Gladys Montgomery

Real Estate Salesperson

Gladys Montgomery

Gladys Montgomery

Real Estate Salesperson

Great Barrington Brokerage

308 Main Street
Great Barrington, MA 01230
Visit my website

It’s exciting for anyone in any profession to know that you excel at it, that all of your skills and experience are being used to the fullest. That’s a feeling of satisfaction that I experience every day of my work life as a realtor in the Berkshire County and contiguous areas of New York State.

Long before I became a realtor in 2007, I spent 25-years as a writer, editor and author specializing in architecture and design. I’ve penned more than 300 home-focused magazine feature articles for regional and national magazines and was the founding editor of Berkshire Living Home + Garden...

It’s exciting for anyone in any profession to know that you excel at it, that all of your skills and experience are being used to the fullest. That’s a feeling of satisfaction that I experience every day of my work life as a realtor in the Berkshire County and contiguous areas of New York State.

Long before I became a realtor in 2007, I spent 25-years as a writer, editor and author specializing in architecture and design. I’ve penned more than 300 home-focused magazine feature articles for regional and national magazines and was the founding editor of Berkshire Living Home + Garden. I’ve also authored several books about historic buildings. Having been on countless photo shoots, I am fortunate to have learned from some of the nation’s foremost architectural photographers. In addition, I spent many years as a professional in international marketing and public relations. My writing, styling, photographic, and marketing acumen translates into great results for my listing clients.

I’m an architecture nerd. I take great pleasure in representing architecturally distinctive properties and to pairing buyers with just the right home, whether it’s contemporary or antique, a fixer upper or replete with every 21st-century amenity. Having restored/renovated three houses myself, I have the hands-on experience to help my buyers evaluate properties that interest them.

I moved 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 where I grew up, Washington D.C., New York’s Upper West Side, a Boston suburb, and abroad for eight years in the Philippines and Japan. Because its lifestyle assets, the Berkshire region is a magnet for people from all over the country and the world––welcoming to new arrivals, eager to share the best of itself. It’s exciting to me to share what I love about the Berkshires and to help others make successful transitions to the area.

As a realtor, I maintain the highest professional and ethical standards. This means having a thorough knowledge of the real estate market, understanding my clients’ needs and surpassing their expectations by being responsive, communicating effectively, providing sound advice, negotiating for results, and handling transactions seamlessly and perfectly. Working with buyers and sellers, my 2015 sales have ranged from under $45,000 for a building lot to more than $3,500,000 for a contemporary estate: quality properties do come in every price range.


 Look forward to speaking with you about your real estate needs. I am licensed in MA, CT and NY.

It’s exciting for anyone in any profession to know that you excel at it, that all of your skills and experience are being used to the fullest. That’s a feeling of satisfaction that I experience every day of my work life as a realtor in the Berkshire County and contiguous areas of New York State.

Long before I became a realtor in 2007, I spent 25-years as a writer, editor and author specializing in architecture and design. I’ve penned more than 300 home-focused magazine feature articles for regional and national magazines and was the founding editor of Berkshire Living Home + Garden. I’ve also authored several books about historic buildings. Having been on countless photo shoots, I am fortunate to have learned from some of the nation’s foremost architectural photographers. In addition, I spent many years as a professional in international marketing and public relations. My writing, styling, photographic, and marketing acumen translates into great results for my listing clients.

I’m an architecture nerd. I take great pleasure in representing architecturally distinctive properties and to pairing buyers with just the right home, whether it’s contemporary or antique, a fixer upper or replete with every 21st-century amenity. Having restored/renovated three houses myself, I have the hands-on experience to help my buyers evaluate properties that interest them.

I moved 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 where I grew up, Washington D.C., New York’s Upper West Side, a Boston suburb, and abroad for eight years in the Philippines and Japan. Because its lifestyle assets, the Berkshire region is a magnet for people from all over the country and the world––welcoming to new arrivals, eager to share the best of itself. It’s exciting to me to share what I love about the Berkshires and to help others make successful transitions to the area.

As a realtor, I maintain the highest professional and ethical standards. This means having a thorough knowledge of the real estate market, understanding my clients’ needs and surpassing their expectations by being responsive, communicating effectively, providing sound advice, negotiating for results, and handling transactions seamlessly and perfectly. Working with buyers and sellers, my 2015 sales have ranged from under $45,000 for a building lot to more than $3,500,000 for a contemporary estate: quality properties do come in every price range.


 Look forward to speaking with you about your real estate needs. I am licensed in MA, CT and NY.

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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

2 Brace Road
Tyringham , MA $2,550,000

2 Brace Road

Tyringham , MA

$2,550,000
  • 6 Beds
  • 4/2 Baths
  • 7,372 Sqft
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 #17
Lenox, MA $2,300,000

165 Kemble St #17

Lenox, MA

$2,300,000
  • 2 Beds
  • 2/1 Baths
  • 2,060 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

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
85 Salmon Kill Rd
Salisbury, CT $2,310,000
SOLD

85 Salmon Kill Rd

Salisbury, CT

$2,310,000
  • 4 Beds
  • 4/2 Baths
  • 4,600 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

Additional Communities

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