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

Consistently a top-selling agent and the #1 Producer in Berkshire County Dollar Volume Sales in 2018,* Gladys prides herself on maintaining the highest standard of client service. Having moved to the Berkshires in 2004, she earned her Massachusetts real estate sales license in 2007; she is also licensed in Connecticut and New York. One of six agents selected to launch Sotheby's Berkshire brokerage in 2013, she was instrumental in helping the company achieve its #1 ranking in Berkshire County market share.

Having lived in many places --- New York’s Upper West Side, a Boston suburb, Long Island, Washington D.C., and for eight years as an expat in Asia --- Gladys understands first-hand what a truly extraordinary community the Berkshires is and delights in helping new arrivals learn about and enjoy their Berkshire experience as much as she does.

Gladys's forté is helping her clients purchase and sell architecturally distinctive properties. Prior to becoming a realtor, she had a 25-year career as a writer, editor and author specializing in residential architecture; she penned more than 300 home-focused articles and supervised numerous photo-shoots; authored three books about historic buildings; and was the founding editor of Berkshire Living Home & Garden. She’s also restored and renovated her own homes and has a background in international strategic marketing.

With this experience and her commitment to providing exceptional service to her clients, she’s a go-to realtor for discerning buyers and sellers in every price range. Her clients especially appreciate her positive attitude, thoughtful advice, and diligence in effecting successful transactions and transitions to their new homes.

* 2018 Berkshire County MLS sales statistic

Consistently a top-selling agent and the #1 Producer in Berkshire County Dollar Volume Sales in 2018,* Gladys prides herself on maintaining the highest standard of client service. Having moved to the Berkshires in 2004, she earned her Massachusetts real estate sales license in 2007; she is also licensed in Connecticut and New York. One of six agents selected to launch Sotheby's Berkshire brokerage in 2013, she was instrumental in helping the company achieve its #1 ranking in Berkshire County market share.

Having lived in many places --- New York’s Upper West Side, a Boston suburb, Long Island, Washington D.C., and for eight years as an expat in Asia --- Gladys understands first-hand what a truly extraordinary community the Berkshires is and delights in helping new arrivals learn about and enjoy their Berkshire experience as much as she does.

Gladys's forté is helping her clients purchase and sell architecturally distinctive properties. Prior to becoming a realtor, she had a 25-year career as a writer, editor and author specializing in residential architecture; she penned more than 300 home-focused articles and supervised numerous photo-shoots; authored three books about historic buildings; and was the founding editor of Berkshire Living Home & Garden. She’s also restored and renovated her own homes and has a background in international strategic marketing.

With this experience and her commitment to providing exceptional service to her clients, she’s a go-to realtor for discerning buyers and sellers in every price range. Her clients especially appreciate her positive attitude, thoughtful advice, and diligence in effecting successful transactions and transitions to their new homes.

* 2018 Berkshire County MLS sales statistic

Consistently a top-selling agent and the #1 Producer in Berkshire County Dollar Volume Sales in 2018,* Gladys prides herself on maintaining the highest standard of client service. Having moved to the Berkshires in 2004, she earned her Massachusetts real estate sales license in 2007; she is also licensed in Connecticut and New York. One of six agents selected to launch Sotheby's Berkshire brokerage in 2013, she was instrumental in helping the company achieve its #1 ranking in Berkshire County market share.

Having lived in many places --- New York’s Upper West Side, a Boston suburb, Long Island, Washington D.C., and for eight years as an expat in Asia --- Gladys understands first-hand what a truly extraordinary community the Berkshires is and delights in helping new arrivals learn about and enjoy their Berkshire experience as much as she does.

Gladys's forté is helping her clients purchase and sell architecturally distinctive properties. Prior to becoming a realtor, she had a 25-year career as a writer, editor and author specializing in residential architecture; she penned more than 300 home-focused articles and supervised numerous photo-shoots; authored three books about historic buildings; and was the founding editor of Berkshire Living Home & Garden. She’s also restored and renovated her own homes and has a background in international strategic marketing.

With this experience and her commitment to providing exceptional service to her clients, she’s a go-to realtor for discerning buyers and sellers in every price range. Her clients especially appreciate her positive attitude, thoughtful advice, and diligence in effecting successful transactions and transitions to their new homes.

* 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

Testimonials

Gladys Montgomery is a fabulous realtor and a wonderful person. Before retaining Gladys we marketed our house for more than a year and received no offers. Gladys brought us to a more realistic listing price and encouraged a few modest home improvements that helped the sale process. She then marketed the house and handled buyer negotiations so effectively that we had a contract for sale and a back up buyer in less than three months. She provided excellent guidance when issues came up during the inspection period. Within weeks of our finding a buyer, Gladys also found us a new home that fit our needs and desires perfectly. She also referred us to a number of excellent vendors who provided services including legal representation, rapid mortgage application processing, home improvements, and sales of the many items we were not taking with us. Gladys was wonderful to work with and to get to know. She is open, warm, humorous, and a caring person, yet, when acting on our behalf and when the situation called for it, she could be tough when she needed to be. We cannot recommend her highly enough. Jerry Congress and Lesley Richman

ron ragusa

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 3,894 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
3,894
sqft
165 Kemble St #8 $1,850,000 link

165 Kemble St #8

Lenox, MA 01240 | Berkshire County
$1,850,000
2 Beds 2/1 Baths 1,683 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
1,683
sqft
165 Kemble St #15 $1,575,000 link

165 Kemble St #15

Lenox, MA 01240 | Berkshire County
$1,575,000
1 Beds 1/1 Baths 1,308 Sqft

A unique opportunity to own a one-bedroom-with-study unit at the premier resort, Canyon Ranch, Lenox. This is the only unit of this design on the market. Canyon Ranch Living defines...

1
bed
1/1
bath
1,308
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
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
2 Brace Road $2,100,000 link

2 Brace Road

Tyringham , MA 01264 | Berkshire County
$2,100,000
6 Beds 4/2 Baths 7,372 Sqft 114.5 Acres

Welcome to South House, a spectacular 115-acre turn-of-the-century estate in one of the loveliest spots in the Berkshires, affording the luxury of escape to a magical place with...

6
bed
4/2
bath
7,372
sqft
86 Interlaken Rd $2,050,000 link

86 Interlaken Rd

Stockbridge, MA 01262 | Berkshire County
$2,050,000
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
165 Kemble St #9 $1,995,000 link

165 Kemble St #9

Lenox, MA 01240 | Berkshire County
$1,995,000
2 Beds 2/1 Baths 1,949 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
1,949
sqft
165 Kemble St #16 $1,900,000 link

165 Kemble St #16

Lenox, MA 01240 | Berkshire County
$1,900,000
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
165 Kemble St #6 $1,835,000 link

165 Kemble St #6

Lenox, MA 01240 | Berkshire County
$1,835,000
2 Beds 2/1 Baths 1,687 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
1,687
sqft
165 Kemble St #10 $1,820,000 link

165 Kemble St #10

Lenox, MA 01240 | Berkshire County
$1,820,000
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
902 West St $1,815,000 link

902 West St

Pittsfield, MA 01201 | Berkshire County
$1,815,000
6 Beds 4 Baths 5,696 Sqft 6.5 Acres

Welcome to Rose Rock Landing, an impressive estate parcel on 6.5 acres on the southern shore of beautiful Lake Onota. This 4,500 square foot home is truly one with nature blending...

6
bed
4
bath
5,696
sqft
151 East Rd $1,700,000 link

151 East Rd

Alford, MA 01266 | Berkshire County
$1,700,000
5 Beds 3/2 Baths 3,750 Sqft 18.79 Acres

A long driveway leads to this magnificently simple contemporary farmhouse with protected views in all directions. For stylishly casual country living: an airy, light-filled plan,...

5
bed
3/2
bath
3,750
sqft