The Shire Group

Real Estate Professional

The Shire Group

The Shire Group

Real Estate Professional

Great Barrington

306 Main Street
Great Barrington, MA 01230

Lenox

34 Church Street
Lenox, MA 01240
Visit our website

The Shire Group/ William Pitt Sotheby’s International Realty

The Shire Group comprises full-time professional realtors whose goal is simple: to provide our buyers and sellers with the best client service in the business. Distinctive service is the key to success, so we listen carefully to our clients and work passionately and tirelessly to surpass their expectations. With significant real estate experience and relevant backgrounds in other fields, we provide the expertise and the dedication to achieve flawless transactions. William Pitt Sotheby’s International Realty offers unparalleled tools for assisting buyers and for presenting our sellers’ properties to their best advantage: we delight in using those tools...

The Shire Group comprises full-time professional realtors whose goal is simple: to provide our buyers and sellers with the best client service in the business. Distinctive service is the key to success, so we listen carefully to our clients and work passionately and tirelessly to surpass their expectations. With significant real estate experience and relevant backgrounds in other fields, we provide the expertise and the dedication to achieve flawless transactions. William Pitt Sotheby’s International Realty offers unparalleled tools for assisting buyers and for presenting our sellers’ properties to their best advantage: we delight in using those tools. Whether it’s a small bit of land with a view, a cottage in the woods or on a lake, a neighborhood home, or a significant estate, luxury really does come in every price range. Let us help you achieve your real estate dreams.

What does “distinctive service” mean? It means that we:

 Make ourselves available to you, if not 24/7, then darn close to it,

 Communicate clearly and often,

 Adhere to the highest ethical and professional standards,

 Represent you effectively,

 Are proactive in anticipating and meeting your needs as a client,

 Make the extra effort for you that earns your trust and respect,

 Treat you as we would want to be treated if we were the client.

About The Shire

Are we Lord of the Rings aficionados? Not as avid as some, but we do think Tolkien was onto something. His Shire, like our Berkshires, is a verdant countryside, a place of rolling fields, light-dappled woods, gentle hills, old mountains, myriad streams, rivers and lakes. When you are out in the larger world, this is a place you want to return to, time and time again. Where you live is more than just the location of your home – it’s where you choose to experience life, pursue inspiration, and connect with your passions. Whether you become a full-time resident or a second-home owner in the Berkshires, this is where your heart will reside.

About Us

Gladys Montgomery: A realtor for 11 years, Gladys is consistently one of the company’s top producers. Formerly an award-winning writer and editor specializing in architecture and design, Gladys has authored three books about historic buildings and is an expert in antique homes; she has styled, supervised photo sessions, and penned some 250 feature articles for national and regional magazines; and she was founding editor of Berkshire Living Home + Garden. She also worked as a marketing professional, with a forté in strategic, creative marketing. A graduate of Syracuse University, Gladys grew up on Long Island; has lived in Washington, D.C., Manhattan, and the Boston area; and was an expatriate in Japan and Southeast Asia for eight years. Having chosen to live in the Berkshires because of its lifestyle advantages, she loves helping others make successful transitions here. She is licensed in Massachusetts, Connecticut, and New York.

Maggie Barry: A native of the Berkshires and a graduate of the University of Massachusetts, Amherst, with a degree in business administration, Maggie has worked in architectural offices and with builders, has lived in Italy and Spain, and is a small-business owner as a principal in the Lake House Inn in Lee, Massachusetts. Having earned her Massachusetts real estate license in 2014, she is a million-dollar producer, who possesses a strong work ethic, works effectively with sellers and buyers, understands strategic marketing on social media, and delights in introducing newcomers to this area.

Leslie Chesloff: After a successful 35-year career as a television executive, Leslie relocated to Great Barrington full-time three years ago and became a licensed real estate agent. She has quickly become one of the top producing agents in Berkshire County.  Having gone through the construction process many times, Leslie has recently built her second home in the Berkshires. Having also built three homes in Boston, Philadelphia and Short Hills NJ, she loves to help clients with interior design and the building process, as well as give recommendations for everything from the best painter to the best restaurant.

Leslie is happy to show you around the Berkshires and share all of her favorite things.

The Berkshires:

If you’d like to know more about the area, please request The Shire Group’s Berkshire LifeStyle Guide.

The Shire Group comprises full-time professional realtors whose goal is simple: to provide our buyers and sellers with the best client service in the business. Distinctive service is the key to success, so we listen carefully to our clients and work passionately and tirelessly to surpass their expectations. With significant real estate experience and relevant backgrounds in other fields, we provide the expertise and the dedication to achieve flawless transactions. William Pitt Sotheby’s International Realty offers unparalleled tools for assisting buyers and for presenting our sellers’ properties to their best advantage: we delight in using those tools. Whether it’s a small bit of land with a view, a cottage in the woods or on a lake, a neighborhood home, or a significant estate, luxury really does come in every price range. Let us help you achieve your real estate dreams.

What does “distinctive service” mean? It means that we:

 Make ourselves available to you, if not 24/7, then darn close to it,

 Communicate clearly and often,

 Adhere to the highest ethical and professional standards,

 Represent you effectively,

 Are proactive in anticipating and meeting your needs as a client,

 Make the extra effort for you that earns your trust and respect,

 Treat you as we would want to be treated if we were the client.

About The Shire

Are we Lord of the Rings aficionados? Not as avid as some, but we do think Tolkien was onto something. His Shire, like our Berkshires, is a verdant countryside, a place of rolling fields, light-dappled woods, gentle hills, old mountains, myriad streams, rivers and lakes. When you are out in the larger world, this is a place you want to return to, time and time again. Where you live is more than just the location of your home – it’s where you choose to experience life, pursue inspiration, and connect with your passions. Whether you become a full-time resident or a second-home owner in the Berkshires, this is where your heart will reside.

About Us

Gladys Montgomery: A realtor for 11 years, Gladys is consistently one of the company’s top producers. Formerly an award-winning writer and editor specializing in architecture and design, Gladys has authored three books about historic buildings and is an expert in antique homes; she has styled, supervised photo sessions, and penned some 250 feature articles for national and regional magazines; and she was founding editor of Berkshire Living Home + Garden. She also worked as a marketing professional, with a forté in strategic, creative marketing. A graduate of Syracuse University, Gladys grew up on Long Island; has lived in Washington, D.C., Manhattan, and the Boston area; and was an expatriate in Japan and Southeast Asia for eight years. Having chosen to live in the Berkshires because of its lifestyle advantages, she loves helping others make successful transitions here. She is licensed in Massachusetts, Connecticut, and New York.

Maggie Barry: A native of the Berkshires and a graduate of the University of Massachusetts, Amherst, with a degree in business administration, Maggie has worked in architectural offices and with builders, has lived in Italy and Spain, and is a small-business owner as a principal in the Lake House Inn in Lee, Massachusetts. Having earned her Massachusetts real estate license in 2014, she is a million-dollar producer, who possesses a strong work ethic, works effectively with sellers and buyers, understands strategic marketing on social media, and delights in introducing newcomers to this area.

Leslie Chesloff: After a successful 35-year career as a television executive, Leslie relocated to Great Barrington full-time three years ago and became a licensed real estate agent. She has quickly become one of the top producing agents in Berkshire County.  Having gone through the construction process many times, Leslie has recently built her second home in the Berkshires. Having also built three homes in Boston, Philadelphia and Short Hills NJ, she loves to help clients with interior design and the building process, as well as give recommendations for everything from the best painter to the best restaurant.

Leslie is happy to show you around the Berkshires and share all of her favorite things.

The Berkshires:

If you’d like to know more about the area, please request The Shire Group’s Berkshire LifeStyle Guide.

Read Less

Read MoreRead Less

Our Listings

36 Pittsfield Rd
Lenox, MA $4,500,000

36 Pittsfield Rd

Lenox, MA

$4,500,000
  • 68.87 Acres
89 Dunmore Ct
Lenox, MA $975,000

89 Dunmore Ct

Lenox, MA

$975,000
  • 5 Beds
  • 4 Baths
  • 5,736 Sqft
20 Wright Ln
Great Barrington, MA $875,000

20 Wright Ln

Great Barrington, MA

$875,000
  • 4 Beds
  • 2/1 Baths
  • 1,880 Sqft
23 Pleasant St
Great Barrington, MA $795,000

23 Pleasant St

Great Barrington, MA

$795,000
  • 5 Beds
  • 3/1 Baths
  • 2,806 Sqft

Our Sales

429 Stratton Rd
Williamstown, MA $1,015,000
SOLD

429 Stratton Rd

Williamstown, MA

$1,015,000
  • 5 Beds
  • 4/2 Baths
  • 3,929 Sqft
120 Blythewood Dr
Pittsfield, MA $669,000
SOLD

120 Blythewood Dr

Pittsfield, MA

$669,000
  • 5 Beds
  • 2 Baths
  • 2,426 Sqft
100 Shore Dr
Hinsdale, MA $620,000
SOLD

100 Shore Dr

Hinsdale, MA

$620,000
  • 4 Beds
  • 2/1 Baths
  • 2,200 Sqft
20 Waubeek Rd
Pittsfield, MA $480,000
SOLD

20 Waubeek Rd

Pittsfield, MA

$480,000
  • 3 Beds
  • 2 Baths
  • 1,684 Sqft

Additional Communities

Click to view listings available
+-