Gladys Montgomery
Real Estate Salesperson
- 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/
Read Less
My Sales
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
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
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
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
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
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
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
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
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
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
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
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

















































