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

 

 

Click here  to view my LifeStyle Guide to the Berkshires

Read my blog: https://www.theviewfrommyporch.com/

 

 

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

 

 

Click here  to view my LifeStyle Guide to the Berkshires

Read my blog: https://www.theviewfrommyporch.com/

 

 

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

 

 

Click here  to view my LifeStyle Guide to the Berkshires

Read my blog: https://www.theviewfrommyporch.com/

 

 

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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

Thanks for helping us negotiate and close on our new home! We're happy to be joining you in the Berkshires.

Christopher and Katie Metter

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

Gladys was a real pro - she brought a huge amount of background knowledge about architecture to our listing and developed a really ambitious, effective marketing plan. She was kind, thoughtful, respectful and patient, but she knew how to get things done. We were very pleased to work with her.

jkucich

We were looking for an historic house to fall in love with and care for. Gladys understood us right away. She showed sophisticated knowledge of the details of the house and design and she shared her vast network of skilled resources, including her personal guide to the best of the Berkshires. She was very fair and transparent working between us and the seller and incredibly responsive to all of us. It was a great pleasure working with her and I would recommend her highly to anyone looking in the area.

user344059

Gladys helped us buy a wonderful home in Alford, MA and she helped us sell our home in Lenox, MA. She was equally masterful in guiding us through the process of buying and selling. There are some rules that are very specific to the Berkshires and she helped us navigate them. Gladys is a great communicator. Our emails were always answered promptly and our phone call returned quickly. We live most of the year in NYC so her great communication skill made the process very enjoyable. She is a wonderful person to work. Once she got to know us she helped us find the home of our dreams. She knows the area very well and helped us get set up in a new town. I have no hesitation in recommending her and I would work with her again in a heartbeat.

Gary Kahn

My Listings

14 Sullivan Rd $18,000,000 link

14 Sullivan Rd

Sandisfield, MA 01255 | Berkshire County
$18,000,000
7 Beds 5/1 Baths 3,800 Sqft 321.43 Acres

Experience the ultimate country escape in the Berkshires, at Atwater Pond, a magical, consummately private 321-acre woodland property, with its own private 33-acre  lake and...

7
bed
5/1
bath
3,800
sqft
443 Johnson Hill Rd $880,000 link

443 Johnson Hill Rd

Washington, MA 01223 | Berkshire County
$880,000
3 Beds 2 Baths 2,034 Sqft 9.69 Acres

An oasis of peace and privacy awaits, with fields, apple trees, woods, pond, a lovely 3-4BR house, barn, guest cottage, spring house, on 9.69 acres abutting conservation...

3
bed
2
bath
2,034
sqft
150 Main St $795,000 link

150 Main St

Lee, MA 01238 | Berkshire County
$795,000
3 Beds 3/2 Baths 6,319 Sqft 0.32 Acres

This marvelous historic building, offering two apartments and a successful restaurant, is readily convertible to a single-family or multi-family residence. Located on Lee's...

3
bed
3/2
bath
6,319
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
9 Buttondown Ln $3,000,000 link

9 Buttondown Ln

Great Barrington, MA 01236 | Berkshire County
$3,000,000
4 Beds 4/1 Baths 4,100 Sqft 9.1 Acres

Situated at the end of a country road overlooking the Williams River is a remarkable Modern home on 9 acres. Amenities include: river frontage, Pines, River Birches, extensive...

4
bed
4/1
bath
4,100
sqft
324 Long Pond Rd $3,000,000 link

324 Long Pond Rd

Great Barrington, MA 01230 | Berkshire County
$3,000,000
5 Beds 4/1 Baths 4,829 Sqft 10.43 Acres

This spectacular 5 bedroom, 4 1/2 bath post and beam home perched on a 10+ acre mountain ridge instantly welcomes you with a beautiful outdoor pool and hot tub overlooking...

5
bed
4/1
bath
4,829
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
190 Torrey Woods Rd $2,217,500 link

190 Torrey Woods Rd

Williamstown, MA 01267 | Berkshire County
$2,217,500
5 Beds 4 Baths 5,052 Sqft 29 Acres

Shadowbrook: This breathtakingly beautiful European-style estate has been completely updated, renovated, and enhanced to be the ideal country retreat. Comprising 29 very private,...

5
bed
4
bath
5,052
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
165 Kemble St #14 $2,075,000 link

165 Kemble St #14

Lenox, MA 01240 | Berkshire County
$2,075,000
2 Beds 2/1 Baths 1,685 Sqft

Discover luxury living and a wellness lifestyle at their finest in this elegant two-bedroom second-floor unit with gorgeous custom details and beautiful westerly views at Canyon...

2
bed
2/1
bath
1,685
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