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 standards 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---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 cottage on a lake, 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 clients deserves the exceptional.

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. Consistently among the top-selling realtors in the county, she founded The Shire Group with Maggie Barry and Leslie Chesloff in mid-2017. With each of its three members ranking in the top 20 of the 560 Berkshire County realtors,* the Shire Group is the top-selling realtor team in Berkshire 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...

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 standards 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---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 cottage on a lake, 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 clients deserves the exceptional.

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. Consistently among the top-selling realtors in the county, she founded The Shire Group with Maggie Barry and Leslie Chesloff in mid-2017. With each of its three members ranking in the top 20 of the 560 Berkshire County realtors,* the Shire Group is the top-selling realtor team in Berkshire 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 made the transition to the Berkshires in 2004, attracted by the region’s unparalleled quality of life. She 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 and The Shire Group 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 standards 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---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 cottage on a lake, 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 clients deserves the exceptional.

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. Consistently among the top-selling realtors in the county, she founded The Shire Group with Maggie Barry and Leslie Chesloff in mid-2017. With each of its three members ranking in the top 20 of the 560 Berkshire County realtors,* the Shire Group is the top-selling realtor team in Berkshire 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 made the transition to the Berkshires in 2004, attracted by the region’s unparalleled quality of life. She 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 and The Shire Group can help you achieve your real estate goals.

* 2018 Berkshire County MLS sales statistic

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  • Awards
    • #1 Producer, Dollar Volume Sales, Berkshire County 2018YTD
    • Platinum Award 2017, 2015
    • Gold, Silver, Bronze Awards 20-13-2016
    • Top Office Producer 2013-2017
    • 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

My Listings

1 Pinecroft Dr $3,450,000 link

1 Pinecroft Dr

Lenox, MA 01240 | Berkshire County
$3,450,000
6 Beds 5/1 Baths 7,816 Sqft 1.14 Acres

Enjoy the ultimate luxury of a turn-key residence, steps from the Canyon Ranch resort and all of its wellness lifestyle amenities. Offered fully furnished, this extraordinary home...

6
bed
5/1
bath
7,816
sqft
36 Pittsfield Rd $2,950,000 link

36 Pittsfield Rd

Lenox, MA 01240 | Berkshire County
$2,950,000
0.00 Baths 25 Acres

Ideally located on Route 7/20 in Lenox, this expansive 25-acre property is allocated for commercial development. One mixed-use building currently on the property contains two businesses...

0.00
bath
25.00
acre
79 Hawthorne St $2,500,000 link

79 Hawthorne St

Stockbridge, MA 01262 | Berkshire County
$2,500,000
4 Beds 4/2 Baths 5,952 Sqft 36.4 Acres

An exquisite traditional Georgian-style brick manor house is the centerpiece of this rare 36-acre Stockbridge estate, which offers both privacy and proximity to Lenox village,...

4
bed
4/2
bath
5,952
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 #14 $2,205,000 link

165 Kemble St #14

Lenox, MA 01240 | Berkshire County
$2,205,000
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