

My Listings

14 Monument Valley Rd
Great Barrington, MA $2,395,000

14 Monument Valley Rd

Great Barrington, MA

$2,395,000
  • 5 Beds
  • 3/2 Baths
  • 6,200 Sqft
165 Kemble St #14
Lenox, MA $2,300,000

165 Kemble St #14

Lenox, MA

$2,300,000
  • 2 Beds
  • 2/1 Baths
  • 1,790 Sqft
165 Kemble St #17
Lenox, MA $2,300,000

165 Kemble St #17

Lenox, MA

$2,300,000
  • 2 Beds
  • 2/1 Baths
  • 2,060 Sqft
2 Brace Road
Tyringham , MA $2,100,000

2 Brace Road

Tyringham , MA

$2,100,000
  • 6 Beds
  • 4/2 Baths
  • 7,372 Sqft

My Sales

3 & 7 Dellea Rd
Alford, MA $3,525,000
SOLD

3 & 7 Dellea Rd

Alford, MA

$3,525,000
  • 8 Beds
  • 6/1 Baths
  • 7,492 Sqft
151 East Rd
Alford, MA $1,700,000
SOLD

151 East Rd

Alford, MA

$1,700,000
  • 5 Beds
  • 3/2 Baths
  • 3,750 Sqft
121 Top Of Dean Hill Rd
Canaan, NY $1,070,000
SOLD

121 Top Of Dean Hill Rd

Canaan, NY

$1,070,000
  • 3 Beds
  • 3 Baths
  • 3,181 Sqft
121 Top Of Dean Hill Rd
Canaan , NY $1,070,000
SOLD

121 Top Of Dean Hill Rd

Canaan , NY

$1,070,000
  • 3 Beds
  • 3 Baths
  • 3,181 Sqft

Additional Communities

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