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
  • 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

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. It’s gratifying to know that my 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.

My 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. 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 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, I have been instrumental in building our business to a #1 market share position in Berkshire County. I am currently #1 in sales (dollar volume) and am consistently among the top-selling realtors in the County. In 2017, I founded The Shire Group with Maggie Barry and Leslie Chesloff. We are now the top-selling realtor team in Berkshire County.

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 my buyers and sellers.

Like many people...

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. It’s gratifying to know that my 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.

My 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. 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 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, I have been instrumental in building our business to a #1 market share position in Berkshire County. I am currently #1 in sales (dollar volume) and am consistently among the top-selling realtors in the County. In 2017, I founded The Shire Group with Maggie Barry and Leslie Chesloff. We are now the top-selling realtor team in Berkshire County.

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 my buyers and 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 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.

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

 

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. It’s gratifying to know that my 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.

My 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. 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 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, I have been instrumental in building our business to a #1 market share position in Berkshire County. I am currently #1 in sales (dollar volume) and am consistently among the top-selling realtors in the County. In 2017, I founded The Shire Group with Maggie Barry and Leslie Chesloff. We are now the top-selling realtor team in Berkshire County.

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 my buyers and 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 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.

 I look forward to speaking with you about how my team and 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
    • Adirondack Writing Center - Nonfiction Award for An Elegant Wilderness
    • Victorian Society of New York Book Award for An Elegant Wilderness
    • City and Regional Magazine Award for Berkshire Living Home + Garden
  • Specialities
    • Architecturally Distinctive Properties
    • Antique Homes

My Listings

36 Pittsfield Rd $4,950,000 link

36 Pittsfield Rd

Lenox, MA 01240 | Berkshire County
$4,950,000
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 $3,795,000 link

1 Pinecroft Dr

Lenox, MA 01240 | Berkshire County
$3,795,000
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
86 Interlaken Rd $2,750,000 link

86 Interlaken Rd

Stockbridge, MA 01262 | Berkshire County
$2,750,000
8.63 Acres

A once-in-a-lifetime opportunity to renovate or potentially to build on an existing 6,328sf footprint, in a prime 8.63-acre spot with significant lake frontage on the west side...

8.63
acre

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