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, Traveling, Cooking
  • 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

The #1 Producer in Berkshire County Dollar Volume Sales in 2018,* Gladys loves her work as a realtor and takes pride in maintaining the highest standard of client service. This means having a thorough knowledge of the real estate market and surpassing the expectations of her buyers and sellers by listening to them, understanding their needs, being responsive, communicating effectively, providing sound advice, negotiating successfully, and handling transactions seamlessly and flawlessly. She is grateful to know that her skills and experience are used to the fullest in helping others find the perfect primary or vacation home in the Berkshire region. Earning her first real estate sales license in 2007, she is currently licensed in Massachusetts, Connecticut, and New York.

Gladys's forte is representing architecturally distinctive properties and pairing buyers with the right home, whether it is a Contemporary or an Antique, a fixer-upper, or one that offers every 21st-century amenity. Her recent sales have ranged from $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 lakefront retreat, a cabin in the woods, a comfortable in-town home, a condominium at Canyon Ranch, or a significant estate, she believes that luxury comes at every price point, and that each of her buyer and seller clients deserves exceptional service and personal attention.

One of six agents selected to launch Sotheby's Berkshire brokerage in 2013, Gladys was instrumental in building the business to a #1 market share position in Berkshire County, a rank the company achieved in 2017 and continued in 2018, when the Berkshire brokerage led its nearest competitor by $60 million in sales. Consistently among the top-selling realtors in the county, Gladys founded a team, The Shire Group in mid-2017. In 2018, her team was the top-selling team in the County. 

In addition to having worked in goverment and the corporate world, Gladys had a 25-year career in international strategic marketing and as a writer, editor, and author specializing in architecture and design. She has written more than 300 home-focused magazine feature articles, was the founding editor of Berkshire Living Home + Garden, and authored several books about historic buildings. Having supervised countless photo shoots, she learned...

The #1 Producer in Berkshire County Dollar Volume Sales in 2018,* Gladys loves her work as a realtor and takes pride in maintaining the highest standard of client service. This means having a thorough knowledge of the real estate market and surpassing the expectations of her buyers and sellers by listening to them, understanding their needs, being responsive, communicating effectively, providing sound advice, negotiating successfully, and handling transactions seamlessly and flawlessly. She is grateful to know that her skills and experience are used to the fullest in helping others find the perfect primary or vacation home in the Berkshire region. Earning her first real estate sales license in 2007, she is currently licensed in Massachusetts, Connecticut, and New York.

Gladys's forte is representing architecturally distinctive properties and pairing buyers with the right home, whether it is a Contemporary or an Antique, a fixer-upper, or one that offers every 21st-century amenity. Her recent sales have ranged from $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 lakefront retreat, a cabin in the woods, a comfortable in-town home, a condominium at Canyon Ranch, or a significant estate, she believes that luxury comes at every price point, and that each of her buyer and seller clients deserves exceptional service and personal attention.

One of six agents selected to launch Sotheby's Berkshire brokerage in 2013, Gladys was instrumental in building the business to a #1 market share position in Berkshire County, a rank the company achieved in 2017 and continued in 2018, when the Berkshire brokerage led its nearest competitor by $60 million in sales. Consistently among the top-selling realtors in the county, Gladys founded a team, The Shire Group in mid-2017. In 2018, her team was the top-selling team in the County. 

In addition to having worked in goverment and the corporate world, Gladys had a 25-year career in international strategic marketing and as a writer, editor, and author specializing in architecture and design. She has written more than 300 home-focused magazine feature articles, was the founding editor of Berkshire Living Home + Garden, and authored several books about historic buildings. Having supervised countless photo shoots, she learned from some of the nation’s foremost architectural photographers how to present a home to its best advantage. This background, and her experience with renovating/restoring antique houses, taught her to evaluate homes in terms of light, flow, and quality, and to articulate these characteristics in a meaningful way, which is of tremendous help to her buyers and sellers.

Like many people choosing a primary or second home here, Gladys was attracted by the Berkshires's unparalleled quality of life when she made the transition to the area in 2004. She has 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, she understands 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. She delights in helping new arrivals make a successful transition to their new homes here.

Gladys looks forward to speaking with you about how she can help you achieve your real estate goals.

* 2018 Berkshire County MLS sales statistic

The #1 Producer in Berkshire County Dollar Volume Sales in 2018,* Gladys loves her work as a realtor and takes pride in maintaining the highest standard of client service. This means having a thorough knowledge of the real estate market and surpassing the expectations of her buyers and sellers by listening to them, understanding their needs, being responsive, communicating effectively, providing sound advice, negotiating successfully, and handling transactions seamlessly and flawlessly. She is grateful to know that her skills and experience are used to the fullest in helping others find the perfect primary or vacation home in the Berkshire region. Earning her first real estate sales license in 2007, she is currently licensed in Massachusetts, Connecticut, and New York.

Gladys's forte is representing architecturally distinctive properties and pairing buyers with the right home, whether it is a Contemporary or an Antique, a fixer-upper, or one that offers every 21st-century amenity. Her recent sales have ranged from $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 lakefront retreat, a cabin in the woods, a comfortable in-town home, a condominium at Canyon Ranch, or a significant estate, she believes that luxury comes at every price point, and that each of her buyer and seller clients deserves exceptional service and personal attention.

One of six agents selected to launch Sotheby's Berkshire brokerage in 2013, Gladys was instrumental in building the business to a #1 market share position in Berkshire County, a rank the company achieved in 2017 and continued in 2018, when the Berkshire brokerage led its nearest competitor by $60 million in sales. Consistently among the top-selling realtors in the county, Gladys founded a team, The Shire Group in mid-2017. In 2018, her team was the top-selling team in the County. 

In addition to having worked in goverment and the corporate world, Gladys had a 25-year career in international strategic marketing and as a writer, editor, and author specializing in architecture and design. She has written more than 300 home-focused magazine feature articles, was the founding editor of Berkshire Living Home + Garden, and authored several books about historic buildings. Having supervised countless photo shoots, she learned from some of the nation’s foremost architectural photographers how to present a home to its best advantage. This background, and her experience with renovating/restoring antique houses, taught her to evaluate homes in terms of light, flow, and quality, and to articulate these characteristics in a meaningful way, which is of tremendous help to her buyers and sellers.

Like many people choosing a primary or second home here, Gladys was attracted by the Berkshires's unparalleled quality of life when she made the transition to the area in 2004. She has 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, she understands 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. She delights in helping new arrivals make a successful transition to their new homes here.

Gladys looks forward to speaking with you about how she can help you achieve your real estate goals.

* 2018 Berkshire County MLS sales statistic

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  • Awards
    • #1 Dollar Volume Sales, per Berkshire County MLS, 2018
    • William Pitt|Julia B. Fee Diamond Award, 2018
    • #4 Dollar Volume Sales, William Pitt| Julia B. Fee Company-Wide Award, 2018
    • #1 Berkshire Office Producer, Units Sold, 2018
    • #1 Berkshire Office Producer, Dollar Volume Sales, 2013-2018
    • Top Office Team Award, 2018:
    • The Shire Group
    • William Pitt|Julia B. Fee Platinum Award 2017, 2015
    • William Pitt|Julia B. Fee Gold, Silver, Bronze Awards, 2013, 2014, 2016
    • Adirondack Writing Center - Nonfiction Award for An Elegant Wilderness
    • Victorian Society of New York Book Award for An Elegant Wilderness (author)
    • City and Regional Magazine Award for Berkshire Living Home + Garden (founding editor)
  • Specialities
    • Architecturally Distinctive Properties
    • Antique Homes
    • Mid-Century Modern & Contemporary Homes
    • Luxury & Estate Properties

My Listings

104 Interlaken Rd $4,000,000 link

104 Interlaken Rd

Stockbridge, MA 01262 | Berkshire County
$4,000,000
5 Beds 4/1 Baths 4,200 Sqft 4.92 Acres

Tranquility reigns in this stunning setting on Stockbridge Bowl, where a spectacular, modern lakefront retreat, designed by award-winning architect R.J. McDonald for himself, affords...

5
bed
4/1
bath
4,200
sqft
1 Pinecroft Dr $3,250,000 link

1 Pinecroft Dr

Lenox, MA 01240 | Berkshire County
$3,250,000
6 Beds 5/1 Baths 7,816 Sqft 1.14 Acres

Enjoy the ultimate Berkshire luxury lifestyle in this turn-key residence, with a preferred membership to Canyon Ranch resort, which is just steps away. This extraordinary home...

6
bed
5/1
bath
7,816
sqft
165 Kemble St. #17 -- $2,300,000 link

165 Kemble St. #17 --

Lenox, MA 01240 | Berkshire County
$2,300,000
2 Beds 2/1 Baths 1,950 Sqft

Unit #17. Enjoy the ultimate luxury of the wellness lifestyle in this residence at Canyon Ranch, Lenox, one of the nation's premier spas. One of only 19 units, it features a spacious...

2
bed
2/1
bath
1,950
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
1 Chanterwood Rd $3,200,000 link

1 Chanterwood Rd

Lee, MA 01238 | Berkshire County
$3,200,000
5 Beds 5/1 Baths 5,600 Sqft 12.3 Acres

CHANTERWOOD: BERKSHIRE WATERFRONT ESTATE ON GOOSE POND-ONE OF NEW ENGLAND'S FINEST LAKES! 300' of shoreline + private sandy beach, dock, privacy, & 12 acres divided into 3 parcels...

5
bed
5/1
bath
5,600
sqft
165 Kemble St #17 $2,231,000 link

165 Kemble St #17

Lenox, MA 01240 | Berkshire County
$2,231,000
2 Beds 2/1 Baths 1,950 Sqft

Enjoy the ultimate luxury of the wellness lifestyle in this residence at Canyon Ranch, Lenox, one of the nation's premier spas. One of only 19 units, it features a spacious...

2
bed
2/1
bath
1,950
sqft