Leslie Glenn Chesloff

Leslie Glenn Chesloff

Real Estate Salesperson

Great Barrington

306 Main Street
Great Barrington, MA 01230

Lenox

26 Church Street
Lenox, MA 01240

Leslie treats her clients like friends and helps them find a slice of heaven in The Berkshires

  • Born In:
    Short Hills, NJ
  • Live In:
    Great Barrington, MA
  • Favorite Movie:
    The Big Chill
  • Passion:
    Great food and friends

After a successful 35-year career as a media executive, Leslie relocated to Great Barrington full-time ten years ago and became a licensed real estate agent. She has quickly became one of the top producing agents in Berkshire County.  Having gone through the construction process many times, Leslie built two homes in the Berkshires. She has 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.  As a media executive in many high profile positions, Leslie brings to her real estate endeavors a well tuned set of negotiation and strategic planning skills, all suited for the Berkshire real estate market. She is a licensed agent in Massachusetts, New York, and Connecticut.

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

After a successful 35-year career as a media executive, Leslie relocated to Great Barrington full-time ten years ago and became a licensed real estate agent. She has quickly became one of the top producing agents in Berkshire County.  Having gone through the construction process many times, Leslie built two homes in the Berkshires. She has 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.  As a media executive in many high profile positions, Leslie brings to her real estate endeavors a well tuned set of negotiation and strategic planning skills, all suited for the Berkshire real estate market. She is a licensed agent in Massachusetts, New York, and Connecticut.

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

After a successful 35-year career as a media executive, Leslie relocated to Great Barrington full-time ten years ago and became a licensed real estate agent. She has quickly became one of the top producing agents in Berkshire County.  Having gone through the construction process many times, Leslie built two homes in the Berkshires. She has 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.  As a media executive in many high profile positions, Leslie brings to her real estate endeavors a well tuned set of negotiation and strategic planning skills, all suited for the Berkshire real estate market. She is a licensed agent in Massachusetts, New York, and Connecticut.

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

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  • Awards
    • 2021 Diamond Award
    • 2021 #1 Dollar Volume Berkshire Office
    • 2020 Platinum Award
    • 2019 Gold Award
    • 2019 #1 Units Sold Berkshire Office
    • 2018 Platinum Award
    • 2018 #2 Dollar Volume Berkshire office
    • 2017 Gold Award
    • Pricing Strategy Advisor

My Listings

802 State Rd $2,250,000 link

802 State Rd

Richmond, MA 01254
$2,250,000
6,000 Sqft 16 Acres

Immerse yourself in the premier equestrian lifestyle with this full-service facility nestled in the Berkshires. Spanning 16 acres of pastoral beauty, it boasts a 6000 sqft heated...

6,000
sqft
802 State Rd $1,500,000 link

802 State Rd

Richmond, MA 01254
$1,500,000
6,232 Sqft 11 Acres

Nestled in the heart of the Berkshires, this historic Richmond compound presents a rare colonial charm. Spanning 11 bucolic acres with sweeping pastoral views, the legendary c1776...

6,232
sqft
2650 Swamp Rd $3,750,000 link

2650 Swamp Rd

Richmond, MA 01254
$3,750,000
5 Beds 7/1 Baths 6,022 Sqft 5.65 Acres

This architectural gem has been carefully restored and enhanced to exceptional standards, preserving its storied heritage while seamlessly integrating contemporary conveniences....

5
bed
7/1
bath
6,022
sqft

My Sales

49 Chanterwood Rd $4,800,000 link

49 Chanterwood Rd

Lee, MA 01238
$4,800,000
5 Beds 6/1 Baths 6,000 Sqft 35 Acres

Exquisite Lakefront Sanctuary in the Heart of the Berkshires. Nestled amidst the ancient boulders of Goose Pond's pristine shores, rare opportunity to own a quintessential...

5
bed
6/1
bath
6,000
sqft
165 Kemble St #18 $3,850,000 link

165 Kemble St #18

Lenox, MA 01240 | Berkshire County
$3,850,000
3 Beds 3/1 Baths 3,348 Sqft

Experience the pinnacle of wellness living in this exquisite Canyon Ranch penthouse in Lenox, a beacon of luxury in one of the nation's most revered destinations. Crafted with...

3
bed
3/1
bath
3,348
sqft
321 West Rd $3,170,000 link

321 West Rd

Alford, MA 01266 | Berkshire County
$3,170,000
5 Beds 4/2 Baths 5,514 Sqft 15.86 Acres

Custom built contemporary home on 15 acres with protected view of fields and mountains. Views from every window! Living room with wood burning fire place, beech flooring and Pella...

5
bed
4/2
bath
5,514
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
1 Pinecroft Dr $2,600,000 link

1 Pinecroft Dr

Lenox, MA 01240 | Berkshire County
$2,600,000
6 Beds 6 Baths 7,816 Sqft 1.14 Acres

Exquisite in every detail, this home graces more than an acre of prime Berkshire property! In a league of it's own as part of the Pinecroft subdivsion of Canyon Ranch, this luxurious...

6
bed
6
bath
7,816
sqft
165 Kemble St #19 $2,575,000 link

165 Kemble St #19

Lenox, MA 01240 | Berkshire County
$2,575,000
3 Beds 3/1 Baths 2,575 Sqft

Canyon Ranch Penthouse available! 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...

3
bed
3/1
bath
2,575
sqft
165 Kemble St #10 $2,300,000 link

165 Kemble St #10

Lenox, MA 01240 | Berkshire County
$2,300,000
2 Beds 2/1 Baths 1,790 Sqft

Enjoy Canyon Ranch Living, the ultimate in luxury in this gated community, that offers gracious living with a focus on health and wellness. This two bedroom condo with home office...

2
bed
2/1
bath
1,790
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
165 Kemble St #16 $2,100,000 link

165 Kemble St #16

Lenox, MA 01240 | Berkshire County
$2,100,000
2 Beds 2/1 Baths 1,685 Sqft

Enjoy Canyon Ranch Living, the ultimate in luxury in this gated community, that offers gracious living with a focus on health and wellness. This turn-key, upgraded two bedroom...

2
bed
2/1
bath
1,685
sqft
1488 State Rd $2,030,000 link

1488 State Rd

Richmond, MA 01254
$2,030,000
4 Beds 4/1 Baths 4,098 Sqft 15 Acres

Picture perfect and ideally situated, this exceptional custom-built home is nestled on 15 private acres of fields and woodlands in the heart of Richmond, Massachusetts, just minutes...

4
bed
4/1
bath
4,098
sqft
165 Kemble St, $2,000,000 link

165 Kemble St,

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

Imagine yourself in a home that is exquisite in every detail. Situated on the grounds of Canyon Ranch in the Berkshires-in a league of it's own as one of the world's most celebrated...

2
bed
2/1
bath
1,685
sqft