Gladys Montgomery

Gladys Montgomery

Real Estate Salesperson

Great Barrington

306 Main Street
Great Barrington, MA 01230

Lenox

26 Church Street
Lenox, MA 01240
  • Born In:
    Huntington, Long Island, New York
  • Live In:
    The Berkshires
  • Favorite Movie:
    On the Waterfront
  • Passion:
    Living Creatively & Fully
  • Interests:
    International Travel, Architecture, Architectural History, Garden Design, Food, Textiles, Art, Traveling, Cooking
  • Favorite Lyric:
    "Always stay humble and kind" -- Tim McGraw
  • Can’t Live Without:
    A positive attitude
  • Inspiration:
    Diverse cultures, Family & Friends, Nature, A clear night sky spangled with stars

One of the six realtors chosen to launch William Pitt Sotheby’s Berkshire Brokerage in 2013, Gladys has been instrumental in helping the firm achieve and maintain its position as the top ranking company in the Berkshire MLS from 2017 to 2022*. Consistently a top-selling agent, she prides herself on providing sound advice and maintaining the highest standard of client service. Her forté is helping her clients purchase and sell architecturally distinctive properties; she is an expert in historic homes.

Prior to earning her Massachusetts real estate license in 2007, Gladys had a 30-year career as an award-winning freelance writer, editor, and author specializing in residential architecture and lifestyle topics. In that capacity, she bylined over 300 magazine feature articles and columns and supervised numerous photo-shoots. She was the founding editor of Berkshire Living Home + Garden and authored three books about historic buildings (published by Rizzoli and by Acanthus Press). She also worked in public relations and in international strategic marketing.

Thanks to this background and to her experience in restoring and renovating her own homes, Gladys excels at presenting her listings to their best advantage and at helping buyers evaluate properties they’re considering.

Also licensed in New York and formerly a realtor in New York City, Gladys maintains strong professional ties there and to other key feeder markets nationally and internationally. Having lived in Manhattan, the Boston area, Long Island, Washington D.C., and as an expat in Asia, she 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.

With this experience and her commitment to providing exceptional client service, Gladys is a go-to realtor for discerning buyers and sellers in every price range. Her clients especially appreciate her professionalism and expertise, positive attitude, thoughtful advice, and diligence in helping them achieve successful transactions and transitions to their new homes.

 

* Berkshire County MLS sales statistic

Click here  to view my LifeStyle Guide to the Berkshires

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

 

 

One of the six realtors chosen to launch William Pitt Sotheby’s Berkshire Brokerage in 2013, Gladys has been instrumental in helping the firm achieve and maintain its position as the top ranking company in the Berkshire MLS from 2017 to 2022*. Consistently a top-selling agent, she prides herself on providing sound advice and maintaining the highest standard of client service. Her forté is helping her clients purchase and sell architecturally distinctive properties; she is an expert in historic homes.

Prior to earning her Massachusetts real estate license in 2007, Gladys had a 30-year career as an award-winning freelance writer, editor, and author specializing in residential architecture and lifestyle topics. In that capacity, she bylined over 300 magazine feature articles and columns and supervised numerous photo-shoots. She was the founding editor of Berkshire Living Home + Garden and authored three books about historic buildings (published by Rizzoli and by Acanthus Press). She also worked in public relations and in international strategic marketing.

Thanks to this background and to her experience in restoring and renovating her own homes, Gladys excels at presenting her listings to their best advantage and at helping buyers evaluate properties they’re considering.

Also licensed in New York and formerly a realtor in New York City, Gladys maintains strong professional ties there and to other key feeder markets nationally and internationally. Having lived in Manhattan, the Boston area, Long Island, Washington D.C., and as an expat in Asia, she 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.

With this experience and her commitment to providing exceptional client service, Gladys is a go-to realtor for discerning buyers and sellers in every price range. Her clients especially appreciate her professionalism and expertise, positive attitude, thoughtful advice, and diligence in helping them achieve successful transactions and transitions to their new homes.

 

* Berkshire County MLS sales statistic

Click here  to view my LifeStyle Guide to the Berkshires

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

 

 

One of the six realtors chosen to launch William Pitt Sotheby’s Berkshire Brokerage in 2013, Gladys has been instrumental in helping the firm achieve and maintain its position as the top ranking company in the Berkshire MLS from 2017 to 2022*. Consistently a top-selling agent, she prides herself on providing sound advice and maintaining the highest standard of client service. Her forté is helping her clients purchase and sell architecturally distinctive properties; she is an expert in historic homes.

Prior to earning her Massachusetts real estate license in 2007, Gladys had a 30-year career as an award-winning freelance writer, editor, and author specializing in residential architecture and lifestyle topics. In that capacity, she bylined over 300 magazine feature articles and columns and supervised numerous photo-shoots. She was the founding editor of Berkshire Living Home + Garden and authored three books about historic buildings (published by Rizzoli and by Acanthus Press). She also worked in public relations and in international strategic marketing.

Thanks to this background and to her experience in restoring and renovating her own homes, Gladys excels at presenting her listings to their best advantage and at helping buyers evaluate properties they’re considering.

Also licensed in New York and formerly a realtor in New York City, Gladys maintains strong professional ties there and to other key feeder markets nationally and internationally. Having lived in Manhattan, the Boston area, Long Island, Washington D.C., and as an expat in Asia, she 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.

With this experience and her commitment to providing exceptional client service, Gladys is a go-to realtor for discerning buyers and sellers in every price range. Her clients especially appreciate her professionalism and expertise, positive attitude, thoughtful advice, and diligence in helping them achieve successful transactions and transitions to their new homes.

 

* 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
    • William Pitt|Julia B. Fee Platinum Award 2015, 2017-2022
    • William Pitt|Julia B. Fee Gold, Silver, Bronze Awards, 2013, 2014, 2016
    • Adirondack Writing Center - Nonfiction Award: An Elegant Wilderness (author)
    • Victorian Society of New York Book Award: An Elegant Wilderness (author)
    • City and Regional Magazine Award: Berkshire Living Home + Garden (editor)
    • Philippine National Book Award: E Masferre, People of the Philippine Cordillera, Photographs, 1934-1956 (co-author)
  • Specialities
    • Architecturally Distinctive Properties
    • Antique Homes
    • Mid-Century Modern & Contemporary Homes
    • Luxury & Estate Properties

My Sales

369 Bullitt Rd $4,500,000 link

369 Bullitt Rd

Ashfield, MA 01330 | Franklin County
$4,500,000
6 Beds 4/1 Baths 10,747 Sqft 104 Acres

What makes us fall in love with a place? Is it the feeling of luxury and security that comes from absolute privacy and the combination of the best building traditions and techniques...

6
bed
4/1
bath
10,747
sqft
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
615 Laurel St $3,450,000 link

615 Laurel St

Lee, MA 01238 | Berkshire County
$3,450,000
17 Beds 16/2 Baths 7,937 Sqft 2 Acres

This historic landmark property, which is now known as The LakeHouse Inn, is situated on a cliff with panoramic views of Laurel Lake and its famous sunsets. Set on two well-manicured...

17
bed
16/2
bath
7,937
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
263 E Hill Rd $2,872,566 link

263 E Hill Rd

New Marlborough, MA 01259 | Berkshire County
$2,872,566
5 Beds 5/1 Baths 5,953 Sqft 77.7 Acres

At the crest of a wooded hill is a place made of space, light, and views. A home where you can glide barefoot over polished wood floors enjoying long views across the treetops...

5
bed
5/1
bath
5,953
sqft
148 Stevens Lake Way $2,400,000 link

148 Stevens Lake Way

Monterey, MA 01245 | Berkshire County
$2,400,000
4 Beds 3/2 Baths 4,941 Sqft 15.42 Acres

Experience the consummate pleasure of life in the Berkshires in this serene, spacious Frank Lloyd Wright inspired home, surrounded by mountains, and set high up to take advantage...

4
bed
3/2
bath
4,941
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
165 Kemble St $2,200,000 link

165 Kemble St

Lenox, MA 01240 | Berkshire County
$2,200,000
2 Beds 2/1 Baths 1,685 Sqft

Canyon Ranch Living Unit No.16 is now available for purchase. A stunning condominium residence located within the gated property of Canyon Ranch in Lenox, MA, The Berkshires. Enjoy...

2
bed
2/1
bath
1,685
sqft