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

Gladys loves her 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 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 perfectly. It’s gratifying to know that her skills and experience are being used to the fullest in helping others. She experiences that satisfaction every day as a realtor in Berkshire County and contiguous areas of Massachusetts, New York State, and Connecticut.

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 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.

One of six agents selected to launch Sotheby's Berkshire brokerage in 2013, she has been instrumental in building the business to a #1 market share position in Berkshire County. She is currently #1 in sales (dollar volume) and am consistently among the top-selling realtors in the County. In 2017, Gladys founded The Shire Group with Maggie Barry and Leslie Chesloff. They are now the top-selling realtor team in Berkshire County.

Before becoming a realtor in 2007, She had a 25-year career in international strategic marketing and as a writer, editor, and author specializing in architecture and design. She penned more than 300 home-focused magazine feature articles and was the founding editor of Berkshire Living Home + Garden. Gladys has also 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...

Gladys loves her 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 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 perfectly. It’s gratifying to know that her skills and experience are being used to the fullest in helping others. She experiences that satisfaction every day as a realtor in Berkshire County and contiguous areas of Massachusetts, New York State, and Connecticut.

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 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.

One of six agents selected to launch Sotheby's Berkshire brokerage in 2013, she has been instrumental in building the business to a #1 market share position in Berkshire County. She is currently #1 in sales (dollar volume) and am consistently among the top-selling realtors in the County. In 2017, Gladys founded The Shire Group with Maggie Barry and Leslie Chesloff. They are now the top-selling realtor team in Berkshire County.

Before becoming a realtor in 2007, She had a 25-year career in international strategic marketing and as a writer, editor, and author specializing in architecture and design. She penned more than 300 home-focused magazine feature articles and was the founding editor of Berkshire Living Home + Garden. Gladys has also 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 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 knows 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.

 Gladys looks forward to speaking with you about how Gladys and her team, can help you achieve your real estate goals.

 

Gladys loves her 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 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 perfectly. It’s gratifying to know that her skills and experience are being used to the fullest in helping others. She experiences that satisfaction every day as a realtor in Berkshire County and contiguous areas of Massachusetts, New York State, and Connecticut.

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 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.

One of six agents selected to launch Sotheby's Berkshire brokerage in 2013, she has been instrumental in building the business to a #1 market share position in Berkshire County. She is currently #1 in sales (dollar volume) and am consistently among the top-selling realtors in the County. In 2017, Gladys founded The Shire Group with Maggie Barry and Leslie Chesloff. They are now the top-selling realtor team in Berkshire County.

Before becoming a realtor in 2007, She had a 25-year career in international strategic marketing and as a writer, editor, and author specializing in architecture and design. She penned more than 300 home-focused magazine feature articles and was the founding editor of Berkshire Living Home + Garden. Gladys has also 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 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 knows 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.

 Gladys looks forward to speaking with you about how Gladys and her team, can help you achieve your real estate goals.

 

Read Less

Read MoreRead Less
  • 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

36 Pittsfield Rd $4,500,000 link

36 Pittsfield Rd

Lenox, MA 01240 | Berkshire County
$4,500,000
68.87 Acres

Ideally located on Route 7/20 in Lenox, this expansive 68-acre property has been divided and approved for Commercial and Residential use. 25 acres are allocated for commercial...

68.87
acre
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
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

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 #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